14-night Europe cruise: Lisbon to San Juan, Puerto Rico on Star Legend
The Star Collector: Atlantic Crossing to the Virgin Islands is a 14-night Europe cruise aboard Star Legend, operated by Windstar Cruises. Departing Lisbon on December 6, 2027 and arriving in San Juan, Puerto Rico on December 20, 2027, the voyage visits 4 ports including Funchal, Jost Van Dyke. Fares start from $7,770 per person.
Fixed editorial images from the places on this itinerary. They stay stable each time you return to this sailing.
Lisbon
Lisbon, the capital of Portugal, is a city open to the sea and carefully planned with 18th-century elegance. Its founder is said to be the legendary Ulysses, but the theory of an original Phoenician settlement is probably more realistic. Known in Portugal as Lisboa, the city was inhabited by the Romans, Visigoths and, beginning in the 8th century, the Moors. Much of the 16th century was a period of great prosperity and overseas expansion for Portugal. Tragedy struck on All Saints' Day in 1755 with a devastating earthquake that killed about 40,000 people. The destruction of Lisbon shocked the continent. As a result, the Baixa (lower city) emerged in a single phase of building, carried out in less than a decade by the royal minister, the Marques de Pombal. His carefully planned layout of a perfect neo-classical grid survived to this day and remains the heart of the city. Evidence of pre-quake Lisbon can still be seen in the Belém suburb and the old Moorish section of the Alfama that sprawls below the Castle of St. George.
Lisbon is a compact city on the banks of the Tagus River. Visitors find it easy to get around as many places of interest are in the vicinity of the central downtown area. There is a convenient bus and tram system and taxis are plentiful. Rossio Square, the heart of Lisbon since medieval times, is an ideal place to start exploring. After a fire destroyed parts of the historic neighborhood behind Rossio in 1988, many of the restored buildings emerged with modern interiors behind the original façades.
The city boasts a good many monuments and museums, such as the Jeronimos Monastery, Tower of Belém, the Royal Coach Museum and the Gulbenkian Museum. High above the Baixa is the Bairro Alto (upper city) with its teeming nightlife. The easiest way to connect between the two areas is via the public elevator designed by Gustave Eiffel.
Cruising up the Tagus River to the ship's berth, you can already spot three of Lisbon's famous landmarks: the Monument to the Discoveries, the Tower of Belém and the Statue of Christ, which welcomes visitors from its hilltop location high above Europe's longest suspension bridge.
Funchal
As you arrive in Funchal on an MSC cruise, your ship will cast anchor in a bay protected by mountains rising straight up behind the port. The name, Funchal, derives from that of the fennel plant, the funcho still used today in the traditional sweets known as rebuçados de funcho, that one can find anywhere on the island of Madeira.
An excursion will take you around the town centre, to visit historic churches, from the A Sé Cathedral, with its inlaid ceiling, to the majestic Church of the Incarnation, to the church of Carmo without a vault.
Another MSC excursion will take you up to the village of Monte, from where one can admire a spectacular view of the Funchal bay. You can visit its 18th century church and the tomb of the last Austrian emperor, Charles I, and stroll around the magnificent botanic gardens. But if you like heights, there’s nothing more impressive than the Cabo Girão and its 589 metre tall cliffs, amongst the highest in the world, at the foot of which lie the cultivated lands known as Fajãs do Cabo Girão.
If you’re looking for an equipped beach during your MSC cruise, another excursion will take you to Machico. Founded in the 15th century, it hosts the oldest religious building on the island, the Capela dos Milagres, and the fortresses of São João Baptista and Nossa Senhora do Amparo built in the beginning of the 16th century.
The more lively tourist attraction is instead in Calheta, on the south-west coast. Splendid yachts cruising across the Atlantic are moored in the port and if you want to go for a swim there are two beautiful beaches of golden sand; in spite of the modern structures Calheta dates back to the mid-15th century. This is where they make the “Aguardente”, the best white rhum, and fundamental ingredient of Madeira’s typical drink, the “Poncha” .
San Juan, Puerto Rico
Blessed with some of the oldest buildings in the Western Hemisphere, San Juan, Puerto Rico’s cap-ital, is romantically charming with its bright pastel Spanish colonial facades, wrought-iron balconies abloom with flowers, narrow cobblestone streets and beloved park squares. Once you arrive on an MSC Caribbean and Antilles cruise at the port, explore Old San Juan (Viejo San Juan), a UNESCO World Heritage district, widely renowned for the fortresses of Castillo San Felipe del Morro and the Castillo San Cristóbal.
The old town occupies the headland of a 2.5-mile-long island (connected by bridge to the mainland) that shelters San Juan Bay, for centuries a key port in the New World. It was originally known as Puerto Rico, or “rich port,” because its location made it the perfect stop for shipping.
Several MSC excursions offer walking tours that let you soak up amazing views of San Juan, while making cultural discoveries of a lifetime. Wander through the old town along the Paseo de la Princesa, San Juan’s oldest tree-lined avenue; head up its southern city wall, La Muralla, which until the late 19th century encircled all of Old San Juan with sandstone; and tour the 16th-century fortress of El Morro, with its six different lines of defence.
Take a coffee-tasting walking tour to explore Puerto Rico’s rich coffee culture, and learn how the island’s rich volcanic soil and climate have contributed to the rise of coffee as one of its main crops. Taste a delicious cup of freshly brewed Puerto Rican café con leche, learn about the island's historical ties with the caffeine-rich beverage, and explore how coffee and the church are connected on this MSC excursion through the streets of Old San Juan.
Or savour San Juan’s culinary delights, in a Martha Stewart excursion curated exclusively for MSC that will have you tasting local cuisine and drinks at five destinations along the route through the fortified colonial city. From Puerto Rican fritters at historic El Convento Hotel, to chocolate tasting at a fourth-generation chocolatier, you won’t want to miss this tour, which ends at La Casita de Rones for a rum lesson and a piña colada, the national drink of Puerto Rico.
With more than 80% of the world's rum coming from Puerto Rico, delve deeper into the spirit on an MSC excursion to Casa Bacardí in the town of Cataño. Discover the story behind Bacardí’s legendary cocktails, sniff the products on display and learn about the rum-making process including wood barrelling, ageing and finishing. For the grand finale, enjoy a fascinating mixology show.
Nature lovers will not want to miss a visit to El Yunque, the only tropical rainforest in the U.S. territory and one of Puerto Rico's finest spots of natural beauty. Marvel at its small horsetail waterfalls, giant ferns and tropical hardwoods.
For an enchanting experience, kayak into the enchanting bioluminescent bay at Laguna Grande of Fajardo on another MSC excursion. Under the blanket of the night sky and the lighthouse of Fajardo, paddle through the water and watch it glow with the bioluminescence of millions and millions of tiny organisms.
Prices come from third-party data feeds via Windstar Cruises and may differ from the cruise line's current fare. Confirm the final price before booking. How our pricing works
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With only 212 guests, a Star Legend cruise will make you feel like you're on board your own private small ship almost as soon as you step aboard.
The sitting area of your spacious, newly refurbished suite gives you an expansive ocean view — making it a welcome retreat.
When you're ready to make an appearance, the lounges, club, and library are waiting to be explored. Take some "you" time in the tranquil WindSpa . . . enjoy a dip in the pool . . . work off that decadent dessert in the Fitness Center . . . and, of course, you are always welcome to visit the Bridge to examine navigation charts with the Captain.
Star Legend is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach.
Take a tour to see her beautiful spaces.
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