Eastern Caribbean

Eastern Caribbean Loop: San Juan, Cruz Bay, Saint John & Castries

San Juan · Cruz Bay, Saint John · Castries · Bridgetown · Philipsburg · Road Town, Tortola · Miami · Grand Turk Island · Willemstad · Kralendijk · Oranjestad

  • 21 nights
  • Miami
  • Eastern Caribbean
  • 11 ports

Map of Eastern Caribbean Loop: San Juan, Cruz Bay, Saint John & Castries. Stops in order: San Juan, Cruz Bay, Saint John, Castries, Bridgetown, Philipsburg, Road Town, Tortola, Miami, Grand Turk Island, Willemstad, Kralendijk, Oranjestad. The same stops are listed under Port by port.

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Embark and disembark port
Port of call

Port by port

21 nights · 11 port calls · 11 countries

  1. Stop #1

    Embark

    Miami

    United States · US East Coast

  2. Stop #2

    San Juan

    Puerto Rico · Eastern Caribbean

    Usually docks

  3. Stop #3

    Cruz Bay, Saint John

    Virgin Islands, U.S. · Eastern Caribbean

    Usually docks

  4. Stop #4

    Castries

    Saint Lucia · Southern Caribbean

    Usually docks

  5. Stop #5

    Bridgetown

    Barbados · Southern Caribbean

    Usually docks

  6. Stop #6

    Philipsburg

    Sint Maarten (Dutch part) · Eastern Caribbean

    Usually docks

  7. Stop #7

    Road Town, Tortola

    Virgin Islands, British · Eastern Caribbean

    Usually tenders

  8. Stop #8

    Miami

    United States · US East Coast

    Usually docks

  9. Stop #9

    Grand Turk Island

    Turks and Caicos Islands · Eastern Caribbean

    Usually docks

  10. Stop #10

    Willemstad

    Curaçao · ABC Islands

    Usually docks

  11. Stop #11

    Kralendijk

    Bonaire, Sint Eustatius and Saba · Southern Caribbean

    Usually docks

  12. Stop #12

    Oranjestad

    Aruba · ABC Islands

    Usually docks

  13. Stop #13

    Disembark

    Miami

    United States · US East Coast

What would you change about this trip?

Explore other routes with different ports, trip lengths, and departure ports.

Best departures

How these are chosen
  • Best overall value: the strongest value signal, a fare furthest below Jibhop's typical fare for the same cabin, among departures with enough price history.
  • Lowest fare: the lowest current starting fare among all listed departures. Cabin categories can differ between departures, so check the cabin shown.
  • Best near-term option: a below-typical fare on a departure within the next 90 days.
  • Currently priced high: a fare above its usual range in Jibhop's observations. Shown as a warning, not a recommendation.
No curated value-ranked sailings are ready yet for this itinerary.

All departures

Each fare is the departure's lowest current fare; the cabin category can differ between departures. Observed fares, not guaranteed availability.

No upcoming departures are available for this itinerary yet.