Ocean Crossings

 
Philipsburg, St. Maarten to Lisbon
Sat Mar 27, 2027 - Sun Apr 11, 2027,
 15 days
 on Wind Surf
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Starting from $2,799 USD
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Philipsburg, St. Maarten to Lisbon
This is a place where dreams really do come true. The place where nothing comes between you and your fondest wishes. Where no schedules intrude, where day-to-day annoyances can’t reach you, where every moment of every hour of every day is yours alone. This is your place – at sea under an open sky – the one place in which you truly can get away from it all. Simply step on board and we’ll take it from there. Meals so delicious they might be sinful are served when, where, and any way you choose. Decadent spa treatments. Lazy hours stretched out on deck. Workouts you’ve been meaning to get around to in the state-of-the-art Fitness Center. Uninterrupted time to spend with new friends, or in exquisite solitude. Best of all, this is the place and the time to reconnect – with each other, with yourself, with your dreams.
voyage map
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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.
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Day 12: Funchal
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.
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Day 13: PORTO SANTO, MADEIRA
PORTO SANTO, MADEIRA
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Day 16: 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.
Popular Highlights
Bridge
Dropping by the Bridge for an impromptu navigation lesson.
cuisine
Extraordinary cuisine – and great fitness equipment to work it off.
Friends
New friendships with like-minded travelers.
Massage
Time for your favorite indulgences – from a relaxing massage to breakfast in bed.
Private yacht lifestyle
Private yacht lifestyle with no interruptions.
stars overhead
More stars overhead than you ever imagined.
vistas from your stateroom
Sweeping ocean vistas from your stateroom or suite.
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Sat Mar 27
Philipsburg, St. Maarten
Arrive:  
Depart:  5:00 PM
Watersports Platform: 
Sun Mar 28
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Mon Mar 29
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Tue Mar 30
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Wed Mar 31
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Thu Apr 1
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Apr 2
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sat Apr 3
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sun Apr 4
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Mon Apr 5
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Tue Apr 6
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Wed Apr 7
Funchal
Arrive:  8:00 AM
Depart:  11:59 PM
Watersports Platform: 
Thu Apr 8
PORTO SANTO, MADEIRA
Arrive:  8:00 AM
Depart:  1:00 PM
Watersports Platform: 
Fri Apr 9
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sat Apr 10
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sun Apr 11
Lisbon
Arrive:  8:00 AM
Depart:  
Watersports Platform: 
Accommodations & Pricing
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar) 
? Call for Availability
Category B
Category B
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $2,799 per guest
? All-inclusive price from $2,799 per guest
Category BX Deluxe
Category BX Deluxe
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $2,899 per guest
? All-inclusive price from $2,899 per guest
Category A
Category A
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $2,999 per guest
? All-inclusive price from $2,999 per guest
Category AX Deluxe
Category AX Deluxe
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $3,199 per guest
? All-inclusive price from $3,199 per guest
Category TX Deluxe
Category TX Deluxe
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $3,399 per guest
? All-inclusive price from $3,399 per guest
Suite
Suite
With 376 square feet, you’ll find the perfect space for time together — and plenty of room for time to yourself. You’ll even enjoy two full separate bathrooms. All the amenities of the staterooms await you, plus a beautiful sitting area, and two flat-screen television sets with DVD players.
? Cruise only from $4,499 per guest
? All-inclusive price from $4,499 per guest
Officer's Suite
Officer's Suite
For the ultimate in nautical experiences, reserve the new Officer’s Suite located close to the Bridge where our own ship’s officers have their quarters. With its unique “insider” location and 242 square feet of comfort, the nautically appointed Officer’s Suite offers an experience you won’t find on any other cruise line.
? Call for Availability
Bridge Suite
Bridge Suite
The ultimate in space and style surrounds you in 495 square feet of pure indulgence. Separate bedroom and living room with an in-suite dining area is an invitation to relaxation. And possibly best of all, your expansive bathroom features both a whirlpool spa tub and a massage shower.
? Call for Availability
The Windstar Life
The Windstar staff-to-guest ratio is 1:1.5, and it shows.The moment you board you’ll feel it: an ever-attentive crew at your service, providing you with what you want and need, when you want and need it.
Friendly and Relaxed Atmosphere
Signature Onboard Barbecue
Cooking Demonstrations
Genuine and Thoughtful Crew
Crew Talent Show
Open Bridge
Local and Live Performances
Relax at the Pool or Hot Tub
Complimentary 24 Hour Room Service
Signature Sail Away
Shopping With The Chef
Take In The Sun
Marina
*Select voyages
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session
ALL DATES &
FARES
Thankful For Travel Sales Event
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited select beer, wine, and cocktails, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sun, Mar 22 - Tue, Apr 7, 2026
STAR PRIDE
$3,099
$3,099
Tue, Apr 28 - Wed, May 6, 2026
STAR SEEKER
$2,199
$2,199
Wed, Sep 2 - Wed, Sep 16, 2026
STAR SEEKER
$3,499
$3,499
Sat, Dec 5 - Sat, Dec 19, 2026
WIND SURF
$2,499
$2,499
Mon, Feb 8 - Mon, Mar 1, 2027
WIND STAR
$4,099
$4,099
Tue, Mar 2 - Wed, Mar 17, 2027
STAR LEGEND
$3,049
$3,049
Sat, Mar 27 - Sun, Apr 11, 2027
WIND SURF
$2,799
$2,799
THIS
SAILING
Thu, May 20 - Tue, Jun 1, 2027
STAR SEEKER
$3,787
$2,599
Tue, May 16 - Sun, May 28, 2028
STAR SEEKER
$3,787
$2,599