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Star Collector: Atlantic Crossing to the Virgin Islands

Summary

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.

Cruise line Windstar Cruises

Duration 21 nights

Type Ocean Cruise

Regions Transatlantic

Itinerary & Map

Cádiz → San Juan (Puerto Rico) 22 days · 9 ports · 2 sea days
Day 1 Cádiz Embark

Believed to be the oldest town on the Iberian Peninsula, the Andalusian port of Cádiz enjoys a stunning location at the edge of a six-mile promontory. The town...

Full description
Day 4 Santa Cruz de Tenerife

The largest of the Canary Islands, Tenerife is a beautiful and scenic island which enjoys year-round sunshine and is dominated by Mount Teide. The mountain rang...

Full description
Day 14 Great Harbour, Jost Van Dyke

Jost Van Dyke, four miles long, is truly known as the 'barefoot island'. The smallest of the British Virgin Islands, it is known as a popular destination for ya...

Full description
Day 15 San Juan (Puerto Rico)

If you associate Puerto Rico's capital with the colonial streets of Old San Juan, then you know only part of the picture. San Juan is a major metropolis, radiat...

Full description
Day 16 At Sea
Day 17 Basseterre, Saint Kitts

Mountainous St. Kitts, the first English settlement in the Leeward Islands, crams some stunning scenery into its 65 square miles (168 square km). Vast, brillian...

Full description
Day 18 Gustavia

You can easily explore all of Gustavia during a two-hour stroll. Some shops close from noon to 3 or 4, so plan lunch accordingly, but stores stay open past 7 in...

Full description
Day 19 Philipsburg

The capital of Dutch St. Maarten stretches about a mile (1½ km) along an isthmus between Great Bay and the Salt Pond and has five parallel streets. Most of the...

Full description
Day 20 Great Harbour, Jost Van Dyke

Jost Van Dyke, four miles long, is truly known as the 'barefoot island'. The smallest of the British Virgin Islands, it is known as a popular destination for ya...

Full description
Day 21 At Sea
Day 22 San Juan (Puerto Rico) Disembark

If you associate Puerto Rico's capital with the colonial streets of Old San Juan, then you know only part of the picture. San Juan is a major metropolis, radiat...

Full description
Scroll for all 22 days
Route overview map
Day 1 Cádiz Embark

Believed to be the oldest town on the Iberian Peninsula, the Andalusian port of Cádiz enjoys a stunning location at the edge of a six-mile promontory. The town...

Full description
Day 4 Santa Cruz de Tenerife

The largest of the Canary Islands, Tenerife is a beautiful and scenic island which enjoys year-round sunshine and is dominated by Mount Teide. The mountain rang...

Full description
Day 14 Great Harbour, Jost Van Dyke

Jost Van Dyke, four miles long, is truly known as the 'barefoot island'. The smallest of the British Virgin Islands, it is known as a popular destination for ya...

Full description
Day 15 San Juan (Puerto Rico)

If you associate Puerto Rico's capital with the colonial streets of Old San Juan, then you know only part of the picture. San Juan is a major metropolis, radiat...

Full description
Day 16 At Sea
Day 17 Basseterre, Saint Kitts

Mountainous St. Kitts, the first English settlement in the Leeward Islands, crams some stunning scenery into its 65 square miles (168 square km). Vast, brillian...

Full description
Day 18 Gustavia

You can easily explore all of Gustavia during a two-hour stroll. Some shops close from noon to 3 or 4, so plan lunch accordingly, but stores stay open past 7 in...

Full description
Day 19 Philipsburg

The capital of Dutch St. Maarten stretches about a mile (1½ km) along an isthmus between Great Bay and the Salt Pond and has five parallel streets. Most of the...

Full description
Day 20 Great Harbour, Jost Van Dyke

Jost Van Dyke, four miles long, is truly known as the 'barefoot island'. The smallest of the British Virgin Islands, it is known as a popular destination for ya...

Full description
Day 21 At Sea
Day 22 San Juan (Puerto Rico) Disembark

If you associate Puerto Rico's capital with the colonial streets of Old San Juan, then you know only part of the picture. San Juan is a major metropolis, radiat...

Full description

Cádiz

Believed to be the oldest town on the Iberian Peninsula, the Andalusian port of Cádiz enjoys a stunning location at the edge of a six-mile promontory. The town itself, with 3,000 years of history, is characterised by pretty white houses with balconies often adorned with colourful flowers. As you wander around be sure to take a stroll through the sizeable Plaza de Espãna, with its large monument dedicated to the first Spanish constitution, which was signed here in 1812. Cádiz has two pleasant seafront promenades which boast fine views of the Atlantic Ocean, and has a lovely park, the Parque Genoves, located close to the sea with an open-air theatre and attractive palm garden. Also notable is the neo-Classical cathedral, capped by a golden dome.

Santa Cruz de Tenerife

The largest of the Canary Islands, Tenerife is a beautiful and scenic island which enjoys year-round sunshine and is dominated by Mount Teide. The mountain range runs through the centre of the island, with fertile valleys on the northern side. In the central part of the range is the gigantic natural crater of the Cañadas del Teide, about 14 miles in diameter. Santa Cruz, the island’s pretty capital, was originally a small fishing village but has now grown into a modern city, and also contains 16th-century civic buildings and ornate private mansions. Near the pier is the Santa Cruz Palmetum, a Botanical Garden covering an area of 29 acres, specialising in palms.

Great Harbour, Jost Van Dyke

Jost Van Dyke, four miles long, is truly known as the 'barefoot island'. The smallest of the British Virgin Islands, it is known as a popular destination for yachts and is celebrated for its casual lifestyle, protected anchorages, fine beaches and beachfront restaurants and bars. The island has fewer than 200 inhabitants and they are widely known as a welcoming people. The island's name conjures up its rich, colorful past. Jost Van Dyke is said to have been named for an early Dutch settler, a former pirate. At Great Harbour, Little Harbour, and White Bay there are safe, protected bays and pristine beaches shaded with coconut palms and seagrape trees. Discover inviting shops selling local treasures, restaurants, and bars. 'The Painkiller', one of the Caribbean’s most popular drinks, originated at the Soggy Dollar Bar. Foxy’s and Gertrude's in White Bay are renowned for drinks made with the island's famous rum, frosty beers, and tales of pirates and sunken treasure. Explore Jost Van Dyke's history in the vegetation-covered ruins of centuries-old sugar mills, or on the old trails that crisscross the island. Revel in the natural beauty of the pristine, untouched beaches. Hike up to the highest spot on the island, Majohnny Point, and take in a stunning 360 degree view of the Caribbean. Relax in the natural 'bubble pool', a popular tourist attraction. Jost Van Dyke conjures up images of what the British Virgin Islands may have looked like many years ago.

San Juan (Puerto Rico)

If you associate Puerto Rico's capital with the colonial streets of Old San Juan, then you know only part of the picture. San Juan is a major metropolis, radiating out from the bay on the Atlantic Ocean that was discovered by Juan Ponce de León. More than a third of the island's nearly 4 million citizens proudly call themselves sanjuaneros. The city may be rooted in the past, but it has its eye on the future. Locals go about their business surrounded by colonial architecture and towering modern structures.By 1508 the explorer Juan Ponce de León had established a colony in an area now known as Caparra, southeast of present-day San Juan. He later moved the settlement north to a more hospitable peninsular location. In 1521, after he became the first colonial governor, Ponce de León switched the name of the island—which was then called San Juan Bautista in honor of St. John the Baptist—with that of the settlement of Puerto Rico ("rich port").Defended by the imposing Castillo San Felipe del Morro (El Morro) and Castillo San Cristóbal, Puerto Rico's administrative and population center remained firmly in Spain's hands until 1898, when it came under U.S. control after the Spanish-American War. Centuries of Spanish rule left an indelible imprint on the city, particularly in the walled area now known as Old San Juan. The area is filled with cobblestone streets and brightly painted, colonial-era structures, and its fortifications have been designated a UNESCO World Heritage Site.Old San Juan is a monument to the past, but most of the rest of the city is planted firmly in the 21st century and draws migrants island-wide and from farther afield to jobs in its businesses and industries. The city captivates residents and visitors alike with its vibrant lifestyle as well as its balmy beaches, pulsing nightclubs, globe-spanning restaurants, and world-class museums. Once you set foot in this city, you may never want to leave.

Basseterre, Saint Kitts

Mountainous St. Kitts, the first English settlement in the Leeward Islands, crams some stunning scenery into its 65 square miles (168 square km). Vast, brilliant green fields of sugarcane (the former cash crop, now slowly being replanted) run to the shore. The fertile, lush island has some fascinating natural and historical attractions: a rain forest replete with waterfalls, thick vines, and secret trails; a central mountain range dominated by the 3,792-foot Mt. Liamuiga, whose crater has long been dormant; and Brimstone Hill, known in the 18th century as the Gibraltar of the West Indies. St. Kitts and Nevis, along with Anguilla, achieved self-government as an associated state of Great Britain in 1967. In 1983 St. Kitts and Nevis became an independent nation. English with a strong West Indian lilt is spoken here. People are friendly but shy; always ask before you take photographs. Also, be sure to wear wraps or shorts over beach attire when you're in public places.

Gustavia

You can easily explore all of Gustavia during a two-hour stroll. Some shops close from noon to 3 or 4, so plan lunch accordingly, but stores stay open past 7 in the evening. Parking in Gustavia is a challenge, especially during vacation times. A good spot to park is rue de la République, alongside the catamarans, yachts, and sailboats.

Philipsburg

The capital of Dutch St. Maarten stretches about a mile (1½ km) along an isthmus between Great Bay and the Salt Pond and has five parallel streets. Most of the village's dozens of shops and restaurants are on Front Street, narrow and cobblestone, closest to Great Bay. It's generally congested when cruise ships are in port, because of its many duty-free shops and several casinos. Little lanes called steegjes connect Front Street with Back Street, which has fewer shops and considerably less congestion. Along the beach is a ½-mile-long (1-km-long) boardwalk with restaurants and several Wi-Fi hot spots.Wathey Square (pronounced watty) is in the heart of the village. Directly across from the square are the town hall and the courthouse, in a striking white building with cupola. The structure was built in 1793 and has served as the commander's home, a fire station, a jail, and a post office. The streets surrounding the square are lined with hotels, duty-free shops, restaurants, and cafés. The Captain Hodge Pier, just off the square, is a good spot to view Great Bay and the beach that stretches alongside.

Date & price

Departs

Mon 6 Dec 2027

from £4,198 pp

Enquire now Call 020 7590 0610

Per person, based on two sharing, cruise only. Updated daily and confirmed when you book.

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