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Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing
Dec 5, 2026 — Dec 26, 2026
Starting from
DATA ART TEST PROMO
Free Laundry for Collectors:
LISBON → PHILIPSBURG, ST. MAARTEN
21 Nights on Wind Surf
Cruise from Portugal across the Atlantic to white Caribbean beaches, vibrant tropical fish and savory West Indies cuisine during this 19-day transatlantic crossing. Relax, unwind and refocus with back-to-back spa days throughout your ocean crossing and dine on award-winning meals. Relive history while sailing aboard a former America's Cup competition sailboat or cook up delicious French meals with a certified chef in Philipsburg, St. Maarten. Roll out in offroad vehicles for an unrushed day of snorkeling on Tortola's secluded beaches. Swim and frolic with dolphins near Jost Van Dyke in the British Virgin Islands. Snorkel above colorful coral and dizzying schools of curious fish on Virgin Gorda in the British Virgin Islands. Glide over a sunken ship in a semi-submersible and take in a glowing Caribbean sunset during a catamaran cruise off Gustavia's tropical beaches on St. Barts.






Popular Highlights
Find time for your favorite indulgences – from a relaxing massage to breakfast in your room during your days crossing the Atlantic.
A late night stay in Gustavia lets you really get time to get the flavor of this distinct place.
Stroll Pusser’s Landing, the charming boardwalk of Soper’s Hole on your way to a secluded beach.
See Virgin Gorda’s lovely beaches like The Baths, Spring Bay and Savannah Bay.
Overnight in Jost Van Dyke with time to snorkel among the sponges and angelfish in Sandy Spit.
Find time for your favorite indulgences – from a relaxing massage to breakfast in your room during your days crossing the Atlantic.
Pack light with complimentary daily laundry service.

The rhythm of Lisbon invites you to join its captivating dance. This splendid capital city on the banks of the Rio Teja offers a warm welcome and an unparalleled blend of architectural styles. Elegant outdoor cafés line the cobbled sidewalks. Turn-of-the-century funiculars climb the scenic hills. Find the UNESCO sites of the Tower of Belem and the Monastery of the Hieronymites. And, everywhere, the city engages you with its easy style and remarkable charm.
Lisbon, Concierge Collection: Half Day Private Car & Guide *
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Lisbon, Majestic Sintras & Cascais With Transfer to Windstar Hotel *

Lisbon by Tuk Tuk *

Lisbon, Highlights with Transfer to Airport *

Lisbon, Concierge Collection: Half Day Private Van & Guide *


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
St.Johns, Concierge Collection: Sail Snorkel and Beach
St. Johns, Segway Fort Conqueror
St. Johns: Presidents Tour
St Johns, Swim with the Stingrays
St Johns, Concierge Collection, Jet Ski Adventure
St Johns, Chocolate and Rum Making
St. Johns, Open Course Canopy Challenge
St. Johns, Beach Escape

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.
St. Maarten, Post Island Tour with Transfer to Hotel
St. Maarten: Americas Cup Sailboat Racing with Transfer to Windstar Hotel
St. Maarten: Americas Cup Sailboat Racing with Transfer to Airport
St. Maarten, Post Island Tour with Transfer to Airport

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
St Barts, Concierge Collection: St. Barthelemy Beach Day
St. Barts, Concierge Collection: Sunset Cruise
St. Barts: Intimate Island Tour
Gustavia, Concierge Collection: Jet Ski
St. Barts: Sailing Catamaran Adventure

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 Harbour, Spectacular Antigua Island Tour
Falmouth Harbour, Open Course Canopy Zipline
Falmouth Harbour, Presidents Tour
Falmouth Harbour, Concierge Collection, Jet Ski Adventure
Falmouth Harbour, Antigua Beach Escape *

Falmouth Harbour, Nelsons Dockyard Walking Tour & Boat around English Harbour
Falmouth Harbour, Make Your Own Rum

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
Road Bay, Shoal Bay Beach Transfer
Road Bay, Island Exploration by Moke
Concierge Collection: Road Bay, Snorkel Adventure by Speedboat
Road Bay, Concierge Collection: Relaxing Day at Savi with Lunch
Road Bay, Iconic Island Highlights with Salt Tasting and Beach Time

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
Tortola, Snorkel Adventure at Peter Island
Soper's Hole: Cane Garden Bay Beach Break
Tortola, Scenic Drive & Beach
Jost Van Dyke, Catamaran Cruise & Swim to Norman Island

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.

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
Virgin Gorda: Snorkel Adventure

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.
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