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Star Collector: Atlantic Crossing to the Virgin Islands
Dec 6, 2027 — Dec 27, 2027
Starting from
Complimentary All-In Package
Free Laundry for Collectors:
Reduced Deposit
CADIZ → SAN JUAN
21 Nights on Star Legend
This extended Atlantic-to-Caribbean sailing follows a rare winter route that links Europe, the open ocean, and the islands of the eastern Caribbean in one continuous journey, with experiences shaped by both destination and time at sea. Begin in Lisbon with its historic neighborhoods and riverfront cafés, then pause in Madeira for botanical gardens, coastal walks, and views from Monte. A true transoceanic crossing follows, offering days to settle into shipboard life before landfall in the Caribbean. Once there, small-ship access opens the door to snorkeling off Jost Van Dyke, beach time at Virgin Gorda’s Prickly Pear, exploring colonial streets in San Juan, and dining ashore in Gustavia after sunset. Cruz Bay and Basseterre invite hiking, sailing, and easy island exploration, creating a journey defined by variety, distance, and unhurried discovery.




Popular Highlights
Admire the incredible views from El Morro’s 16th century ramparts, a UNESCO World Heritage Site, in San Juan
Let the Bubbly Pool on Jost Van Dyke wash your cares away
Visit Madeira for gardens, coastal viewpoints, and island walks before turning west toward open water.
Arrive in the Caribbean with small-ship access to places larger vessels cannot reach, including Jost Van Dyke and Cruz Bay.
Enjoy a long stretch of days at sea that allows time to settle into shipboard life and onboard enrichment.
Snorkel clear waters, relax on secluded beaches, and sail calm bays in the British Virgin Islands

Cádiz is the most southern province of the Iberian Peninsula. It is extremely rich in natural beauty and some of the most important Natural Parks of Spain and Europe are found here including Sierra de Grazalema and los Alcornocales. Both are rich in flora and fauna, including species under threat of extinction. Many birds find their resting and feeding place here just after or before making the jump from or to Africa.

Here in this privileged setting you'll discover two UNESCO World Heritage Site beaches of tantalizing beauty; San Cristóbal de La Laguna; and the island's symbol, Teide National Park. Wide avenues, exotic landscapes, and striking examples of modernist architecture complete one of the world's most popular destinations.
Available Excursions
Santa Cruz de Tenerife
Time
8:00 AMDuration
4.5 HoursActivity Level
ModerateAdd during booking
$105
Santa Cruz de Tenerife
Time
8:00 AMDuration
5.5 HoursActivity Level
ModerateAdd during booking
$139
Santa Cruz de Tenerife
Time
8:00 AMDuration
5.5 HoursActivity Level
ModerateAdd during booking
$119
Santa Cruz de Tenerife
Time
9:45 AMDuration
5 HoursActivity Level
Easy-ModerateAdd during booking
$165
Santa Cruz de Tenerife
Time
9:30 AMDuration
4.5 HoursActivity Level
ModerateAdd during booking
$105

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 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.
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Available Excursions
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AMDuration
2.5 HoursActivity Level
EasyAdd during booking
$99
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AMDuration
3.5 HoursActivity Level
ModerateAdd during booking
$139
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$149
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$139

With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean's small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.
Available Excursions
Basseterre
Time
8:30 AMDuration
3.25 HoursActivity Level
Easy-ModerateAdd during booking
$89
Basseterre
Time
8:30 AMDuration
4 HoursActivity Level
StrenuousAdd during booking
$129
Basseterre
Time
8:30 AMDuration
3 HoursActivity Level
StrenuousAdd during booking
$139
Basseterre
Time
9:00 AMDuration
3.5 HoursActivity Level
EasyAdd during booking
$99
Basseterre
Time
10:30 AMDuration
2.5 HoursActivity Level
ModerateAdd 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.

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.

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.
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Available Dates
No other dates are available.