Barefoot Break in the British Virgin Islands
Dec 2, 2025 — Dec 7, 2025
Starting from $4,300 Displayed pricing is based off of double occupancy per person. Pricing subject to change based on occupancy and cabin selection.
See more routes around CaribbeanPHILIPSBURG, ST. MAARTEN → PHILIPSBURG, ST. MAARTEN
5 Nights in Wind Surf
Popular Highlights

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.

Arrive at the boardwalk of Pusser's Landing and mingle with other yachtsmen in the utterly charming marina at Soper's Hole. Find a deserted stretch of beach to kick back and ponder this tiny port's rich heritage of romance, pirates, and adventure. An evening departure features a once-in-a-lifetime romantic sunset Sail Away.
Soper's Hole: Cane Garden Bay Beach Break
Soper's Hole: Cane Garden Bay Beach Break
Kick start your adventure at Soper's Hole Marina. After a quick safety brief, you will have a 30-minute drive through Zion Hill with beautiful views of Capoons, Carrot and Apple Bays. Enjoy 3 hours free time at Myetts Beach Lounge, a bright colorful, beach bar and restaurant. The beach bar sun loungers and picnic tables are set right at the edge of a white sandy beach. With a drink in one hand and toes in the sand, music drifting out from the bar, you know you have left your worries far behind for a taste of everything Irie (that's Jamaican for pleasing). Swim, relax or take a stroll on the beautiful shores. Your driver will be waiting to take you back to the Marina after a relaxing day. Please note: Swimming is at your own risk, so always use caution. The buses used for the transfer are island style open air buses. Guests must be able to board with minimal assistance. Social distancing is highly encouraged. Wear your swimsuit under your clothing and beach shoes; bring a towel, reef-safe/biodegradable sunscreen, a cover-up for further protection from the sun, and a hat.
Tortola, Scenic Drive & Beach
Tortola, Scenic Drive & Beach
From your tender dock, you will take an open-air safari bus on a scenic drive through the capital Roadtown , featuring both coasts of this beautiful island. Follow the Ridge Road and ascend Fort Hill , pausing for photos and commentary along the way. The views towards Anegada, the U.S. Virgin Islands, and many of the British Virgin Islands are unparalleled. After passing the local village of Long Trench with its colorful wall mural depicting historical scenes of island life, you will glimpse the settlement of Fahie Hill . More outstanding views continue as you follow along the ridge, before descending Ross Path to beautiful Cane Garden Bay for a one-hour stay Swim and relax in the crystal clear water at this spectacular white-sand beach and enjoy a complimentary beverage . Changing/showering facilities, a restaurant, and bar (for additional extra-charge drinks) are also available. Your return to Roadtown will include a short visit to the historic Callwoods Rum Distillery and trace the scenic north shore, past Zion Hill and the Sir Francis Drake Channel. Please note : This tour is operated using open safari tour buses that are accessed by three steps and involves driving over winding, steep hills. The buses drive on the left hand side of the road. You will have free time at the beach where a lifeguard will be present. Wear your swimwear under your clothes and bring a towel. Beach chairs and umbrellas are available for rent at the beach.
Tortola, Snorkel Adventure at Peter Island
Tortola, Snorkel Adventure at Peter Island
Board your catamaran at the pier. Your friendly crew will greet you and conduct a short safety briefing to make sure you are well-settled before the Captain sets off. Cruise approximately 45 minutes across the Sir Francis Drake Channel to one of the British Virgin Island's prime snorkel sites. Your approximately 60-minute snorkeling adventure is all about enjoying the beautiful clear waters of the Virgin Islands, the myriad marine life and an idyllic Caribbean beach. Upon arriving at your snorkel site, an experienced instructor will guide you around the underwater world of a secluded location on Peter Island. Back on board, enjoy some drinks before moving on to your 2nd snorkel spot. You can choose to relax on board, swim or enjoy a 2nd guided snorkel tour. Finally, reboard your catamaran and cruise approximately 45 minutes back to the pier in Soper's Hole. Please note : Alternative snorkel locations may be selected according to sea and weather conditions. Wear your swimsuit under your clothing; bring a towel, reef-safe/biodegradable sunscreen, a cover-up for further protection from the sun, and a hat. Masks, snorkels and snorkel vests are provided as well as instruction for novices. You will have approximately 1-1/2 hour snorkel time. Water will be available on board.
Tortola, Tortola Jeep & Beach Tour
Tortola, Tortola Jeep & Beach Tour
Kick start your adventure at Soper's Hole Marina. After a quick safety briefing, you'll set out caravan style and follow your guide in the lead vehicle. Communicating by VHF radio, you'll head offroad and park your vehicle at the stunning, secluded Smugglers Beach. Stroll along the shoreline of one of Tortola's most inviting beaches. Bask in the sun, swim, or simply admire the natural beauty and serenity of the sea. Back in the Jeep, you'll wind through Long Bay and skirt the beautiful western shores of Apple Bay and the fishing village of Carrot Bay. Ascending Windy Hill, you'll take photos from a 360 degree view up at Sky world, before you continue to Cane Garden Bay and back to Nanny Cay Marina. Enjoy your scenic drive back to the ship. Please note : Minimum age is 4 years (car seat provided). Four guests per vehicle; you can take turns driving. Bring your driver's license (must be 25 to drive). Wear your swimsuit under your clothing; bring a towel, reef-safe/biodegradable sunscreen, a cover-up for further protection from the sun, and a hat. Drinks at Peg Legs Beach Bar include soft drinks, beers and water.

For an island comprised of a mere eight square miles, it's amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis Drake Waterway. After all that, you'll be ready for an evening drink on the beach - where you can admire your Windstar ship aglow in the harbor.

For an island comprised of a mere eight square miles, it's amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis Drake Waterway. After all that, you'll be ready for an evening drink on the beach - where you can admire your Windstar ship aglow in the harbor.
Jost Van Dyke, Sail and Snorkel
Jost Van Dyke, Sail and Snorkel
Step aboard a sleek catamaran for a fun and relaxing cruise through the islands surrounding Jost Van Dyke. After an hour of sailing your catamaran will anchor off the beautiful desert island Sandy Cay. From here you can choose to swim in the crystal-clear water, bask in the sun on the pristine white-sand beach, or stay on board and enjoy a complimentary drink. Cruise to Diamond Cay, a tiny islet surrounded by powdery white sand, azure blue waters, and an underwater world filled with colorful marine life . Enjoy an hour of exploring the fascinating reefs, or take a stroll to Foxy's Taboo. Refreshments and snacks are available at Foxy's Taboo (additional cost), as well as a pleasant little gift shop. The crew will sound the horn for another hour of catamaran cruising with rum punch and music. Please note : Wear your swimwear under your clothes and bring a towel, dry t-shirt or sweatshirt, a hat, and sunscreen. Snorkeling and swimming destinations may vary according to sea and weather conditions. Guests must be able to step on and off the catamaran and in and out of the water via a dive ladder. Refreshments are included on board.
Jost Van Dyke, Catamaran Cruise & Swim to Norman Island
Jost Van Dyke, Catamaran Cruise & Swim to Norman Island
This outing contains all the right ingredients for a fun-filled and memorable day on the water in the BVI. Board a power catamaran from Great Harbor and take in the breathtaking and incredible views of the islands of both the USVI and BVI. Your captain and crew have extensive local knowledge and will share geographical and nautical facts and lore with you. The boat will dock at Pirates Bight on Norman Island, famously known as Treasure Island. The reputed history of piracy on this island is immortalized in Robert Louis Stevenson's famous book Treasure Island . Here, you have free time to snorkel from the beach, enjoy a stroll or simply relax. Please note : Wear your swimsuit under your clothing; bring a towel, sunscreen, and a hat. Guests with heart problems, epilepsy or asthma are not allowed to participate in snorkeling. A waiver must be signed, and medical conditions disclosed. Guests participating in snorkeling should be able to swim and be in good physical condition.

The beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called "The Baths," which form huge underground pools and caverns
Virgin Gorda: Highlights & Bath Tour
Virgin Gorda: Highlights & Bath Tour
Enjoy the best that Virgin Gorda has to offer when you take this Island Tour to the world famous Baths. Board your open air safari bus at Gun Creek and wind up the hills to Gorda Peak where you will have the opportunity to photograph the impressive archipelago of the B.V.I. Your route will take you on down the spine of this beautiful island. From here you will drive to The Baths. These massive granite boulders stand out against powdery white sand and crystal-clear waters, so seize this chance to scramble through narrow gaps, intricate pools and passages which comprise this adventurous footpath before it opens out to the spectacular white sands of Devil's Bay. The beach at The Baths boasts an appealing bar, souvenir stand and restrooms. For those not physically inclined, you can still be witness to these dramatic batholiths should you take a drink at the Top of The Baths, or the less strenuous path direct down to Devils Bay. Before boarding the safari busses, sample a complimentary rum punch, punch or water at the gazebo above the Baths, and then enjoy the remainder of your circular island tour via Nail Bay with homes of the rich and famous and Hog's Heaven for some stunning shots of the ship anchored in North Sound. Please note : Wear your swimsuit under your clothes, bring reef-friendly sun screen, towel, camera, reef or aqua shoes to explore the Baths, flip-flops are not recommended. This tour is not recommended for those with mobility issues. Use caution while walking down the trail and through the boulders in the caves. Path is uneven and slippery. On some days expect crowds. Please be aware of the National Flag Warning System and adhere to it at all times. Red Flag: Danger - No Swimming. Yellow Flag: Caution - Weak swimmers are discouraged from entering the water. Purple Flag: Jellyfish Warning. The only way to experience this natural wonder is with our pre- arranged shore excursion being offered onboard.
Virgin Gorda: Snorkel Adventure
Virgin Gorda: Snorkel Adventure
Board a 36-foot Newton Dive Special vessel for a fun and relaxing cruise through the islands surrounding Virgin Gorda. Motor across the stunning Virgin Gorda waters with views of neighboring islands. The boat will moor at your first snorkel spot, chosen by the Captain as the best location for the day. The crew will assist with getting your snorkel gear ready, give a safety briefing and guide you in the water while pointing out interesting sea life. Once back on board, the Captain will pick out a second snorkel spot for you to enjoy. The tour will end with refreshments on board and a cruise back to shore in time for your beach barbecue. Please note: wear your swimsuit under your clothes, bring a towel, a dry t-shirt or sweatshirt, reef friendly sunscreen, waterproof camera (if you want to record the boulders ashore), and a hat. Participants must sign a waiver before departing the dock. Depending on weather and sea state the snorkel locations might have to be adjusted. Minimum age is 7 years. The only way to experience this natural wonder is with our pre- arranged shore excursion being offered onboard.

Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by.
St. Barts: Independent Explorer by Car
St. Barts: Independent Explorer by Car
Here is a chance for the adventuresome to get away from the crowds, get behind the wheel, and enjoy the lush countryside on a self-guided tour . You will be escorted from the pier to the nearby starting point and after brief formalities you will be given the keys to your rental car. Armed with a map of the island, some suggested itineraries, and some details about historical facts and points of interest, you're ready to explore this beautiful island at your own pace . The cost is for the car; one to four people can explore at just one rate. Please note : Participants must be comfortable driving winding and hilly conditions. Bring your swimsuit, a credit card, and a current driver's license. The tour price is per car and includes CDW insurance, a $1200 euro deductible which will be fully or partially charged to the driver's credit card in the event the car is returned damaged. Fuel costs are included. Pricing is per car, and can hold up to 4 guests. Only one person in the party needs to purchase the tour. Your tour time may vary depending on when your ship docks.
Gustavia, Concierge Collection: Scuba Dive 2 Tank
Gustavia, Concierge Collection: Scuba Dive 2 Tank
Explore the vibrant flora and fauna of St. Barthélemy with our expert, accredited instructors as they guide you through the stunning sites of the Protected Marine Reserve on this two tank dive. Please note: any electronic devices (such as cell phones, cameras, etc.) and valuable items should be securely stored in a waterproof, sealable dry bag. Guests are responsible for any damage to these items. Please bring copies of your PADI scuba certification.
St Barts, Concierge Collection: St. Barthelemy Beach Day
St Barts, Concierge Collection: St. Barthelemy Beach Day
You will find Le Barthélemy Resort and Spa at the end of a beautiful bay right on a stunning beach. Le Barthélemy is sheer luxury, so let yourself be spoiled. In the rare beauty of the natural setting, you will understand the spirit of St. Barts; elegance, refinement, and discretion. Enjoy your lunch, swim, make use of the non-motorized watersport equipment provided, or do nothing at all, enjoy yourself. Le Barthélemy lets you forget all worries for the day and slips you into a cocoon of comfort and contentment. ENJOY! This is the life, St. Bart's style. This excursion was arranged specifically for and is exclusive to Windstar guests. Please note : Bring your swimsuit, sunscreen, and a cover up for the restaurant. Lunch is included at the resort restaurant.
St. Barts, Concierge Collection: Sunset Cruise
St. Barts, Concierge Collection: Sunset Cruise
Boarding your sailing cat you will depart from Gustavia's tender pier. Your Captain will give a safety briefing as you set sail. You will have a peaceful and quiet sailing time in the vicinity of the harbor area to enjoy scenic views of the sunset. You will appreciate the scenic panorama, passing the mega yachts at anchor. The Captain will offer you Champagne, mineral water, soft drinks or beer and some assorted light snacks. The crew will be attentive and helpful. Please note : You will board the ship with a gangway that can be tricky because of the recurrent swell in Gustavia harbor. You will have to remove your shoes and be barefoot before boarding the vessel. The Captain is solely responsible and has the right to refuse boarding to a guest who would be judged unable to participate. Cancellations must be made 48 hours prior to cruise time for refunds.
Gustavia, Concierge Collection: Jet Ski
Gustavia, Concierge Collection: Jet Ski
Embark on an exciting adventure to discover St. Barth's most stunning beaches! Accompanied by professional instructors, you'll begin your journey from Gustavia Harbor, making stops at the picturesque Shell Beach, the secluded Gouverneur Beach, and the beautiful Salines Beach, before heading south to Coco Island, located 0.62 miles from St. Barth. Along the way, enjoy a 15-minute swim break in the calm waters before hopping back onto your jet-ski for the return ride to Gustavia. Please note: participants must be at least 16 years old. You will be required to sign a waiver prior to participating in this tour.
Gustavia, Concierge Collection: Scuba Dive 1 Tank
Gustavia, Concierge Collection: Scuba Dive 1 Tank
Explore the vibrant flora and fauna of St. Barthélemy with our expert, accredited instructors as they guide you through the stunning sites of the Protected Marine Reserve on this one tank dive. Please note: any electronic devices (such as cell phones, cameras, etc.) and valuable items should be securely stored in a waterproof, sealable dry bag. Guests are responsible for any damage to these items. Please bring copies of your PADI scuba certification.
St. Barts: Sailing Catamaran Adventure
St. Barts: Sailing Catamaran Adventure
Caribbean music and the friendly crew of a well-appointed, full-sail catamaran will welcome you aboard. This boat is specially designed to offer shade and refreshing breezes as you sail along the beautiful west coast of the island to the Marine Park at Colombier Bay . You will anchor about 80 feet offshore, close to coral reefs teeming with schools of colorful fish. A professional instructor will give you a full orientation and explain the use of the snorkel equipment. You will have time to swim and snorkel, or simply bask in the sun. On the return to Gustavia, soft drinks, beer, or refreshing rum punch or fruit punch will be offered. Please note : This exclusive experience is limited to 12 guests and sells out quickly. No previous sailing experience necessary. The catamaran will offer refreshments throughout the trip. Restrooms are located on board the catamaran. Bring sunscreen, hat, swimsuit, and underwater camera and towel. Snorkeling gear is available on the boat.
Gustavia, Concierge Collection: Savor St Barts
Gustavia, Concierge Collection: Savor St Barts
St. Barthélemy offers a unique culinary experience that blends French and Caribbean flavors into a delicious fusion. Stroll through the charming streets of Gustavia, where luxury boutiques and hidden gems await, all while savoring some of the island's finest gastronomic delights at every stop. Your culinary adventure begins with a classic French treat: a crepe, served with a choice of lemon and sugar or warm homemade chocolate. Discover the origins of this beloved dish from the Bretagne region, and enjoy it with a refreshing glass of hard apple cider. Next, head to the iconic "Le Select" bar, famous for being the place where Jimmy Buffett wrote his hit song "Cheeseburger in Paradise" in 1978. Known for its legendary rum punch, called "Planteur" (available with or without alcohol), this stop promises a fun and flavorful experience. Then, wander to a cozy restaurant nestled in the heart of Gustavia, where you'll enjoy a healthy "Tartine," a French open-faced sandwich topped with smoked salmon, lemon Greek yogurt, avocado, and sesame seeds, paired with a chilled Passion Fruit Iced Tea. The grand finale of your culinary tour takes you to the elegant Barons de Rothschild lounge, where you'll indulge in two glasses of their signature champagne: the Blanc de Blanc and the Rose Champagne, accompanied by the unforgettable Baron de Rothschild cheese. It's the perfect way to unwind and savor the finest flavors of St. Barth. At the end of the tour, your guide will escort you back to the tender, or you may choose to stay and explore the shops of Gustavia at your own pace.
St. Barts: Intimate Island Tour
St. Barts: Intimate Island Tour
This is an exclusive panorama island tour for five people with a local, English speaking driver/guide in an air-conditioned vehicle. Experience the local highlights as you wish, at your pace. Please note : Wear comfortable shoes and clothes.

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.

Available Staterooms
Amenities
- Queen Size Bed with Luxurious Linens
- Fully-Stocked Mini-Bar/Refrigerator
- L'Occitane Bath Amenities
- Fresh Fruit
- Hair Dryers and 110/220 Outlets
- Waffle Weave Robe and Slippers
- Safe
- Granite Vanity with Magnifying Mirror
- Bathroom with Granite Countertop and Shower
- Wi-Fi (Internet cards can be purchased at reception)
- TV with DVD Player
Category A

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.
Amenities
- Queen Size Bed with Luxurious Linens
- Fully-Stocked Mini-Bar/Refrigerator
- L'Occitane Bath Amenities
- Fresh Fruit
- Hair Dryers and 110/220 Outlets
- Waffle Weave Robe and Slippers
- Safe
- Granite Vanity with Magnifying Mirror
- Bathroom with Granite Countertop and Shower
- Wi-Fi (Internet cards can be purchased at reception)
- TV with DVD Player
Category AX Deluxe

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.
Amenities
- Queen Size Bed with Luxurious Linens
- Fully-Stocked Mini-Bar/Refrigerator
- L'Occitane Bath Amenities
- Fresh Fruit
- Hair Dryers and 110/220 Outlets
- Waffle Weave Robe and Slippers
- Safe
- Granite Vanity with Magnifying Mirror
- Bathroom with Granite Countertop and Shower
- Wi-Fi (Internet cards can be purchased at reception)
- TV with DVD Player
Category BX Deluxe

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.
Amenities
- Queen Size Bed with Luxurious Linens
- Fully-Stocked Mini-Bar/Refrigerator
- Fully Upgraded Bath Amenity Line Including Pure Pampering L'Occitane
- Fruit Basket with Berries
- Hair Dryers and 110/220 Outlets
- Upgraded High End Quality Bath Robes
- Safe
- Fresh Flowers
- Granite Vanity with Magnifying Mirror
- Bathroom with Granite Countertop and Shower
- Free Internet Service (1 Voucher per Suite)
- Preferred on Board Check In
- Invitation to Captain or Senior Officer Table
- Personalized Wake-Up Call Service with Preferred Beverage Coffee/Tea/Juice
- Preferred Specialty Restaurant Dining
- Preferred Canapes Service
- Maschio Prosecco
- Illy Espresso Machine
- Binoculars
- TV with DVD Player
Suite

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.
Amenities
- Queen Size Bed with Luxurious Linens
- Fully-Stocked Mini-Bar/Refrigerator
- L'Occitane Bath Amenities
- Fresh Fruit
- Hair Dryers and 110/220 Outlets
- Waffle Weave Robe and Slippers
- Safe
- Granite Vanity with Magnifying Mirror
- Bathroom with Granite Countertop and Shower
- Wi-Fi (Internet cards can be purchased at reception)
- TV with DVD Player
Category B

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.
Amenities
- Queen Size Bed with Luxurious Linens
- Fully-Stocked Mini-Bar/Refrigerator
- L'Occitane Bath Amenities
- Fresh Fruit
- Hair Dryers and 110/220 Outlets
- Waffle Weave Robe and Slippers
- Safe
- Granite Vanity with Magnifying Mirror
- Bathroom with Granite Countertop and Shower
- Wi-Fi (Internet cards can be purchased at reception)
- TV with DVD Player
Category TX Deluxe

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.