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EXPLORA III · Caribbean & Central America

13 nights, San Juan to San Juan

November 15, 2026 – November 29, 2026 · 13 nights · 10 stops · round-trip

Explora's name for it: An Extended Journey of Tropical Harmony & Natural Wonders

Thirteen nights, ten stops, San Juan to San Juan: a slow loop through the eastern Caribbean with one long northwest leg up to Miami and back. The pace is unhurried for the islands, but a couple of calls are about contrast more than depth. The anchor is the start. Explora ties up at the Old San Juan piers on Marina Street, so the cobbled grid of the walled colonial town begins a few steps from the gangway, and El Morro is a morning's walk uphill. From there the route reads as a string of small, water-first islands. At Road Bay you tender straight onto Sandy Ground Beach in Anguilla, no terminal, just sand and bar shacks. Terre-de-Haut in the Saintes anchors you at the village dock in Le Bourg, where Fort Napoléon closes around 12:30 and the tourment d'amour is still baked the old way. Frederiksted lands you alongside a pier that doubles as a shore-diving site, with its 1848 emancipation story a short walk from the gangway.

This rewards a traveler who likes beach-and-village days over packed touring, and who accepts that Miami is a logistics waypoint, not a Caribbean call. If you want every day to be a new culture, the long run up to Florida and back will feel like filler. If you want unhurried sand, small Creole and Danish-colonial towns, and a dock you can walk off, this is the loop.

Explora III is all-suite and all-oceanfront.

San Juan (open port guide)San JuanRoad Bay (open port guide)St. John's (Antigua) (open port guide)Frederiksted (Saint Croix) (open port guide)Catalina Island (open port guide)Puerto Plata (open port guide)Miami (open port guide)Cruz Bay (Saint John) (open port guide)Terre-de-Haut (Îles des Saintes) (open port guide)Philipsburg (open port guide)Philipsburg

The itinerary, port by port

10 calls over 13 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
  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 →

Fares on this departure, decoded

Reading the fare fine print is the job. Here's what this sailing currently carries:

Invitation to Discover More
Explora's discovery fare, available across most of the calendar. Onboard credit where the offer applies.
Founders Fare
A founding-era fare on a selected set of sailings. Onboard credit where the offer applies.
Air-Inclusive Fare
A fare that folds airfare into the voyage price on a smaller set of sailings.

The ship and your suite

This sailing is aboard EXPLORA III, all-suite, every suite with a private ocean-front terrace. Suites run from the entry Ocean Terrace to the Owner's Residence; the right tier depends on how you travel. Compare suites → · What's included →


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