Special Sale: Ways to Winter Sales Event (view details)
14-Night Caribbean (Caribbean - Extended)
Wind Surf
Windstar Cruises
Offer: Up to $1,000 Onboard Credit per stateroom on sailings through March 2026
Offer Details:
Booking Window: Now - 10/7/25
Applicable Sailings: All sailings through March 2026
Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) and up to $1,000 Onboard Credit per suite ($500 per guest) for all sailings through March 31, 2026.
Premium suites on sailings 14 days or longer will receive $1,000 onboard credit per suite ($500 per guest). Premium suites on sailings up to 13 days will receive $400 onboard credit per suite ($200 per guest). Standard staterooms or suites on sailings 14 days or longer will receive $400 onboard credit per stateroom ($200 per guest). Standard staterooms or suites on sailings up to 13 days will receive $200 onboard credit per stateroom ($100 per guest).
Premium Suites include the following categories: On Wind Star and Wind Spirit: Owner's Suite (OW). On Wind Surf: Broadmoor/Sea Island Suites (BRS), Owners Suites (OS), and Suites (STE). On Star Breeze, Star Legend and Star Pride: Owners Suites (OW), Broadmoor/Sea Island Suites (CS), and Deluxe Suites (DS). On Star Seeker and Star Explorer: Horizon Owners Suite (OW), Star Suites (CS2), Classic Suites (CS) and Deluxe Suites (DS).
Standard Stateroom/Suites include the following categories: On Wind Star, Wind Spirit and Wind Surf: Ocean View Suites (TX, AX, A, BX & B) and Guaranteed (Y & YB). On Star Breeze, Star Legend and Star Pride: Balcony Suites (SBS1, BS1, SBS & BS) and Ocean View Suites (S3, S2, SS1, S1 & S), Porthole Suites (SP) and Guaranteed Suites (Y & YB). On Star Seeker and Star Explorer: all Verandah Suites (VVB, VS3, VS2, VS1, VSS & VS), Infinity Suites (IN3, IN2, IN1 & IN), Oceanview Suites (OV) and Guaranteed Suites (Y & YB).
All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category. Government Taxes & Fees are additional and are published. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made. This offer cannot be applied retroactively. Single and Triple guests in a stateroom or suite are also eligible for this promotion; the shipboard credit will be awarded at a per guest rate. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer expires on October 7, 2025. Ships’ registry: Bahamas.
Special Sale: Travel Is Better When You're All-In (view details)
14-Night Caribbean (Caribbean - Extended)
Wind Surf
Windstar Cruises
Offer: Complimentary All-Inclusive Package on sailings through March 2026
Booking Window: Now - 11/15/25
Applicable Sailings: All sailings through 3/31/26
Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) for voyages through March 31, 2026. All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made. This offer cannot be applied retroactively. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer expires on November 15, 2025. Ships’ registry: Bahamas.
On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea.
Day #
Date
Port
Arrive
Depart
1
Sunday, 12/7/25
About Philipsburg
An exquisite blend of Dutch and French cultures, St. Martin boasts stunning beaches, crystal clear waters, and incredible duty-free shopping. Whether you lunch at a charming French cafe or explore the lively Dutch capital of Philipsburg, you will find the dichotomy of St. Maarten perfectly charming.
Philipsburg Attractions
Compete in an actual race on an America's Cup shortened course. Grind a winch, trim a sail or just sit back and enjoy. Professional sailors will give you a quick lesson, then you're off to compete on Stars and Stripes, one of the most famous sailboats in the world.
Philipsburg Activities
Rendezvous at one of the newest and trendiest restaurants in French St. Maarten. Explore Orient Bay, the French Riviera of the Caribbean, with over 1 1/2 miles of white-sand beaches.
Admire the delicate nature and dazzling colors of hundreds of butterflies as you tour St. Maarten's popular Butterfly Farm.
Recently ranked #4 in a list of "Best Destination Cities" in North America by Travel and Leisure readers, Charleston offers something for everyone, from its beautiful beaches to a fascinating historic district. With great hotels, interesting tours, and fabulous restaurants, Charleston draws visitors from far and near and makes them feel welcome with a charm and grace that is rarely found anymore.
Charleston Attractions
Tour the historic section of Charleston and visit St. Michael's Church and the Joseph Manigault House. City tours by horse carriage and tours to nearby Boone Hall Plantation are also available.
Charleston Activities
Your visit to Charleston isn't complete without experiencing the ships, planes and exhibits of Patriots Point. The museum centerpiece is the massive aircraft carrier YORKTOWN, one of the most decorated and famous warships of World War II. Go deep inside the vessels to experience what life was like for the sailors who lived, fought and sometimes paid the ultimate price for preserving our nation's freedom.
The South Carolina Aquarium is a regional resource inspiring conservation by excelling in education, and in the care, display, and study of aquatic life.
Take a walking tour of Charleston's pre-revolution dungeon tour, an uncensored look at Charleston's past, a nighttime tour of one of the oldest graveyards in the country or an inside look at Charleston's haunted Old City Jail.
Roseau is a charming costal village of Dominica and your gateway to one of the Caribbean's most untouched islands. With its lush forested mountains, countless rivers, and black-sand beaches, you'll see why it's called the "Nature Island of the Caribbean." If you've ever wondered what an authentic Caribbean island was like, this is it.
Roseau Attractions
Go snorkeling at Champagne Beach. These actual effervescent waters produce a "fizzing effect" due to the sub-aquatic surroundings. Don't miss this once-in-a-lifetime chance to swim alongside parrot fish in bubbly waters.
Roseau Activities
Soak the day away with a beauty bath in the rejuvenating Sulphur Springs.
History buffs should take a peek into Colonial island life and volcanic geology at the Dominica Museum.
See if you can spot the 150 species of plants and rare Dominica parrots at the Botanical Gardens.
Get a good dose of vitamin D on the island's beautiful black-sand beaches.
Pigeon Island National Landmark (don't let the name lead you astray) is a 44-acre island reserve just off the north coast of St. Lucia. Connected to the mainland by the construction of a man-made causeway in 1972, the island park is hailed as a monument to St. Lucia's history and its role in 18th-century maritime trade. An interpretation center located within the confines of the park traces the history of long ago battles between English and French troops struggling to control the strategically important outpost.
Explore the beaches of Grand-Terre and the French fort ruins and volcanic mountaintop of Basse-Terre.
Pointe a Pitre Attractions
The town center is place de la Victoire, a park shaded by palm trees and poincianas. Here you'll see some old sandbox trees said to have been planted by Victor Hugues, the mulatto who organized a revolutionary army of both whites and blacks to establish a dictatorship. In this square he kept a guillotine busy, and the death-dealing instrument stood here until modern times.
You can easily explore all of Gustavia during a two-hour stroll. Some shops close from noon to 3 or 4, so plan lunch accordingly, but stores stay open past 7 in the evening. Parking in Gustavia is a challenge, especially during vacation times. A good spot to park is rue de la République, alongside the catamarans, yachts, and sailboats.
Authentic Caribbean foods at Basseterre, and a peaceful setting virtually untouched by tourism are among St Kitts most enchanting features. For breathtaking views, visit Brimstone Hill Fort, an impressive construction atop Mt Liamuiga that is one of the wonders of the Caribbean.
Basseterre Attractions
Whether you're a history buff or just want to take in the scenery, be sure to visit the 350-year-old estate, Romney Manor, once owned by a British earl. The beautiful grounds include magnificent gardens, exotic plants and an amazing African Saman tree, which covers half an acre and is believed to be as old as the estate itself.
Basseterre Activities
Explore Brimstone Hill Fortress National Park. Climb to the top of the main hill to take in amazing views of St. Eustatius and Sandy Point Town.
Walk through Independence Square. Now a small public park, it was built in 1790 for slave auctions and council meetings.
Visit St. George's Cathedral. While originally christened Notre Dame in 1670 by the French, it was destroyed more than once and was most recently rebuilt in 1869 in typical Georgian style.
An exquisite blend of Dutch and French cultures, St. Martin boasts stunning beaches, crystal clear waters, and incredible duty-free shopping. Whether you lunch at a charming French cafe or explore the lively Dutch capital of Philipsburg, you will find the dichotomy of St. Maarten perfectly charming.
Philipsburg Attractions
Compete in an actual race on an America's Cup shortened course. Grind a winch, trim a sail or just sit back and enjoy. Professional sailors will give you a quick lesson, then you're off to compete on Stars and Stripes, one of the most famous sailboats in the world.
Philipsburg Activities
Rendezvous at one of the newest and trendiest restaurants in French St. Maarten. Explore Orient Bay, the French Riviera of the Caribbean, with over 1 1/2 miles of white-sand beaches.
Admire the delicate nature and dazzling colors of hundreds of butterflies as you tour St. Maarten's popular Butterfly Farm.
Tour Nelson's Dockyard, which was originally built as a way station in the 18th century for warships of the British Royal Navy. This historic district has been restored to its former glory and you can sit upon the old fortifications and observation posts that line the harbor. As you evoke the port's nautical past, close your eyes and you can hear the revelry of sailors coming ashore for leave.
Twenty-one-square-mile Tortola is the largest of the British Virgin Islands, an unspoiled archipelago that lies in the path of welcome trade winds. Try fishing, snorkeling and sailing excursions out of Road Towns serene harbor or horseback riding in the shadow of Mount Sage.
Tortola Attractions
Rent a private boat and forge your way out to Norman Isle, a former pirate den across Drake Channel from Tortola and real life deserted island today. Legend has it that Norman Isle served as Robert Louis Stevenson's inspiration for Treasure Island. You can venture into caves, some of which are excellent snorkeling spots. Or hike to Spy Glass Hill. This is a journey you'll never forget.
Tortola Activities
Sage Mountain National Park is located over 1700 ft. above sea level, and contains the British Virgin Islands' highest peak.
Trails lead through a primeval rainforest overlooking neighboring islets.
The wreck of the HMS Rhone is a 310-foot ship that sank in 1867 near Salt Island. Its remains have become a fascinating underwater habitat for marine life and it is known as a premier dive spot in the Caribbean. Get the party started with a visit to Bomba's Shack at Cappoon's Bay. Live entertainment, rum punch and infamous full moon parties.
Great Harbour is the main anchorage on Jost Van Dyke and the center for nightlife on this beautiful island. The holding for anchors in Great Harbour can be tricky and now there are some mooring balls to make life easier. Great Harbour has the island’s police station and customs and immigration office. It’s “main road” is just a sandy strip. A small beach, dotted with dinghy docks, runs the length of the bay.
Great Harbour is the main anchorage on Jost Van Dyke and the center for nightlife on this beautiful island. The holding for anchors in Great Harbour can be tricky and now there are some mooring balls to make life easier. Great Harbour has the island’s police station and customs and immigration office. It’s “main road” is just a sandy strip. A small beach, dotted with dinghy docks, runs the length of the bay.
Leverick Bay, Virgin Gorda, British Virgin Islands
8:00am
5:00pm
14
Saturday, 12/20/25
About Gustavia
You can easily explore all of Gustavia during a two-hour stroll. Some shops close from noon to 3 or 4, so plan lunch accordingly, but stores stay open past 7 in the evening. Parking in Gustavia is a challenge, especially during vacation times. A good spot to park is rue de la République, alongside the catamarans, yachts, and sailboats.
An exquisite blend of Dutch and French cultures, St. Martin boasts stunning beaches, crystal clear waters, and incredible duty-free shopping. Whether you lunch at a charming French cafe or explore the lively Dutch capital of Philipsburg, you will find the dichotomy of St. Maarten perfectly charming.
Philipsburg Attractions
Compete in an actual race on an America's Cup shortened course. Grind a winch, trim a sail or just sit back and enjoy. Professional sailors will give you a quick lesson, then you're off to compete on Stars and Stripes, one of the most famous sailboats in the world.
Philipsburg Activities
Rendezvous at one of the newest and trendiest restaurants in French St. Maarten. Explore Orient Bay, the French Riviera of the Caribbean, with over 1 1/2 miles of white-sand beaches.
Admire the delicate nature and dazzling colors of hundreds of butterflies as you tour St. Maarten's popular Butterfly Farm.
On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea.
Year Built
1990
Capacity
342
Meeting Rooms
Yes
Year Refurbished
2003
Elevators
2
Casino
No
Registry
Bahamas
Restaurants
2
Disco
Yes
Tonnage
14,745
Bars
2
Fitness Center
Yes
Cabins
154
Pools
2
Children's Program
No
Handicap Cabins
N/A
Theaters
N
Internet Cafe
No
Shops
Yes
Library
Yes
Spa
Yes
Cabin Categories | Decks
Bridge Suite
CATEGORY A
CATEGORY AX DELUXE
Category B
CATEGORY BX DELUXE
CATEGORY TX DELUXE
Officer's Suite
Opulent Bridge Suite
Suite
Cabin Details
BRIDGE SUITE
Deck Bridge Midship
CABIN TYPE: SUITE
495 SQ FT
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.
BRIDGE SUITE
Deck Bridge Midship
CABIN TYPE: SUITE
495 SQ FT
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.
CATEGORY A
Deck 2 Forward/Aft
CABIN TYPE: STATEROOM
188 sq. feet
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.
CATEGORY AX DELUXE
Deck 2 Midship
CABIN TYPE: STATEROOM
188 sq. feet
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.
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.
With 188 square feet, 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.
CATEGORY TX DELUXE
Deck 3 Forward/Aft or Midship
CABIN TYPE: STATEROOM
188 sq. feet
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 & reg; 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.
For the ultimate in nautical experiences, reserve the new Officer’s Suite located close to the Bridge where our 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.
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.
SUITE
Deck 3 Forward/Aft or Midship
CABIN TYPE: SUITE
376 sq. feet
With 376 square feet, 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.
Star Deck
Bridge Deck
Main Deck
Deck Three
Deck Two
Deck One
Request Additional Information
Departure Port:
Philipsburg
Sailing Date:
Sunday, 12/07/25
Return Date:
Sunday, 12/21/25
Nights:
14
Ship:
Wind Surf
Cruise Line:
Windstar Cruises
Checking For Available Shore Excursions From ShoreTrips®
Prices are per person, double occupancy, cruise only and on select sailings. Prices shown are for stateroom categories as noted and are shown in US Dollars. Government taxes and fees are additional. Airfare is not included. Prices and itineraries are based on availability and are subject to change without notice.
Checking For Available Shore Excursions From ShoreTrips®
Recently ranked #4 in a list of "Best Destination Cities" in North America by Travel and Leisure readers, Charleston offers something for everyone, from its beautiful beaches to a fascinating historic district. With great hotels, interesting tours, and fabulous restaurants, Charleston draws visitors from far and near and makes them feel welcome with a charm and grace that is rarely found anymore. 
Authentic Caribbean foods at Basseterre, and a peaceful setting virtually untouched by tourism are among St Kitts most enchanting features. For breathtaking views, visit Brimstone Hill Fort, an impressive construction atop Mt Liamuiga that is one of the wonders of the Caribbean. 
Tour Nelson's Dockyard, which was originally built as a way station in the 18th century for warships of the British Royal Navy. This historic district has been restored to its former glory and you can sit upon the old fortifications and observation posts that line the harbor. As you evoke the port's nautical past, close your eyes and you can hear the revelry of sailors coming ashore for leave. 
retrieving destinations 