Windward Ways & Tobago Cays

Dec 4, 2026 — Dec 12, 2026

Starting from

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BRIDGETOWN, BARBADOS → ORANJESTAD, ARUBA

8 Nights on Star Legend

Dive, snorkel and swim with fish and sea turtles in Tobago Cays Marine Park, Bonaire National Marine Park and the proposed Speyside Marine Protected Area. Swim in a picture-perfect waterfall pool surrounded by the oldest protected rainforest in the Western Hemisphere, the Main Ridge Forest Reserve. Take in the volcanic beauty of the Pitons on St. Lucia, where rainforest meets some of the healthiest coral reefs in the Caribbean. And discover Bonaire, with its stunning desert-palette motifs like pink flamingos on white salt pans. Those who are looking for the classic Caribbean will find it in Mayreau — fewer than 300 inhabitants, and just 1.5 square miles, making it a port exclusive to yachts. And those who love colonial harbors will enjoy British Bridgetown as well as the triple Dutch treat of Kralendijk, Willemstad and Oranjestad.

Popular Highlights

Additional Information

Map routes may vary by sailing. Actual itineraries are listed below.
1
DEC 04, 2026
Bridgetown
EMBARK
1:00 PM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
1

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.

Bridgetown: Barbados Island Tour with Airport Transfer

Time
6:30 AM
Duration
4.5 Hours
Activity Level
Moderate
Price
$129
2
DEC 05, 2026
Rodney Bay
TYPE
Sail
DETAIL
RODNEY BAY

Rodney Bay, Saint Lucia

The Pitons
ARRIVE
5:30 PM
DEPART
6:30 PM
MARINA
NO
SHORE EXCURSIONS
0

Located near the town of Soufriere, St. Lucia the Pitons are a UNESCO World Heritage Site and a spectacular landmark. Gros Piton is 2,619 feet high (798 meters) and Petit Piton is 2,438 feet high (743 meters). Gros Piton is home to at least 148 plant species and 27 bird species (5 of them endemic) and Petit Piton has 97 plant species with 8 rare tree species.

3
DEC 06, 2026
Scarborough, Tobago
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
0

Scarborough, Tobago

4
DEC 07, 2026
Bequia
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
5

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.

Bequia, Taste of Bequia

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate
Price
$149

Bequia, Bequia Fort & Lower Beach Getaway *

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

Bequia Highlights

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

Bequia Snorkel Adventure

Time
8:30 AM
Duration
3 Hours
Activity Level
Strenuous
Price
$119

Bequia, Mustique Magic with Lunch

Time
8:30 AM
Duration
6 Hours
Activity Level
Moderate
Price
$269
5
DEC 08, 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
6
DEC 09, 2026
AT SEA
7
DEC 10, 2026
Kralendijk
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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

8
DEC 11, 2026
Willemstad
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

9
DEC 12, 2026
Oranjestad
ARRIVE
6:00 AM
DISEMBARK
7:00 AM
MARINA
NO
SHORE EXCURSIONS
0

Known for having some of the best beaches in the Caribbean, this Dutch port makes it easy to just ... take it easy. Walk through town to choose your favorite carved wooden door, or spend the day like the Arubans do playing dominos at a beachside table.

Star Legend

number of decks
6 Decks
yacht length
440 ft (134 meters)
yacht crew size
140 Crew Members
yacht guest capacity
312 Guests

Staterooms

Room Size 575 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 468 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 400 sq ft
Max. Occupancy 2 Passengers
Amenities

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities
Expand all

Available Dates

No other dates are available.

Windward Ways & Tobago Cays

BRIDGETOWN, BARBADOS → ORANJESTAD, ARUBA

8 Nights on Star Legend

Dec 4, 2026 — Dec 12, 2026

Dive, snorkel and swim with fish and sea turtles in Tobago Cays Marine Park, Bonaire National Marine Park and the proposed Speyside Marine Protected Area. Swim in a picture-perfect waterfall pool surrounded by the oldest protected rainforest in the Western Hemisphere, the Main Ridge Forest Reserve. Take in the volcanic beauty of the Pitons on St. Lucia, where rainforest meets some of the healthiest coral reefs in the Caribbean. And discover Bonaire, with its stunning desert-palette motifs like pink flamingos on white salt pans. Those who are looking for the classic Caribbean will find it in Mayreau — fewer than 300 inhabitants, and just 1.5 square miles, making it a port exclusive to yachts. And those who love colonial harbors will enjoy British Bridgetown as well as the triple Dutch treat of Kralendijk, Willemstad and Oranjestad.

1
DEC 04, 2026
Bridgetown
EMBARK
1:00 PM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
1

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.

Bridgetown: Barbados Island Tour with Airport Transfer

Your tour will begin with a leisurely drive along the Gold Coast , home to many wealthy residents, and will take you to the stunning area of Bathsheba . This is where the Atlantic surf pounds the coastline and it is a famous spot for international and local surfing competitions. A walk on the beach is a must. Heading into the hills, you will arrive at St. John's Church . There are stunning views from the churchyard - a perfect photo opportunity. The church contains an interesting sculpture depicting the Madonna and Child with the infant St. John. The graveyard contains the tomb of Ferdinand Paleologus, a descendant of the Byzantine Imperial family. The present building was constructed in 1836, and the pulpit is constructed from six different kinds of wood: ebony, locust, Barbados mahogany, manchineel, oak and pine. Through sleepy country villages and sugar cane fields, you will make your way to Sunbury House dating back to 1650. The house was destroyed by fire in 1995, and was gracefully restored and re-opened in 1996. It possesses one of the country's superior collections of antiques. The cellar houses a unique collection of antique carriages, the largest collection in the Caribbean, as well as many items used in the domestic life of the plantation. It also houses a very old collection of optical machinery and sight testing equipment, some of the first to come to the West Indies including the first lens grinding plant. Enjoy a light deli-style lunch with a complimentary rum or fruit punch. A short drive will take you to the airport where you will be met and assisted with your luggage and airline check-in. Please note : There are about 20 steps to climb at Sunbury House and 10 steps down to the cellar. This tour will end with a drop off at the Grantley Adams International Airport or the Accra Beach Hotel.
Port
Bridgetown
Time
6:30 AM
Duration
4.5 Hours
Activity Level
Moderate

Add during booking

$129 USD

2
DEC 05, 2026
Rodney Bay
TYPE
Sail
DETAIL
RODNEY BAY

Rodney Bay, Saint Lucia

The Pitons
ARRIVE
5:30 PM
DEPART
6:30 PM
MARINA
NO
SHORE EXCURSIONS
0

Located near the town of Soufriere, St. Lucia the Pitons are a UNESCO World Heritage Site and a spectacular landmark. Gros Piton is 2,619 feet high (798 meters) and Petit Piton is 2,438 feet high (743 meters). Gros Piton is home to at least 148 plant species and 27 bird species (5 of them endemic) and Petit Piton has 97 plant species with 8 rare tree species.

3
DEC 06, 2026
Scarborough, Tobago
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
0

Scarborough, Tobago

4
DEC 07, 2026
Bequia
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
5

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.

Bequia, Taste of Bequia

Embark on a tantalizing culinary expedition across Bequia, awakening your taste buds with an array of flavors. Your guide will greet you as your adventure commences with a leisurely stroll along the Belmont Waterfront Boardwalk. Your first destination is the famed Frangipani's waterfront open-air restaurant and bar, recognized among the world's top 100 bars. Indulge in an assortment of Caribbean-infused cocktails featuring enticing flavors like mango, passion fruit, golden apple, and the renowned Frangi Fever. This establishment serves gourmet West Indian cuisine with global influences, highlighting fresh fruits, vegetables, and locally sourced seafood from the Grenadines. Relish a sampling platter of the island's specialties before proceeding to your next venue. Your next stop is Mac's, renowned for over 40 years for their exceptional pizzas boasting a selection of more than 45 toppings, including lobster during its season, you'll experience a casual, laid-back atmosphere against the backdrop of the Caribbean Sea. Engage your senses fully: taste the delectable pizza, feel the gentle Caribbean breeze, admire the natural surroundings, and immerse yourself in the ambient background music. Your last stop of the tour is the Plantation Restaurant and Bar. Serenaded by the soothing sounds of waves, capture the postcard-perfect views of Admiralty Bay while anticipating a delightful selection of freshly baked sweet island delicacies. As your culinary voyage draws to a close, you'll journey back to the port, cherishing the delightful memories created during your time exploring the culinary delights of Bequia. Please note: we recommend you wear comfortable walking shoes and bring local currency.
Port
Bequia
Time
8:30 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate

Add during booking

$149 USD

Bequia, Bequia Fort & Lower Beach Getaway *

Enjoy a scenic drive from the port to Fort Hamilton where there are beautiful views of the harbor of Port Elizabeth. A wonderful location to take memorable pictures of your visit. Then you will drive to Lower Bay Beach where you will get a beach chair and choice of a local rum punch, local beer or soft drink (juice). Relax on the beach, take a swim and enjoy a few hours relaxing in the sun until it is time to return to the port. Please note: Bring your swimsuit, local currency, sunscreen, a hat, and towels.
Port
Bequia
Time
8:30 AM
Duration
3 Hours
Activity Level
Easy-Moderate

Add during booking

$99 USD

Bequia Highlights

Hop into the back of a covered safari-style jeep, the island's signature mode of transportation, and embark on an exciting tour of Bequia. Starting in the bustling town of Port Elizabeth, we'll drive towards Fort Hamilton, an historic fort perched 300 feet above sea level. From here, you'll enjoy panoramic views of Admiralty Bay and the surrounding area, while learning about the French cannons once used in their conflict with the British centuries ago. Next, we'll head to Mount Pleasant, where you can take in breathtaking views of charming local homes and the stunning bays that surround the island. Continuing along the scenic Atlantic coastline, we'll stop at Spring and visit the Firefly Plantation. Here, a guided tour will introduce you to the island's diverse fruit trees and lush vegetation. After exploring Bequia's highlights, we'll return to the harbor and head back to the ship, having experienced the island's natural beauty and rich history from a unique perspective. Please note : Bring sunscreen and wear comfortable walking shoes.
Port
Bequia
Time
8:30 AM
Duration
2.5 Hours
Activity Level
Easy-Moderate

Add during booking

$89 USD

Bequia Snorkel Adventure

What better way to enjoy the Caribbean than to engage in what the area is best known for! A coastal scenic trip and a bit of snorkeling are just the right combination to provide some adventure. You will climb aboard an adventure power boat and set off towards one of the island's snorkel sites. See tiny shellfish in their natural habitat and watch the schools of fish dart playfully around you. After a while in the water you will return to your boat where the Captain's famous rum punch will be served. Enjoy the scenery as you sip on your beverage and your boat takes you back to the pier and your waiting yacht. Please note : Wear your swimsuit under your clothing and bring a towel. You may stay on board and enjoy the atmosphere if you choose not to snorkel.
Port
Bequia
Time
8:30 AM
Duration
3 Hours
Activity Level
Strenuous

Add during booking

$119 USD

Bequia, Mustique Magic with Lunch

Enjoy power cruising over to the island of the rich and famous. Discover Mustique, a 14-acre gem with fertile valleys surrounded by coral reef, coves and dazzling beaches. You will enjoy a coastal tour while boating in along the coast, the history and homes of this exotic getaway of the rich and famous are pointed out at this time. Upon arrival visit the unique shops, relax on one of Mustique's white-sand beaches or enjoy the vividness and beauty of the underwater marine life or take an optional taxi tour around the island. The tour continues with a delicious local lunch at an island restaurant . Have a swim before heading back to Bequia. Please note : This power boat experience may have waves and splashing and is not recommended for persons with back problems. Wear your swimsuit under your clothing and bring a towel. Bring a hat, local and US currency and sunscreen.
Port
Bequia
Time
8:30 AM
Duration
6 Hours
Activity Level
Moderate

Add during booking

$269 USD

5
DEC 08, 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

This exclusive sail-away tour will take you through part of the Grenadines archipelago experiencing coastlines garlanded with white-sand beaches as you make your way to Mopion . Along the way, you will sail past Palm Island, a private island is a resort named after the hundreds of coconut palms planted by the original owner over 30 years ago. Continuing on, you will head for Mopion - an islet resembling an atoll in the South Pacific surrounded by a reef lagoon. Upon arrival to Mopion, your mind will be set back decades, as this perfect setting is the antidote for the stresses of everyday life. The crystal-clear waters and white sand are breathtaking - life does not get more ideal than this! On your return, you can enjoy the Captain's special rum punch . But watch out as it has a kick! Please note: Remember your sunblock and beach towels. You may bring along your own snorkel gear from the yacht and you will be taken ashore by small boat as it is illegal to anchor on the reef.
Port
Mayreau
Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate

Add during booking

$89 USD

6
DEC 09, 2026
AT SEA
7
DEC 10, 2026
Kralendijk
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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

8
DEC 11, 2026
Willemstad
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

9
DEC 12, 2026
Oranjestad
ARRIVE
6:00 AM
DISEMBARK
7:00 AM
MARINA
NO
SHORE EXCURSIONS
0

Known for having some of the best beaches in the Caribbean, this Dutch port makes it easy to just ... take it easy. Walk through town to choose your favorite carved wooden door, or spend the day like the Arubans do playing dominos at a beachside table.