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Sailings

14 Nights Caribbean
departing from Philipsburg, St. Maarten
Cruise Line Windstar Cruises
Ship Wind Surf
Departing Sat, 4 Jan 2025
Return Port Philipsburg, St. Maarten
Ports of Call Philipsburg, St. Maarten | Port of Charlestown, Nevis, St. Kitts and Nevis | Roseau, Dominica | Pigeon Island, St. Lucia |...
Windstar Cruises
Philipsburg, St. Maarten | Port of Charlestown, Nevis, St. Kitts and Nevis | Roseau, Dominica | Pigeon Island, St. Lucia | Les Saintes, Guadeloupe | Gustavia, St. Barts | Port of Basseterre, St. Kitts, St. Kitts and Nevis | Falmouth Harbour, Antigua | Jost Van Dyke, British Virgin Islands | Sopers Hole, British Virgin Islands | Virgin Gorda, British Virgin Islands | Road Bay, Anguilla
Prices starting from
  • Inside
    Oceanview
    Balcony
    Suite
  • $12,431 NZD $887.95 NZD per day
Taxes and fees of $216 NZD included. Port charges of $988 NZD included.

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Itinerary
  • Date Date Location Location Arrival Arrival Departure Departure
  • Sat, 4 Jan 2025 PHILIPSBURG, ST. MAARTEN -- 7:00 pm
    Sun, 5 Jan 2025 CHARLESTOWN 8:00 am 5:00 pm
    Mon, 6 Jan 2025 ROSEAU, DOMINICA 8:00 am 5:00 pm
    Tue, 7 Jan 2025 PIGEON ISLAND, ST. LUCIA 8:00 am 5:00 pm
    Wed, 8 Jan 2025 LES SAINTES, GUADELOUPE 8:00 am 5:00 pm
    Thu, 9 Jan 2025 GUSTAVIA, ST. BARTHELEMY 8:00 am 10:00 pm
    Fri, 10 Jan 2025 BASSETERRE, ST. KITTS 8:00 am 9:00 pm
    Sat, 11 Jan 2025 PHILIPSBURG, ST. MAARTEN 6:00 am 7:00 pm
    Sat, 11 Jan 2025 PHILIPSBURG, ST. MAARTEN 7:00 am --
    Sun, 12 Jan 2025 FALMOUTH HARBOUR, ANTIGUA 8:00 am 6:00 pm
    Mon, 13 Jan 2025 GUSTAVIA, ST. BARTHELEMY 8:00 am 7:00 pm
    Tue, 14 Jan 2025 SOPER'S HOLE, TORTOLA, BVI 8:00 am 6:00 pm
    Tue, 14 Jan 2025 GREAT HARBOUR, JOST VAN DYKE 7:00 pm --
    Wed, 15 Jan 2025 GREAT HARBOUR, JOST VAN DYKE -- 10:00 pm
    Thu, 16 Jan 2025 VIRGIN GORDA/PRICKLY PEAR, BVI 8:00 am 5:00 pm
    Fri, 17 Jan 2025 ROAD BAY, ANGUILLA 8:00 am 6:00 pm
    Sat, 18 Jan 2025 PHILIPSBURG, ST. MAARTEN 6:00 am --
    Sat, 18 Jan 2025 PHILIPSBURG, ST. MAARTEN 7:00 am --
Click on a port for more information
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Windstar Cruises
General

TAKING SMALL SHIP CRUISING IN A DIFFERENT DIRECTION

Any cruise ship lets you see the world. Windstar brings it close enough so you can fully live it. See, hear, smell, taste and feel what it's like to sail on a lovely ship into a small port, explore a hidden beach, see Moroccan goats standing in trees, taste a spicy Norwegian Bacalao stew and altogether lose yourself in a strange and wondrous culture. Our elegant, 148 - 310-guest cruise ships open up captivating new worlds and leave indelible, lifetime memories.

Windstar's small cruise ships and personalized approach bring you closer to each destination and every port, so you can see the world from new perspectives. Share intimate moments away from the crowds, and immerse yourself in local, exotic cultures, all on a cruise ship where surprise and delight are constant companions.

And of course, part of the Windstar magic is our incredible personal service. Enjoy undivided attention from a crew who delights in remembering your name and preferences. Both gracious hosts and ambassadors, they delight in surprising you in discrete ways - satisfying your sweet tooth with an extra chocolate on your pillow or sharing the location of a favorite seaside cafe.

This is 180 degrees from ordinary, where all your senses are indulged and your sense of wonder is awakened.

Ship
Wind Surf
Overview
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 bowl of 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 underwent a significant renovation 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. An Officer’s Suite, which might be the only one of its kind, provides you with 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.

Windstar has always been known for our iconic sailing ships, and now we are embarking on a multi-year refresh of the Wind Class ships. The initiative, Setting Sails: A Wind Class Refresh, brings the tight-knit connection of the Windstar community to the forefront through the redesign of public spaces and staterooms. From a revamped lobby to a new pool and larger pool bar, new World Spa by Windstar to a redesigned lounge, this initiative also includes intricate details like new teak decks and decor for a timeless and welcoming experience. Wind Surf will complete her redesign in 2024 and 2026.
World Class Dining Experience

We've upped the onboard dining game with our culinary program, featuring an array of fresh, seasonal ingredients sourced from each port along the journey. Each nightly menu is crafted to highlight the spectacular flavors of the regional cuisine.

  1. Cooked to Order Meals at Your Request
  2. Focus on Local & Sustainable Food Selections
  3. Cooking Demos & Classes Available

Dining Choices

Every meal is just what you'd expect on your private yacht - perfect. You're free to dine when, where, and with whomever you please.

Veranda

It's breakfast alfresco, full service or buffet-style, anytime till 9:30 a.m. No need to hurry. Again, the choices are many in Veranda. Choose the sumptuous, seemingly endless buffet. Or, order from the lunch menu between noon and 2:30 p.m.

AmphorA

Here, the dining room manager seats you, but where is your decision. There are no pre-assigned tables or first or second seatings. When you dine and with whom are entirely up to you. Seating usually begins at 6:30 p.m. and will be printed in the ship's daily program. Each delightful dish is prepared exactly to your liking - an exquisite dinner served course-by-course with a fine selection of vintage wines.

Stella Bistro

Treat your palate to the French-inspired cafe cuisine of Stella Bistro, Wind Surf's alternative restaurant. You'll find delightfully indulgent desserts and a wonderful array of wines specifically paired to the meal. (Wind Surf only)

Candles

Here's the perfect place for a romantic tete-a-tete under the stars in Candles, Windstar's signature outdoor restaurant transformed by night into a dreamlike paradise. Delectable cuisine, memorable surroundings, inspired wine airings.

Activities & Entertainment

Activities: Other cruise lines have bingo and trivia nights. Windstar has a Watersports Platform that opens directly from the back of our ships and includes complimentary kayaks, paddleboards, water trampolines, and water skis. Spend time in the Lounge regaling your fellow guests about the bears you saw catching fish from the river or simply relax in the Library with an intriguing book. Take some "you" time in the tranquil World Spa by Windstar...enjoy a dip in the pool...work off that decadent dessert in the Fitness Center...and, of course, you are always welcome to visit the Bridge to examine navigation charts with the Captain.

  • Tastings 
  • Enjoy our Yacht Club
  • Yoga Al Fresco
  • Meet the Captain on The Bridge 
  • Relax by The Pool or Hot Tub
  • Enjoy Fun In the Sun with Our Watersports Platform
  • Take In The Sun
  • Enjoy Our Crew Talent Show
  • Local and Regional Dining
  • Live Music Duet 
  • Signature Sail Away 
  • Complimentary Room Service

Entertainment: A day on board your Windstar ship is a day of choices, all of them good. Perhaps you’ll begin with a relaxing massage in World Spa by Windstar. Or maybe an invigorating workout in the Fitness Center. Even better, why not both? After a sumptuous lunch in Veranda, make a splash from the Watersports Platform off the ship’s stern. Everything you can think of for fun in the water is there — swimming, kayaking, sail-boarding, even water skiing. And it’s all complimentary, of course. Sun yourself on deck, take a dip in the whirlpool, then catch up on email or order a cheese plate for your stateroom or suite. After dinner, dance to live music in the Lounge. This is your yacht, so of course you’re welcome on the Bridge, where the Captain and officers are delighted to share charts, routes, and vistas with you.

All Inclusive Cruise Services

Make Your Cruise As Inclusive as You Like

One call. It's that simple. With a single call to a Windstar Vacation Planner you or your travel professional can take care of every aspect of your vacation - air travel, ground transportation, shore excursions, pre- or post-cruise experiences and extensions, the right Optional Travel Protection Plan to secure your peace of mind. It's all as easy as a phone call.

Beverage Packages

While all non-alcoholic beverages are complimentary, you may enjoy a pre-dinner cocktail under the setting sun or a champagne toast at the evening Sail Away with our beverage packages for wine, beer, cocktails and more. Find the perfect wine pairing with your meal and then end the night sipping scotch as you contemplate the stars.

Luggage Shipping

Eliminate the hassles of carrying and checking bags or clearing customs with our luggage shipping service. Your bags will be picked up from home and delivered directly aboard your ship and then sent back once you're ready to go home. Thanks to our partnership with Luggage Forward, you just board your flight and meet your bags at your destination.

Personal Onboard Laundry Service

Pack light when you add our convenient 24-hour onboard professional laundry service. Simply leave your laundry outside your stateroom or suite before you retire and it will be waiting for you, crisp and clean, when you return from your day's explorations. It adds the easy to our easy-going style.

Stay Connected

Keep in touch with your loved ones back home and share your cruise experiences during your voyage. Whether you want to check email or post updates to Facebook, we have multiple options to help you stay connected.

Your Windstar Voyage Includes:
  • All Meals 
  • Non-alcoholic Beverages 
  • Welcome Cocktail
  • Water Sports Equipment 
  • Live Entertainment 
  • Fitness Center & Classes
  • Destination Briefings
Enrichment Programs

At Windstar, we don't just take you to fascinating destinations, we take you into them, giving you unique access to knowledge and activities that enhance your understanding of the places you visit. Complimentary Destination Discovery Events treat you to iconic experiences that capture the essence of your locale. Guest Lecturers intrigue you with regional topics, adding new dimensions to your voyage. And small group excursions take you to meet locals who are delighted to share their homes, cuisines, and cultures with you.


Guest Lecturers

On select Windstar voyages, satisfy your curiosity and enhance your understanding of the local culture by listening to our onboard lecturers. We’ve curated a group of speakers designed to bring you an insider’s perspective on a multitude of intriguing topics. Listen raptly as your voyage becomes more than just a vacation – and a thought-provoking exploration of enchanting lands.


Windstar Signature Expeditions

Introducing the Windstar Signature Expeditions program. Helmed by a team of on board expedition experts who sail with the cruise the entire time, they'll provide more insight, understanding, and commentary to show you an Alaska you've never seen before. Consisting of naturalists, glaciologists, historians and more, this team of experts will also lead guided tours, sometimes directly from the ship to some of the most remote areas of the Alaskan frontier.

Each once-in-a-lifetime experience will leave you hungry for more of the real flavors of Alaska. Book your Alaska cruise and Signature Expeditions today.


Culinary Shore Excursions

Tantalize your taste buds with a variety of flavorful shore excursions. Choose from wine, brewery and distillery tours as well as hands-on cooking classes with seasoned chefs practiced in the art of perfecting traditional and modern recipes. Ship to shore, we'll intoxicate your senses.


Shore Excursions

Get to the heart of local cultures with Windstar shore excursions.

You don’t want to just dip a toe in local culture, you want to dive into the deep end, and that’s exactly what Windstar shore excursions are designed to do. All of our excursions are created to provide authentic local experience – the kind travelers like you are looking for. And with more than 2,500 excursions to choose from, you can experience your destination in whatever way is most meaningful to you. Whether you’re an outdoor enthusiast, a foodie, a history buff or someone who loves to get to know the faces behind the many places we travel.

We make sure the hot springs are hot and the pinot grigio is chilled.


180 degrees Onboard Magazine

Discover Windstar's onboard magazine, 180 degrees. Focused on immersive, vibrant travel experiences, the magazine introduces our most popular destinations, with handy notes after each article noting which itineraries visit the port. Read about the history and culture of our most popular destinations over breakfast al fresco, or by the poolside as you sunbathe. Start planning your next cruise with the included cruise calendar or simply be transported to wondrous lands. 180 degrees is available onboard now and online.

Onboard Spaces
  • Lounge 
  • Lounge Bar
  • Yacht Club Cafe
  • Compass Rose Bar
  • Spa
  • Stella Bistro
  • Veranda Restaurant 
  • Pool Bar
  • Deck
  • Captain's Bridge
Ship Facts
  • Capacity: 342 Guests
  • Crew: 210 international staff
  • Ship's Registry: Bahamas
  • Length: 535 ft (162 m) at waterline; 617 ft (187m) including bowsprit
  • Draft: 16.5 ft (5 m)
  • Tonnage: 14,745 (grt)
  • Beam: 66 ft (20 m)
  • Speed: 10 to 12 knots with engines only; up to 15 knots wind and engine assisted
Decks
Stateroom Legend
  • Stateroom Legend
  • A Category A
  • AX AX Deluxe
  • B Category B
  • BS Opulent Bridge Suite
  • BX BX Deluxe
  • OW Spacious Suite
  • TX Gracious Stateroom
Stateroom Symbol Legend
  • Stateroom Symbol Legend
  • MODIFIED ACCESSIBLE SUITES
  • SHOWER ONLY (STAR PRIDE)
  • SHOWER ONLY
  • QUEEN BED ONLY ON STAR BREEZE and STAR LEGEND. (STAR PRIDE can convert to twins.)
  • STAR LEGEND HAS A SINGLE SINK
  • ELEVATOR
  • ONE QUEEN SIZE BED ONLY (no twin option)
  • ADJOINING SUITES - STAR LEGEND and STAR BREEZE
  • RESTRICTED VIEW
Please select the deck plan you will like to see below

Star Deck

Choose your cabin on Star Deck
Destination
Caribbean
Sleeping under a palm tree, strolling on endless beaches and eating ice cream while floating in a turquoise sea. What could be further from your everyday world? When you sail the Caribbean you'll discover how relaxing, entertaining and just plain fun a week really can be. Visit a variety of beautiful islands and escape to paradise on your next vacation.
Ports of Call
Philipsburg, St. Maarten

Dutch St. Maarten is a great place to stop just to shop. Its capital is Philipsburg and fills a narrow stretch of land between Great Bay and the Great Salt Pond. It is a bustling center of international trade with lively shopping streets, cafes, and hotels. Strangely enough it has two main streets called Front Street and Back Street.

On Front Street, which is the main thoroughfare, duty-free shops line the road as far as the eye can see. These duty-free shops offer everything from Italian leather goods and Japanese cameras to native crafts. Don't be afraid to venture the alleyways that will lead you to arcades and courtyards filled with flowers.

The Courthouse is the most prominent landmark on Front Street. It is a grand white wooden structure topped with a cupola built in 1793. Front Street also includes the Simartin Museum so that visitors can get and excellent introduction to local St. Maartin history. There are also historical forts that are monuments to Philipsburg's strategic importance in St. Maarten's history.

Philipsburg has not been left behind in the time, however. It has combined its historical legacy with 20th century excitement. Since its waterfront has become a popular stop for cruise ships, the shore of this town is covered with restaurants, cafes and nightclubs that offer entertainment well into the night.

Port of Charlestown, Nevis, St. Kitts and Nevis
City Nevis

...St. Kitts is still relatively uncrowded, and the white-sand beaches stretch for miles. The 18th century architecture of St. Kitts is magnificent, and the extravagant man-made buildings are complemented fantastically by the lush rain forests that encapsulate the majority of the island. This is exactly what makes St. Kitts so incredibly exciting. The diversity all around the island is amazing, as locals can be seen shirtless wearing sandals, while others prefer to suit up in thousand dollar linens, while sipping martinis in one of the posh dining facilities.

Roseau, Dominica
City Roseau

Pigeon Island, St. Lucia
City Pigeon Island

Les Saintes, Guadeloupe

Gustavia, St. Barts
City Gustavia

The tiny island of St. Barts is picture-perfect. So much so that it has become a haunt for the very rich who come for the privacy, gorgeous beaches and exquisite French cuisine. It has over 20 magnificent beaches, linked roads that are hilly and narrow. The quaint streets of the Lilliputian port of Gustavia lead past small markets and bakeries. Included among these markets are dozens of small shops selling French perfumes, sportswerar, watches, and crystal. It is no wonder why the port of Gustavia is preferred by many of the luxury cruise lines as a port-of-call.

Port of Basseterre, St. Kitts, St. Kitts and Nevis

This fertile isle is a land of rain forests, tropical flowers, and abundant sugar cane. After a stroll around the charming colonial streets and shops of the capital, Basseterre, tour the island or visit Brimstone Hill Fort, an impressive construction that is one of the wonders of the Caribbean world.

Falmouth Harbour, Antigua
City Falmouth

Because Falmouth Harbour is a large, protected, horseshoe-shaped bay you are able to find two main centers of activity. On the north side of the harbour you can casually mingle with the residents of the small village of Falmouth. If you are more interested in the visitor oriented tourist spots travel to the east side of Falmouth Harbour where you will be walking distance from Nelson's Dockyard.

Nelson's Dockyard is named after a Royal Navy Captain that set up his base there in 1785. Now, Nelson's Dockyard evokes the presence of the greatest naval Commander in history by means of its faded pink brick and weather-worn bollards. Just to the south is English Harbour, probably one of the most atmospheric ports you'll ever come across. These dockyard and many others, including the marinas, old inns, pubs, and crowds of yacht crews may remind you a bit of Newport or Annapolis, because this is the epicenter of the Caribbean yachting world.

Jost Van Dyke, British Virgin Islands
City Jost Van Dyke

If you''re looking for the ultimate laid back island adventure, Jost Van Dyke is the island for you. Jost Van Dyke has amazing beaches, appetizing restaurants, and tempting bars for your indulging pleasure. This four mile long island is known as the "barefoot" island for its casual inviting atmosphere.

Sopers Hole, British Virgin Islands
City Sopers Hole

Are you looking for the ideal place to anchor and enjoy beautiful scenery? This extraordinary city is engulfed in mountains and would be the perfect place for you to explore. Soper Hole lies on the west end of Tortola Island of the British Virgin Islands. Sopers Hole is known for plenty of its main attractions for its visitors as well as its natives. Its watering holes are a favorite of the visiting yacht members. One of the main attractions of this city would be the Marina is equipped with moorings, docking, water ice, and plenty of services for the boaters. Dining includes the perfect waterfront surroundings, live entertainment, outdoor bar, and a variety of dishes for your eating pleasure.

Virgin Gorda, British Virgin Islands
City Virgin Gorda

Two outstanding sights highlight this port of call. First is "The Baths." Unique in all the Caribbean, this natural wonder consists of giant boulders that form labyrinthine caves and clear, salt-water pools illuminated by the rays of the sun. Second is Gorda Sound, a protected anchorage known the world over by seasoned yachtsmen.

Road Bay, Anguilla

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