56-Day Windstar Grand Caribbean Cruise

Explore Warm Winter in the Caribbean on this Star Collector Voyage!

Explore the depth and breadth of the Caribbean on this 56-Day Odyssey, from tiny yachtsman favorites, to glitzy celebrity getaways, historic colonial towns, to the incredible jungles of wildlife. Go cave tubing in Belize and diving in Bonaire. Snorkel with friendly sea turtles and rays in waters as clear as glass. Climb the battlements of colonial forts and the arrowhead peak of Gros Piton in St. Lucia. It's the ultimate cruise, circling the Caribbean, discovering the brilliant colors, textures and fascinating history found here.
Receive exclusive $300 Onboard Credit per stateroom from Cruise & Travel Experts!
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.

*Prices are per person based on double occupancy, availability and subject to change without notice. Taxes, fees and port expenses are additional at approximately $1,190 per person. Prices reflect all discounts that are available. Other restrictions may apply. Ships Registry: Bahamas