Windward Ways & Tobago Cays

Jan 25, 2026 — Feb 1, 2026

Starting from $6,048 Displayed pricing is based off of double occupancy per person. Pricing subject to change based on occupancy and cabin selection.

See more routes around Caribbean

BRIDGETOWN, BARBADOS → ORANJESTAD, ARUBA

7 Nights in Wind Surf

1
JAN 25, 2026
Bridgetown
EMBARK
1:00 PM
DEPART
6:00 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.

2
JAN 26, 2026
Bequia
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
0

The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia's whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island's famed model boat builders at work on their miniature masterpieces.

3
JAN 27, 2026
Mayreau
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
1

With fewer than 300 inhabitants and miles of secluded beaches, it's easy to feel as if you're on your own private island. Saline Bay is a delightful anchorage that separates the Caribbean from the Atlantic - and a perfect place to play with some of the toys from the Watersports Platform.

Mayreau, Grenadines Island Escape

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$89
4
JAN 28, 2026
Soufriere
ARRIVE
8:00 AM
DEPART
4:00 PM
MARINA
NO
SHORE EXCURSIONS
5

Nestled in the shadows of the UNESCO Pitons, Soufriere represents the heart and soul of St. Lucia. The tiny town center is full of street vendors and stores and some of the best resorts on the island can be found here. Nearby are secluded waterfalls and the waters here boast some of the best diving around. Sights to see include the Edmund Rainforest Trail, fond Doux Holiday plantation, Robot Estate and the Gros Piton Nature Trail.

Soufriere, Bean to Bar & Market Style Lunch

Time
9:30 AM
Duration
4 Hours
Activity Level
Easy-Moderate
Price
$235

Soufriere, Snorkel at Marine Park

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Moderate-Strenuous
Price
$109

Soufriere, Botanical Gardens, Toraille Waterfall & Beach

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy-Moderate
Price
$69

Soufriere, Chocolate Heritage tour at Fond Doux Estate

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Easy-Moderate
Price
$99

Soufriere, Concierge Collection: Taste of St. Lucia

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Easy-Moderate
Price
$179
5
JAN 29, 2026
6
JAN 30, 2026
Kralendijk
ARRIVE
1:00 PM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
7

The ice cream colors of the stucco houses will draw your lens, as will the pink flamingos on the salt pans. But you'll need a waterproof camera to complete the portrait since more than 400 fish species and 50 types of coral wait beneath the surface

Kralendijk, Kayak, Beach & Snorkel

Time
1:30 PM
Duration
2.5 Hours
Activity Level
Moderate-Strenuous
Price
$69

Kralendijk, Bonaire Glass Bottom Boat

Time
1:30 PM
Duration
1.5 Hours
Activity Level
Easy
Price
$59

Kralendijk, Snorkel Safari by Sustainable Catamaran

Time
1:30 PM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$79

Kralendijk, Samur Sail, Beach & Snorkel

Time
1:30 PM
Duration
3 Hours
Activity Level
Moderate
Price
$79

Kralendijk, Kralendijk by Eco Powered Tuk-Tuk

Time
1:30 PM
Duration
1 Hours
Activity Level
Easy
Price
$39

Kralendijk, Experience Bonaire's Fishing (Easy-Moderate)

Time
1:30 PM
Duration
4 Hours
Activity Level
Moderate-Strenuous
Price
$349

Kralendijk, Bonaire Highlights

Time
1:30 PM
Duration
2.75 Hours
Activity Level
Easy
Price
$79
7
JAN 31, 2026
Willemstad
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
6

Savor the pastel colors of the historic UNESCO site Old Town and the way the elaborate Dutch gables cut baroque curlicues from the sky. It's the perfect appetizer for a day of watersports or an adventure below ground at the magical Hato Caves-filled with eerie limestone formations and ancient petroglyphs.

Willemstad, Caves and City Tour

Time
8:30 AM
Duration
2.75 Hours
Activity Level
Strenuous
Price
$89

Willemstad, Panoramic Tour

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$49

Willemstad, Off Road Adventures in the Wild West

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy-Moderate
Price
$89

Willemstad, Naural Wonders with Snack

Time
8:30 AM
Duration
5 Hours
Activity Level
Moderate-Strenuous
Price
$149

Willemstad, Day at Corendon Mangrove Beach Resort With Lunch

Time
9:00 AM
Duration
5 Hours
Activity Level
Easy-Moderate
Price
$159

Willemstad, Walking Tour

Time
8:30 AM
Duration
1.5 Hours
Activity Level
Moderate-Strenuous
Price
$39

Wind Surf

number of decks
6 Decks
yacht length
535 ft (163 meters)
yacht crew size
191 Crew Members
yacht guest capacity
342 Guests

Available Staterooms

Category A

Cabin
29 Cabins
Max. Occupancy
2 Passengers
Room Size
188 Sqft
Amenities

Category AX Deluxe

Cabin
34 Cabins
Max. Occupancy
2 Passengers
Room Size
188 Sqft
Amenities

Suite

Cabin
18 Cabins
Availability
Limited
Max. Occupancy
3 Passengers
Room Size
376 Sqft
Amenities

Category BX Deluxe

Cabin
34 Cabins
Max. Occupancy
3 Passengers
Room Size
188 Sqft
Amenities

Category TX Deluxe

Cabin
32 Cabins
Max. Occupancy
2 Passengers
Room Size
188 Sqft
Amenities

Available Dates