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Ocean Crossings + Ponta Delgada, Azores
 
Philipsburg, St. Maarten to Lisbon
Sat Mar 29, 2025 - Sat Apr 12, 2025,
 14 days
 on Wind Surf
?All-inclusive from
$2,499
?Cruise Only From
$2,499
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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. One delightful stop in Ponta Delgada, the Azores Islands en route to Lisbon for an outdoor activity or relaxing on the beach.  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 11: Ponta Delgada
Ponta Delgada is the capital of São Miguel Island, gateway to the crater lakes and volcano of Sete Cidades and to the Azores Archipelago of Portugal. There is much to do here including horseback riding, golfing, and inviting beaches with volcanic sand, tidal pools and inviting surfing or body boarding.  Sites to see include the impressive, 3-arched city gates and the Gothic-style Church of St. Sebastian near the harbor, the Hermitage of Our Lady of Peace Temple, the quirky street art and the Carlos Machado Museum with a variety of artifacts of  the Azorean culture.
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Day 15: 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
Drop by the Bridge for an impromptu navigation lesson.
Friends
Make new friendships with like-minded travelers Savor extraordinary cuisine then use the great fitness equipment to work it off.
Massage
Find you have time for your favorite indulgences – from a relaxing massage to breakfast in bed.
Monastery of St. Jerome
See the ornate architecture and the Monastery of St. Jerome, a UNESCO site in Lisbon.
Ponta Delgada
Enjoy the charming Azores port of Ponta Delgada and look for the quirky street art.
relax
Rediscover how to relax with delightful days at sea to do as you please as you cross the Atlantic.
stars overhead
Discover more stars overhead than you ever imagined.
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports Platform: 
Sat Mar 29
Philipsburg, St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sun Mar 30
AT SEA
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Depart:  
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Mon Mar 31
AT SEA
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Tue Apr 1
AT SEA
Arrive:  
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Wed Apr 2
AT SEA
Arrive:  
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Thu Apr 3
AT SEA
Arrive:  
Depart:  
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Fri Apr 4
AT SEA
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Sat Apr 5
AT SEA
Arrive:  
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Sun Apr 6
AT SEA
Arrive:  
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Mon Apr 7
AT SEA
Arrive:  
Depart:  
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Tue Apr 8
Ponta Delgada
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Apr 9
AT SEA
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Depart:  
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Thu Apr 10
AT SEA
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Fri Apr 11
AT SEA
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Sat Apr 12
Lisbon
Arrive:  7:00 AM
Depart:  
Watersports Platform: 
Wind Surf
On any day, our 342-guest flagship, Wind Surf, the world’s largest sailing ship, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. During their cruise, you will find the perfect setting for ‘making an entrance’ in the beautiful reception area – and, appropriately, that’s only the beginning.
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Accommodations & Pricing
Boutique cruising with fewer than 350 guests. Our expertly designed itineraries and unexpected shore excursions bring you closer to each destination.
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 $2,499 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 $2,599 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 $2,699 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 $2,899 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 $3,099 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.
? Cruise only from $4,599 per guest
? All-inclusive price from $4,599 per guest
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.
? Cruise only from $5,999 per guest
? All-inclusive price from $5,999 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.
? 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
Watersports Platform
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session
ALL DATES &
FARES
Complimentary All-Inclusive Upgrade
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited beer, wine, and cocktails, and gratuities. From $89 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sat, Mar 29 - Sat, Apr 12, 2025
WIND SURF
$2,499
$2,499
THIS
SAILING