Knot Your Average Crossing

 
Philipsburg, St. Maarten to Lisbon
Sat Apr 4, 2026 - Sat Apr 18, 2026,
 14 days
 on Wind Surf
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Starting from $2,599 USD
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Philipsburg, St. Maarten to Lisbon
Set sail on an unforgettable ocean crossing aboard one of our majestic sailing ships, where you’ll immerse yourself in the timeless art of seafaring. This voyage features a guest speaker offering fascinating talks on navigation history, legendary explorers, and even swashbuckling pirates. You’ll learn to read charts, tie sailor’s knots, and even navigate the vessel on the Flying Bridge alongside our Officers. Enjoy stargazing and star mapping sessions, and hear navigational insights directly from the Captain himself. Throughout the journey, hands-on workshops and immersive activities will deepen your connection to the sea — and for a final splash of fun, join our lively "Pirates of the Atlantic” themed party, so don’t forget to pack your nautical outfits!
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
Learn how to navigate the vessel on the Flying Bridge.
cuisine
Indulge in gourmet dining options with dishes created by James Beard Foundation award winning chefs.
Private Yacht Lifestyle
Private yacht lifestyle with no interruptions.
Massage
Time for your favorite indulgences – from a relaxing massage to breakfast in bed.
stars overhead
Star gaze and map the constellations with one of the ships Officers.
knot tying workshop
Learn how to read a navigational chart and participate in a knot tying workshop
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Sat Apr 4
Philipsburg, St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sun Apr 5
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Mon Apr 6
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Tue Apr 7
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Wed Apr 8
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Thu Apr 9
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Apr 10
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sat Apr 11
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sun Apr 12
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Mon Apr 13
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Tue Apr 14
Ponta Delgada
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Apr 15
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Thu Apr 16
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Apr 17
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sat Apr 18
Lisbon
Arrive:  7:00 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 $2,599 per guest
? All-inclusive price from $2,599 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 $2,699 per guest
? All-inclusive price from $2,699 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 $2,799 per guest
? All-inclusive price from $2,799 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 $2,999 per guest
? All-inclusive price from $2,999 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 $3,199 per guest
? All-inclusive price from $3,199 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 $4,299 per guest
? All-inclusive price from $4,299 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
Sat, Mar 28 - Sun, Apr 12, 2026
WIND SPIRIT
$3,099
$3,099
Sat, Apr 4 - Sat, Apr 18, 2026
WIND SURF
$2,599
$2,599
THIS
SAILING
Tue, Nov 10 - Tue, Nov 24, 2026
WIND STAR
$2,899
$2,899