- Itinerary
- Highlights
- Yacht
- Staterooms
-
Book Now
Island Trails: Aruba to the Virgin Islands
Mar 6, 2028 — Mar 13, 2028
Starting from
ORANJESTAD, ARUBA → SAN JUAN
7 Nights on Star Pride
Discover natural wonders along northern and southern Caribbean beaches during this seven night voyage ranging from islands off South America to Puerto Rico. Roll into Curacao's lush wilds on a 4x4 tour seeking sunning lizards and pink flamingos. Snorkel between coral reefs and undulating sea grass at Bonaire Marine Park, a 6,700-acre sanctuary rich in tarpon, parrotfish, reef perch, and several sea turtle species. Sip sparkling wine or your preferred beverage during a romantic sunset sailing beyond the twinkling lights of Gustavia Harbor's nightlife. Swim and play with friendly dolphins on balmy Jost Van Dyke. Explore the landmark Baths--massive granite boulders--on the white powdery sands of Virgin Gorda prior to spending the afternoon on this warm beach or in Devil's Bay's clear waters.
Popular Highlights
Wander through the Baths’ massive granite boulders on Virgin Gorda before relaxing on powder-white sands.
Explore Oranjestad’s Dutch-Caribbean architecture while sampling Aruba’s local pastechi and fresh seafood.
Sail past Gustavia’s glowing harbor lights during a romantic sunset cruise with sparkling wine in hand.
Spot wild pink flamingos and sunning iguanas on a rugged 4x4 adventure through Curacao’s backcountry.
Join a marine guide in Bonaire to identify colorful reef fish thriving in protected waters.
Enjoy Windstar’s Signature Beach Party, where the Caribbean spirit is in full swing.

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.

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

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
Available Excursions
Kralendijk
Time
7:30 AMDuration
3 HoursActivity Level
Moderate-StrenuousAdd during booking
$79
Kralendijk
Time
7:30 AMDuration
2.5 HoursActivity Level
Moderate-StrenuousAdd during booking
$79
Kralendijk
Time
7:30 AMDuration
1 HoursActivity Level
EasyAdd during booking
$49
Kralendijk
Time
7:30 AMDuration
2.75 HoursActivity Level
EasyAdd during booking
$79
Kralendijk
Time
7:30 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$89
Kralendijk
Time
7:30 AMDuration
4 HoursActivity Level
Moderate-StrenuousAdd during booking
$369
Kralendijk
Time
7:30 AMDuration
1.5 HoursActivity Level
EasyAdd during booking
$69

Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by.

For an island comprised of a mere eight square miles, it's amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis Drake Waterway. After all that, you'll be ready for an evening drink on the beach - where you can admire your Windstar ship aglow in the harbor.

The beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called "The Baths," which form huge underground pools and caverns
Available Excursions
Virgin Gorda / Prickly Pear, British Virgin Islands
Time
8:30 AMDuration
4 HoursActivity Level
StrenuousAdd during booking
$99
Virgin Gorda / Prickly Pear, British Virgin Islands
Time
8:30 AMDuration
2.75 HoursActivity Level
Moderate-StrenuousAdd during booking
$299

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.
Staterooms
Starting from
Starting from
Starting from
Starting from
Starting from
Starting from
Starting from
Starting from
Starting from
Available Dates
No other dates are available.