Windstar 22 Nights Transatlantic

Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing

Wind Surf • Embarkation: St Maarten (Philipsburg)

Voyage Overview

Embark Date 12-Mar-2028
Disembark Date 03-Apr-2028
Duration 22 Nights
Vessel Wind Surf

Day-by-Day Itinerary

Day 1: PHILIPSBURG, ST MAARTEN

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 2: ST JOHNS, ANTIGUA

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.

Day 3: GUSTAVIA, ST BARTHELEMY

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: SOPERS HOLE, TORTOLA, BVI

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

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

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 7: VIRGIN GORDA/PRICKLY PEAR, BVI

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

Day 8: ROAD BAY, ANGUILLA

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 9: PHILIPSBURG, ST MAARTEN

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 10: SEAD

SEAD

Day 11: SEAD

SEAD

Day 12: SEAD

SEAD

Day 13: SEAD

SEAD

Day 14: SEAD

SEAD

Day 15: SEAD

SEAD

Day 16: SEAD

SEAD

Day 17: SEAD

SEAD

Day 18: SEAD

SEAD

Day 19: SEAD

SEAD

Day 20: PORTO SANTO, MADEIRA

PORTO SANTO, MADEIRA

Day 21: FUNCHAL, MADEIRA

Considered one of Portugal's main tourist attractions and home of world-famous footballer Cristiano Ronaldo, Funchal is known for its style and beauty.  Visit Cabo Girao, the highest sea cliff in Europe or take a trip to the Pica da Torre for an incredible view of Camara de Lobos, a delightful fishing village. With a long history of Madeira winemaking, there'll be time here for a little wine tasting, a meal at one of the many 5-star restaurants, sightseeing to 15th century Cathedral of Our Lady of the Assumption, shopping the bargains to be found here, or experiencing the vibrant night life.

Day 22: SEAD

SEAD

Day 23: SEAD

SEAD

Day 24: LISBON

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.

About Wind Surf

Wind Surf
  • Cruise Line: Windstar
  • Guest Capacity: 2 guests
  • Vessel Type: Ocean Liner / Mega-Cruise Ship
  • IMO Registration: 8700785
Starting From
$4,388
per person / based on double occupancy
Category Estimates
Inside Cabin: Call
Oceanview Cabin: $4,388
Private Balcony: Call
Luxury Suite: $6,478
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