SMALL SHIP OCEAN CROSSINGS CRUISES







Experience Ocean Crossings in Windstar Style
Sail in style on one of our Wind Class yachts, complete with billowing white sails.
Absorb every shade of blue, from cerulean to cobalt.
Invariably, the deckside hot tub is one of the best seats in the house for whale watching.
Star Breeze, of our all-suite Star Class.
Wind Star, of our iconic Wind Class.
Enjoy romantic moments at the bow.
Take in sunsets presenting every color nature offers.








The Wind and the Stars Know the Way
Indulge yourself in leisurely, unscheduled days where time suspends in the magic of the sea. Sleep late. Dine early. Establish your own rhythm in sync with the waves and the arc of the sun and moon overhead. Watch the constellations drift and let your mind shake off all the cobwebs of shore. Feast on the impossible beauty of liquid sunsets, and let your soul dance with the dolphins in the spray off the bow.
Watch Whales With Windstar
On many of our voyages, you'll have ample opportunity to whale watch (as well as look out for dolphins, flying fish, and sea birds of all shapes and sizes). We've compiled a handy list of the 12 best destinations to view these incredible animals.

Windstar Ocean Crossing Voyages
Sample body copy to show what it looks like.

*NEW Star Collector: Montreal to San Jaun
MONTREAL, QC to SAN JUANi*NEW Star Collector: Montreal to San Jaun
19 Nights in Star Pride Yacht

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

Star Collector: Classic Crossing to Spain & More
BARCELONA to BRIDGETOWN, BARBADOSiIdeal for anyone seeking equal portions of relaxing time at sea and port visits, this transatlantic crossing features a combination of leisurely, uninterrupted sea crossing time balanced with the best ports in the Western Mediterranean. Spend time crossing the Atlantic and enjoy the romance of sailing as you make your way to your ultimate destination. Sip port wines in Lisbon, Portugal, browse wares in the bustling Grand Souk in Tangier, Morocco, and wander the medieval cobbled streets of Tarragona, Spain.
24 Nights in Wind Spirit Yacht

14 Nights in Wind Spirit Yacht

14 Nights in Wind Surf Yacht

Barefoot Break in the British Virgin Islands
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTENiBarefoot Break in the British Virgin Islands
5 Nights in Wind Surf Yacht

16 Nights in Star Seeker Yacht

Star Collector: Caribbean Beats & Transatlantic Treats
BRIDGETOWN, BARBADOS to LISBONiStar Collector: Caribbean Beats & Transatlantic Treats
22 Nights in Wind Spirit Yacht

Transatlantic Crossing Bridgetown to Amsterdam
BRIDGETOWN, BARBADOS to AMSTERDAMiTransatlantic Crossing Bridgetown to Amsterdam
16 Nights in Star Pride Yacht

15 Nights in Wind Spirit Yacht

Star Collector: Classic Crossing to Spain & More
BRIDGETOWN, BARBADOS to BARCELONAiIdeal for anyone seeking equal portions of relaxing time at sea and port visits, this transatlantic crossing features a combination of leisurely, uninterrupted sea crossing time balanced with the best ports in the Western Mediterranean. Spend time crossing the Atlantic and enjoy the romance of sailing as you make your way to your ultimate destination. Sip port wines in Lisbon, Portugal, browse wares in the bustling Grand Souk in Tangier, Morocco, and wander the medieval cobbled streets of Tarragona, Spain.
25 Nights in Wind Spirit Yacht

Star Collector: Classic Crossing to Spain & More
BRIDGETOWN, BARBADOS to BARCELONAiIdeal for anyone seeking equal portions of relaxing time at sea and port visits, this transatlantic crossing features a combination of leisurely, uninterrupted sea crossing time balanced with the best ports in the Western Mediterranean. Spend time crossing the Atlantic and enjoy the romance of sailing as you make your way to your ultimate destination. Sip port wines in Lisbon, Portugal, browse wares in the bustling Grand Souk in Tangier, Morocco, and wander the medieval cobbled streets of Tarragona, Spain.
25 Nights in Wind Spirit Yacht

Star Collector: Spectacular Transatlantic Journey - Caribbean to the Azores
PHILIPSBURG, ST. MAARTEN to LISBONiStar Collector: Spectacular Transatlantic Journey - Caribbean to the Azores
21 Nights in Wind Surf Yacht

Ocean Crossings + Ponta Delgada, Azores
PHILIPSBURG, ST. MAARTEN to LISBONiOcean Crossings + Ponta Delgada, Azores
14 Nights in Wind Surf Yacht

Star Collector: Atlantic Interludes & Iberian Indulgences
PHILIPSBURG, ST. MAARTEN to BARCELONAiStar Collector: Atlantic Interludes & Iberian Indulgences
22 Nights in Wind Surf Yacht

14 Nights in Star Seeker Yacht