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7-night Classic Caribbean Cruise

Roundtrip St. Maarten (Philipsburg)

Voyage Overview

Embarkation
St. Maarten (Philipsburg)
Disembarkation
St. Maarten (Philipsburg)
Destination Highlight

The island of St. Martin is divided between French St. Martin in the north and Dutch St. Maarten in the south. Although the cultural flow transcends any borders, each side manages to retain its own distinct flavor. This 37-square-mile island promises beautiful vistas, first-rate water sports and stunning beaches. Philipsburg is the capital of Dutch St. Maarten. Its two main streets, Frontstreet and Backstreet, are bustling thoroughfares lined with shops and restaurants.

About the Ship
On any day, the 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.

Daily Itinerary
Feb 06, 2028 - St. Maarten (Philipsburg)

The island of St. Martin is divided between French St. Martin in the north and Dutch St. Maarten in the south. Although the cultural flow transcends any borders, each side manages to retain its own distinct flavor. This 37-square-mile island promises beautiful vistas, first-rate water sports and stunning beaches. Philipsburg is the capital of Dutch St. Maarten. Its two main streets, Frontstreet and Backstreet, are bustling thoroughfares lined with shops and restaurants.

Feb 07, 2028 - Charlestown

Charlestown is a Caribbean town with remnants of the Colonial era. It’s the capital of the island of Nevis of Saint Kitts and Nevis in the West Indies. The town was developed as early as the 17th century by the British building Fort Charles and mounting 26 cannons to protect its harbor. The British had a lucrative sugar trade much profitable than that of North America. Historical figure Anthony Hamilton, the first US Secretary of Treasury was born and raised in Charlestown. 

Travelers visiting Charlestown can tour the Nelson Museum, Philatelic Bureau or Museum of Nevis History. Visitors can either horseback ride by the beach or relax by it under the Caribbean sun!

Feb 08, 2028 - Roseau, Dominica

With the island’s colonial background, the capital Roseau features both historic and modern buildings. Situated above town, on the slopes of Morne Bruce, are the beautiful Botanic Gardens with rare native and imported plants. The prominent 18th-century Fort Young is now part of the Fort Young Hotel complex.

Feb 09, 2028 - Mayreau, Grenadines

Tossed like a tiny emerald among the Grenadines' 100 islands is Mayreau. In this idyllic spot there are no cars, just one tiny village and one resort, hidden away in the palms.

Feb 10, 2028 - Iles des Saintes

Pastoral and far off the beaten track, the Saintes are a cluster of eight islands off the southern coast of Guadeloupe. In Bourg, the charming hamlet on Terre-de-Haut, the largest isle, you can wander peaceful streets past small houses, then follow the narrow road out of town through fields and hills to a sweeping strand of secluded beach.

Feb 11, 2028 - Basseterre, St. Kitts

Basseterre, St. Kitts’ capital, still shows signs of colonial architecture. However, its setting against the emerald green hills ensures a distinct Caribbean ambiance. Many travelers agree Basseterre is one of the prettiest of the Caribbean’s small capitals.

Feb 12, 2028 - Gustavia

There was never any hope of lucrative sugar plantations in St.Barths. It was too dry, too steep, too rocky, and, finally, too small. Unsuitable for agriculture, the island was never coveted as a prize during the colonial wars of the 18th century. The place had a serviceable harbor, and this allowed the town that grew around it, Gustavia, to play a key role in that intermittent conflict, a role that was to presage much of its future. Overflowing warehouses surrounded a harbor packed with ships from many nations, and a mercantile and architectural tradition was established that has lingered to the present day. Today, Gustavia has adjusted itself to satisfy the increasing number of visiting tourists. Restaurants, boutiques, and gift shops now line streets once busy with merchants, merchant seamen, and adventurers.

Feb 13, 2028 - St. Maarten (Philipsburg)

The island of St. Martin is divided between French St. Martin in the north and Dutch St. Maarten in the south. Although the cultural flow transcends any borders, each side manages to retain its own distinct flavor. This 37-square-mile island promises beautiful vistas, first-rate water sports and stunning beaches. Philipsburg is the capital of Dutch St. Maarten. Its two main streets, Frontstreet and Backstreet, are bustling thoroughfares lined with shops and restaurants.

Stateroom Options

Deluxe Ocean View Stateroom
Deluxe Ocean View Stateroom (Cat TX)
$3,377

Size: 188 square feet (18 square meters). 
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers. Note: Staterooms with 3rd Berths: 117–139; all suites (excluding 501). Staterooms with One Queen Size Bed Only (no twin option): 101, 102, 157, 301-304.

Officer's Suite
Officer's Suite (Cat OS)
$6,982

Size: 242 square feet (22.5 square meters) and 1 bathroom.
For the ultimate in nautical experiences, reserve the new Officer’s Suite located close to the Bridge where the own ship’s officers have their quarters. With its unique “insider” location and 242 square feet of comfort, the nautically appointed Officer’s Suite offers an experience you won’t find on any other cruise line.

Suite
Suite (Cat STE)
$5,232

Size: 242-376 square feet (22.5-35 square meters). Some Suites have 2 bathrooms. 
You’ll find the perfect space for time together — and plenty of room for time to yourself. You’ll even enjoy two full separate bathrooms. All the amenities of the staterooms await you, plus a beautiful sitting area, and two flat-screen television sets with DVD players.

Bridge Suite
Bridge Suite (Cat BRS)
$8,732

Size: 495 square feet (46 square meters).
The ultimate in space and style surrounds you in 495 square feet of pure indulgence. Separate bedroom and living room with an in-suite dining area is an invitation to relaxation. And possibly best of all, your expansive bathroom features both a whirlpool spa tub and a massage shower.

Deluxe Ocean View Stateroom
Deluxe Ocean View Stateroom (Cat AX)
$3,062

Size: 188 square feet (18 square meters). 
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.

Deluxe Ocean View Stateroom
Deluxe Ocean View Stateroom (Cat BX)
$2,712

Size: 188 square feet (18 square meters). 
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers. Note: Staterooms with 3rd Berths: 117–139; all suites (excluding 501). Staterooms with One Queen Size Bed Only (no twin option): 101, 102, 157, 301-304.

Ocean View Stateroom
Ocean View Stateroom (Cat A)
$2,817

Size: 188 square feet (18 square meters). 
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.

Ocean View Stateroom
Ocean View Stateroom (Cat B)
$2,537

Size: 188 square feet (18 square meters). 
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers. Note: Staterooms with 3rd Berths: 117–139; all suites (excluding 501). Staterooms with One Queen Size Bed Only (no twin option): 101, 102, 157, 301-304.

Guarantee Stateroom
Guarantee Stateroom (Cat Y)
$2,537

With this selection, you are guaranteed to receive a stateroom within a selected category, anywhere on the ship. However, the actual room assignment and location on the ship may be determined at any time after your reservation has been completed and paid in full up to the day of sailing.

Included Amenities

Exclusive Bonus: Contact us for exclusive perks available on this sailing.
  • 7-night Cruise
  • Meals
  • Entertainment

Additional Departure Dates for This Itinerary

Select an upcoming departure below to view availability or lock in exclusive Signature Travel Network perks.

Dec 26, 2026
7-night Classic Caribbean Cruise
7 Nights • Wind Surf • Roundtrip St. Maarten (Philipsburg)
Jan 09, 2027
7-night Classic Caribbean Cruise
7 Nights • Wind Surf • Roundtrip St. Maarten (Philipsburg)
Jan 23, 2027
7-night Classic Caribbean Cruise
7 Nights • Wind Surf • Roundtrip St. Maarten (Philipsburg)
Feb 06, 2027
7-night Classic Caribbean Cruise
7 Nights • Wind Surf • Roundtrip St. Maarten (Philipsburg)

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Starting From
$2,537
Rates are cruise only, per person, based on double occupancy and include government fees/taxes. Optional transfers and airfare (unless otherwise stated) additional for all guests.

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Trip Summary
Ship Name Wind Surf
Departure Date February 06, 2028
Duration 7 Nights
Offer ID 1707637
Ship Facts
Built 1989
Guests 310
Crew 200
Call Vincent Vacations: 1 (888) 883-0460

Prices are per person, based on double occupancy and include government fees and taxes. Optional airfare and transfers additional.

All fares are quoted in US Dollars.