Barefoot Break in the British Virgin Islands Windstar Cruises

What's Included

  • 30 Nov - 07 Dec 2025
  • Return flights from the UK
  • 5 Nights onboard Wind Surf
  • 2 nights hotel stay pre cruise
  • Water sports toys*
  • Inclusion package upgrades available on request*
  • Soft drinks*
  • Complimentary Dining*
  • Entertainment*
*included onboard your cruise
Cabin & Fares
Inside Not
Available
Outside Available
Balcony Not
Available
Suite Available
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Promotions

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  • 35% savings on select 2025 voyages*
  • Reduced single supplement on select voyages*
*Select voyages. T's and C's apply

Your Itinerary

  • Day 1

    Philipsburg, Sint Maarten (Dutch part)

    The capital of Dutch St. Maarten stretches about a mile (1½ km) along an isthmus between Great Bay and the Salt Pond and has five parallel streets. Most of the village's dozens of shops and restaurants are on Front Street, narrow and cobblestone, closest to Great Bay. It's generally congested when cruise ships are in port, because of its many duty-free shops and several casinos. Little lanes called steegjes connect Front Street with Back Street, which has fewer shops and considerably less congestion. Along the beach is a ½-mile-long (1-km-long) boardwalk with restaurants and several Wi-Fi hot spots.Wathey Square (pronounced watty) is in the heart of the village. Directly across from the square are the town hall and the courthouse, in a striking white building with cupola. The structure was built in 1793 and has served as the commander's home, a fire station, a jail, and a post office. The streets surrounding the square are lined with hotels, duty-free shops, restaurants, and cafés. The Captain Hodge Pier, just off the square, is a good spot to view Great Bay and the beach that stretches alongside.

  • Day 2

    Sopers Hole, Tortola, British Virgin Islands

  • Day 2

    Great Harbour, Jost Van Dyke, British Virgin Islands

    Jost Van Dyke, four miles long, is truly known as the 'barefoot island'. The smallest of the British Virgin Islands, it is known as a popular destination for yachts and is celebrated for its casual lifestyle, protected anchorages, fine beaches and beachfront restaurants and bars. The island has fewer than 200 inhabitants and they are widely known as a welcoming people. The island's name conjures up its rich, colorful past. Jost Van Dyke is said to have been named for an early Dutch settler, a former pirate. At Great Harbour, Little Harbour, and White Bay there are safe, protected bays and pristine beaches shaded with coconut palms and seagrape trees. Discover inviting shops selling local treasures, restaurants, and bars. 'The Painkiller', one of the Caribbean’s most popular drinks, originated at the Soggy Dollar Bar. Foxy’s and Gertrude's in White Bay are renowned for drinks made with the island's famous rum, frosty beers, and tales of pirates and sunken treasure. Explore Jost Van Dyke's history in the vegetation-covered ruins of centuries-old sugar mills, or on the old trails that crisscross the island. Revel in the natural beauty of the pristine, untouched beaches. Hike up to the highest spot on the island, Majohnny Point, and take in a stunning 360 degree view of the Caribbean. Relax in the natural 'bubble pool', a popular tourist attraction. Jost Van Dyke conjures up images of what the British Virgin Islands may have looked like many years ago.

  • Day 3

    Great Harbour, Jost Van Dyke, British Virgin Islands

    Jost Van Dyke, four miles long, is truly known as the 'barefoot island'. The smallest of the British Virgin Islands, it is known as a popular destination for yachts and is celebrated for its casual lifestyle, protected anchorages, fine beaches and beachfront restaurants and bars. The island has fewer than 200 inhabitants and they are widely known as a welcoming people. The island's name conjures up its rich, colorful past. Jost Van Dyke is said to have been named for an early Dutch settler, a former pirate. At Great Harbour, Little Harbour, and White Bay there are safe, protected bays and pristine beaches shaded with coconut palms and seagrape trees. Discover inviting shops selling local treasures, restaurants, and bars. 'The Painkiller', one of the Caribbean’s most popular drinks, originated at the Soggy Dollar Bar. Foxy’s and Gertrude's in White Bay are renowned for drinks made with the island's famous rum, frosty beers, and tales of pirates and sunken treasure. Explore Jost Van Dyke's history in the vegetation-covered ruins of centuries-old sugar mills, or on the old trails that crisscross the island. Revel in the natural beauty of the pristine, untouched beaches. Hike up to the highest spot on the island, Majohnny Point, and take in a stunning 360 degree view of the Caribbean. Relax in the natural 'bubble pool', a popular tourist attraction. Jost Van Dyke conjures up images of what the British Virgin Islands may have looked like many years ago.

  • Day 4

    At sea

  • Day 5

    Gustavia, Saint Barthélemy

    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.

  • Day 6

    Philipsburg, Sint Maarten (Dutch part)

    The capital of Dutch St. Maarten stretches about a mile (1½ km) along an isthmus between Great Bay and the Salt Pond and has five parallel streets. Most of the village's dozens of shops and restaurants are on Front Street, narrow and cobblestone, closest to Great Bay. It's generally congested when cruise ships are in port, because of its many duty-free shops and several casinos. Little lanes called steegjes connect Front Street with Back Street, which has fewer shops and considerably less congestion. Along the beach is a ½-mile-long (1-km-long) boardwalk with restaurants and several Wi-Fi hot spots.Wathey Square (pronounced watty) is in the heart of the village. Directly across from the square are the town hall and the courthouse, in a striking white building with cupola. The structure was built in 1793 and has served as the commander's home, a fire station, a jail, and a post office. The streets surrounding the square are lined with hotels, duty-free shops, restaurants, and cafés. The Captain Hodge Pier, just off the square, is a good spot to view Great Bay and the beach that stretches alongside.

View full itinerary Close itinerary

On Board

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. 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.

 

Outside Available

Officer's Suite

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.

Owner's Suite

One of the best secrets in the cruise industry, this unique suite is located directly behind the Bridge. The Owner’s Suite, previously named the Officer’s Suite, is the only public accommodation near the officers’ quarters. Following the renovation, expect an elevated nautical look for true insider-y yacht life in a tucked away location.

All Accommodations Feature

  • Queen Size Bed with Luxurious Linens
  • Waffle Weave Robe and Slippers
  • Fully Stocked Mini Bar/Refrigerator
  • Hair Dryers and 110/220 outlets
  • Bathroom with granite countertop and shower
  • Granite vanity with magnifying mirror
  • Safe
  • L'Occitane Bath Amenities
  • Fresh Fruit
  • Wi-Fi access
  • Television

Suite Available

Gracious Staterooms

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.

Spacious Suites

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.

Opulent Bridge Suites

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.

Introduction

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 flavours of the regional cuisine.

Amphora Restaurant

Wind Surf’s main dining room has been entirely refreshed setting the scene for a timeless dining experience. Amphora’s new design concept draws from elements of the sea, such as pearls, smooth stones, and sea glass, which guests will see integrated into the new architecture and furniture details. The complementing colour tones were inspired by the horizon at sunset. New seating arrangements include curved booths to seat 2-8 people, new larger dining chairs for comfort. 

Stella Bistro

Treat your palate to the French-inspired café 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) 

Veranda Restaurant

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

24-Hour Room Service

Stay in tonight and even order from the main Amphora dining menu.

Introduction

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, and stand-up paddleboarding. 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.

As you prepare for another amazing Windstar day, enjoy a nightcap anywhere you like — on deck, in the Lounge, or why not let us bring it to your suite or stateroom? Your day ends just as it began, blissfully.

Compass Rose Bar

The ship’s Compass Rose features comfortable, modern décor with pops of blue and orange, a chic bar, and a new multi-purpose stage area ideal for live music and local performances. 

Pool Deck & Bar

This space will now maximise Wind Surf’s ocean views and create a more convivial vibe for poolside lounging and top-shelf mixology. Tropical scenes and greenery at the bar pull in a natural, outdoor atmosphere. Soothing natural colours convey a beach scene and new arty tiling on the two whirlpools take the form of ocean waves. Look for a variety of new outdoor furniture as well. 

Star Boutique

A larger retail area with upscale details, reminiscent of a luxury brand store’s shopping experience. 

Reception

A new, more welcoming location that’s better able to serve guests with additional seating options, plus an updated and fresh (yet still nautical) vibe akin to a boutique hotel. 

Onboard Entertainment

Onboard entertainment facilities include: a casino, a watersports platform, the Compass Rose Cocktail Bar, The Lounge, and The Terrace Bar.

Lounge

An expanded lounge with new lights and sound for upcoming stage performances.

Yacht Club Café

The Yacht Club Café can be found on the Main Deck.

Wine Room

Located on the Main Deck

Bridge

Located on Bridge Deck

Introduction

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, and stand-up paddleboarding. 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.

As you prepare for another amazing Windstar day, enjoy a nightcap anywhere you like — on deck, in the Lounge, or why not let us bring it to your suite or stateroom? Your day ends just as it began, blissfully.

Enquire about this cruise with our team of experts.

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