14 nights, San Juan to San Juan

The itinerary, port by port

10 calls over 14 nights, round-trip from San Juan. 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
   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 →

3. 3
   St. John's (Antigua)

   St. Port guide →

4. 4
   Frederiksted (Saint Croix)

   Frederiksted is the quieter, west-end town of St Croix and the island's only deep-water cruise call, a low-rise grid of Danish colonial and Victorian buildings facing the Caribbean. Port guide →

5. 5
   Catalina Island

   Catalina is a low-key island an hour off the Southern California coast, where the small port town of Avalon ends at clear, kelp-forested water that draws snorkelers and glass-bottom boats. Port guide →

6. 6
   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 →

7. 7
   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 →

8. 8
   Cruz Bay (Saint John)

   Saint John is the quietest of the U.S. Port guide →

9. 9
   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 →

10. Disembark
    Philipsburg

    Philipsburg is the Dutch-side capital of Sint Maarten, a narrow strip of town wedged between Great Bay and a salt pond. Port guide →