San Juan
San Juan 11/30/2025
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.
|
11/30/2025 |
11/30/2025 |
Cruz Bay, St. John
Cruz Bay, St. John 12/01/2025
Cruz Bay is a vibrant waterfront town located on St. John, one of the U.S. Virgin Islands. Known for its stunning beaches, crystal-clear waters, and laid-back atmosphere, it's a popular destination for tourists seeking relaxation, hiking, and water sports. As the island's main port and hub, Cruz Bay offers a charming blend of local shops, restaurants, and historical sites.
|
12/01/2025 |
12/01/2025 |
Gustavia
Gustavia 12/02/2025
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.
|
12/02/2025 |
12/02/2025 |
Basseterre, St. Kitts
Basseterre, St. Kitts 12/03/2025
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.
|
12/03/2025 |
12/03/2025 |
St. Maarten (Philipsburg)
St. Maarten (Philipsburg) 12/04/2025
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.
|
12/04/2025 |
12/04/2025 |
Jost Van Dyke
Jost Van Dyke 12/05/2025
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.
|
12/05/2025 |
12/05/2025 |
Virgin Gorda
Virgin Gorda 12/06/2025
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. Although 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.
Please note: only guests with shore excursions booked through Windstar can be tendered to Gun Creek.
|
12/06/2025 |
12/06/2025 |
San Juan
San Juan 12/07/2025
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.
|
12/07/2025 |
12/07/2025 |
Santo Domingo
Santo Domingo 12/08/2025
La Capital, as Santo Domingo is affectionately known, is a UNESCO site and one of the oldest cities in the Caribbean, with Zona Colonial buildings dating back to the 1500s. Santo Domingo is also considered the most modern metropolis in the Caribbean doing a great job of converging old and new. At the heart of the Zona Colonial, a pedestrian-friendly maze of cobblestones and interesting architecture is the first cathedral built in the New World. Find time to sample the aromatic coffee and cacao.
|
12/08/2025 |
12/08/2025 |
At Sea
|
12/09/2025 |
12/09/2025 |
Cartagena (Colombia)
Cartagena (Colombia) 12/10/2025
Welcome to the sparkling city of Cartagena, where the gold and jewels of the Spanish Main awaited shipment across the Atlantic. No pirate could resist, nor will you be able to when you visit this historic city. The Old Town, a UNESCO World Heritage Site, is surrounded by 400-year-old walls and contains a plethora of churches, fortresses, and restored colonial mansions. Outside the walls are more treasures: Climb the massive Castillo de San Felipe to investigate its maze of hidden tunnels, or shop for the perfect emerald.
|
12/10/2025 |
12/10/2025 |
Cartagena (Colombia)
Cartagena (Colombia) 12/11/2025
Welcome to the sparkling city of Cartagena, where the gold and jewels of the Spanish Main awaited shipment across the Atlantic. No pirate could resist, nor will you be able to when you visit this historic city. The Old Town, a UNESCO World Heritage Site, is surrounded by 400-year-old walls and contains a plethora of churches, fortresses, and restored colonial mansions. Outside the walls are more treasures: Climb the massive Castillo de San Felipe to investigate its maze of hidden tunnels, or shop for the perfect emerald.
|
12/11/2025 |
12/11/2025 |
San Blas Islands
San Blas Islands 12/12/2025
The San Blas Islands of Panama is an archipelago comprising approximately 378 islands and cays, of which 49 are inhabited, some by the Kuna people. Scattered over an area of about 100 square miles, the islands are the number 1 vacation destination in Panama although the Kuna work hard to protect their land against overwhelming tourism and keep the islands healthy and lovely, unique and untouched by culture. These white-sand and palm tree lined islands are encompassed by a coral reef and warm, crystal-clear water that is perfect for snorkeling and is home to a variety of marine life including dolphins, sharks and giant manta rays.
|
12/12/2025 |
12/12/2025 |
Colon (Panama)
Colon (Panama) 12/13/2025
Explore the inner workings of the Panama Canal, head into the jungle to meet with Embera Indians, or take an aerial tram ride through the rainforest canopy.
|
12/13/2025 |
12/13/2025 |