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EXPLORA III · Caribbean & Central America

15 nights, San Juan to San Juan

December 28, 2026 – January 13, 2027 · 15 nights · 11 stops · round-trip

Explora's name for it: An Extended Journey of Caribbean Celebrations and Island Horizons

This is a fifteen-night round trip from San Juan that works the eastern Caribbean in detail rather than racing through it: eleven calls across nine countries, with a single sea day to break up the run. The shape is a wide loop touching Puerto Rico, the Lesser Antilles, the Virgin Islands, and a swing west to the Dominican Republic and Miami before the return. The hooks are concrete. In San Juan the ship ties up at the Old San Juan piers themselves, so the walled colonial grid and El Morro are a short walk from the gangway. Gustavia anchors offshore at St Barths, a French island that has deliberately kept big ships out, so the harbor never feels crowded. Road Town is your launch point for the 30-minute ferry to The Baths on Virgin Gorda, a far better sight than anything in town. Samaná trades shopping for whales, waterfalls, and mangrove parks.

This itinerary rewards someone who wants range and is comfortable with logistics. Several calls are tender ports (Cruz Bay, Gustavia, Samaná), where swell and queue timing govern the day, and a few towns, St. John's and Road Town among them, are really gateways to one excursion rather than destinations themselves. If you want fewer, deeper stops or a port-step-off-and-walk pace throughout, look elsewhere. If fifteen nights and an island-a-day cadence sounds right, this is a strong one.

Explora III is all-suite and all-oceanfront. Send me your dates and the suite tier you are weighing, and I will have live pricing in your inbox within two hours.

San Juan (open port guide)San JuanSt. John's (Antigua) (open port guide)Pointe-à-Pitre (open port guide)At Sea - FireworksCruz Bay (Saint John) (open port guide)SamanáPuerto Plata (open port guide)Miami (open port guide)Gustavia (open port guide)Road Town (Tortola) (open port guide)Basseterre (open port guide)Basseterre

The itinerary, port by port

11 calls over 15 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
  3. 3
    Pointe-à-Pitre

    Pointe-à-Pitre is the commercial capital of Guadeloupe, a French overseas region, and the city wears that dual identity openly: Creole markets and a French colonial grid, euros and Caribbean spice. Port guide →

  4. 4
    At Sea - Fireworks
  5. 5
    Cruz Bay (Saint John)

    Saint John is the quietest of the U.S. Port guide →

  6. 6
    Samaná

    Samana sits on a green peninsula at the head of a wide bay on the Dominican Republic's northeast coast, a quieter, more nature-led call than the island's resort ports.

  7. 7
    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 →

  8. 8
    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 →

  9. 9
    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 →

  10. 10
    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 →

  11. 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 →

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.
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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Send me the dates and the suite tier you have in mind and I'll come back with a confirmed live number and my read on the sailing within two hours. Best available price, and I make it worth more.

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