Beach Fun & Sun: A Remote Caribbean Getaway

Jan 30, 2027 — Feb 6, 2027

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See more routes around Caribbean

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
JAN 30, 2027
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 31, 2027
Road Bay
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
YES
SHORE EXCURSIONS
6

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, Concierge Collection: Relaxing Day at Savi with Lunch

Time
8:30 AM
Duration
5 Hours
Activity Level
Easy-Moderate
Price
$459

Road Bay, Iconic Island Highlights with Salt Tasting and Beach Time

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

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, French Invasion Hike

Time
8:30 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
3
FEB 01, 2027
Soper's Hole
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
YES
SHORE EXCURSIONS
5

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, Scenic Drive & Beach

Time
8:30 AM
Duration
4.5 Hours
Activity Level
Easy
Price
$119

Soper's Hole: Cane Garden Bay Beach Break

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

Jost Van Dyke, Catamaran Cruise & Swim to Norman Island

Time
7:30 PM
Duration
Invalid Duration
Activity Level
Moderate-Strenuous
Price
$259

Tortola, Snorkel Adventure at Peter Island

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$149

Tortola, Tortola Jeep & Beach Tour

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

4
FEB 02, 2027
Jost Van Dyke, Great Harbour
ARRIVE
12:00 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
FEB 03, 2027
Virgin Gorda / Prickly Pear, British Virgin Islands
ARRIVE
8:00 AM
DEPART
10:00 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: Highlights & Bath Tour

Time
8:00 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$89

Virgin Gorda: Snorkel Adventure

Time
8:30 AM
Duration
2.75 Hours
Activity Level
Moderate-Strenuous
Price
$269
6
FEB 04, 2027
Gustavia
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
9

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

Time
8:30 AM
Duration
6 Hours
Activity Level
Easy-Moderate
Price
$349

Gustavia, Concierge Collection: Scuba Dive 1 Tank

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

Gustavia, Concierge Collection: Savor St Barts

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

Gustavia, Concierge Collection: Jet Ski

Time
8:30 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$509

St. Barts: Intimate Island Tour

Time
8:30 AM
Duration
1 Hours
Activity Level
Easy
Price
$139

St Barts, Concierge Collection: St. Barthelemy Beach Day

Time
8:30 AM
Duration
6 Hours
Activity Level
Easy-Moderate
Price
$519

Gustavia, Concierge Collection: Scuba Dive 2 Tank

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

St. Barts, Concierge Collection: Sunset Cruise

Time
8:30 AM
Duration
1.5 Hours
Activity Level
Easy-Moderate
Price
$199

St. Barts: Sailing Catamaran Adventure

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$299
7
FEB 05, 2027
Falmouth Harbour
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
9

It's said that Antigua has 365 beaches - one for every day of the year. See how many you can discover as our stay in port stretches into the evening to accommodate them all. Watch the stars come out as darkness falls and imagine how residents of Andromeda must envy you.

Falmouth Harbor, Chocolate and Rum Making

Time
8:30 AM
Duration
3.25 Hours
Activity Level
Easy-Moderate
Price
$209

Falmouth Harbour , Concierge Collection, Tuk Tuk Rainforest and Beach

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Easy
Price
$379

Falmouth Harbour, Open Course Canopy Zipline

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

Falmouth Harbour, Swim with the Stingrays

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$119

Falmouth Harbour, Spectacular Antigua Island Tour

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$99

Falmouth Harbour, Presidents Tour

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$129

Falmouth Harbour, Concierge Collection, Jet Ski Adventure

Time
8:30 AM
Duration
1.75 Hours
Activity Level
Moderate-Strenuous
Price
$379

Falmouth Harbour, Nelsons Dockyard Walking Tour & Boat around English Harbour

Time
8:30 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$79

Falmouth Harbour, Antigua Beach Escape *

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$89

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