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Learn about Spanish colonial history in Old San Juan

Caribbean Yachting Hideaways

San Juan - St John's - Example 8 Day Cruise aboard Emerald Kaia
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Embark on an 8-day Caribbean cruise aboard the Emerald Kaia, departing from the capital city of San Juan, Puerto Rico. Sail to Vieques Island to explore the coastal town of Esperanza, observing its active social environment along a distinct waterfront area. Continue toward Cruz Bay, located on St. John Island, where striking architectural designs and a relaxed regional lifestyle provide an excellent environment for walking through the town center. Navigate through both the United States and the British Virgin Islands, making a dedicated stop at Jost Van Dyke to experience pristine white sand beaches and clear coastal waters. Travel to the island of Saint Barthelemy to visit Gustavia, noting the distinct French cultural influences present within the local stores and restaurants. Conclude in St. John's, Antigua.
A traveler looking back to the towards the White Bay beach of Jost Van Dyke Island, British Virgin Islands.Sunset over PhilipsburgThe crystal blue water of Jost van DykeRelax on the beaches of St. MaartenRelax on the pristine beaches of the Virgin IslandsLearn about the history of the CaribbeanThe looming fort walls of San JuanLearn about Spanish colonial history in Old San Juan
Highlights
  • Visit Culebra to discover Flamenco Beach and vivid reefs
  • Tour St. John to admire architecture in Mongoose Junction
  • Discover Cruz Bay to shop and dine along the bustling bay
  • Walk Philipsburg to peruse lively street markets and crafts
Activity Level: Variable
Activity options vary depending on destination and operator. Activity level is determined by the range and intensity of activities you choose to participate in. Discuss with your Trip Planner which options are best for you.
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Full Itinerary

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Day 1: San Juan, Puerto Rico | Embark

Your unforgettable maritime journey commences in San Juan, the deeply historic capital of Puerto Rico and the oldest European-founded city in the Americas. Following your arrival, enjoy a seamless transfer directly to an Emerald Cruises luxury yacht to begin a truly magical exploration of the most idyllic yachting hideaways throughout the Caribbean.

To guarantee a perfectly smooth embarkation process, please arrange for an inbound flight arriving in San Juan prior to 5:00 PM.

Day 2: Vieques Island, Puerto Rico

The charming Puerto Rican coastal town of Esperanza features stunning beaches and a highly picturesque waterfront framed by a lively collection of restaurants, bars, and inviting guesthouses. Take time to stroll leisurely along the scenic boulevard, visiting various local establishments to fully immerse your senses in the vibrant regional culture and engaging activities available throughout the area. Embrace the authentic island lifestyle by spending a deeply relaxing afternoon at Sun Bay, the primary urban beach gracefully situated on the eastern edge of the town.

Day 3: St. John, U.S. Virgin Islands | Jost Van Dyke, British Virgin Islands

Welcome to Cruz Bay, the economic and social hub of St. John, the smallest of the three U.S. Virgin Islands located amid the Caribbean Sea. Here, a busy inter-island ferry dock connects with the other beautiful islands in the region. The busting  bay is lined with restaurants and shops, while striking Caribbean architecture in Mongoose Junction can be admired on a leisurely stroll through town.  

In the evening, set sail for Jost Van Dyke.

Day 4: Jost Van Dyke, British Virgin Islands

Today, arrive in Jost Van Dyke, the smallest of all four main islands comprising the British Virgin Islands. Covering approximately eight-square kilometers (three-square-miles), lush and beautiful Jost Van Dyke is known as ‘The Last Virgin Island.’ Discover White Bay Beach, distinctive for its rugged, rocky scenery and colorful local culture. This pretty bay offers one of the loveliest beaches by far to relax and soak up the splendid Caribbean views.

Day 5: Philipsburg, Sint Maarten | Gustavia, Saint Barthelemy

With its blend of Dutch and Caribbean influences, Philipsburg presents a bustling port town with a vibrant atmosphere, striking colonial architecture, and stunning beaches. Situated on the Dutch side of Saint Martin, this capital of Sint Maarten offers a fascinating array of activities and attractions, including historic sites and a lively street market. where you can sample the local cuisine and peruse the islands’ arts and crafts. In the evening, sail to Gustavia.

Day 6: Gustavia, Saint Barthelemy

Named after Sweden’s King Gustav III, who boldly declared it his own island getaway in 1785, Gustavia is the charming capital and main seaport of chic island, Saint Barthélemy, also known as St. Barth's. Saint Barthélemy is often considered to be one of the most beautiful islands in the Caribbean and a tropical paradise infused with French flair. Today, enjoy the beauty of the island’s idyllic beaches and delicious French-Creole cuisine, as well as the charms of Gustavia and its colorful, old wooden houses.

Day 7: Little Bay, Montserrat | St. John’s, Antigua, Antigua and Barbuda

Welcome to what is regarded as one of the most unusual and fascinating islands in the Caribbean. Prior to the recent volcanic eruptions that commenced in 1995, for those in the know, Montserrat was considered one of the most sought-after Caribbean islands. It was also home to producer George Martin’s Air Studios Montserrat recording studio, where some of the world’s most celebrated recording artists, including Eric Clapton and Paul McCartney among others, used to cut their albums. Recent history has dealt some unfortunate blows to the island ranging from hurricanes (Hugo in 1989) to multiple volcanic eruptions that destroyed the picturesque capital, Plymouth. In the evening, cruise to St. John’s on the lovely island of Antigua.

Day 8: St. John’s, Antigua, Antigua and Barbuda | Disembark

  • 1 Breakfast
Your memorable voyage and time on board your Emerald Cruises luxury yacht comes to an end in St. John’s, capital of the Caribbean island-nation of Antigua and Barbuda. After bidding farewell to the crew and your fellow guests, from the yacht, be transferred to the airport for your return flight home, or to continue your holiday.

Please book your flight to depart out of St John's after 11:00 AM.

This itinerary is a guide only and may be amended for operational reasons. As such, Emerald Cruises cannot guarantee the cruise will be operated unaltered from the itinerary stated above.

Ship/Hotel

Emerald Kaia

Dates & Prices

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Enjoy an additional savings of $150 per person when you add an extension to your Europe river cruise. This promotion is valid for new bookings made between May 12 and June 30, 2026. A deposit is required at the time of booking. Additional restrictions may apply. Please contact us for more details.
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Per person starting at
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Oceanview Stateroom
Suite size: 21-23m²
Balcony Suite B
Suite size: 30m²-32m²
Balcony Suite A
Suite size: 32m²
Balcony Suite AB
Suite size: 32m²
Deluxe Balcony Suite
Suite size: 44m²
Terrace Suite
Yacht Suites offer a spacious 77m² layout, including a wraparound terrace
Yacht Suite
Yacht Suites offer a spacious 82m² layout, including a wraparound terrace
Owner's Suite
Larger suites at 131m² feature a Spa Pool a deux on the private terrace
Included
  • 7 Breakfasts, 6 Lunches, 7 Dinners
  • 7 Nights Accommodations
  • Accommodations as listed
  • Ground transportation as listed
  • Activities as listed
  • Meals as listed
  • Access to a 24-7 Emergency line while traveling
  • Choice between Emerald Plus and Emerald Active Excursions
  • Wifi
  • Complimentary Wine, Beer and Soft drinks with lunch and dinner on board
  • The services of an Emerald Cruises Tour Manager
  • Airport transfers to and from the ship
  • Port taxes and charges
  • All tipping and gratuities
  • Including a Welcome and Farewell Reception & Dinner
  • Open bar (except for premium wines)
Excluded
  • Travel Insurance
  • Personal Expenses
  • Flight costs (please request a quote)
  • Additional excursions during free time
  • Fuel and transportation surcharges (when applicable)
  • Travelers are urged to arrange comprehensive travel insurance to cover any unforeseen circumstances that may occur during the tour

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This was our first trip to South America and we were a little nervous. But Adventure Life made things so easy! All our questions were answered before we left, and our guide, Vidal, was amazing! He gave us enough space to explore without rushing us along. He also knew where the best picture taking opportunities were, which was great.
Lindsay Gompf

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