56-Day Windstar Grand Caribbean Cruise
Explore Warm Winter in the Caribbean on this Star Collector Voyage!

Ship: | Wind Surf |
Cruise Line: | Windstar Cruises |
Sail Date: | January 8, 2022 |
From/To: | Roundtrip St. Maarten |
Length: | 7-Nights |

Ocean View Stateroom Cat. B (Deck 1-aft/forward-188 sq. ft.) From | Ocean View Stateroom Cat. BX Deluxe (Deck 1-Midship-188 sq. ft.) From | Ocean View Stateroom Cat. AX Deluxe (Deck 2-Midship-188 sq. ft) From | Suite (Deck 3-Forward/Aft-376 sq. ft.) From |
---|---|---|---|
$11,999 per person |
$12,899 per person |
$14,599 per person |
$22,099 per person |
Popular Highlights:
- Take a catamaran cruise to St. Lucia’s twin Pitons, a UNESCO World Heritage Site — “I highly recommend this cruise; the island’s west coast is stunning, and the Pitons are an absolute must-see”
- Stroll the streets of pastel-painted UNESCO-designated Willemstad, or head into Curacao’s famous Hato Caves, where “sloping trails lead through the coral-limestone chambers past still pools and even a fresh-water waterfall — a rare sight on this dry island”
- Explore a shipwreck while snorkeling the colorful reef off Isla San Andres, a UNESCO Biosphere Reserve
- Take advantage of late departures in St. Barts to “enjoy a sunset sail, linger over dinner at Eden Rock, and check out the night life at Nikki Beach”
- Explore Bequia, one of John’s favorite spots in the Caribbean — “This is truly a small-ship port … soak in the view of Admiralty Bay from Fort Hamilton, then grab a slice of Mac’s famous lobster pizza”
This incredible voyage visits 25 countries and 36 ports across the British Virgin Islands, Colombia, Panama, Costa Rica, Honduras, Mexico, and beyond,
“I love that this is a complete circumnavigation of the Caribbean Sea,” says Chris Prelog, Windstar’s President. “I don’t know of another cruise line doing that.” Guests can take full advantage of Wind Surf’s onboard Watersports Platform with plenty of late-evening departures, as well as overnights in Jost Van Dyke, Virgin Gorda, and St. Lucia’s Pigeon Island — while being among the first to enjoy the ship’s redesigned spa, one of many new enhancements coming this fall. Chris is particularly excited about calls in Costa Maya and Cozumel, two locations that Windstar hasn’t visited in years: “Cruising into Costa Maya on the world’s largest sailing ship will be beyond spectacular.”
Sat Jan 8
7:00 PM
St. Maarten
Sun Jan 9
8:00 AM
10:00 PM
Falmouth Harbour
Mon Jan 10
AT SEA
Tue Jan 11
8:00 AM
6:00 PM
Soper’s Hole
✓
Tue Jan 11
7:00 PM
Jost Van Dyke, Great Harbour
✓
Wed Jan 12
3:00 PM
Jost Van Dyke, Great Harbour
✓
Wed Jan 12
6:00 PM
Virgin Gorda
✓
Thu Jan 13
5:00 PM
Virgin Gorda
✓
Fri Jan 14
8:00 AM
10:00 PM
Gustavia
✓
Sat Jan 15
6:00 AM
7:00 PM
St. Maarten
Sun Jan 16
8:00 AM
9:00 PM
Basseterre
Mon Jan 17
8:00 AM
10:00 PM
Gustavia
✓
Tue Jan 18
8:00 AM
10:00 PM
Little Bay
✓
Wed Jan 19
8:00 AM
5:00 PM
Les Saintes
✓
Thu Jan 20
8:00 AM
5:00 PM
Roseau
Fri Jan 21
7:00 AM
4:00 PM
Pigeon Island
Sat Jan 22
5:00 AM
6:00 PM
Bridgetown
Sun Jan 23
8:00 AM
Pigeon Island
Mon Jan 24
6:00 AM
Pigeon Island
Mon Jan 24
8:00 AM
3:00 PM
Castries
Mon Jan 24
5:30 PM
5:30 PM
The Pitons
Tue Jan 25
8:00 AM
6:00 PM
Anse Mitan
Wed Jan 26
8:00 AM
6:00 PM
Mayreau
Thu Jan 27
8:00 AM
10:00 PM
St. George’s
Fri Jan 28
8:00 AM
5:00 PM
Bequia
✓
Sat Jan 29
5:00 AM
6:00 PM
Bridgetown
Sun Jan 30
8:00 AM
5:00 PM
Man-O-War Bay
✓
Mon Jan 31
8:00 AM
6:00 PM
Mayreau
Tue Feb 1
8:00 AM
4:00 PM
Soufriere
Wed Feb 2
8:00 AM
5:00 PM
St. George’s
Thu Feb 3
AT SEA
Fri Feb 4
8:00 AM
10:00 PM
Kralendijk
Sat Feb 5
8:00 AM
6:00 PM
Willemstad
Sun Feb 6
6:00 AM
6:00 PM
Oranjestad
Mon Feb 7
AT SEA
Tue Feb 8
7:00 AM
6:00 PM
Santa Marta
Wed Feb 9
8:00 AM
3:30 PM
Cartegena
Thu Feb 10
AT SEA
Fri Feb 11
12:00 PM
6:00 PM
Bocas del Toro
Sat Feb 12
6:00 AM
6:00 PM
Puerto Limón/Moin
Sun Feb 13
AT SEA
Mon Feb 14
7:00 AM
4:00 PM
Colón
Tue Feb 15
10:00 AM
4:00 PM
Bocas del Toro
Wed Feb 16
1:00 PM
7:00 PM
Isla San Andres
Thu Feb 17
AT SEA
Fri Feb 18
AT SEA
Sat Feb 19
9:00 AM
5:00 PM
Roatan
Sun Feb 20
9:00 AM
7:00 PM
Belize City
Mon Feb 21
8:00 AM
5:00 PM
Costa Maya
Tue Feb 22
8:00 AM
6:00 PM
Cozumel
Wed Feb 23
AT SEA
Thu Feb 24
8:00 AM
6:00 PM
Grand Cayman
Fri Feb 25
7:00 AM
1:00 PM
Cayman Brac
Sat Feb 26
12:00 PM
6:00 PM
Port Antonio
Sun Feb 27
AT SEA
Mon Feb 28
1:00 PM
10:00 PM
Santo Domingo
Tue Mar 1
7:00 AM
5:00 PM
La Romana
Wed Mar 2
AT SEA
Thu Mar 3
8:00 AM
11:59 PM
Jost Van Dyke, Great Harbour
✓
Fri Mar 4
8:00 AM
5:00 PM
Virgin Gorda
✓
Sat Mar 5
6:00 AM
St. Maarten
On any day, our 342-guest flagship, Wind Surf, the world’s largest sailing ship, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. During their cruise, you will find the perfect setting for ‘making an entrance’ in the beautiful reception area – and, appropriately, that’s only the beginning.
When you return to your stateroom, the luxury gets personal. Windstar’s signature bowls of flowers and fresh fruit will still be waiting for you, along with rich tufted headboards, soft seascape colors, beautiful new upholstery, and fine count Egyptian cotton linens welcome you to an oasis of relaxing indulgence.
Wind Surf recently underwent a significant renovation in November 2019 of public spaces and suites, including an expanded lounge with new lights and sound for upcoming stage performances. Relax into the destinations you’re visiting at the new World Spa by Windstar, which will offer regional spa treatments, including massage styles like Swedish, Japanese Shiatsu and Hawaiian Lomi Lomi. A new Officer’s Suite, which might be the only one of its kind, provides you the chance to stay in the heart of the officer quarters tucked right behind the Bridge.
Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.