14 days - Star Collector: Lovely Leewards [San Juan to San Juan]
![14 days - Star Collector: Lovely Leewards [San Juan to San Juan]](/images/packages/extraimages/3190_14Days-Star-Collector-Lovely-Leewards26112022.jpg "14 days - Star Collector: Lovely Leewards [San Juan to San Juan]")
Starting from
$4,099*
San Juan to San Juan
Ship: Star Pride | Star Seeker
Departure Date : Nov 02 2025 | Nov 09 2025 | Nov 16 2025 | Nov 23 2025 | Jan 23 2026 | Jan 30 2026 | Feb 06 2026 | Feb 13 2026 | Feb 20 2026 | Feb 27 2026 | Mar 06 2026
Itinerary
Day San Juan, Puerto RicoDepart 10:00 PM
"Back in the 1500s, Puerto Rico was one of the first Caribbean islands to be settled, and its capital, today's San Juan, became a vital hub of Spains New World colonies. The historic part of the city, known as Old San Juan, is now a UNESCO World Heritage Site; it's also a National Historic Site within the U.S. National Park Service. Strolling the narrow cobblestoned streets of Old San Juan, you'll discover a historic treasure surrounded by massive city walls. You can climb the ramparts of imposing fortresses like El Morro, at the entrance to the bay, and visit the Cathedral of San Juan Bautista, one of the oldest churches in the Americas and the final resting place of the citys founder, Ponce de León. Modern San Juan extends well beyond the historic district and offers diversions of its own. Condado, a lively beachfront neighborhood, has high-rise resorts and trendy waterfront bars. Visitors may sample one of Puerto Ricos best-known products at Casa Bacardí, the rum distillery across the bay. And stunning natural wonders await just outside the city, including the rain forest and waterfalls of El Yunque National Forest and the otherworldly lights of Fajardos bioluminescent bay. "
"Back in the 1500s, Puerto Rico was one of the first Caribbean islands to be settled, and its capital, today's San Juan, became a vital hub of Spains New World colonies. The historic part of the city, known as Old San Juan, is now a UNESCO World Heritage Site; it's also a National Historic Site within the U.S. National Park Service. Strolling the narrow cobblestoned streets of Old San Juan, you'll discover a historic treasure surrounded by massive city walls. You can climb the ramparts of imposing fortresses like El Morro, at the entrance to the bay, and visit the Cathedral of San Juan Bautista, one of the oldest churches in the Americas and the final resting place of the citys founder, Ponce de León. Modern San Juan extends well beyond the historic district and offers diversions of its own. Condado, a lively beachfront neighborhood, has high-rise resorts and trendy waterfront bars. Visitors may sample one of Puerto Ricos best-known products at Casa Bacardí, the rum distillery across the bay. And stunning natural wonders await just outside the city, including the rain forest and waterfalls of El Yunque National Forest and the otherworldly lights of Fajardos bioluminescent bay. "
Day Gustavia, Saint BarthelemyArrive 10:00 AM Departs 10:00PM
"St. Barts, a French territory in the Caribbean's Leeward Islands, is the ultimate jet-set beach destination. Its 14 pristine beaches are jewels set in sparkling waters, the cuisine is infused with a French flair and the scene is cosmopolitan chic. Other islands in the region might be casual and laid-back, but here the dress code is stylish caftans, oversize sunglasses and sky-high heels. And the preferred mode of transportation is the yacht. Gustavia, the capital and main port of St. Barts (also spelled St. Barths), embodies the island's international appeal. A former fishing village, it was named for King Gustav III of Swedenthe Swedes occupied the island in the early 19th century, leaving a legacy of names and sites. The town's winding streets are lined with high-end boutiques, excellent restaurants and plenty of bars where you can toast your visit with a glass of refreshing rosé. A handful of historic sites, including forts and a lighthouse, add to the attractions. "
"St. Barts, a French territory in the Caribbean's Leeward Islands, is the ultimate jet-set beach destination. Its 14 pristine beaches are jewels set in sparkling waters, the cuisine is infused with a French flair and the scene is cosmopolitan chic. Other islands in the region might be casual and laid-back, but here the dress code is stylish caftans, oversize sunglasses and sky-high heels. And the preferred mode of transportation is the yacht. Gustavia, the capital and main port of St. Barts (also spelled St. Barths), embodies the island's international appeal. A former fishing village, it was named for King Gustav III of Swedenthe Swedes occupied the island in the early 19th century, leaving a legacy of names and sites. The town's winding streets are lined with high-end boutiques, excellent restaurants and plenty of bars where you can toast your visit with a glass of refreshing rosé. A handful of historic sites, including forts and a lighthouse, add to the attractions. "
Day Little Bay, Montserrat, BWIArrives 08:00 AM Departs 5:00 PM
Today we visit Pompeii of the Caribbeanan island that is half lush and green, half gray and covered in ash by a volcano in 1995. And if a half-buried city isnt intriguing enough, there are black-sand beaches and a perplexing Irish heritage to explore.
Today we visit Pompeii of the Caribbeanan island that is half lush and green, half gray and covered in ash by a volcano in 1995. And if a half-buried city isnt intriguing enough, there are black-sand beaches and a perplexing Irish heritage to explore.
Day Philipsburg, Sint MaartenArrives 07:00 AM Departs 10:00 PM
"This Leeward island has been famously bisected into French and Dutch territories since 1648, and is referred to both as Saint Martin and Sint Maarten. In their respective capitals�Marigot and Philipsburg�there are ancient stone forts and candy-colored buildings lining winding streets. The Dutch side has a slightly larger population but is a bit smaller, at 34 square kilometers (13 square miles), versus the 53-square-kilometer (20-square-mile) Saint Martin. Named for its founder John Philips, Philipsburg, the capital of the Dutch side, has some excellent international art galleries, thumping discos and popular casinos. Farther afield are beautiful beaches and a seemingly endless array of nature conservancies. With them come extensive opportunities for adventure�hiking, biking and zip lining�and amazing wildlife sightings in the sea, on land and in the sky."
"This Leeward island has been famously bisected into French and Dutch territories since 1648, and is referred to both as Saint Martin and Sint Maarten. In their respective capitals�Marigot and Philipsburg�there are ancient stone forts and candy-colored buildings lining winding streets. The Dutch side has a slightly larger population but is a bit smaller, at 34 square kilometers (13 square miles), versus the 53-square-kilometer (20-square-mile) Saint Martin. Named for its founder John Philips, Philipsburg, the capital of the Dutch side, has some excellent international art galleries, thumping discos and popular casinos. Farther afield are beautiful beaches and a seemingly endless array of nature conservancies. With them come extensive opportunities for adventure�hiking, biking and zip lining�and amazing wildlife sightings in the sea, on land and in the sky."
Day Jost Van Dyke, Great Harbour, B.V.I.Arrives 08:00 AM Departs 11:59 PM
For an island comprised of a mere eight square miles, its 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, youll be ready for an evening drink on the beach where you can admire your Windstar ship aglow in the harbor.
For an island comprised of a mere eight square miles, its 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, youll be ready for an evening drink on the beach where you can admire your Windstar ship aglow in the harbor.
Day Virgin Gorda, Prickly Pear Beach, B.V.IArrive 08:00 AM Depart 05:00 PM
A beautiful coral reef wavers just beneath you as your ship makes the break into exclusive North Sound. You can imagine the reaction of the locals watching from The Bitter End Yacht Club as your ship comes around the corner under full canvas. At the other end of the island lies the curious assembly of house-sized boulders called The Baths, which form huge underground pools and caverns that youre free to explore.
A beautiful coral reef wavers just beneath you as your ship makes the break into exclusive North Sound. You can imagine the reaction of the locals watching from The Bitter End Yacht Club as your ship comes around the corner under full canvas. At the other end of the island lies the curious assembly of house-sized boulders called The Baths, which form huge underground pools and caverns that youre free to explore.
Day San Juan, Puerto RicoArrives 07:00 AM Departs 07:00 PM
"Back in the 1500s, Puerto Rico was one of the first Caribbean islands to be settled, and its capital, today's San Juan, became a vital hub of Spains New World colonies. The historic part of the city, known as Old San Juan, is now a UNESCO World Heritage Site; it's also a National Historic Site within the U.S. National Park Service. Strolling the narrow cobblestoned streets of Old San Juan, you'll discover a historic treasure surrounded by massive city walls. You can climb the ramparts of imposing fortresses like El Morro, at the entrance to the bay, and visit the Cathedral of San Juan Bautista, one of the oldest churches in the Americas and the final resting place of the citys founder, Ponce de León. Modern San Juan extends well beyond the historic district and offers diversions of its own. Condado, a lively beachfront neighborhood, has high-rise resorts and trendy waterfront bars. Visitors may sample one of Puerto Ricos best-known products at Casa Bacardí, the rum distillery across the bay. And stunning natural wonders await just outside the city, including the rain forest and waterfalls of El Yunque National Forest and the otherworldly lights of Fajardos bioluminescent bay. "
"Back in the 1500s, Puerto Rico was one of the first Caribbean islands to be settled, and its capital, today's San Juan, became a vital hub of Spains New World colonies. The historic part of the city, known as Old San Juan, is now a UNESCO World Heritage Site; it's also a National Historic Site within the U.S. National Park Service. Strolling the narrow cobblestoned streets of Old San Juan, you'll discover a historic treasure surrounded by massive city walls. You can climb the ramparts of imposing fortresses like El Morro, at the entrance to the bay, and visit the Cathedral of San Juan Bautista, one of the oldest churches in the Americas and the final resting place of the citys founder, Ponce de León. Modern San Juan extends well beyond the historic district and offers diversions of its own. Condado, a lively beachfront neighborhood, has high-rise resorts and trendy waterfront bars. Visitors may sample one of Puerto Ricos best-known products at Casa Bacardí, the rum distillery across the bay. And stunning natural wonders await just outside the city, including the rain forest and waterfalls of El Yunque National Forest and the otherworldly lights of Fajardos bioluminescent bay. "
Day At Sea
Day St. George's, GrenadaArrive 09:00 AM Depart 10:00 PM
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.
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.
Day Bequia, St. Vincent & the GrenadinesArrive 08:00 AM Depart 10:00 PM
The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequias whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the islands famed model boat builders at work on their miniature masterpieces.
The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequias whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the islands famed model boat builders at work on their miniature masterpieces.
Day Pigeon Island, St. LuciaArrive 08:00 AM Depart 05:00 PM
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.
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.
Day Les Saintes, GuadeloupeArrive 08:00 AM Depart 5:00 PM
This is the Caribbean as youve 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.
This is the Caribbean as youve 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.
Day Philipsburg, Sint MaartenArrive 08:00 AM Depart 2:00 PM
"This Leeward island has been famously bisected into French and Dutch territories since 1648, and is referred to both as Saint Martin and Sint Maarten. In their respective capitals�Marigot and Philipsburg�there are ancient stone forts and candy-colored buildings lining winding streets. The Dutch side has a slightly larger population but is a bit smaller, at 34 square kilometers (13 square miles), versus the 53-square-kilometer (20-square-mile) Saint Martin. Named for its founder John Philips, Philipsburg, the capital of the Dutch side, has some excellent international art galleries, thumping discos and popular casinos. Farther afield are beautiful beaches and a seemingly endless array of nature conservancies. With them come extensive opportunities for adventure�hiking, biking and zip lining�and amazing wildlife sightings in the sea, on land and in the sky."
"This Leeward island has been famously bisected into French and Dutch territories since 1648, and is referred to both as Saint Martin and Sint Maarten. In their respective capitals�Marigot and Philipsburg�there are ancient stone forts and candy-colored buildings lining winding streets. The Dutch side has a slightly larger population but is a bit smaller, at 34 square kilometers (13 square miles), versus the 53-square-kilometer (20-square-mile) Saint Martin. Named for its founder John Philips, Philipsburg, the capital of the Dutch side, has some excellent international art galleries, thumping discos and popular casinos. Farther afield are beautiful beaches and a seemingly endless array of nature conservancies. With them come extensive opportunities for adventure�hiking, biking and zip lining�and amazing wildlife sightings in the sea, on land and in the sky."
Day San Juan, Puerto RicoArrive 07:00 AM
"Back in the 1500s, Puerto Rico was one of the first Caribbean islands to be settled, and its capital, today's San Juan, became a vital hub of Spains New World colonies. The historic part of the city, known as Old San Juan, is now a UNESCO World Heritage Site; it's also a National Historic Site within the U.S. National Park Service. Strolling the narrow cobblestoned streets of Old San Juan, you'll discover a historic treasure surrounded by massive city walls. You can climb the ramparts of imposing fortresses like El Morro, at the entrance to the bay, and visit the Cathedral of San Juan Bautista, one of the oldest churches in the Americas and the final resting place of the citys founder, Ponce de León. Modern San Juan extends well beyond the historic district and offers diversions of its own. Condado, a lively beachfront neighborhood, has high-rise resorts and trendy waterfront bars. Visitors may sample one of Puerto Ricos best-known products at Casa Bacardí, the rum distillery across the bay. And stunning natural wonders await just outside the city, including the rain forest and waterfalls of El Yunque National Forest and the otherworldly lights of Fajardos bioluminescent bay. "
"Back in the 1500s, Puerto Rico was one of the first Caribbean islands to be settled, and its capital, today's San Juan, became a vital hub of Spains New World colonies. The historic part of the city, known as Old San Juan, is now a UNESCO World Heritage Site; it's also a National Historic Site within the U.S. National Park Service. Strolling the narrow cobblestoned streets of Old San Juan, you'll discover a historic treasure surrounded by massive city walls. You can climb the ramparts of imposing fortresses like El Morro, at the entrance to the bay, and visit the Cathedral of San Juan Bautista, one of the oldest churches in the Americas and the final resting place of the citys founder, Ponce de León. Modern San Juan extends well beyond the historic district and offers diversions of its own. Condado, a lively beachfront neighborhood, has high-rise resorts and trendy waterfront bars. Visitors may sample one of Puerto Ricos best-known products at Casa Bacardí, the rum distillery across the bay. And stunning natural wonders await just outside the city, including the rain forest and waterfalls of El Yunque National Forest and the otherworldly lights of Fajardos bioluminescent bay. "
Day San Juan, Puerto RicoArrive 07:00 AM
"Back in the 1500s, Puerto Rico was one of the first Caribbean islands to be settled, and its capital, today's San Juan, became a vital hub of Spains New World colonies. The historic part of the city, known as Old San Juan, is now a UNESCO World Heritage Site; it's also a National Historic Site within the U.S. National Park Service. Strolling the narrow cobblestoned streets of Old San Juan, you'll discover a historic treasure surrounded by massive city walls. You can climb the ramparts of imposing fortresses like El Morro, at the entrance to the bay, and visit the Cathedral of San Juan Bautista, one of the oldest churches in the Americas and the final resting place of the citys founder, Ponce de León. Modern San Juan extends well beyond the historic district and offers diversions of its own. Condado, a lively beachfront neighborhood, has high-rise resorts and trendy waterfront bars. Visitors may sample one of Puerto Ricos best-known products at Casa Bacardí, the rum distillery across the bay. And stunning natural wonders await just outside the city, including the rain forest and waterfalls of El Yunque National Forest and the otherworldly lights of Fajardos bioluminescent bay. "
"Back in the 1500s, Puerto Rico was one of the first Caribbean islands to be settled, and its capital, today's San Juan, became a vital hub of Spains New World colonies. The historic part of the city, known as Old San Juan, is now a UNESCO World Heritage Site; it's also a National Historic Site within the U.S. National Park Service. Strolling the narrow cobblestoned streets of Old San Juan, you'll discover a historic treasure surrounded by massive city walls. You can climb the ramparts of imposing fortresses like El Morro, at the entrance to the bay, and visit the Cathedral of San Juan Bautista, one of the oldest churches in the Americas and the final resting place of the citys founder, Ponce de León. Modern San Juan extends well beyond the historic district and offers diversions of its own. Condado, a lively beachfront neighborhood, has high-rise resorts and trendy waterfront bars. Visitors may sample one of Puerto Ricos best-known products at Casa Bacardí, the rum distillery across the bay. And stunning natural wonders await just outside the city, including the rain forest and waterfalls of El Yunque National Forest and the otherworldly lights of Fajardos bioluminescent bay. "
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