23 nights, San Juan to Barcelona

The itinerary, port by port

11 calls over 23 nights, San Juan to Barcelona. 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
   St. John's (Antigua)

   St. Port guide →

3. 3
   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 →

4. 4
   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 →

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
   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 →

8. 8
   Funchal (Madeira)

   Funchal is the capital of Madeira, a Portuguese volcanic island in the Atlantic, and the port sits a short walk from a working city built up a steep amphitheater of hills. Port guide →

9. 9
   Cadiz

   Cádiz sits on a narrow Atlantic peninsula in Andalusia and is among the oldest continuously inhabited cities in Western Europe, a compact old town ringed by sea on three sides. Port guide →

10. 10
    Málaga

    Málaga is the working capital of the Costa del Sol and the birthplace of Picasso, and its old town packs a Moorish hilltop fortress, a 1st-century BC Roman theater, and an unfinished Renaissance cathedral… Port guide →

11. Disembark
    Barcelona

    Barcelona packs Gaudí's modernisme, a 2,000-year-old Roman and medieval core, and a working Mediterranean waterfront into a single dense, walkable city. Port guide →