SMALL SHIP CARIBBEAN CRUISES
Experience the Caribbean in Windstar Style
Anguilla has some of the most beautiful sunsets and delicious rum punch to be found in the Caribbean. It is also home to Cuban tree frogs, red-footed tortoise, green iguanas, and five species of bats.
With its protected shoreline, calm surf, spectacular coral reefs, and sugar-soft beaches, Road Bay has become a destination for boaters, eager to visit its delightful restaurants, bars, and shops.
Visit ports reserved for small ships and private yachts like Mayreau, Bequia, Jost Van Dyke, and Virgin Gorda.
Kayak, paddleboard or swim directly off the complimentary Marina Platform located at the back of the yacht, and enjoy your own set of personalized snorkel gear to use throughout your cruise.
Enjoy Windstar’s Signature Beach Party and a Signature Onboard Barbecue on every itinerary — events that are always a highlight for our guests.
Get Closer to the Caribbean
The perfect island itinerary would look a lot like these. Ports of call would include tiny towns and hidden harbors known only to small ships and private yachts like ours. Schedules would allow for dropping the Marina Platform in cerulean seas and raising sails on the way to your next island rendezvous. And the laid-back island vibe continues on board with a mouthwatering Signature Onboard Barbecue. Best of all, every sailing includes a landing on a secluded beach for Windstar’s Signature Beach Party, elaborate buffet and watersports included.
Yachtsman's Secrets
Shh. There are still secret places here that the big ships pass by. Places where there’s only one beach bar in sight, closed if the proprietor decides to go spear fishing. Your Windstar yacht has an uncanny ability to find places like this. Places where your day’s activities are timed by the rumble of your stomach, the drowsiness following a good swim, an iridescent sunset that heralds “sailor’s delight” on the morrow. But then, one glance at your itinerary already told you that.
Windstar Voyages to Caribbean
Sample body copy to show what it looks like.
Bermuda Bliss
MANHATTAN, NEW YORK to SAN JUANiEmbark on an ocean crossing from Manhattan to San Juan with an overnight in St. George’s, Bermuda. Commence your adventure amid the iconic skyline of Manhattan, absorbing the grandeur of the Statue of Liberty and the Brooklyn Bridge. Indulge in the bliss of multiple sea days, where you’ll have uninterrupted relaxation. As you traverse the cobblestone streets of St. George, a UNESCO World Heritage Site, the brilliant hues of azure water pastel-colored buildings evoke a sense of timeless charm. Immerse yourself in the culture and history, from the imposing silhouette of St. Peter's Church to the architectural marvel of the Town Hall. Discover a serenity that rejuvenates the soul during an overnight in Bermuda before a few more tranquil days at sea. Arrive in the historic and vibrant city of San Juan, Puerto Rico, a city welcoming you with a blend of history and Caribbean flair.
7 Nights in Star Pride Yacht
San Juan & the Virgin Islands
SAN JUAN to SAN JUANiBegin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. As you continue on this bewitching Caribbean cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen — like you. Skip more common and commercial ports like St. Thomas in favor of less-visited destinations like Montserrat. Bypass the major cruise terminals in favor of marinas and anchorages exclusive to small yachts on this Caribbean cruise. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant yacht is already there.
7 Nights in Star Pride Yacht
14 Nights in Star Pride Yacht
San Juan & the Virgin Islands
SAN JUAN to SAN JUANiBegin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. As you continue on this bewitching Caribbean cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen — like you. Skip more common and commercial ports like St. Thomas in favor of less-visited destinations like Montserrat. Bypass the major cruise terminals in favor of marinas and anchorages exclusive to small yachts on this Caribbean cruise. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant yacht is already there.
7 Nights in Star Pride Yacht
14 Nights in Star Pride Yacht
San Juan & the Virgin Islands
SAN JUAN to SAN JUANiBegin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. As you continue on this bewitching Caribbean cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen — like you. Skip more common and commercial ports like St. Thomas in favor of less-visited destinations like Montserrat. Bypass the major cruise terminals in favor of marinas and anchorages exclusive to small yachts on this Caribbean cruise. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant yacht is already there.
7 Nights in Star Pride Yacht
14 Nights in Star Pride Yacht
San Juan & the Virgin Islands
SAN JUAN to SAN JUANiBegin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. As you continue on this bewitching Caribbean cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen — like you. Skip more common and commercial ports like St. Thomas in favor of less-visited destinations like Montserrat. Bypass the major cruise terminals in favor of marinas and anchorages exclusive to small yachts on this Caribbean cruise. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant yacht is already there.
7 Nights in Star Pride Yacht
14 Nights in Star Pride Yacht
San Juan & the Virgin Islands
SAN JUAN to SAN JUANiBegin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. As you continue on this bewitching Caribbean cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen — like you. Skip more common and commercial ports like St. Thomas in favor of less-visited destinations like Montserrat. Bypass the major cruise terminals in favor of marinas and anchorages exclusive to small yachts on this Caribbean cruise. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant yacht is already there.
7 Nights in Star Pride Yacht
Star Collector: Central America & the Caribbean - Cloud Forest, Canal Locks & Calypso Concerts
SAN JUAN to PUERTO CALDERA, SAN JOSE'iStar Collector: Central America & the Caribbean - Cloud Forest, Canal Locks & Calypso Concerts
20 Nights in Star Pride Yacht
Star Collector: Ivory Beaches & Sapphire Seas of the Caribbean
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiStar Collector: Ivory Beaches & Sapphire Seas of the Caribbean
12 Nights in Wind Surf Yacht
Classic Caribbean
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiFrom the stunning drama of the Pitons to the captivating charm of Les Saintes; hidden coves and secret beaches to exotic markets and lively cafés, you’ll discover the best of this region with one single Caribbean voyage. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.
7 Nights in Wind Surf Yacht
Classic Caribbean
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiFrom the stunning drama of the Pitons to the captivating charm of Les Saintes; hidden coves and secret beaches to exotic markets and lively cafés, you’ll discover the best of this region with one single Caribbean voyage. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.
7 Nights in Wind Surf Yacht
Star Collector: Caribbean Explorations
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiStar Collector: Caribbean Explorations
14 Nights in Wind Surf Yacht
Beach Fun & Sun: A Remote Caribbean Getaway
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiBask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from our yacht’s onboard Marina Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.
7 Nights in Wind Surf Yacht
Beach Fun & Sun: A Remote Caribbean Getaway
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiBask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from our yacht’s onboard Marina Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.
7 Nights in Wind Surf Yacht
Star Collector: Caribbean Explorations
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiStar Collector: Caribbean Explorations
14 Nights in Wind Surf Yacht
*NEW Oranjestad to Bridgetown
ORANJESTAD, ARUBA to BRIDGETOWN, BARBADOSi*NEW Oranjestad to Bridgetown
8 Nights in Wind Spirit Yacht
*NEW Star Collector: Oranjestad to Bridgetown
ORANJESTAD, ARUBA to BRIDGETOWN, BARBADOSi*NEW Star Collector: Oranjestad to Bridgetown
15 Nights in Wind Spirit Yacht
Classic Caribbean
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiFrom the stunning drama of the Pitons to the captivating charm of Les Saintes; hidden coves and secret beaches to exotic markets and lively cafés, you’ll discover the best of this region with one single Caribbean voyage. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.
7 Nights in Wind Surf Yacht
Classic Caribbean
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiFrom the stunning drama of the Pitons to the captivating charm of Les Saintes; hidden coves and secret beaches to exotic markets and lively cafés, you’ll discover the best of this region with one single Caribbean voyage. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.
7 Nights in Wind Surf Yacht
Star Collector: Caribbean Explorations
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiStar Collector: Caribbean Explorations
14 Nights in Wind Surf Yacht
*NEW Star Collectory: Bridgetown to Philipsburg
BRIDGETOWN, BARBADOS to PHILIPSBURG, ST. MAARTENi*NEW Star Collectory: Bridgetown to Philipsburg
17 Nights in Wind Spirit Yacht
Beach Fun & Sun: A Remote Caribbean Getaway
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiBask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from our yacht’s onboard Marina Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.
7 Nights in Wind Surf Yacht
Beach Fun & Sun: A Remote Caribbean Getaway
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiBask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from our yacht’s onboard Marina Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.
7 Nights in Wind Surf Yacht
Windward Island Delights
BRIDGETOWN, BARBADOS to BRIDGETOWN, BARBADOSiWindward Island Delights
7 Nights in Wind Spirit Yacht
*NEW Bridgetown to Philipsburg
BRIDGETOWN, BARBADOS to PHILIPSBURG, ST. MAARTENi*NEW Bridgetown to Philipsburg
10 Nights in Wind Spirit Yacht
Beach Fun & Sun: A Remote Caribbean Getaway
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiBask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from our yacht’s onboard Marina Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.
7 Nights in Wind Surf Yacht
Beach Fun & Sun: A Remote Caribbean Getaway
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiBask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from our yacht’s onboard Marina Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.
7 Nights in Wind Surf Yacht
Star Collector: A Lesser Antilles Odyssey
PHILIPSBURG, ST. MAARTEN to BRIDGETOWN, BARBADOSiStar Collector: A Lesser Antilles Odyssey
21 Nights in Wind Surf Yacht
Star Collector: Grand Caribbean Adventure
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiStar Collector: Grand Caribbean Adventure
55 Nights in Wind Surf Yacht
Star Collector: Leeward & Windward Caribbean Havens
PHILIPSBURG, ST. MAARTEN to BRIDGETOWN, BARBADOSiStar Collector: Leeward & Windward Caribbean Havens
14 Nights in Wind Surf Yacht
Star Collector: The Best of the Windward & Leeward Isles
PHILIPSBURG, ST. MAARTEN to ORANJESTAD, ARUBAiStar Collector: The Best of the Windward & Leeward Isles
28 Nights in Wind Surf Yacht
Lush & Lovely Islands of the Lesser Antilles
PHILIPSBURG, ST. MAARTEN to BRIDGETOWN, BARBADOSiLush & Lovely Islands of the Lesser Antilles
7 Nights in Wind Surf Yacht
Star Collector: Antilles Adventures
PHILIPSBURG, ST. MAARTEN to BRIDGETOWN, BARBADOSiStar Collector: Antilles Adventures
14 Nights in Wind Surf Yacht
Blue Waters of the Leeward Islands
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiExplore the Leeward Islands of the Caribbean from panoramic summit views to sunny seashores. Swim with gentle Antigua stingrays near Falmouth Harbour. Take in expansive views of Martinique from Fort de France and admire colorful flowers in the quiet shade of small port Anse Mitan’s botanical garden. Learn how to crush local cocoa nibs into liquefied chocolate during a delicious chocolatier class in Castries on St. Lucia. Sail on a catamaran beyond Soper’s Hole and across turquoise waters to Norman Island, a lush and sandy setting that inspired Robert Lewis Stevenson’s classic Treasure Island. Extend your British Virgin Island shore explorations to include succulent lobster, grilled tuna and sweet rum cocktails during overnight port stays in Jost Van Dyke and Virgin Gorda. Remain comfortably dry while viewing colorful reef fish and coral during a semi-submersible cruise near Gustavia.
10 Nights in Wind Spirit Yacht
Blue Waters of the Leeward Islands
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiExplore the Leeward Islands of the Caribbean from panoramic summit views to sunny seashores. Swim with gentle Antigua stingrays near Falmouth Harbour. Take in expansive views of Martinique from Fort de France and admire colorful flowers in the quiet shade of small port Anse Mitan’s botanical garden. Learn how to crush local cocoa nibs into liquefied chocolate during a delicious chocolatier class in Castries on St. Lucia. Sail on a catamaran beyond Soper’s Hole and across turquoise waters to Norman Island, a lush and sandy setting that inspired Robert Lewis Stevenson’s classic Treasure Island. Extend your British Virgin Island shore explorations to include succulent lobster, grilled tuna and sweet rum cocktails during overnight port stays in Jost Van Dyke and Virgin Gorda. Remain comfortably dry while viewing colorful reef fish and coral during a semi-submersible cruise near Gustavia.
10 Nights in Wind Spirit Yacht
Star Collector: Hidden Gems of the Caribbean
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiStar Collector: Hidden Gems of the Caribbean
17 Nights in Wind Spirit Yacht
8 Nights in Star Seeker Yacht
Jewels of the Windward Islands
BRIDGETOWN, BARBADOS to BRIDGETOWN, BARBADOSiThis is the Caribbean of days gone by — deep blue waters, quiet coves and tropical islands dotted with powdery beaches and lush green hillsides. Sail from the rugged natural beauty of St. Lucia to little-known isles that are off the tourist radar. From colorful Bequia and Mayreau in St. Vincent & the Grenadines to the open-air markets of exotic St. George’s, you’ll discover a part of the Caribbean that remains authentic and unspoiled. This is everything that makes the Caribbean synonymous with paradise.
7 Nights in Wind Surf Yacht
Jewels of the Windward Islands
BRIDGETOWN, BARBADOS to BRIDGETOWN, BARBADOSiThis is the Caribbean of days gone by — deep blue waters, quiet coves and tropical islands dotted with powdery beaches and lush green hillsides. Sail from the rugged natural beauty of St. Lucia to little-known isles that are off the tourist radar. From colorful Bequia and Mayreau in St. Vincent & the Grenadines to the open-air markets of exotic St. George’s, you’ll discover a part of the Caribbean that remains authentic and unspoiled. This is everything that makes the Caribbean synonymous with paradise.
7 Nights in Wind Surf Yacht
Star Collector: Captivating Caribbean
BRIDGETOWN, BARBADOS to ORANJESTAD, ARUBAiStar Collector: Captivating Caribbean
14 Nights in Wind Surf Yacht
San Juan & the Virgin Islands
SAN JUAN to SAN JUANiBegin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. As you continue on this bewitching Caribbean cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen — like you. Skip more common and commercial ports like St. Thomas in favor of less-visited destinations like Montserrat. Bypass the major cruise terminals in favor of marinas and anchorages exclusive to small yachts on this Caribbean cruise. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant yacht is already there.
7 Nights in Star Seeker Yacht
14 Nights in Star Seeker Yacht
Classic Caribbean
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiFrom the stunning drama of the Pitons to the captivating charm of Les Saintes; hidden coves and secret beaches to exotic markets and lively cafés, you’ll discover the best of this region with one single Caribbean voyage. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.
7 Nights in Wind Spirit Yacht
Classic Caribbean
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiFrom the stunning drama of the Pitons to the captivating charm of Les Saintes; hidden coves and secret beaches to exotic markets and lively cafés, you’ll discover the best of this region with one single Caribbean voyage. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.
7 Nights in Wind Spirit Yacht
Windward Ways & Tobago Cays
BRIDGETOWN, BARBADOS to ORANJESTAD, ARUBAiWindward Ways & Tobago Cays
7 Nights in Wind Surf Yacht
14 Nights in Star Seeker Yacht
7 Nights in Star Seeker Yacht
Beach Fun & Sun: A Remote Caribbean Getaway
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiBask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from our yacht’s onboard Marina Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.
7 Nights in Wind Spirit Yacht
Beach Fun & Sun: A Remote Caribbean Getaway
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiBask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from our yacht’s onboard Marina Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.
7 Nights in Wind Spirit Yacht
Star Collector: Caribbean Explorations
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiStar Collector: Caribbean Explorations
14 Nights in Wind Spirit Yacht
San Juan & the Virgin Islands
SAN JUAN to SAN JUANiBegin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. As you continue on this bewitching Caribbean cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen — like you. Skip more common and commercial ports like St. Thomas in favor of less-visited destinations like Montserrat. Bypass the major cruise terminals in favor of marinas and anchorages exclusive to small yachts on this Caribbean cruise. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant yacht is already there.
7 Nights in Star Seeker Yacht
14 Nights in Star Seeker Yacht
Classic Caribbean
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiFrom the stunning drama of the Pitons to the captivating charm of Les Saintes; hidden coves and secret beaches to exotic markets and lively cafés, you’ll discover the best of this region with one single Caribbean voyage. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.
7 Nights in Wind Spirit Yacht
Classic Caribbean
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiFrom the stunning drama of the Pitons to the captivating charm of Les Saintes; hidden coves and secret beaches to exotic markets and lively cafés, you’ll discover the best of this region with one single Caribbean voyage. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.
7 Nights in Wind Spirit Yacht
Star Collector: Caribbean Explorations
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiStar Collector: Caribbean Explorations
14 Nights in Wind Spirit Yacht
14 Nights in Star Seeker Yacht
7 Nights in Star Seeker Yacht
Beach Fun & Sun: A Remote Caribbean Getaway
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiBask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from our yacht’s onboard Marina Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.
7 Nights in Wind Spirit Yacht
Beach Fun & Sun: A Remote Caribbean Getaway
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiBask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from our yacht’s onboard Marina Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.
7 Nights in Wind Spirit Yacht
San Juan & the Virgin Islands
SAN JUAN to SAN JUANiBegin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. As you continue on this bewitching Caribbean cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen — like you. Skip more common and commercial ports like St. Thomas in favor of less-visited destinations like Montserrat. Bypass the major cruise terminals in favor of marinas and anchorages exclusive to small yachts on this Caribbean cruise. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant yacht is already there.
7 Nights in Star Seeker Yacht
14 Nights in Star Seeker Yacht
Beach Fun & Sun: A Remote Caribbean Getaway
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiBask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from our yacht’s onboard Marina Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.
7 Nights in Wind Spirit Yacht
Beach Fun & Sun: A Remote Caribbean Getaway
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiBask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from our yacht’s onboard Marina Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.
7 Nights in Wind Spirit Yacht
Star Collector: A Lesser Antilles Odyssey
PHILIPSBURG, ST. MAARTEN to BRIDGETOWN, BARBADOSiStar Collector: A Lesser Antilles Odyssey
21 Nights in Wind Spirit Yacht
Star Collector: Grand Caribbean & Panamanian Adventure
PHILIPSBURG, ST. MAARTEN to BRIDGETOWN, BARBADOSiStar Collector: Grand Caribbean & Panamanian Adventure
28 Nights in Wind Spirit Yacht
Star Collector: Leeward & Windward Caribbean Havens
PHILIPSBURG, ST. MAARTEN to BRIDGETOWN, BARBADOSiStar Collector: Leeward & Windward Caribbean Havens
14 Nights in Wind Spirit Yacht
14 Nights in Star Seeker Yacht
7 Nights in Star Seeker Yacht
Classic Caribbean
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiFrom the stunning drama of the Pitons to the captivating charm of Les Saintes; hidden coves and secret beaches to exotic markets and lively cafés, you’ll discover the best of this region with one single Caribbean voyage. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.
7 Nights in Wind Surf Yacht
Classic Caribbean
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiFrom the stunning drama of the Pitons to the captivating charm of Les Saintes; hidden coves and secret beaches to exotic markets and lively cafés, you’ll discover the best of this region with one single Caribbean voyage. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.
7 Nights in Wind Surf Yacht
Lush & Lovely Islands of the Lesser Antilles
PHILIPSBURG, ST. MAARTEN to BRIDGETOWN, BARBADOSiLush & Lovely Islands of the Lesser Antilles
7 Nights in Wind Spirit Yacht
Star Collector: Antilles Adventures
PHILIPSBURG, ST. MAARTEN to BRIDGETOWN, BARBADOSiStar Collector: Antilles Adventures
14 Nights in Wind Spirit Yacht
Star Collector: Caribbean Explorations
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiStar Collector: Caribbean Explorations
14 Nights in Wind Surf Yacht
San Juan & the Virgin Islands
SAN JUAN to SAN JUANiBegin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. As you continue on this bewitching Caribbean cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen — like you. Skip more common and commercial ports like St. Thomas in favor of less-visited destinations like Montserrat. Bypass the major cruise terminals in favor of marinas and anchorages exclusive to small yachts on this Caribbean cruise. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant yacht is already there.
7 Nights in Star Seeker Yacht
14 Nights in Star Seeker Yacht
Beach Fun & Sun: A Remote Caribbean Getaway
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiBask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from our yacht’s onboard Marina Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.
7 Nights in Wind Surf Yacht
Beach Fun & Sun: A Remote Caribbean Getaway
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiBask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from our yacht’s onboard Marina Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.
7 Nights in Wind Surf Yacht
Jewels of the Windward Islands
BRIDGETOWN, BARBADOS to BRIDGETOWN, BARBADOSiThis is the Caribbean of days gone by — deep blue waters, quiet coves and tropical islands dotted with powdery beaches and lush green hillsides. Sail from the rugged natural beauty of St. Lucia to little-known isles that are off the tourist radar. From colorful Bequia and Mayreau in St. Vincent & the Grenadines to the open-air markets of exotic St. George’s, you’ll discover a part of the Caribbean that remains authentic and unspoiled. This is everything that makes the Caribbean synonymous with paradise.
7 Nights in Wind Spirit Yacht
Jewels of the Windward Islands
BRIDGETOWN, BARBADOS to BRIDGETOWN, BARBADOSiThis is the Caribbean of days gone by — deep blue waters, quiet coves and tropical islands dotted with powdery beaches and lush green hillsides. Sail from the rugged natural beauty of St. Lucia to little-known isles that are off the tourist radar. From colorful Bequia and Mayreau in St. Vincent & the Grenadines to the open-air markets of exotic St. George’s, you’ll discover a part of the Caribbean that remains authentic and unspoiled. This is everything that makes the Caribbean synonymous with paradise.
7 Nights in Wind Spirit Yacht
Star Collector: Blue Seas of the Windward Islands
BRIDGETOWN, BARBADOS to BRIDGETOWN, BARBADOSiStar Collector: Blue Seas of the Windward Islands
14 Nights in Wind Spirit Yacht
7 Nights in Star Seeker Yacht
Beach Fun & Sun: A Remote Caribbean Getaway
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiBask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from our yacht’s onboard Marina Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.
7 Nights in Wind Surf Yacht
Beach Fun & Sun: A Remote Caribbean Getaway
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiBask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from our yacht’s onboard Marina Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.
7 Nights in Wind Surf Yacht
Star Collector: Blue Seas of the Windward Islands
BRIDGETOWN, BARBADOS to BRIDGETOWN, BARBADOSiStar Collector: Blue Seas of the Windward Islands
14 Nights in Wind Spirit Yacht
Star Collector: Caribbean Explorations
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiStar Collector: Caribbean Explorations
14 Nights in Wind Surf Yacht
Windward Island Delights
BRIDGETOWN, BARBADOS to BRIDGETOWN, BARBADOSiWindward Island Delights
7 Nights in Wind Spirit Yacht
Windward Ways & Tobago Cays
ORANJESTAD, ARUBA to BRIDGETOWN, BARBADOSiWindward Ways & Tobago Cays
7 Nights in Star Pride Yacht
Classic Caribbean
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiFrom the stunning drama of the Pitons to the captivating charm of Les Saintes; hidden coves and secret beaches to exotic markets and lively cafés, you’ll discover the best of this region with one single Caribbean voyage. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.
7 Nights in Wind Surf Yacht
Classic Caribbean
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiFrom the stunning drama of the Pitons to the captivating charm of Les Saintes; hidden coves and secret beaches to exotic markets and lively cafés, you’ll discover the best of this region with one single Caribbean voyage. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.
7 Nights in Wind Surf Yacht
Jewels of the Windward Islands
BRIDGETOWN, BARBADOS to BRIDGETOWN, BARBADOSiThis is the Caribbean of days gone by — deep blue waters, quiet coves and tropical islands dotted with powdery beaches and lush green hillsides. Sail from the rugged natural beauty of St. Lucia to little-known isles that are off the tourist radar. From colorful Bequia and Mayreau in St. Vincent & the Grenadines to the open-air markets of exotic St. George’s, you’ll discover a part of the Caribbean that remains authentic and unspoiled. This is everything that makes the Caribbean synonymous with paradise.
7 Nights in Wind Spirit Yacht
Jewels of the Windward Islands
BRIDGETOWN, BARBADOS to BRIDGETOWN, BARBADOSiThis is the Caribbean of days gone by — deep blue waters, quiet coves and tropical islands dotted with powdery beaches and lush green hillsides. Sail from the rugged natural beauty of St. Lucia to little-known isles that are off the tourist radar. From colorful Bequia and Mayreau in St. Vincent & the Grenadines to the open-air markets of exotic St. George’s, you’ll discover a part of the Caribbean that remains authentic and unspoiled. This is everything that makes the Caribbean synonymous with paradise.
7 Nights in Wind Spirit Yacht
Star Collector: Caribbean Explorations
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiStar Collector: Caribbean Explorations
14 Nights in Wind Surf Yacht
10 Nights in Star Seeker Yacht
Star Collector: Historic Caribbean - Legendary Islands, Colombia and Panama
SAN JUAN to PUERTO CALDERA, SAN JOSE'iStar Collector: Historic Caribbean - Legendary Islands, Colombia and Panama
24 Nights in Star Seeker Yacht
17 Nights in Star Seeker Yacht
Beach Fun & Sun: A Remote Caribbean Getaway
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiBask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from our yacht’s onboard Marina Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.
7 Nights in Wind Surf Yacht
Beach Fun & Sun: A Remote Caribbean Getaway
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiBask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from our yacht’s onboard Marina Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.
7 Nights in Wind Surf Yacht
7 Nights in Star Seeker Yacht
Star Collector: Rainforest Refuges of Panama & Costa Rica via the Panama Canal
SAN JUAN to PUERTO CALDERA, SAN JOSE'iStar Collector: Rainforest Refuges of Panama & Costa Rica via the Panama Canal
14 Nights in Star Seeker Yacht
