16 nights, San Juan to Miami

The itinerary, port by port

9 calls over 16 nights, San Juan to Miami. Open any port for my full day-ashore guide, what to see, when to go, and how the day actually runs.

Getting there: Flights to San Juan (SJU) are already bookable for these dates. I watch the fare for booked clients so you book at the right moment. When to book your flights →

1. Embark
   San Juan

   San Juan's old quarter is a walled Spanish colonial town on a headland, founded in the early 1500s, with two stone forts run by the U.S. Port guide →

2. 2
   Charlotte Amalie (Saint Thomas)

   Charlotte Amalie is the capital of the U.S. Port guide →

3. 3
   St. John's (Antigua)

   St. Port guide →

4. 4
   Terre-de-Haut (Îles des Saintes)

   Terre-de-Haut is the main inhabited island of the Saintes, a small archipelago off Guadeloupe's south coast, settled by Breton and Norman fishing families whose descendants still run the place. Port guide →

5. 5
   Puerto Plata

   Puerto Plata is the Dominican Republic's north-coast amber capital, a town of faded Victorian gingerbread houses sitting under the green wall of Mount Isabel de Torres. Port guide →

6. 6
   Miami

   Miami is the busiest cruise port in the United States, set on Dodge Island in Biscayne Bay a mile or two off downtown. Port guide →

7. 7
   Cayo Levantado (Samaná Bay)

   Cayo Levantado is a small palm-covered island in Samana Bay off the northeast coast of the Dominican Republic, nicknamed Bacardi Island after a rum commercial filmed here, with white sand and warm sheltered… Port guide →

8. 8
   Spanish Town (Virgin Gorda)

   Spanish Town is the small main settlement on Virgin Gorda, but the reason the day exists is a few miles south of it: The Baths, a stretch of coast where house-size granite boulders pile into grottoes,… Port guide →

9. Disembark
   Road Bay

   Road Bay is Anguilla's main harbor, sheltering the small fishing village of Sandy Ground on a wide curve of pale sand. Port guide →