Beach Fun & Sun: A Remote Caribbean Getaway

Jan 3, 2028 — Jan 9, 2028

Starting from

See more routes around Caribbean

PHILIPSBURG, ST. MAARTEN → PHILIPSBURG, ST. MAARTEN

6 Nights on Wind Surf

Bask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from our yacht’s onboard Marina Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.

Map routes may vary by sailing. Actual itineraries are listed below.
1
JAN 03, 2028
Philipsburg, St. Maarten
EMBARK
1:00 PM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

2
JAN 04, 2028
Road Bay
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
YES
SHORE EXCURSIONS
0

With its protected shoreline, calm surf, spectacular coral reefs and sugar-soft beaches, Road Bay has become a destination for boaters, with its delightful restaurants, bars, and shops. Anguilla has some of the most beautiful sunsets and delicious rum punch to be found in the Caribbean.  It is also home to Cuban tree frogs, red-footed tortoise, green iguanas and five species of bats.  Worth checking out is Wallblake House, a heritage plantation house and museum said to be the oldest building on the island and located nearby.

3
JAN 05, 2028
Gustavia
ARRIVE
8:00 AM
DEPART
7:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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.

4
JAN 06, 2028
Jost Van Dyke, Great Harbour
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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.

5
JAN 07, 2028
Virgin Gorda / Prickly Pear, British Virgin Islands
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
2

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

Available Excursions

Virgin Gorda / Prickly Pear, British Virgin Islands

Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous

Add during booking

$99

Virgin Gorda / Prickly Pear, British Virgin Islands

Time
8:30 AM
Duration
2.75 Hours
Activity Level
Moderate-Strenuous

Add during booking

$299

6
JAN 08, 2028
Soper's Hole
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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. 

7
JAN 09, 2028
Philipsburg, St. Maarten
ARRIVE
6:00 AM
DISEMBARK
7:00 AM
MARINA
NO
SHORE EXCURSIONS
0

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.

Wind Surf

number of decks
6 Decks
yacht length
535 ft (163 meters)
yacht crew size
191 Crew Members
yacht guest capacity
342 Guests

Staterooms

Room Size 495 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 242 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 376 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 188 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 188 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 188 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 188 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 188 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size sq ft
Max. Occupancy 2 Passengers
Amenities

Available Dates

Date Yacht
Starting from
Actions
Dec 19 (Sat) – Dec 26 (Sat), 2026December 19 (Sat) – December 26 (Sat), 2026Wind Surf
Jan 2 (Sat) – Jan 9 (Sat), 2027January 2 (Sat) – January 9 (Sat), 2027Wind Surf
Jan 16 (Sat) – Jan 23 (Sat), 2027January 16 (Sat) – January 23 (Sat), 2027Wind Surf
Jan 30 (Sat) – Feb 6 (Sat), 2027January 30 (Sat) – February 6 (Sat), 2027Wind Surf
Feb 13 (Sat) – Feb 20 (Sat), 2027February 13 (Sat) – February 20 (Sat), 2027Wind Surf
Feb 27 (Sat) – Mar 6 (Sat), 2027February 27 (Sat) – March 6 (Sat), 2027Wind Surf
Mar 13 (Sat) – Mar 20 (Sat), 2027March 13 (Sat) – March 20 (Sat), 2027Wind Surf
Nov 20 (Sat) – Nov 28 (Sun), 2027November 20 (Sat) – November 28 (Sun), 2027Wind Surf
Dec 5 (Sun) – Dec 12 (Sun), 2027December 5 (Sun) – December 12 (Sun), 2027Wind Surf
Dec 19 (Sun) – Dec 27 (Mon), 2027December 19 (Sun) – December 27 (Mon), 2027Wind Surf
Jan 16 (Sun) – Jan 23 (Sun), 2028January 16 (Sun) – January 23 (Sun), 2028Wind Surf
Jan 30 (Sun) – Feb 6 (Sun), 2028January 30 (Sun) – February 6 (Sun), 2028Wind Surf
Feb 13 (Sun) – Feb 20 (Sun), 2028February 13 (Sun) – February 20 (Sun), 2028Wind Surf
Feb 27 (Sun) – Mar 5 (Sun), 2028February 27 (Sun) – March 5 (Sun), 2028Wind Surf
Mar 12 (Sun) – Mar 19 (Sun), 2028March 12 (Sun) – March 19 (Sun), 2028Wind Surf

Beach Fun & Sun: A Remote Caribbean Getaway

PHILIPSBURG, ST. MAARTEN → PHILIPSBURG, ST. MAARTEN

6 Nights on Wind Surf

Jan 3, 2028 — Jan 9, 2028

Bask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from our yacht’s onboard Marina Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.

1
JAN 03, 2028
Philipsburg, St. Maarten
EMBARK
1:00 PM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

2
JAN 04, 2028
Road Bay
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
YES
SHORE EXCURSIONS
0

With its protected shoreline, calm surf, spectacular coral reefs and sugar-soft beaches, Road Bay has become a destination for boaters, with its delightful restaurants, bars, and shops. Anguilla has some of the most beautiful sunsets and delicious rum punch to be found in the Caribbean.  It is also home to Cuban tree frogs, red-footed tortoise, green iguanas and five species of bats.  Worth checking out is Wallblake House, a heritage plantation house and museum said to be the oldest building on the island and located nearby.

3
JAN 05, 2028
Gustavia
ARRIVE
8:00 AM
DEPART
7:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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.

4
JAN 06, 2028
Jost Van Dyke, Great Harbour
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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.

5
JAN 07, 2028
Virgin Gorda / Prickly Pear, British Virgin Islands
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
2

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

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.

Port
Virgin Gorda / Prickly Pear, British Virgin Islands
Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous

Add during booking

$99 USD

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.

Port
Virgin Gorda / Prickly Pear, British Virgin Islands
Time
8:30 AM
Duration
2.75 Hours
Activity Level
Moderate-Strenuous

Add during booking

$299 USD

6
JAN 08, 2028
Soper's Hole
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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. 

7
JAN 09, 2028
Philipsburg, St. Maarten
ARRIVE
6:00 AM
DISEMBARK
7:00 AM
MARINA
NO
SHORE EXCURSIONS
0

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.