Classic Caribbean

  • 20 Feb ‘28
  • 7 nights
  • Departing from Philipsburg
  • Wind Surf
  • Outside price from
    $2,999*/pp
  • Balcony price from
    Call for price
  • Suite price from
    $3,899*/pp

YOUR ITINERARY

Philipsburg, St. Martin - Charlestown, Nevis - Roseau, Dominica - Mayreau, Grenadines - Les Saintes, F.W.I. - Basseterre, St. Kitts - Gustavia, St. Barthelemy - Philipsburg, St. Martin

Date
Port
Info
Arrive
Depart
Day 1
20th Feb 2028
Philipsburg, St. Martin

Philipsburg is the capital of Sint Maarten, the Dutch side of ...

Philipsburg is the capital of Sint Maarten, the Dutch side of the Caribbean island Saint Martin. Beachfront bars line the boardwalk along Great Bay. Voorstraat, or Front Street, has duty-free shops and casinos. The St. Maarten Zoo is home to parrots, monkeys and a playground. Sint Maarten Museum displays artifacts from the indigenous Arawak people. The ruins of 17th-century Fort Amsterdam stand on a nearby peninsula.

Arrive
13:00
Depart
19:00
Day 2
21st Feb 2028
Charlestown, Nevis

Charlestown is a historic waterfront neighborhood...

Charlestown is a historic waterfront neighborhood with Irish-American roots. The Freedom Trail climbs streets lined with brick townhouses and clapboard triple-decker homes to the Bunker Hill Monument, site of a key Revolutionary War battle. The 1797 U.S.S. Constitution warship and its museum are in the Charlestown Navy Yard. Main Street’s traditional pubs and stylish restaurants draw young professionals and families

Arrive
08:00
Depart
17:00
Day 3
22nd Feb 2028
Roseau, Dominica

Roseau is the capital of the Caribbean island nation...

Roseau is the capital of the Caribbean island nation of Dominica. It’s on the southwest coast and known for its 18th-century Creole architecture. Its cobblestone Old Market, formerly a slave auction site, sells crafts and fruit. It’s next to the Dominica Museum, with exhibits on the country’s natural and cultural history. The Dominica Botanic Gardens showcase tropical flora and native Sisserou parrots.

Arrive
08:00
Depart
16:00
Day 4
23rd Feb 2028
Mayreau, Grenadines

In the north of Mayreau is Salt Whistle Bay, a perfect hal...

In the north of Mayreau is Salt Whistle Bay, a perfect half moon beach, separating the Atlantic from the Caribbean side with a sand spit only 50 yards wide, fringed by palm trees. The windward side of Mayreau is one huge deserted beach; you could spend days picnicking, sunbathing and snorkeling in the underwater world of Mayreau Garden. The southwestern, leeward beach is Saline Bay, nearly a mile of white sand with calm, clear water – ideal to bring your family!

Arrive
08:00
Depart
17:00
Day 5
24th Feb 2028
Les Saintes, F.W.I.

The Îles des Saintes, or Les Saintes, are dependency ...

The Îles des Saintes, or Les Saintes, are dependency islands of Guadeloupe, a French overseas territory in the Caribbean. The main island, Terre-de-Haut, is known for Pain de Sucre Beach’s coral-rich waters and palm-lined Les Saintes Bay. Overlooking the bay is 19th-century Fort Napoléon, with a museum and cactus garden. Trails cross the volcanic landscape of Terre-de-Bas Island, home to tranquil Grand Anse Beach.

Arrive
12:00
Depart
18:00
Day 6
25th Feb 2028
Basseterre, St. Kitts

Basseterre, set against the irresistible backdrop of St. K...

Basseterre, set against the irresistible backdrop of St. Kitts’ emerald green hills and punctuated by elegant Georgian architecture, is one of the best of the Caribbean’s small capitals.

Arrive
08:00
Depart
22:00
Day 7
26th Feb 2028
Gustavia, St. Barthelemy

Gustavia is the main town and capital of the island of Saint Ba...

Gustavia is the main town and capital of the island of Saint Barthélemy. Originally called Le Carénage, it was renamed in honor of King Gustav III of Sweden.

Arrive
08:00
Depart
22:00
Day 8
27th Feb 2028
Philipsburg, St. Martin

Philipsburg is the capital of Sint Maarten, the Dutch...

Philipsburg is the capital of Sint Maarten, the Dutch side of the Caribbean island Saint Martin. Beachfront bars line the boardwalk along Great Bay. Voorstraat, or Front Street, has duty-free shops and casinos. The St. Maarten Zoo is home to parrots, monkeys and a playground. Sint Maarten Museum displays artifacts from the indigenous Arawak people. The ruins of 17th-century Fort Amsterdam stand on a nearby peninsula.

Arrive
06:00
Depart
07:00

YOUR SHIP - The Wind Surf

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.

Bar
Compass Rose
Degrees
Poolside Bar
Terrace Bar
Veranda

Hot Tubs
Massage
Spa
Whirlpool

Library
Outdoor Pool

Description

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.

Food and Drink

Bar
Compass Rose
Degrees
Poolside Bar
Terrace Bar
Veranda

Relaxation

Hot Tubs
Massage
Spa
Whirlpool

Recreational

Library
Outdoor Pool

STATEROOMS

    suite

    outside

SIMILAR CRUISES

  • Date
    Trip
    Cruise Ship
    Nights
    Price
  • 2027-12-12
    Classic Caribbean
    Wind Surf- 7Nights
    7
    $2,799* /per person
  • 2027-12-27
    Classic Caribbean
    Wind Surf- 7Nights
    7
    $3,199* /per person
  • 2028-01-09
    Classic Caribbean
    Wind Surf- 7Nights
    7
    $2,999* /per person
  • 2028-01-23
    Classic Caribbean
    Wind Surf- 7Nights
    7
    $2,999* /per person
  • 2028-02-06
    Classic Caribbean
    Wind Surf- 7Nights
    7
    $2,999* /per person

*Based on Twinshare cabin

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