Ocean Crossings
 
Lisbon to Philipsburg, St. Maarten
Tue Nov 18, 2025 - Tue Dec 2, 2025,
 14 days
 on Wind Surf
VIEW ALL DATES
Starting from $2,499 USD
ADD TO
WISH LIST
REMOVE
FROM
WISH LIST
VIEW THE JOURNEY
Lisbon to Philipsburg, St. Maarten
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
VIEW THE JOURNEY
Day 1: 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.
VIEW THE JOURNEY
Day 14: St. John's
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.
VIEW THE JOURNEY
Day 15: 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.
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: 
Tue Nov 18
Lisbon
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Wed Nov 19
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Thu Nov 20
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Nov 21
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sat Nov 22
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sun Nov 23
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Mon Nov 24
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Tue Nov 25
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Wed Nov 26
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Thu Nov 27
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Nov 28
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sat Nov 29
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sun Nov 30
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Mon Dec 1
St. John's
Arrive:  8:00 AM
Depart:  7:00 PM
Watersports Platform: 
Tue Dec 2
Philipsburg, St. Maarten
Arrive:  6:00 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 $2,499 per guest
? All-inclusive price from $3,885 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 $2,599 per guest
? All-inclusive price from $3,985 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 $2,699 per guest
? All-inclusive price from $4,085 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 $2,899 per guest
? All-inclusive price from $4,285 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 $3,099 per guest
? All-inclusive price from $4,485 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 $4,149 per guest
? All-inclusive price from $5,535 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
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session
ALL DATES &
FARES
Early Booking Offer 2026 & 2027
Pick Your Perk
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
Tue, Nov 18 - Tue, Dec 2, 2025
WIND SURF
$3,885
$2,499
THIS
SAILING
Sun, Mar 22 - Tue, Apr 7, 2026
STAR PRIDE
$4,083
$2,499
Sat, Mar 28 - Sun, Apr 12, 2026
WIND SPIRIT
$3,984
$2,499
Tue, Apr 28 - Wed, May 6, 2026
STAR SEEKER
$2,991
$2,199
Wed, Sep 2 - Wed, Sep 16, 2026
STAR SEEKER
$4,485
$3,099
Tue, Nov 10 - Tue, Nov 24, 2026
WIND STAR
$2,499
$2,499