• Copied

Ocean Crossing

Nov 5, 2027 — Nov 20, 2027

Starting from

Complimentary All-In Package

Free Laundry for Collectors:

Reduced Deposit
Request a quote Other Available Dates
See more routes around Ocean Crossing

LISBON → PHILIPSBURG, ST. MAARTEN

15 Nights on Wind Surf

Indulge yourself in leisurely, unscheduled days where time suspends in the magic of the sea. Sleep late. Dine early. Establish your own rhythm in sync with the waves and the arc of the sun and moon overhead. Watch the constellations drift and let your mind shake off all the cobwebs of shore. Feast on the impossible beauty of liquid sunsets, and let your soul dance with the dolphins in the spray off the bow.

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
7

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.

Available Excursions

Funchal

Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate

Add during booking

$75

Funchal

Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate

Add during booking

$145

Funchal

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate

Add during booking

$95

Funchal

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Easy-Moderate

Add during booking

$115

Funchal

Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate

Add during booking

$119

Funchal

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate

Add during booking

$85

Funchal

Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous

Add during booking

$109

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
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
See More Voyages

Staterooms

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 495 sq ft
Max. Occupancy 3 Passengers
Amenities

Room Size 242 sq ft
Max. Occupancy 2 Passengers
Amenities

Room Size sq ft
Max. Occupancy 2 Passengers
Amenities

Available Dates

Date Yacht
Starting from
Actions
Nov 10 (Tue) – Nov 24 (Tue), 2026November 10 (Tue) – November 24 (Tue), 2026Wind Star
Nov 12 (Thu) – Nov 27 (Fri), 2026November 12 (Thu) – November 27 (Fri), 2026Star Legend
Feb 8 (Mon) – Mar 1 (Mon), 2027February 8 (Mon) – March 1 (Mon), 2027Wind Star
Mar 2 (Tue) – Mar 17 (Wed), 2027March 2 (Tue) – March 17 (Wed), 2027Star Legend
Mar 27 (Sat) – Apr 11 (Sun), 2027March 27 (Sat) – April 11 (Sun), 2027Wind Surf
Mar 30 (Tue) – Apr 15 (Thu), 2027March 30 (Tue) – April 15 (Thu), 2027Star Pride
May 20 (Thu) – May 31 (Mon), 2027May 20 (Thu) – May 31 (Mon), 2027Star Seeker
Sep 1 (Wed) – Sep 14 (Tue), 2027September 1 (Wed) – September 14 (Tue), 2027Star Seeker
Dec 6 (Mon) – Dec 20 (Mon), 2027December 6 (Mon) – December 20 (Mon), 2027Star Legend
Jan 6 (Thu) – Jan 10 (Mon), 2028January 6 (Thu) – January 10 (Mon), 2028Star Breeze
Jan 24 (Mon) – Jan 28 (Fri), 2028January 24 (Mon) – January 28 (Fri), 2028Star Breeze
Mar 19 (Sun) – Apr 3 (Mon), 2028March 19 (Sun) – April 3 (Mon), 2028Wind Surf
Apr 3 (Mon) – Apr 19 (Wed), 2028April 3 (Mon) – April 19 (Wed), 2028Star Pride
Aug 30 (Wed) – Sep 12 (Tue), 2028August 30 (Wed) – September 12 (Tue), 2028Star Seeker
Nov 5 (Sun) – Nov 19 (Sun), 2028November 5 (Sun) – November 19 (Sun), 2028Wind Surf
May 25 (Fri) – Jun 5 (Tue), 2029May 25 (Fri) – June 5 (Tue), 2029Star Seeker

Ocean Crossing

LISBON → PHILIPSBURG, ST. MAARTEN

15 Nights on Wind Surf

Nov 5, 2027 — Nov 20, 2027

Indulge yourself in leisurely, unscheduled days where time suspends in the magic of the sea. Sleep late. Dine early. Establish your own rhythm in sync with the waves and the arc of the sun and moon overhead. Watch the constellations drift and let your mind shake off all the cobwebs of shore. Feast on the impossible beauty of liquid sunsets, and let your soul dance with the dolphins in the spray off the bow.

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
7

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.

Funchal, Cabo Girao & Ribeira Brava *

Spend a relaxing day exploring the small towns and picturesque countryside of Madeira . Begin with a trip to the Pico da Torre viewpoint for an incredible view of Camara de Lobos, a quintessential fishing village characterized by brightly painted boats in the harbor. Taste the famous poncha , a delightful local drink made of rum and honey on your way to Cabo Girao , the highest sea cliff in Europe and the second highest in the world. It features a skywalk with an amazing glass floor balcony (1,932 feet up). Enjoy a brief photo opportunity here to capture the magnificent sights before heading to Ribeira Brava, a historic town filled with quaint shops, wonderful cafés, and endless island charm. Please note : Wear comfortable walking shoes. Visibility from all scenic outlooks is dependent upon the weather and therefore cannot be guaranteed. Itinerary may be operated in reverse order but all sites will be covered. Guests prone to motion sickness should take precautions. Guests must be of legal age to consume alcohol.

Port
Funchal
Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate

Add during booking

$75 USD

Funchal, Forest 4X4 with Wine Tasting

Leave the pier behind and set out on an off-road journey through Madeira’s wild and dramatic landscapes. Begin with a scenic drive toward the lush Serra de Água valley, followed by a stop at the Encumeada Pass—an impressive viewpoint perched 1,000 meters above sea level. From here, enjoy panoramic views stretching from the island’s northern to southern coasts, framed by the green valleys of Ribeira Brava and São Vicente.

Continue your adventure through the island’s UNESCO-listed Laurisilva Forest, one of the world’s few remaining laurel forests and a sanctuary of rare plants and bird species. Experience the thrill of open-roof Land Rover travel as you navigate winding trails surrounded by dense vegetation and mountain peaks.

Your journey concludes with a visit to Quinta do Barbusano, a picturesque vineyard nestled among terraced hills. Savor a tasting of Madeira’s local red, white, and rosé wines paired with regional snacks, while taking in peaceful views of the surrounding countryside.

Relax on the scenic return drive to Funchal, carrying with you memories of Madeira’s natural beauty, cultural heritage, and adventurous spirit.

Tour sequence may vary depending on local conditions.

Port
Funchal
Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate

Add during booking

$145 USD

Funchal, Walking Tour with Wine Tasting *

Start this walking tour with a visit to Parque de Santa Catarina, one of the most important parks of the city. Continue towards Avenida Arriaga, one of the busiest avenues in the city and taste the famous Madeira wine accompanied by local snacks in a wine cellar located there. The tour will continue towards the Cathedral (outside visit), passing by the market area and finishing at the old town. Please note: Wear comfortable walking shoes and weather appropriate clothing. Must be of legal age to consume alcohol. This tour is not suitable for people with mobility issues or a wheelchair.

Port
Funchal
Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate

Add during booking

$95 USD

Funchal, Quinta House with Tea and Gardens

Step back in time and discover an 18th century Madeiran Quinta where you'll enjoy a tea service and stroll through the Quinta's stunning botanical garden. Your adventure begins with incredible views of Funchal from the Pico dos Barcelos Viewpoint. Then, travel to an authentic 18th century Quinta, a beautiful traditional estate with sprawling gardens. Sit down to an exquisite tea service paired with scones and homemade jams, a slice of cake and sandwiches. Then, stroll the estate's lush gardens. Learn about the 500 species of plants and flowers cultivated at the Quinta Jardins do Lago. See rare species of old trees and delicate flowers while wandering through the aromatic blooms. After your walk through the gardens, board your bus for a short drive back to the pier. Please note : Various scones, pasties, sandwiches, tea, and a glass of sparkling wine are included in the tea service.

Port
Funchal
Time
8:30 AM
Duration
2.5 Hours
Activity Level
Easy-Moderate

Add during booking

$115 USD

Funchal, Panoramic Drive & Tuk Tuk Stroll *

This tour is a new and exciting way to discover the charms and beauties of Funchal. By using two means of transportation, you will be able to admire fantastic views of Funchal by visiting the most important viewpoints of the city with a minivan. Leaving the pier by minivan or motor coach you will proceed towards Pico dos Barcelos , where you can see distant Funchal and the surrounding villages scattered over the green slopes. Continue towards Cabo Girão , the highest sea cliff in Europe and the second highest in the world. Soaring 1,900 feet, its etched face tells the tale of its volcanic origins. From this impressive promontory, you will have breathtaking views along the island's southern coast. Passing by Estreito de Camara de Lobos , known for its vineyards, you will reach Camara de Lobos , a well-known fishing village. There, you will see its lovely, quaint setting of red-tile-roofed houses clustered on the rocky point and the brightly painted fishing boats anchored in the harbor.The second part of this tour will be by Tuk Tuk , built upon ecological and innovative criteria, directly inspired by the Italian Dolce Vita glamorous style and the iconic 3-wheeled Ape Calessino. It offers those who visit Funchal an exclusive perspective along with an intimate approach to our history and culture. Please note : Wear comfortable walking shoes. Order of sights visited my vary. Tuk Tuk suspension is not recommended for people with any sort of back problems. This tour is not suitable for guests with limited mobility or in a wheelchair. Visibility from all scenic outlooks is dependent upon the weather and therefore cannot be guaranteed.

Port
Funchal
Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate

Add during booking

$119 USD

Funchal, Tobogan Ride & Pico dos Barcelos *

Get ready to fall in love with the lush landscape of Madeira. A 25-minute motor coach drive will take you to Monte situated high in the hills. You will indulge in the fun local past-time of toboggan riding as you take a ride in a wicker chariot through the streets! Next stop will be Pico dos Barcelos from where you can admire breathtaking views over the island of Madeira before you return to the ship. Please note : Tour order may vary but all sites will be covered. This tour is not available for guests in wheelchairs and others with mobility challenges .The toboggan is closed on Sundays and Holy Friday.

Port
Funchal
Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate

Add during booking

$85 USD

Funchal, City Highlights and Cable Car *

Explore the adventurous city of Funchal, capital of Madeira and Portugal's largest town. You will board your motor coach for the short 10-minute drive to the center of town. Walk through the vibrant local market, explore the Old Town where the first settlement of the city was born. This old part of the city is characterized by its narrow sidewalk streets and façades of old houses and is considered a historical area of great architectural and patrimonial value. You will climb to Monte by cable car. This village located at an elevation of 1,772 feet high was the last residence of Carlos I of Austria, who is buried in the Church of Our Lady of Monte. Finally you will have a 25-minute drive to visit the Old Blandy Wine Lodge in the center of Funchal which acts as an excellent show place for many the finest wines of Madeira. You will taste four 5-years-old wines accompanied by some delicious snacks. Please note: Wear comfortable walking shoes. Guests must be legal age to consume alcohol. The market and the Old Blandy Lodge are closed Saturday afternoons, Sundays and public holidays all day. A visit to the church of Monte is not included and is closed on Sundays and public holidays. Should guests wish to visit it, it is free of charge and they have to be able to climb 171 steps up and 68 steps down. Tour order may vary but all sites will be covered. Shops are closed during public holidays. This tour is not available for guests in wheelchairs and others with mobility challenges.

Port
Funchal
Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous

Add during booking

$109 USD

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
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.