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EXPLORA III · Caribbean & Central America

13 nights, San Juan to Bridgetown

March 7, 2027 – March 21, 2027 · 13 nights · 11 stops

Explora's name for it: An Extended Journey from Ocean Calm to Vibrant Culture

Thirteen nights, eleven calls, San Juan to Bridgetown without doubling back to where you started. That ratio tells you the shape: this moves. You start tied up at the Old San Juan piers, where the walled colonial grid and El Morro are a short walk up from the gangway, then run the northern islands before swinging down the eastern arc to Barbados. The standouts are easy to name. Gustavia, where St Barths has kept big ships out by design, so the ship anchors and tenders into a harbor that never feels crowded. Grand Turk, where the offshore reef wall sits close enough that this is one of the rare ports with real wall snorkeling steps from the beach. And Roseau, your foot-of-the-mountains gateway into Dominica's rainforest. Bequia and Bridgetown close it out on Admiralty Bay and Carlisle Bay.

Be honest with yourself about two things. This itinerary detours to Miami midway through, a busy US port that breaks the island rhythm and trades a Caribbean day for a city one. And several calls are tender ports, Gustavia, Providenciales, and Bequia among them, where a windy morning can thin the boats. If you want slow and uniform, this isn't it. If you want range and don't mind a brisk pace, it delivers.

Explora III is all-suite, all-oceanfront. I've sailed the line and I'll tell you which suite to skip.

San Juan (open port guide)San JuanPhilipsburg (open port guide)Gustavia (open port guide)Basseterre (open port guide)Grand Turk (open port guide)Miami (open port guide)Providenciales (open port guide)St. John's (Antigua) (open port guide)Roseau (open port guide)Bequia (open port guide)Bridgetown (open port guide)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
  9. 9
    Roseau

    Roseau is Dominica's small capital, a grid of weathered French- and English-colonial streets pressed between the sea and the green wall of the Morne Trois Pitons mountains. 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 →

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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