Beach Fun & Sun: A Remote Caribbean Getaway

Mar 28, 2026 — Apr 4, 2026

Starting from

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PHILIPSBURG, ST. MAARTEN → PHILIPSBURG, ST. MAARTEN

7 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.

1
MAR 28, 2026
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
MAR 29, 2026
St. John's
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
8

St. John's is a city of Old World charm and elegance which lingers in the varied architecture of Georgian, Victorian, Vernacular, Romantic and International flavors.  The picturesque seafront where tiny, colorful boats are moored, the cheerful wooden buildings carefully refurbished to retain their original features, the vibrant Market Street offering vegetables, fruit and fish and the duty-free Heritage Quay shopping area provide a delightful atmosphere to captivate you.  Sites to see include St. John's Cathedral with its white Baroque towers, the Botanical Garden, St. John's Antigua Lighthouse, and Fort James.

St. Johns, Spectacular Antigua

Time
9:30 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$99

St John's , Caribbean Cooking Culinary Experience

Time
10:45 AM
Duration
4 Hours
Activity Level
Easy-Moderate
Price
$239

St. Johns, Open Course Canopy Challenge

Time
9:30 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$139

St Johns, Concierge Collection, Jet Ski Adventure

Time
9:30 AM
Duration
1.75 Hours
Activity Level
Moderate-Strenuous
Price
$379

St. Johns, Concierge Collection: Antigua Helicopter Adventure

Time
9:30 AM
Duration
2 Hours
Activity Level
Easy
Price
$429

St. Johns, Beach Escape

Time
10:00 AM
Duration
4 Hours
Activity Level
Easy
Price
$89

St Johns, Swim with the Stingrays

Time
9:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$119

St. Johns: Presidents Tour

Time
9:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$129
3
MAR 30, 2026
Road Bay
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
YES
SHORE EXCURSIONS
5

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.

Road Bay, French Invasion Hike

Time
9:00 AM
Duration
2.5 Hours
Activity Level
Strenuous
Price
$159

Concierge Collection: Road Bay, Snorkel Adventure by Speedboat

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$329

Road Bay, Island Exploration by Moke

Time
9:00 AM
Duration
2.5 Hours
Activity Level
Strenuous
Price
$579

Road Bay, Shoal Bay Beach Transfer

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$129

Road Bay, Concierge Collection: Relaxing Day at Savi with Lunch

Time
9:30 AM
Duration
5 Hours
Activity Level
Easy-Moderate
Price
$459
4
MAR 31, 2026
Soper's Hole
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
YES
SHORE EXCURSIONS
3

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. 

Tortola, Tortola Jeep & Beach Tour

Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate
Price
$199

Soper's Hole: Cane Garden Bay Beach Break

Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate
Price
$109

Tortola, Scenic Drive & Beach

Time
8:30 AM
Duration
4.5 Hours
Activity Level
Easy
Price
$119
Jost Van Dyke, Great Harbour
ARRIVE
7:00 PM
DEPART
11:59 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
APR 01, 2026
Jost Van Dyke, Great Harbour
ARRIVE
12:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
1

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, Catamaran Cruise & Swim to Norman Island

Time
8:15 AM
Duration
4.5 Hours
Activity Level
Moderate-Strenuous
Price
$259
6
APR 02, 2026
Virgin Gorda / Prickly Pear, British Virgin Islands
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
YES
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: Snorkel Adventure

Time
9:00 AM
Duration
2.75 Hours
Activity Level
Moderate-Strenuous
Price
$269

Virgin Gorda: Highlights & Bath Tour

Time
8:15 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$89
7
APR 03, 2026
Gustavia
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
3

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.

Gustavia, Concierge Collection: Savor St Barts

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Moderate
Price
$349

Gustavia, Concierge Collection: Scuba Dive 2 Tank

Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$499

Gustavia, Concierge Collection: Scuba Dive 1 Tank

Time
8:30 AM
Duration
3 Hours
Activity Level
Strenuous
Price
$349

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 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 242 sq ft
Max. Occupancy 2 Passengers
Amenities

Room Size sq ft
Max. Occupancy 2 Passengers
Amenities