Ocean Crossings

 
Bridgetown to Lisbon
Tue Mar 2, 2027 - Wed Mar 17, 2027,
 15 days
 on Star Legend
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Starting from $3,049 USD
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Bridgetown 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: Bridgetown
Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you’ll find historic sugar plantations and the fairyland magic of Harrison’s Cave.
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Day 11: 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 12: PORTO SANTO, MADEIRA
PORTO SANTO, MADEIRA
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Day 14: Casablanca, Morocco
The siren call of Morocco is irresistible. Amid the whitewashed alleyways and stunning ocean views, make time for an optional excursion to the medina of Marrakech, a UNESCO World Heritage Site.  Explore the souks and medinas in the footsteps of Sir Winston Churchill and Yves St. Laurent, who both called this extraordinary blend of east and west their home.
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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: 
Tue Mar 2
Bridgetown
Arrive:  
Depart:  5:00 PM
Watersports Platform: 
Wed Mar 3
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Thu Mar 4
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Mar 5
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sat Mar 6
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sun Mar 7
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Mon Mar 8
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Tue Mar 9
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Wed Mar 10
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Thu Mar 11
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Mar 12
Funchal
Arrive:  8:00 AM
Depart:  11:59 PM
Watersports Platform: 
Sat Mar 13
PORTO SANTO, MADEIRA
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Sun Mar 14
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Mon Mar 15
Casablanca, Morocco
Arrive:  7:00 AM
Depart:  11:59 PM
Watersports Platform: 
Tue Mar 16
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Wed Mar 17
Lisbon
Arrive:  8:00 AM
Depart:  
Watersports Platform: 
Accommodations & Pricing
Guaranteed Suite** (chosen by Windstar)
Guaranteed Suite** (chosen by Windstar)
Guaranteed Suite** (chosen by Windstar)
? Call for Availability
Star Porthole Suite
Star Porthole Suite
These rooms represent a nod to the sailing tradition of porthole windows. And while sailors might have had cramped quarters, your 277 square foot stateroom is wonderfully spacious and furnished with all the modern amenities and comforts of home.
? Cruise only from $3,049 per guest
? All-inclusive price from $3,049 per guest
Ocean View Suite
Ocean View Suite
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, and savor a treat from the fresh fruit bowl.
? Cruise only from $3,149 per guest
? All-inclusive price from $3,149 per guest
Ocean View Suite 1
Ocean View Suite 1
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $3,249 per guest
? All-inclusive price from $3,249 per guest
Star Ocean View Suite 1
Star Ocean View Suite 1
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Cruise only from $3,299 per guest
? All-inclusive price from $3,299 per guest
Ocean View Suite 2
Ocean View Suite 2
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $3,349 per guest
? All-inclusive price from $3,349 per guest
Ocean View Suite 3
Ocean View Suite 3
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $3,499 per guest
? All-inclusive price from $3,499 per guest
Balcony Suite
Balcony Suite
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $3,949 per guest
? All-inclusive price from $3,949 per guest
Star Balcony Suite
Star Balcony Suite
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Cruise only from $4,049 per guest
? All-inclusive price from $4,049 per guest
Balcony Suite 1
Balcony Suite 1
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $4,149 per guest
? All-inclusive price from $4,149 per guest
Star Balcony Suite 1
Star Balcony Suite 1
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Cruise only from $4,349 per guest
? All-inclusive price from $4,349 per guest
Deluxe Suite
Deluxe Suite
Brand new Deluxe Suites welcome you with 468 square feet of casually elegant living space and an ocean viewing French balcony. All these suites feature 3rd berths, and a sleep-inducing queen bed.
? Cruise only from $5,049 per guest
? All-inclusive price from $5,049 per guest
Classic Suite
Classic Suite
Relax in 400 spacious square feet. Your living area offers beautiful views from the forward-facing window and French doors onto your private veranda. Two spacious closets give you plenty of room to unpack.
? Cruise only from $5,949 per guest
? All-inclusive price from $5,949 per guest
Owner's Suite
Owner's Suite
With 575 square feet, your Owner’s Suite offers separate living room and dining areas. A veranda, Interactive TVs, and a full master bath and separate powder room indulge you in spacious comfort. 
? Cruise only from $6,549 per guest
? All-inclusive price from $6,549 per guest
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
THIS
SAILING
Sat, Mar 27 - Sun, Apr 11, 2027
WIND SURF
$2,799
$2,799
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