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San Juan to Puerto Caldera

Set sail on a 24-day journey, visiting 20 different ports, to experience endless adventures. Begin in the Caribbean, visiting the U.S.V.I., Antigua & Barbuda, Guadeloupe, St. Lucia, Grenada, St. Barthelemy, B.V.I., Puerto Rico, and the Dominican Republic. Savor fresh seafood, walk the cobblestone streets of Old San Juan and Santo Domingo, learn about local rum production, snorkel or scuba dive exquisite coral reefs, and lounge on the most beautiful beaches across the Caribbean. Your journey continues to Colombia, Panama, and Costa Rica for even cultural wonders. Enjoy a taste of Colombian coffee, take a cooking class that highlights local ingredients and traditional recipes, and explore Getsemani in Cartagena, known for its vibrant street art. Celebrate the mid-journey with a Windstar Signature Beach Party in the San Blas Islands, meeting the Kuna Tribe and relaxing on Panama’s beautiful beaches. Witness the engineering marvel of the Panama Canal, one of the Seven Wonders of the Modern World, as you transit through on your way to Costa Rica. Explore a variety of wellness activities once you arrive in Costa Rica, from yoga and paddling to nature walks and birdwatching. You’ll end your voyage with a deeper understanding of the unique cultures and natural beauty that can be found across the Caribbean Sea.

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Day 1: San Juan

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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Day 2: CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)

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.

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Day 3: St. John's

St. John’s is a city of Old World charm and elegance which lingers in the varied architecture of Georgian, Victorian, Vernacular, Romantic and International flavors. The picturesque seafront where tiny, colorful boats are moored, the cheerful wooden buildings carefully refurbished to retain their original features, the vibrant Market Street offering vegetables, fruit and fish and the duty-free Heritage Quay shopping area provide a delightful atmosphere to captivate you. Sites to see include St. John’s Cathedral with its white Baroque towers, the Botanical Garden, St. John’s Antigua Lighthouse, and Fort James.

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Day 4: Les Saintes

This is the Caribbean as you’ve always imagined it, with yacht-filled harbors set against volcanic mountains and endless stretches of palm-fringed beach. The underwater world here attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters.

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Day 5: Pigeon Island

The UNESCO site Pitons’ with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.

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Day 6: St. George's

Inhale the intoxicating aroma of the “Isle of Spice” as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must.

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Day 8: Gustavia

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.

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Day 9: Jost Van Dyke, Great Harbour

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.

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Day 10: Virgin Gorda / Prickly Pear, British Virgin Islands

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.

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Day 11: San Juan

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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Day 12: Isla Catalina

Small Isla Catalina boasts gleaming white-sand beaches ringed by coral reefs beckoning snorkelers. The island is a protected Natural Park where one beach is completely protected from the wind and the sea is delightfully calm. While beaches occupy more than 2/3 of the coastline, Isla Catalina also has unique rocky coasts and cliffs. One of the best diving sites of the Dominican Republic, Muro, can be found here. It boasts an impressive underwater wall over 328 feet deep. Isla Catalina is also the only place in the D.R. where raccoons and wild hares can be found.

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Day 13: Santo Domingo

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.

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Day 15: Cartagena

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.

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Day 16: Cartagena

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.

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Day 17: San Blas, Panama

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.

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Day 18: Colón

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.

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Day 19: Panama Canal

At nearly 48 miles long, on your transit through the Panama Canal you will enter three sets of locks that raise and lower the vessel 85 feet between the calm Pacific Ocean and the shimmering waters of the Atlantic. Your voyage features a daylight hours transit with numerous observation vantage points for outside viewing and comfortable indoor air-conditioned lounges. Expert onboard commentary enhances your journey as you watch the day to day workings of this bucket list experience.

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Day 19: Balboa / Fuerte Amador

One of the entrances to the Panama Canal on the Pacific side, Balboa/Fuerte Amador was founded in 1519 and is a short distance from Panama City. In 2012 Balboa was ranked #1 in Latin America in the category of world's busiest container ports. Sightseeing highlights include the colonial homes, the Administration Building, the Goethals Memorial, the Prado, and the local handicraft markets of traditional Panamanian crafts.

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Day 20: Balboa / Fuerte Amador

One of the entrances to the Panama Canal on the Pacific side, Balboa/Fuerte Amador was founded in 1519 and is a short distance from Panama City. In 2012 Balboa was ranked #1 in Latin America in the category of world's busiest container ports. Sightseeing highlights include the colonial homes, the Administration Building, the Goethals Memorial, the Prado, and the local handicraft markets of traditional Panamanian crafts.

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Day 22: Isla Parida

Located within a Nature Preserve of 50 islands, and part of Chiriqui Marine National Park lovely Isla Parida boasts magnificent beaches, one of which is over 1,300 feet long. The crystal clear waters stay at 82 degrees year round and are filled with marine life. There are numerous hardwood trees like teak, mahogany, and eucalyptus, and fruit trees like mango, banana and coconut trees. Here you will be treated to Windstar's Signature Beach Party on a secluded beach that faces the Pacific Ocean.

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Day 23: Golfo Dulce

Picture Jurassic foliage growing down steep hillsides all the way to the waterline, the hoots of monkeys echoing through trees choked by orchids. Golfo Dulce is one of Costa Rica’s most biodiverse areas, where both the jungle and the sea brim with life. Explore the canals by kayak in search of javelinas, butterflies, and more bird species than in all of North America. This port is accessed with a wet landing.

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Day 24: Quepos

The former banana-exporting town of Quepos is your basecamp for a day of rainforest adventure. Take a walk along trails that weave up to waterfalls, or ride horseback to a beautiful jungle pool. A float trip through a mangrove swamp populated by monkeys, crocodiles, egrets, and herons is also available. Or you may choose a nature walk through Manuel Antonio National Park, with its lovely beaches, easy trails, and abundant animal life.

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Day 25: Puerto Caldera

Located on the Gulf of Nicoya, the small town of Puerto Caldera is one of Costa Rica’s top attractions, perfect for travelers who like more off the beaten path destinations where the native Tico lifestyle can be experienced. It is the gateway to San Jose, Jaco and the big city of Puntarenas, plus Los Suenos and Tortuga Island. Carara National Park is nearby, the rainforest home to crocodiles, over 400 species of birds and is considered the most likely place to see scarlet macaws.