| Trip Name | From | Days | Summary |
|---|---|---|---|
| Quintessential Caribbean | $7,990 | 8 | Embark on an 8-day Caribbean cruise aboard the Emerald Sakara. Explore the vibrant culture of San Juan, the charm of Saint John, the tranquil beaches of Nevis, the picturesque village of Deshaies, the historic allure of Falmouth Harbor, the lively streets of Gustavia, and the pristine beauty of Prickly Pear Cays. |
| Caribbean Escapade | $7,590 | 8 | Set sail on an 8-day Caribbean cruise aboard the Emerald Sakara. Explore Grand Turk's pristine beaches and historic landmarks, discover Long Island's tranquil Gordon's Beach, and dive into San Salvador's vibrant coral reefs and historic sites. |
| Splendours of the Caribbean | $9,190 | 7 | Sail through the Caribbean on a 7-day cruise aboard Emerald Sakara, from San Juan to Saint Thomas. Visit Saint John, Nevis, Antigua, Saint Barthelemy, and Virgin Gorda. Discover colonial towns, quiet beaches, and historic sites. |
| Quintessential Caribbean | $9,990 | 8 | Explore the Caribbean on an 8-day cruise from Saint Thomas to San Juan aboard Emerald Sakara. Visit Saint John, Nevis, Guadeloupe, Antigua, Saint Barthélemy, and the British Virgin Islands. Discover UNESCO-listed landmarks, swim in clear waters, and experience regional architecture, food, and history throughout the journey. |
| San Juan to San Juan | $5,000 | 8 | Depart from San Juan and explore Caribbean islands on an 8-day cruise aboard Silver Dawn. Visit St John, Gustavia, Antigua, Martinique, St Kitts, and Jost Van Dyke. Swim in clear waters, snorkel vibrant reefs, hike rainforest trails, and relax on white sand beaches. Discover a mix of nature, culture, and coastal views. |
| Caribbean Yachting Hideaways | $6,845 | 8 | Set sail on an 8-day Caribbean cruise aboard the Emerald Kaia from San Juan, Puerto Rico, exploring Vieques, Cruz Bay, and Jost Van Dyke's stunning beaches. Visit Gustavia in Saint Barthelemy, experiencing its unique French culture before concluding the journey in St. John's, Antigua. |
| Caribbean Yachting Discovery | $6,745 | 8 | Set sail on an 8-day Caribbean cruise aboard the Emerald Kaia from Antigua, visiting St. Kitts, Guadeloupe, and Saint-Barthelemy, before exploring the British Virgin Islands' iconic sites. End your journey in San Juan, Puerto Rico, the oldest European settlement in the Americas. |
Best San Juan, Puerto Rico Small Ship Cruise Line for 2026-2027
Our team is waiting and ready to talk with you about your next adventure. So go ahead and book an appointment with one of our specialized trip planners.
Let's ChatReceive personal attention and concierge-level service for the same cost as booking direct. Gain access to exclusive rates, perks, and insider expertise on how to maximize the value for your dollar.
We guide you through every detail beyond the cruise—from flights to pre- and post-trip stays—so your journey feels effortless.
Secure your 5% Past Traveler Rewards across a wide range of ships and destinations - not a single brand and not just cruises.
No cost, no commitment. Talk with our experts about your dream trip.
Share your travel style—we match you with the right itinerary or create one just for you.
Lock in knowing every detail is handled and you’re fully supported.
Enjoy a seamless journey—and unlock 5% off your next adventure.