13 nights, San Juan to Bridgetown

The itinerary, port by port

11 calls over 13 nights, San Juan to Bridgetown. 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
   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 →

3. 3
   Gustavia

   Gustavia is the harbor capital of St Barths, a small French island that has deliberately kept large cruise ships out, so only luxury lines anchor offshore and tender in. Port guide →

4. 4
   Basseterre

   Basseterre is the Georgian-era capital of St Kitts, a small twin-island Caribbean nation where the cruise pier puts you a five-minute walk from a colonial town center built around a circular junction… Port guide →

5. 5
   Grand Turk

   Grand Turk is the small, low-rise capital island of the Turks and Caicos, a former salt-raking colony of donkeys, ponds, and pastel Bermudian houses that never urbanized. 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
   Providenciales

   Providenciales (Provo) is the tourism hub of the Turks and Caicos, and its reason for being on an itinerary is Grace Bay: a 12-mile run of white sand and turquoise shallows fronting a barrier reef,… Port guide →

8. 8
   St. John's (Antigua)

   St. Port guide →

9. 9
   Pointe-à-Pitre

   Pointe-à-Pitre is the commercial capital of Guadeloupe, a French overseas region, and the city wears that dual identity openly: Creole markets and a French colonial grid, euros and Caribbean spice. Port guide →

10. 10
    Bequia

    Bequia is the largest of the Grenadines, a seven-square-mile island in St Vincent and the Grenadines with a deep sailing and whaleboat-building heritage and a single small harbor town, Port Elizabeth, on… Port guide →

11. Disembark
    Bridgetown

    Barbados's capital is a UNESCO-listed Georgian port town wrapped around a careenage, with British colonial bones, a Parliament still in session, and a turtle-filled bay a short taxi away. Port guide →