23 nights, San Juan to San Juan

The itinerary, port by port

15 calls over 23 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
   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 →

3. 3
   Saint-Pierre

   Saint-Pierre was Martinique's cultural capital, the Paris of the Caribbean, until Mont Pelee erupted on May 8, 1902 and a pyroclastic flow killed roughly 30,000 people in minutes. Port guide →

4. 4
   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 →

5. 5
   Port of Spain (Trinidad)

   Port of Spain is the capital of Trinidad and Tobago, a genuine working Caribbean city rather than a cruise-built one, with a multicultural street life that shows in its food, its architecture, and its…

6. 6
   Macapá

   Macapá is the capital of Amapá state, sitting directly on the equator at the northern mouth of the Amazon, where the line literally runs through the city's Marco Zero monument and even through the midfield… Port guide →

7. 7
   Santarem (Pará)

   Santarem sits where the clear blue-green Tapajos River meets the silt-brown Amazon, a port city founded by the Portuguese in 1661 and one of the oldest in the Brazilian Amazon. Port guide →

8. 8
   Boca da Valeria

   Boca da Valeria is a tiny riverside village of roughly 75 people at the mouth of the Valeria River, about 850 miles up the Amazon near the Pará-Amazonas border. Port guide →

9. 9
   Manaus

   Manaus is the million-person Amazonian capital that grew rich on the rubber boom of the 1890s to 1910s and spent that money on European architecture set down in the middle of the rainforest, a thousand… Port guide →

10. 10
    Parintins

    Parintins is a river town of about 100,000 on an island in the Amazon, famous for the Boi-Bumba folklore festival, a three-day spectacle each June built around the legend of a resurrected ox and a rivalry… Port guide →

11. 11
    Alter do Chão

    Alter do Chão is a small river village on the Tapajós about 30 km upstream from Santarém, where the water runs clear and blue instead of the muddy brown of the main Amazon. Port guide →

12. 12
    Devil's Island

    The Îles du Salut are three small granite islands off French Guiana that France ran as a penal colony from 1852 until the 1940s, the system the wider world remembers as Devil's Island. Port guide →

13. 13
    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 →

14. 14
    Castries

    Castries is St. Port guide →

15. Disembark
    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 →