Beach Fun & Sun: A Remote Caribbean Getaway
Bask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboa...
Cruise only — prices from Solo cruise only — from
Ports of Call & Itinerary
8-night voyage departing Philipsburg.
Printable Itinerary (PDF)Route Map
Beach Fun & Sun: A Remote Caribbean Getaway
7 ports plotted · click a marker for details
Day 1
Philipsburg , Sint Maarten (Dutch part)
Sunday, 19/12/2027
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.
Day 3
Gustavia , Saint Barthélemy
Tuesday, 21/12/2027
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.
Day 4
Road Bay , Anguilla
Wednesday, 22/12/2027
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.
Day 5
Sopers Hole, Tortola , British Virgin Islands
Thursday, 23/12/2027
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.
Day 5
Great Harbour, Jost Van Dyke , British Virgin Islands
Thursday, 23/12/2027
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.
Day 6
Great Harbour, Jost Van Dyke , British Virgin Islands
Friday, 24/12/2027
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.
Day 9
Philipsburg , Sint Maarten (Dutch part)
Monday, 27/12/2027
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.
Room Type & Prices
All prices per person based on double occupancy. Solo traveller prices — single occupancy. Contact our cruise experts for the latest availability and best fares.
Category B
188 sqft · Up to 2 guests
Category BX Deluxe
188 sqft · Up to 2 guests
Category A
188 sqft · Up to 2 guests
Category AX Deluxe
188 sqft · Up to 2 guests
Category TX Deluxe
188 sqft · Up to 2 guests
Suite
376 sqft · Up to 3 guests
Broadmoor Suite/Sea Island Suite
495 sqft · Up to 3 guests
More Departures
10 nights
Grand Japan
16/10/2026
From
£5,491
7 nights
Enchanting Greece & the Amalfi Coast
17/10/2026
From
£2,071
14 nights
Star Collector: Ancient to Avant-Garde Mediterranean
17/10/2026
From
£3,989
8 nights
Aegean Sea Odyssey via the Corinth Canal
19/10/2026
From
£3,207
16 nights
Star Collector: Aegean & Bosporus Escapades
19/10/2026
From
£6,021
70 nights
Star Collector: Grand Mediterranean and Latin America Adventure
19/10/2026
From
£18,809
Your Ship
Wind Surf
Windstar's Flagship Sailing Yacht
As part of our Wind Class, our 342-guest Wind Surf offers a sailing experience like no other — one with real working sails.