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EXPLORA III · Caribbean & Central America

13 nights, San Juan to San Juan

November 1, 2026 – November 15, 2026 · 13 nights · 10 stops · round-trip

Explora's name for it: An Extended Journey into Island Delights, Hidden Coves & Chic Coastlines

Thirteen nights, ten calls, a loop out of San Juan and back. The arc runs through the northern Leewards and Virgins, then west to Miami, before turning south through Turks and Caicos and the Dominican Republic. It is a full schedule with little water between islands, so expect short hops and busy mornings rather than long sea days. The ship ties up at the Old San Juan piers themselves, so the cobbled grid of plazas and the cathedral start a few steps from the gangway. In Tortola, the Road Town ferry terminal sits about a 12-minute walk away and the crossing to The Baths on Virgin Gorda runs roughly 30 minutes, a better sight than anything on Tortola itself. St Barths keeps large ships out by design, so Gustavia's red-roofed harbor never feels crowded. On Anguilla you tender onto Sandy Ground Beach itself, then taxi to Shoal Bay East for the sand the island is known for.

This sailing rewards anyone who wants the islands at a working clip, with beach days at Grace Bay and Jost Van Dyke balanced against forts and old towns at San Juan, Basseterre, and Puerto Plata. Several stops are weather-dependent tender ports, so go early when the trades blow. Skip it if you want unhurried sea days, or if a Miami call in the middle of a Caribbean loop reads as a wasted day to you.

EXPLORA III is all-suite and all-oceanfront.

San Juan (open port guide)San JuanRoad Town (Tortola) (open port guide)Basseterre (open port guide)Gustavia (open port guide)Road Bay (open port guide)Miami (open port guide)Providenciales (open port guide)Puerto Plata (open port guide)La RomanaJost Van Dyke (open port guide)Jost Van Dyke

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 Town (Tortola)

    Road Town is the capital of the British Virgin Islands, and your ship lands you at its doorstep on the south coast of Tortola. Port guide →

  3. 3
    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 →

  4. 4
    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 →

  5. 5
    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 →

  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
    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 →

  9. 9
    La Romana

    La Romana is a former sugar town on the Dominican Republic's southeast coast, and its cruise terminal sits between the town and Casa de Campo, one of the Caribbean's large resort estates.

  10. Disembark
    Jost Van Dyke

    Jost Van Dyke is a four-mile sliver of the British Virgin Islands with roughly 300 residents, no traffic lights, and a beach-bar culture that built the BVI's reputation. 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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