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Ocean Crossing

Nov 5, 2027 — Nov 20, 2027

Starting from

Early Booking Offer All-In Package

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LISBON → PHILIPSBURG, ST. MAARTEN

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
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
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.

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.

See Detail
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
See More Voyages

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

Date Yacht
Starting from
Actions
Sep 2 (Wed) – Sep 16 (Wed), 2026September 2 (Wed) – September 16 (Wed), 2026Star Seeker
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
Dec 5 (Sat) – Dec 19 (Sat), 2026December 5 (Sat) – December 19 (Sat), 2026Wind Surf
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
Feb 28 (Mon) – Mar 14 (Tue), 2028February 28 (Mon) – March 14 (Tue), 2028Star Legend
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
May 16 (Tue) – May 28 (Sun), 2028May 16 (Tue) – May 28 (Sun), 2028Star Seeker

Ocean Crossing

LISBON → PHILIPSBURG, ST. MAARTEN

15 Nights on Wind Surf

Nov 5, 2027 — Nov 20, 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
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
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.