7 days - Windward Islands Surf & Sunsets
Starting from
$2,699*
San Juan to San Juan
Ship: Star Pride
Departure Date : Nov 08 2026 | Nov 22 2026 | Dec 06 2026 | Dec 20 2026 | Jan 03 2027
Optional tours are available from most ports for an additional charge.
Itinerary
Day San Juan, Puerto RicoDepart 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
Days at Sea
Days 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 05:00 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 02:00 PM
Philipsburg, the bustling capital of the Dutch side of Sint Maarten, offers visitors a fascinating mix of cultures, scenic beaches, and excellent shopping opportunities. From the historic Fort Amsterdam to the vibrant Boardwalk, Philipsburg invites travelers to immerse in its lively atmosphere and Dutch heritage, while just a short trip away, the French side of the island offers its own distinct charm and culinary delights.
Philipsburg, the bustling capital of the Dutch side of Sint Maarten, offers visitors a fascinating mix of cultures, scenic beaches, and excellent shopping opportunities. From the historic Fort Amsterdam to the vibrant Boardwalk, Philipsburg invites travelers to immerse in its lively atmosphere and Dutch heritage, while just a short trip away, the French side of the island offers its own distinct charm and culinary delights.
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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