Cruise only (Please call for flight options)
Setting sail from San Juan
Founded by the Spanish in 1521, Puerto Rico's capital is the second oldest European settlement in the Americas. Modern San Juan is a bustling city, home to over a third of the island's population, but the cobbled streets of the Old Town remain the biggest tourist draw. The colonial-era fortifications have been awarded UNESCO World Heritage status, crowned by the imposing waterfront El Morro fortress, and the Old Town is full of attractive, brightly coloured houses. Outside of the Old Town you can find designer shopping on Avenida Ashford, and the north of the city is fringed by beautiful beaches, including fashionable Condado with its hip hotels and bars.
Hunt out the very best chuletas Can-Can and pastelillos – local food at its best is great. Don’t settle for sorry imitations.
Puerto Rico: Isla Culebra
Saint Barthélemy: Gustavia
The tiny French Caribbean island of St Barths is renowned as a haunt of the rich and the famous, and you can certainly live well here if you’ve got the means; the petite capital, Gustavia, boasts an array of gourmet restaurants and chic boutiques aimed squarely at the A-list. The beautiful beaches, on the other hand, are free and open to all.
Montserrat garnered global attention in 1995 when the Soufrière Hills volcano erupted, burying the island’s capital, Plymouth. Although an exclusion zone is still in place in the south, visitors are often surprised by how lush and unspoilt the rest of the island is, home to a colourful variety of birdlife.
Sint Maarten: Philipsburg
Philipsburg is the gateway to an intriguing little Caribbean island with a dual personality: the Dutch side, St. Maarten, is the livelier of the two, with shopping malls, casinos and more of a nightlife scene, while French-speaking St. Martin is a more refined (and more expensive) affair, with a laid-back, continental air and a host of exclusive resorts and restaurants.
British Virgin Islands: Jost Van Dyke
The idyllic island of Jost Van Dyke, named after an early Dutch settler, is known for its laid back vibe and friendly beach bars, including the famous Foxy’s, which counts Keith Richards amongst its past customers. It’s a place to kick back and relax, and the clear blue waters are also perfect for snorkelling.
British Virgin Islands: Virgin Gorda
Languid, laid-back Virgin Gorda is blessed with beautiful beaches and wonderfully friendly people. Life proceeds at a slower pace here, and highlights include The Baths, an unusual collection of granite boulders, grottoes and pools on the island’s southwest shore.
Arriving in San Juan
Here in Puerto Rico it’s all about the history and the sea – you can’t miss the fabulous beaches, and you will enjoy the historic military buildings.
Your home from home
Recent additions to the Windstar fleet, these former Seabourn ships are hugely popular little vessels, for good reason.
What we love
These small ships accommodate just 212 guests in large and recently refurbished all suite accommodation. There's a choice of restaurants and comfortable lounges and plenty of deck space. The ship's marina ensures you can enjoy the complimentary watersports when anchored in hidden bays and tiny coves.
|Crew||140 International Staff|
|Style||This is laid-back luxury at its best with relaxed informal days, refined yet comfortable evenings and a friendly and welcoming crew.|
Tailor-make your trip
Where to stay in Puerto Rico
If you want to stay in San Juan itself, El Convento is definitely the nicest choice. For resort hotels, we love the Ritz Carlton Reserve at Dorado Beach.
Explore Puerto Rico
In the El Yunque rainforest you will find the habitat of Puerto Rico's endangered wildlife - not to mention beautiful views.