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Beach Fun & Sun: A Remote Caribbean Getaway
Jan 2, 2027 — Jan 9, 2027
Starting from
Complimentary All-In Package
Reduced Deposit
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.





Popular Highlights
Relax on the sands of Norman Island, inspiration for Robert Louis Stevenson’s Treasure Island.
Find your perfect spot on the beach while you sample some of the most delicious rum punch found in the Caribbean at Road Bay.
Stroll Pusser’s Landing, the charming boardwalk of Soper’s Hole, on your way to a secluded beach.
Overnight in Virgin Gorda with plenty of time to see lovely beaches like The Baths, Spring Bay and Savannah Bay.
Snorkel among the sea sponges and angelfish in Jost Van Dyke’s Sandy Spit.
Discover the culinary delights of both the Signature Beach Party and the Signature Onboard Barbecue.

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 Excursions
Philipsburg, St. Maarten
Time
8:30 AMDuration
4 HoursActivity Level
EasyAdd during booking
$639
Philipsburg, St. Maarten
Time
8:30 AMDuration
2.75 HoursActivity Level
Moderate-StrenuousAdd during booking
$189
Philipsburg, St. Maarten
Time
7:30 AMDuration
4.5 HoursActivity Level
EasyAdd during booking
$99
Philipsburg, St. Maarten
Time
8:30 AMDuration
4.5 HoursActivity Level
Easy-ModerateAdd during booking
$99
Philipsburg, St. Maarten
Time
11:30 AMDuration
2.75 HoursActivity Level
Moderate-StrenuousAdd during booking
$189

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.
Available Excursions
Falmouth Harbour
Time
8:30 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$129
Falmouth Harbour
Time
10:30 AMDuration
3 HoursActivity Level
Easy-ModerateAdd during booking
$89
Falmouth Harbour
Time
9:30 AMDuration
4 HoursActivity Level
EasyAdd during booking
$99
Falmouth Harbour
Time
9:30 AMDuration
4 HoursActivity Level
StrenuousAdd during booking
$149
Falmouth Harbour
Time
8:45 AMDuration
2 HoursActivity Level
Easy-ModerateAdd during booking
$149

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.
Available Excursions
Road Bay
Time
9:00 AMDuration
2.5 HoursActivity Level
StrenuousAdd during booking
$599
Road Bay
Time
8:30 AMDuration
4 HoursActivity Level
EasyAdd during booking
$139
Road Bay
Time
8:30 AMDuration
3 HoursActivity Level
Moderate-StrenuousAdd during booking
$339
Road Bay
Time
8:30 AMDuration
4 HoursActivity Level
EasyAdd during booking
$219

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.
Available Excursions
Soper's Hole
Time
8:30 AMDuration
4.5 HoursActivity Level
EasyAdd during booking
$119
Soper's Hole
Time
8:30 AMDuration
3 HoursActivity Level
Moderate-StrenuousAdd during booking
$149
Soper's Hole
Time
8:30 AMDuration
4 HoursActivity Level
ModerateAdd during booking
$199
Soper's Hole
Time
8:30 AMDuration
4 HoursActivity Level
ModerateAdd during booking
$109

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.
Available Excursions
Jost Van Dyke, Great Harbour
Time
8:30 AMDuration
4.5 HoursActivity Level
Moderate-StrenuousAdd during booking
$259

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 AMDuration
2.75 HoursActivity Level
Moderate-StrenuousAdd during booking
$299
Virgin Gorda / Prickly Pear, British Virgin Islands
Time
8:00 AMDuration
4 HoursActivity Level
StrenuousAdd during booking
$99

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.
Available Excursions
Gustavia
Dive into St. Barth’s Protected Marine Reserve and discover vibrant reefs, colorful marine life, and crystal-clear waters.
Time
8:30 AMDuration
3 HoursActivity Level
StrenuousAdd during booking
$359
Gustavia
Toast the sunset aboard a sailing catamaran, cruise Gustavia Harbor & admire mega yachts with Champagne and scenic views.
Time
5:00 PMDuration
1.5 HoursActivity Level
Easy-ModerateAdd during booking
$209
Gustavia
Dive St. Barth’s Protected Marine Reserve and discover vibrant coral reefs, tropical fish, and incredible marine life.
Time
8:30 AMDuration
4 HoursActivity Level
StrenuousAdd during booking
$499
Gustavia
Leisurely sail St. Barth’s coast to crystal-clear waters of Colombier Beach, relax in crystal waters & spot colorful marine life.
Time
8:30 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$319
Gustavia
Explore the island at your own pace with a self-drive adventure through lush countryside and scenic hidden gems.
Time
8:30 AMDuration
6 HoursActivity Level
Easy-ModerateAdd during booking
$359
Gustavia
Savor Gustavia’s French-Caribbean flavors with crêpes, Le Select, gourmet bites & Champagne as you explore the town.
Time
8:30 AMDuration
2.5 HoursActivity Level
ModerateAdd during booking
$369
Gustavia
Enjoy an exclusive island panorama tour — explore local highlights at your pace with a private driver and guide!
Time
8:30 AMDuration
1 HoursActivity Level
EasyAdd during booking
$149
Gustavia
Jet ski from Gustavia to Shell, Gouverneur & Salines beaches, then swim in the crystal-clear waters near Coco Island.
Time
8:30 AMDuration
2 HoursActivity Level
StrenuousAdd during booking
$529
Gustavia
Relax at Le Barthélemy Resort — unwind on a stunning St. Barts beach, swim, savor lunch, and enjoy luxury by the sea.
Time
8:30 AMDuration
6 HoursActivity Level
Easy-ModerateAdd during booking
$579

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.
Staterooms
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Starting from
Starting from
Starting from
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