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EXPLORA III · Caribbean & Central America

13 nights, San Juan to San Juan

January 29, 2027 – February 12, 2027 · 13 nights · 10 stops · round-trip

Explora's name for it: An Extended Journey of Secluded Isles & Coastal Havens

Thirteen nights, ten calls, a loop that starts and ends in San Juan. That math tells you the most important thing up front: this is a busy itinerary with very little time at sea, so you trade slow days on the ship for a new island almost every morning. The arc runs from the eastern Caribbean down through the Leewards, swings west to the Florida Keys and Miami, then back. The hooks are concrete. In San Juan you tie up at the Old San Juan piers themselves, so the cobbled colonial grid and El Morro start a few steps from the gangway. Road Town is a launch pad, not a destination: a roughly 30-minute ferry from near the ship reaches The Baths on Virgin Gorda, a far better sight than Tortola itself. Providenciales is all about Grace Bay, and Gustavia, on St Barths, anchors offshore into a tight harbor of red roofs and French bistros that small ships keep uncrowded.

Who it rewards: travelers who want range over depth and don't mind a brisk cadence of beaches, forts, and colonial capitals. Who should skip it: anyone craving sea days or a single region's character, and beach-day purists, because three calls here (Providenciales, Gustavia, Cruz Bay) are tender ports where a windy morning can thin or delay the operation. Plan those for early in the day.

The ship is all-suite and all-oceanfront. Send me your dates.

San Juan (open port guide)San JuanRoad Town (Tortola) (open port guide)St. John's (Antigua) (open port guide)Providenciales (open port guide)Key West (open port guide)Miami (open port guide)Philipsburg (open port guide)Gustavia (open port guide)Basseterre (open port guide)Cruz Bay (Saint John) (open port guide)Cruz Bay (Saint John)

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
  4. 4
    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 →

  5. 5
    Key West

    Key West is the last island in the Florida Keys chain, a compact Old Town of conch houses, literary history, and a daily ritual built around watching the sun drop into the Gulf. 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
    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 →

  9. 9
    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 →

  10. Disembark
    Cruz Bay (Saint John)

    Saint John is the quietest of the U.S. 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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