Windward Ways & Tobago Cays

Mar 15, 2026 — Mar 22, 2026

Starting from

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ORANJESTAD, ARUBA → BRIDGETOWN, BARBADOS

7 Nights on Star Pride

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.

Additional Information

1
MAR 15, 2026
Oranjestad
EMBARK
1:00 PM
DEPART
6:00 PM
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.

2
MAR 16, 2026
Kralendijk
ARRIVE
8:00 AM
DEPART
8:00 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, Samur Sail, Beach & Snorkel

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$79

Kralendijk, Bonaire Highlights

Time
9:00 AM
Duration
2.75 Hours
Activity Level
Easy
Price
$79

Kralendijk, Snorkel Safari by Sustainable Catamaran

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$79

Kralendijk, Kralendijk by Eco Powered Tuk-Tuk

Time
10:00 AM
Duration
1 Hours
Activity Level
Easy
Price
$45

Kralendijk, Kayak, Beach & Snorkel

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Moderate-Strenuous
Price
$75

Kralendijk, Bonaire Glass Bottom Boat

Time
8:30 AM
Duration
1.5 Hours
Activity Level
Easy
Price
$65

Kralendijk, Experience Bonaires Fishing (Easy-Moderate)

Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate-Strenuous
Price
$349
3
MAR 17, 2026
AT SEA
4
MAR 18, 2026
Kingstown
ARRIVE
7:00 AM
DEPART
12:30 PM
MARINA
NO
SHORE EXCURSIONS
4

Charming Kingstown, the capital and main commercial center of St. Vincent & the Grenadines is known for its churches, cobblestone streets, colonial buildings and the St. Vincent Botanical Gardens, founded in 1765.  Steep hills surround the town, with Fort Charlotte sitting high on a ridge north of the city, offering panoramic views of Kingstown and the surrounding islands.  Other sites to see include St. George's Anglican Cathedral, an 1820s structure adorned with stained glass windows, St. Mary's Catholic Cathedral, built in 1823, with its lovely Gothic spires and Romanesque columns and arches.

Kingstown, South Coast Cruise Walk and Snorkel

Time
8:00 AM
Duration
3 Hours
Activity Level
Strenuous
Price
$109

Kingstown, Dolphin Watching with Black Sand Swimming

Time
8:00 AM
Duration
3 Hours
Activity Level
Moderate
Price
$109

Kingstown, Vermont Nature Trail

Time
8:00 AM
Duration
4.5 Hours
Activity Level
Strenuous
Price
$119

Kingstown, Discover St. Vincent

Time
8:00 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$99
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.

5
MAR 19, 2026
Bequia
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
6

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, Concierge Collection: Rum Tasting at Firefly Plantation

Time
10:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$169

Bequia Snorkel Adventure

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

Bequia, Bequia Fort & Lower Beach Getaway *

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

Bequia Highlights

Time
9:00 AM
Duration
2.5 Hours
Activity Level
Easy-Moderate
Price
$89

Bequia, Mustique Magic with Lunch

Time
8:30 AM
Duration
6 Hours
Activity Level
Moderate
Price
$269

Bequia, Taste of Bequia

Time
10:00 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate
Price
$149
6
MAR 20, 2026
Mayreau
ARRIVE
8:00 AM
DEPART
5:00 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
7
MAR 21, 2026
Scarborough, Tobago
ARRIVE
7:00 AM
DEPART
4:00 PM
MARINA
NO
SHORE EXCURSIONS
5

Scarborough, Tobago

Scarborough, Pigeon Point Beach Trip

Time
10:00 AM
Duration
4 Hours
Activity Level
Easy
Price
$49

Scarborough, Tobago Cocoa Discovery

Time
8:45 AM
Duration
4 Hours
Activity Level
Moderate
Price
$109

Scarborough, Angel Reef by Glass Bottom Boat

Time
9:00 AM
Duration
2.5 Hours
Activity Level
Moderate
Price
$89

Scarborough, Tobago Rainforest Hike

Time
8:30 AM
Duration
5 Hours
Activity Level
Strenuous
Price
$109

Scarborough, Argyle Waterfalls

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

Star Pride

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 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 400 sq ft
Max. Occupancy 2 Passengers
Amenities

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Room Size 277 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.