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Knot Your Average Crossing

Nov 10, 2026 — Nov 24, 2026

Starting from

Complimentary All-In Package

Free Laundry for Collectors:

Reduced Deposit
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LISBON → BRIDGETOWN, BARBADOS

14 Nights on Wind Star

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!.

Map routes may vary by sailing. Actual itineraries are listed below.
1
NOV 10, 2026
Lisbon
EMBARK
1:00 PM
DEPART
3:00 PM
MARINA
NO
SHORE EXCURSIONS
5

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.

Available Excursions

Lisbon

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy

Add during booking

$749

Lisbon

Time
8:30 AM
Duration
3 Hours
Activity Level
Easy-Moderate

Add during booking

$425

Lisbon

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy

Add during booking

$875

Lisbon

Time
8:30 AM
Duration
3 Hours
Activity Level
Easy

Add during booking

$109

Lisbon

Time
8:30 AM
Duration
4.5 Hours
Activity Level
Moderate

Add during booking

$135

2
NOV 11, 2026
AT SEA
3
NOV 12, 2026
AT SEA
4
NOV 13, 2026
AT SEA
5
NOV 14, 2026
AT SEA
6
NOV 15, 2026
AT SEA
7
NOV 16, 2026
AT SEA
8
NOV 17, 2026
AT SEA
9
NOV 18, 2026
AT SEA
10
NOV 19, 2026
AT SEA
11
NOV 20, 2026
AT SEA
12
NOV 21, 2026
AT SEA
13
NOV 22, 2026
AT SEA
14
NOV 23, 2026
AT SEA
15
NOV 24, 2026
Bridgetown
ARRIVE
11:00 AM
DISEMBARK
12:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

See Detail

Wind Star

number of decks
4 Decks
yacht length
360 ft (110 meters)
yacht crew size
90 Crew Members
yacht guest capacity
148 Guests
See More Voyages

Staterooms

Room Size 188 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 188 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 188 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 188 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 220 sq ft
Max. Occupancy 2 Passengers
Amenities

Room Size sq ft
Max. Occupancy 2 Passengers
Amenities

Available Dates

Date Yacht
Starting from
Actions
Nov 12 (Thu) – Nov 27 (Fri), 2026November 12 (Thu) – November 27 (Fri), 2026Star Legend
Feb 8 (Mon) – Mar 1 (Mon), 2027February 8 (Mon) – March 1 (Mon), 2027Wind Star
Mar 2 (Tue) – Mar 17 (Wed), 2027March 2 (Tue) – March 17 (Wed), 2027Star Legend
Mar 27 (Sat) – Apr 11 (Sun), 2027March 27 (Sat) – April 11 (Sun), 2027Wind Surf
Mar 30 (Tue) – Apr 15 (Thu), 2027March 30 (Tue) – April 15 (Thu), 2027Star Pride
May 20 (Thu) – May 31 (Mon), 2027May 20 (Thu) – May 31 (Mon), 2027Star Seeker
Sep 1 (Wed) – Sep 14 (Tue), 2027September 1 (Wed) – September 14 (Tue), 2027Star Seeker
Nov 5 (Fri) – Nov 20 (Sat), 2027November 5 (Fri) – November 20 (Sat), 2027Wind Surf
Dec 6 (Mon) – Dec 20 (Mon), 2027December 6 (Mon) – December 20 (Mon), 2027Star Legend
Jan 6 (Thu) – Jan 10 (Mon), 2028January 6 (Thu) – January 10 (Mon), 2028Star Breeze
Jan 24 (Mon) – Jan 28 (Fri), 2028January 24 (Mon) – January 28 (Fri), 2028Star Breeze
Mar 19 (Sun) – Apr 3 (Mon), 2028March 19 (Sun) – April 3 (Mon), 2028Wind Surf
Apr 3 (Mon) – Apr 19 (Wed), 2028April 3 (Mon) – April 19 (Wed), 2028Star Pride
Aug 30 (Wed) – Sep 12 (Tue), 2028August 30 (Wed) – September 12 (Tue), 2028Star Seeker
Nov 5 (Sun) – Nov 19 (Sun), 2028November 5 (Sun) – November 19 (Sun), 2028Wind Surf
May 25 (Fri) – Jun 5 (Tue), 2029May 25 (Fri) – June 5 (Tue), 2029Star Seeker

Knot Your Average Crossing

LISBON → BRIDGETOWN, BARBADOS

14 Nights on Wind Star

Nov 10, 2026 — Nov 24, 2026

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!.

1
NOV 10, 2026
Lisbon
EMBARK
1:00 PM
DEPART
3:00 PM
MARINA
NO
SHORE EXCURSIONS
5

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.

Lisbon, Concierge Collection: Half Day Private Car & Guide *

Explore at your leisure with a private vehicle, driver, and English-speaking guide. This exclusive tour will allow you to customize your time ashore and explore the most interesting sites in the comfort and privacy of your own car. With your private vehicle, and the personalized attention of your driver and English-speaking guide, you will have the flexibility and independence to design your itinerary ashore. See the iconic sites of the city, or create your own personal stops to make the experience your own. Please note : Capacity: 1-2 guests. Private cars are ordered per vehicle (not per person). This tour includes transport in a private car, driver and English Speaking Guide. Itinerary can be adjusted with tour guide as long as it's in the area and does not exceed the duration of 4 hours. Recommended for physically challenged guests.

Port
Lisbon
Time
8:30 AM
Duration
4 Hours
Activity Level
Easy

Add during booking

$749 USD

Lisbon by Tuk Tuk

From the ship your tuk tuk will take you on a journey through the city in an up close and personal way. Lisbon is a city of contrasts and during your ride you can admire both the modern and historic aspects. As you travel through the streets, allow yourself to become immersed in the atmosphere. Admire the city's fine architecture, enjoy splendid views across the River Tagus and take a step back in time in the Old Town with its narrow alleyways and cobblestone streets. During your tour, several photo stops will be made along the way. You'll also have the opportunity to sample regional cheese, bread and port wine, as well as one of Lisbon's famous custard cream cakes. Please note: Wear comfortable walking shoes and sunscreen and bring your camera. This tour returns to the pier and does not include a transfer to the airport or hotel. It is intended for in transit guests. Price is per Tuk Tuk not per person.

Port
Lisbon
Time
8:30 AM
Duration
3 Hours
Activity Level
Easy-Moderate

Add during booking

$425 USD

Lisbon, Concierge Collection: Half Day Private Van & Guide *

Explore at your own pace with a private vehicle, driver and English-speaking guide at your service. You will have the flexibility and independence to design your itinerary ashore according to your own interests. On this half day option you can combine an itinerary in Lisbon only or choose its charming surroundings as Sintra, Cascais, Guincho or Cabo da Roca. Please note: Capacity: 3 - 6 guests. Private vans are ordered per vehicle (not per person).This tour includes transport in a private van, driver and English Speaking Guide. Itinerary in Lisbon, Sintra, Cascais, Guincho or Cabo da Roca areas and for 4 hours duration.

Port
Lisbon
Time
8:30 AM
Duration
4 Hours
Activity Level
Easy

Add during booking

$875 USD

Lisbon, Highlights with Transfer to Airport

Lisbon is a city of contrasts, where modern trends merge with ancient ones, accentuating Lisbon's variety and intensity of color. You will continue along Liberty Avenue a charming old boulevard place of several international stores (such as Prada or Armani) lined with gardens and known for its unique black and white mosaics on the sidewalks on the way to Marquês de Pombal Square. The highlight of your visit is the church of the Jeronimos Monastery (outside visit only), a masterpiece of Manueline architecture, widely acknowledged to be the finest sight in Lisbon, built in the 16th century to commemorate the discoveries of Portuguese navigators. Nearby, you will see the lavishly decorated Belem Tower, and the Monument to the Discoveries, built to celebrate the 500th anniversary of the death of Prince Henry the Navigator. On the way to the hotel or to the airport, you will see, stretching across the Tagus River, the April 25th Bridge, sister to the Golden Gate, and the towering Christ the King statue on the far side. Please note: This tour is only for guests who have a flight later than 2:00 p.m. or an overnight stay in Lisbon. This tour includes transport in a private bus and a qualified English-speaking guide. Tour order may vary but all sites will be covered.

Port
Lisbon
Time
8:30 AM
Duration
3 Hours
Activity Level
Easy

Add during booking

$109 USD

Lisbon, Majestic Sintras & Cascais With Transfer to Windstar Hotel

Your motor coach and English-speaking guide will take you via the beautiful coastal road bordering the River Tagus, driving through the fashionable resort of Estoril - the home of several international royal exiles during the Second World War - to the lively scenic village of Cascais. Here you will have a guided tour around its plaza and enjoy its colorful setting of seaside café terraces , small shops, and sailboats. For six centuries Sintra was the favorite summer residence of the kings of Portugal, who were attracted by the cool climate and the lush beauty of the town's setting. Writers and poets in general - Lord Byron, Alfred Tennyson, Hans Christian Andersen, and Isaac Bashevis Singer chose Sintra as a preferred destination. The tall conical chimneys of the National Palace and the fabulous Pena Palace, are two unmistakable landmarks of this area. You will have the opportunity to taste local pastry in one of the cafés in Sintra followed by a guided walk to explore this town recognized as a UNESCO World Heritage Site since 1995. Return back to your Windstar Hotel in Lisbon. Please note: Tour order may vary but all sites will be covered.

Port
Lisbon
Time
8:30 AM
Duration
4.5 Hours
Activity Level
Moderate

Add during booking

$135 USD

2
NOV 11, 2026
AT SEA
3
NOV 12, 2026
AT SEA
4
NOV 13, 2026
AT SEA
5
NOV 14, 2026
AT SEA
6
NOV 15, 2026
AT SEA
7
NOV 16, 2026
AT SEA
8
NOV 17, 2026
AT SEA
9
NOV 18, 2026
AT SEA
10
NOV 19, 2026
AT SEA
11
NOV 20, 2026
AT SEA
12
NOV 21, 2026
AT SEA
13
NOV 22, 2026
AT SEA
14
NOV 23, 2026
AT SEA
15
NOV 24, 2026
Bridgetown
ARRIVE
11:00 AM
DISEMBARK
12:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.