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Windward Ways & Tobago Cays
Dec 4, 2026 — Dec 12, 2026
Starting from
Complimentary All-In Package
Reduced Deposit
BRIDGETOWN, BARBADOS → ORANJESTAD, ARUBA
8 Nights on Star Legend
Dive, snorkel and swim with fish and sea turtles in Tobago's newly established Speyside Marine Protected Area and Tobago Cays Marine Park. 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. 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
Four magical colonial towns (including two that are UNESCO-listed) contrast with out-of-the-way ports and bays.
Snorkel the impressive coral reefs of Tobago Cays at the confluence of the Atlantic Ocean and Caribbean Sea.
The dramatic twin volcanic spires of the Pitons rise majestically from St. Lucia's lush coastline, creating one of the Caribbean's most breathtaking sailing backdrops.
Visit Mayreau, the smallest island of the Grenadines, and enjoy the exclusive Signature Beach Party.
Willemstad is a UNESCO site known for its brightly colored architecture.
Additional Information

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.
Available Excursions
Bridgetown
Time
6:30 AMDuration
4.5 HoursActivity Level
ModerateAdd during booking
$129

Rodney Bay, Saint Lucia
Available Excursions
Rodney Bay
Time
9:00 AMDuration
3.5 HoursActivity Level
ModerateAdd during booking
$159
Rodney Bay
Time
9:30 AMDuration
2 HoursActivity Level
Easy-ModerateAdd during booking
$129
Rodney Bay
Time
9:45 AMDuration
3 HoursActivity Level
Easy-ModerateAdd during booking
$189
Rodney Bay
Time
8:30 AMDuration
5 HoursActivity Level
EasyAdd during booking
$169
Rodney Bay
Time
9:30 AMDuration
3 HoursActivity Level
Moderate-StrenuousAdd during booking
$139
Rodney Bay
Time
8:30 AMDuration
5 HoursActivity Level
Moderate-StrenuousAdd during booking
$119
Rodney Bay
Time
9:00 AMDuration
3 HoursActivity Level
EasyAdd during booking
$59
Rodney Bay
Time
9:00 AMDuration
2.5 HoursActivity Level
ModerateAdd during booking
$109

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.

Scarborough, Tobago
Available Excursions
Scarborough, Tobago
A relaxed half-day escape to Tobago's most iconic beach, with time to swim, sunbathe, and enjoy beachside dining.
Time
10:00 AMDuration
5 HoursActivity Level
EasyAdd during booking
$79
Scarborough, Tobago
Time
1:00 PMDuration
2.5 HoursActivity Level
ModerateAdd during booking
$89
Scarborough, Tobago
Time
8:30 AMDuration
5 HoursActivity Level
StrenuousAdd during booking
$119
Scarborough, Tobago
A guided nature tour through Tobago's Adventure Farm bird sanctuary and the historic Fort Bennett overlooking Great Courland Bay.
Time
9:15 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$79
Scarborough, Tobago
Time
8:45 AMDuration
2.5 HoursActivity Level
ModerateAdd during booking
$89
Scarborough, Tobago
A guided nature tour through Tobago's Adventure Farm bird sanctuary and the historic Fort Bennett overlooking Great Courland Bay.
Time
12:30 PMDuration
3 HoursActivity Level
ModerateAdd during booking
$79
Scarborough, Tobago
Time
8:30 AMDuration
4 HoursActivity Level
ModerateAdd during booking
$99
Scarborough, Tobago
Time
9:00 AMDuration
4 HoursActivity Level
ModerateAdd during booking
$119

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.
Available Excursions
Bequia
A scenic powerboat cruise along Bequia's coastline with a snorkeling stop at Petit Nevis.
Time
8:30 AMDuration
3 HoursActivity Level
StrenuousAdd during booking
$129
Bequia
Time
8:30 AMDuration
3 HoursActivity Level
Easy-ModerateAdd during booking
$109
Bequia
A guided walking and culinary tour through Bequia's waterfront restaurants, sampling authentic Caribbean dishes and cocktails.
Time
8:30 AMDuration
3.5 HoursActivity Level
Easy-ModerateAdd during booking
$149
Bequia
Time
8:30 AMDuration
2.5 HoursActivity Level
Easy-ModerateAdd during booking
$89
Bequia
A boat excursion to the exclusive island of Mustique for beach time, shopping, and a waterfront lunch at the famous Basil's Bar.
Time
8:30 AMDuration
6 HoursActivity Level
ModerateAdd during booking
$299

Mayreau is the smallest inhabited island of St. Vincent and the Grenadines, covering just about 1.5 square miles with a population of only a few hundred people. Tucked between Union Island and the Tobago Cays in the southern Grenadines, it's known for its laid-back, off-the-grid charm—there are no airports, no banks, and only one small village (Old Wall) perched on a hillside.

Inhale the intoxicating aroma of the "Isle of Spice" as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must.
Available Excursions
St. George's
Time
8:30 AMDuration
4 HoursActivity Level
Easy-ModerateAdd during booking
$69
St. George's
Time
8:30 AMDuration
2 HoursActivity Level
Moderate-StrenuousAdd during booking
$119
St. George's
Time
8:30 AMDuration
3 HoursActivity Level
Moderate-StrenuousAdd during booking
$89
St. George's
Time
8:30 AMDuration
7.5 HoursActivity Level
EasyAdd during booking
$179
St. George's
Time
8:30 AMDuration
4.25 HoursActivity Level
Moderate-StrenuousAdd during booking
$329
St. George's
Time
8:30 AMDuration
3.5 HoursActivity Level
Moderate-StrenuousAdd during booking
$109
St. George's
Time
8:30 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$79
St. George's
Time
8:30 AMDuration
4.5 HoursActivity Level
ModerateAdd during booking
$289
St. George's
Time
8:30 AMDuration
3 HoursActivity Level
Easy-ModerateAdd during booking
$119
St. George's
Time
8:30 AMDuration
3.5 HoursActivity Level
Moderate-StrenuousAdd during booking
$229

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.
Available Excursions
Willemstad
Time
8:30 AMDuration
2.75 HoursActivity Level
StrenuousAdd during booking
$89
Willemstad
Time
8:30 AMDuration
5 HoursActivity Level
Easy-ModerateAdd during booking
$169
Willemstad
Time
8:30 AMDuration
5 HoursActivity Level
Moderate-StrenuousAdd during booking
$149
Willemstad
Time
8:30 AMDuration
1.5 HoursActivity Level
Moderate-StrenuousAdd during booking
$39
Willemstad
Time
8:30 AMDuration
4 HoursActivity Level
Easy-ModerateAdd during booking
$89
Willemstad
Time
8:30 AMDuration
4 HoursActivity Level
EasyAdd during booking
$49

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.
Staterooms
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Available Dates
| Date | Yacht | Starting from | Actions |
|---|---|---|---|
| Feb 22 (Mon) – Mar 2 (Tue), 2027February 22 (Mon) – March 2 (Tue), 2027 | Star Legend |