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

Nov 5, 2027 — Nov 28, 2027

Starting from

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LISBON → PHILIPSBURG, ST. MAARTEN

23 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

Map routes may vary by sailing. Actual itineraries are listed below.
1
NOV 05, 2027
Lisbon
EMBARK
1:00 PM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

2
NOV 06, 2027
AT SEA
3
NOV 07, 2027
AT SEA
4
NOV 08, 2027
Funchal
ARRIVE
8:00 AM
DEPART
3:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

5
NOV 09, 2027
AT SEA
6
NOV 10, 2027
AT SEA
7
NOV 11, 2027
AT SEA
8
NOV 12, 2027
AT SEA
9
NOV 13, 2027
AT SEA
10
NOV 14, 2027
AT SEA
11
NOV 15, 2027
AT SEA
12
NOV 16, 2027
AT SEA
13
NOV 17, 2027
AT SEA
14
NOV 18, 2027
AT SEA
15
NOV 19, 2027
Jost Van Dyke, Great Harbour
ARRIVE
8:00 AM
DEPART
6:00 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.

16
NOV 20, 2027
Philipsburg, St. Maarten
ARRIVE
6:00 AM
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.

17
NOV 21, 2027
Gustavia
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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.

18
NOV 22, 2027
St. John's
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

19
NOV 23, 2027
Deshaies
ARRIVE
7:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
0

Situated near the Grand Anse beach, Deshaies has the deepest bay of all the Caribbean coasts with the best natural protection which made it a shelter for pirates of days gone by and is said to still be housing treasures on the Island. Grand Anse beach is one of the most beautiful of the islands with its over half a mile of fine golden sand and coconut palms.

20
NOV 24, 2027
Road Bay
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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.

21
NOV 25, 2027
Soper's Hole
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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. 

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.

22
NOV 26, 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.

23
NOV 27, 2027
Virgin Gorda / Prickly Pear, British Virgin Islands
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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

24
NOV 28, 2027
Philipsburg, St. Maarten
ARRIVE
6:00 AM
DISEMBARK
7:00 AM
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.

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 242 sq ft
Max. Occupancy 2 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 sq ft
Max. Occupancy 2 Passengers
Amenities

Available Dates

No other dates are available.

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

LISBON → PHILIPSBURG, ST. MAARTEN

23 Nights on Wind Surf

Nov 5, 2027 — Nov 28, 2027

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.

1
NOV 05, 2027
Lisbon
EMBARK
1:00 PM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

2
NOV 06, 2027
AT SEA
3
NOV 07, 2027
AT SEA
4
NOV 08, 2027
Funchal
ARRIVE
8:00 AM
DEPART
3:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

5
NOV 09, 2027
AT SEA
6
NOV 10, 2027
AT SEA
7
NOV 11, 2027
AT SEA
8
NOV 12, 2027
AT SEA
9
NOV 13, 2027
AT SEA
10
NOV 14, 2027
AT SEA
11
NOV 15, 2027
AT SEA
12
NOV 16, 2027
AT SEA
13
NOV 17, 2027
AT SEA
14
NOV 18, 2027
AT SEA
15
NOV 19, 2027
Jost Van Dyke, Great Harbour
ARRIVE
8:00 AM
DEPART
6:00 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.

16
NOV 20, 2027
Philipsburg, St. Maarten
ARRIVE
6:00 AM
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.

17
NOV 21, 2027
Gustavia
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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.

18
NOV 22, 2027
St. John's
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

19
NOV 23, 2027
Deshaies
ARRIVE
7:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
0

Situated near the Grand Anse beach, Deshaies has the deepest bay of all the Caribbean coasts with the best natural protection which made it a shelter for pirates of days gone by and is said to still be housing treasures on the Island. Grand Anse beach is one of the most beautiful of the islands with its over half a mile of fine golden sand and coconut palms.

20
NOV 24, 2027
Road Bay
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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.

21
NOV 25, 2027
Soper's Hole
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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. 

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.

22
NOV 26, 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.

23
NOV 27, 2027
Virgin Gorda / Prickly Pear, British Virgin Islands
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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

24
NOV 28, 2027
Philipsburg, St. Maarten
ARRIVE
6:00 AM
DISEMBARK
7:00 AM
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.