Ocean Crossing

Mar 27, 2027 — Apr 11, 2027

Starting from

DATA ART TEST PROMO

Free Laundry for Collectors:

See more routes around Ocean Crossing

PHILIPSBURG, ST. MAARTEN → LISBON

15 Nights on Wind Surf

Step aboard an extraordinary wellness cruise with Debbie Dixon, renowned author, life coach, and wellness expert. This transformative journey is designed to nurture your mind, body, and spirit. Offering an immersive experience that combines daily yoga, meditation, and breathwork sessions to help restore balance and inner peace, adding the space to reconnect with yourself, others, and your dreams. Along the way, you’ll indulge in gourmet meals that are both nourishing and indulgent, enjoy decadent spa treatments, and unwind at a specialized Elixir Bar Pop-Up offering mind-body elixirs that rejuvenate and restore. Every moment, from sunrise to sunset, is yours to enjoy, whether you choose to spend it reflecting in solitude or connecting with new friends. Simply step on board, and we’ll take it from there – your dream getaway awaits.

Popular Highlights

Map routes may vary by sailing. Actual itineraries are listed below.
1
MAR 27, 2027
Philipsburg, St. Maarten
EMBARK
1:00 PM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
4

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 Airport

Time
7:30 AM
Duration
4.5 Hours
Activity Level
Easy
Price
$99

St. Maarten, Post Island Tour with Transfer to Hotel

Time
7:30 AM
Duration
4.5 Hours
Activity Level
Easy-Moderate
Price
$99

St. Maarten: Americas Cup Sailboat Racing with Transfer to Windstar Hotel

Time
7:30 AM
Duration
2.75 Hours
Activity Level
Moderate-Strenuous
Price
$179

St. Maarten: Americas Cup Sailboat Racing with Transfer to Airport

Time
7:30 AM
Duration
2.75 Hours
Activity Level
Moderate-Strenuous
Price
$179
2
MAR 28, 2027
AT SEA
3
MAR 29, 2027
AT SEA
4
MAR 30, 2027
AT SEA
5
MAR 31, 2027
AT SEA
6
APR 01, 2027
AT SEA
7
APR 02, 2027
AT SEA
8
APR 03, 2027
AT SEA
9
APR 04, 2027
AT SEA
10
APR 05, 2027
AT SEA
11
APR 06, 2027
AT SEA
12
APR 07, 2027
Funchal
ARRIVE
8:00 AM
DEPART
11:59 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.

13
APR 08, 2027
PORTO SANTO, MADEIRA
ARRIVE
8:00 AM
DEPART
1:00 PM
MARINA
NO
SHORE EXCURSIONS
2

PORTO SANTO, MADEIRA

Porto Santo, Hike Pico do Castelo

Time
9:00 AM
Duration
3 Hours
Activity Level
Strenuous
Price
$79

Porto Santo, Island Horseback Riding

Time
9:30 AM
Duration
1.5 Hours
Activity Level
Moderate
Price
$145
14
APR 09, 2027
AT SEA
15
APR 10, 2027
AT SEA
16
APR 11, 2027
Lisbon
ARRIVE
8:00 AM
DISEMBARK
9:00 AM
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.

Meet Debbie Dixon

Meet Debbie Dixon

Debbie Dixon is the author of The Path to Freedom: Your Guide to Living the Life of Your Dreams and What if...You could have it all?, a yoga teacher, life coach, and inspirational speaker who leads transformational retreats worldwide. With a focus on empowering others, Debbie combines yoga, meditation, and coaching to help people reconnect with their highest potential and create lives filled with freedom, joy, and purpose. Her mission is to ignite spiritual health in others and support them in living vibrant, authentic lives.

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 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
Mar 19 (Sun) – Apr 3 (Mon), 2028March 19 (Sun) – April 3 (Mon), 2028Wind Surf

Ocean Crossing

PHILIPSBURG, ST. MAARTEN → LISBON

15 Nights on Wind Surf

Mar 27, 2027 — Apr 11, 2027

Step aboard an extraordinary wellness cruise with Debbie Dixon, renowned author, life coach, and wellness expert. This transformative journey is designed to nurture your mind, body, and spirit. Offering an immersive experience that combines daily yoga, meditation, and breathwork sessions to help restore balance and inner peace, adding the space to reconnect with yourself, others, and your dreams. Along the way, you’ll indulge in gourmet meals that are both nourishing and indulgent, enjoy decadent spa treatments, and unwind at a specialized Elixir Bar Pop-Up offering mind-body elixirs that rejuvenate and restore. Every moment, from sunrise to sunset, is yours to enjoy, whether you choose to spend it reflecting in solitude or connecting with new friends. Simply step on board, and we’ll take it from there – your dream getaway awaits.

1
MAR 27, 2027
Philipsburg, St. Maarten
EMBARK
1:00 PM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
4

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 Airport

The best way to experience 80 different cultures in one day is to take the "Saint-Martin/Saint-Maarten Island Tour. " You will depart from Philipsburg and head to Oyster Pond, a charming little locale with a picturesque marina on the French side of the island. From there, following Coralita Road, along the coast, you will stop at a lookout point from where you can see St. Barth and Tintamare Island. You will continue past famous Orient Beach, well known for its clothing optional beach, past Grand Case, the Culinary Capital of the Caribbean, on your way to Marigot, capitol of the French side. Marigot is best known for its seaside, open-air market , where you can find truly charming souvenirs of your Caribbean vacation. If you are "shopped out", try one of the French cafés right next door, for a café au lait with a croissant. Upon leaving Marigot, you will make one more photo stop on Cay Hill, from where you have a wonderful view over Simpson Bay Lagoon. Our last stop will be Philipsburg, capital of the Dutch side, best known for its jewelry-, electronics-, and high end clothing stores. On the Boardwalk you will find quaint restaurants for a quick bite to eat before your flight and an excellent photo opportunity of your yacht lying in Philipsburg Harbor. From there, you will be taken straight to the airport. Please note : Wear comfortable walking shoes.
Port
Philipsburg, St. Maarten
Time
7:30 AM
Duration
4.5 Hours
Activity Level
Easy

Add during booking

$99 USD

St. Maarten, Post Island Tour with Transfer to Hotel

The best way to experience 80 different cultures in one day is to take the "Saint-Martin/Saint-Maarten Island Tour." You will depart from Philipsburg and head to Oyster Pond, a charming little locale with a picturesque marina on the French side of the island. From there, following Coralita Road, along the coast, you will stop at a l ookout point from where you can see St. Barth and Tintamare Island . You will continue past famous Orient Beach, well known for its clothing optional beach, past Grand Case, the Culinary Capital of the Caribbean, on your way to Marigot, capitol of the French side. Marigot is best known for its seaside, open-air market, where you can find truly charming souvenirs of your Caribbean vacation. If you are "shopped out", try one of the French cafés right next door, for a café au lait with a croissant. Upon leaving Marigot, you will make one more photo stop on Cay Hill, from where you have a wonderful view over Simpson Bay Lagoon . Our last stop will be Philipsburg, capital of the Dutch side, best known for its jewelry-, electronics-, and high end clothing stores. On the Boardwalk you will find quaint restaurants for a quick bite to eat before your flight and an excellent photo opportunity of your yacht lying in Philipsburg Harbor. From there, you will be taken straight to your Windstar Hotel Please note : Wear comfortable walking shoes.
Port
Philipsburg, St. Maarten
Time
7:30 AM
Duration
4.5 Hours
Activity Level
Easy-Moderate

Add during booking

$99 USD

St. Maarten: Americas Cup Sailboat Racing with Transfer to Windstar Hotel

Experience the thrill of racing multi-million dollar America's Cup Race sailboat s in the warm blue waters and brisk trade winds of St. Maarten. Previous sailing experience is not necessary for this excursion, which is one of the highest rated in the Caribbean. You will depart directly from your yacht in Marigot to Philipsburg, where after a briefing you will take a 10-minute tender ride out to your allocated sailboat. Either Dennis Conner's America's Cup winning Stars & Stripes, Canada II, or True North are yours for this once-in-a-lifetime adventure . The expert crew will show you exactly what to do if you want to take a "crew member's" position. Then it's off to the racecourse - grind a winch - trim a sail - punch a stopwatch, or just sit back, relax and enjoy the included refreshments. After the race enjoy a victory rum punch party and browse through the museum souvenir boutique before your transfer to your Windstar hotel. Please note : Wear suitable footwear for the sailboat. This event is weather/wind dependent.
Port
Philipsburg, St. Maarten
Time
7:30 AM
Duration
2.75 Hours
Activity Level
Moderate-Strenuous

Add during booking

$179 USD

St. Maarten: Americas Cup Sailboat Racing with Transfer to Airport

Experience the thrill of racing multi-million dollar America's Cup Race sailboats in the warm blue waters and brisk trade winds of St. Maarten. Previous sailing experience is not necessary for this excursion, which is one of the highest rated in the Caribbean. You will be tendered out from the 12 Metre Clubhouse dock at Dock Maarten, where after a briefing you will take a 10-minute tender ride out to your allocated sailboat. Either Dennis Conner's America's Cup winning Stars & Stripes , Canada II, or True North IV are yours for this once-in-a-lifetime adventure. The expert crew will show you exactly what to do if you want to take a "crew member's" position. Then it's off to the racecourse - grind a winch - trim a sail - punch a stopwatch, or just sit back, relax and enjoy the included refreshments. After the race enjoy a victory rum punch party at the 12 Metre Clubhouse before your transfer to the airport. Please note : Wear soft-soled suitable footwear for the sailboat. This event is weather/wind dependent. Your flight must depart at 2:30pm or later to book this tour.
Port
Philipsburg, St. Maarten
Time
7:30 AM
Duration
2.75 Hours
Activity Level
Moderate-Strenuous

Add during booking

$179 USD

2
MAR 28, 2027
AT SEA
3
MAR 29, 2027
AT SEA
4
MAR 30, 2027
AT SEA
5
MAR 31, 2027
AT SEA
6
APR 01, 2027
AT SEA
7
APR 02, 2027
AT SEA
8
APR 03, 2027
AT SEA
9
APR 04, 2027
AT SEA
10
APR 05, 2027
AT SEA
11
APR 06, 2027
AT SEA
12
APR 07, 2027
Funchal
ARRIVE
8:00 AM
DEPART
11:59 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.

13
APR 08, 2027
PORTO SANTO, MADEIRA
ARRIVE
8:00 AM
DEPART
1:00 PM
MARINA
NO
SHORE EXCURSIONS
2

PORTO SANTO, MADEIRA

Porto Santo, Hike Pico do Castelo

Begin with a short transfer from the pier to the starting point of your hike at Pico do Castelo, one of Porto Santo’s most iconic peaks. The trail winds through reforested areas of pine and native vegetation, a striking contrast to the island’s naturally dry landscape. As you climb toward the 437-meter summit, enjoy sweeping views over the island’s coastline and inland valleys, with several scenic points perfect for photography along the way. Upon reaching the top, take in panoramic vistas of the Atlantic Ocean and surrounding terrain before descending along the same path. Following your hike, a short transfer will take you to Campo de Cima for a brief refreshment stop before returning to the pier. Tour itinerary may vary depending on local conditions.
Port
PORTO SANTO, MADEIRA
Time
9:00 AM
Duration
3 Hours
Activity Level
Strenuous

Add during booking

$79 USD

Porto Santo, Island Horseback Riding

Experience the natural beauty of Porto Santo from a new perspective on a guided horseback adventure through scenic island trails. After a short transfer to the Porto Santo Equestrian Center, you’ll be greeted by professional guides and matched with a well-trained horse suited to your experience level. Following a safety briefing, set out on a relaxing ride across volcanic landscapes, sandy paths, and open countryside, taking in peaceful views of the island’s hills and coastline. This slow-paced excursion offers an enjoyable and accessible way to connect with nature, ideal for both beginners and experienced riders alike. Please note: The tour includes horses and riding gear, a safety briefing, and an escort from the Equestrian Center; no prior riding experience is required.
Port
PORTO SANTO, MADEIRA
Time
9:30 AM
Duration
1.5 Hours
Activity Level
Moderate

Add during booking

$145 USD

14
APR 09, 2027
AT SEA
15
APR 10, 2027
AT SEA
16
APR 11, 2027
Lisbon
ARRIVE
8:00 AM
DISEMBARK
9:00 AM
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.