Eastern Caribbean cruises

Eastern Caribbean Loop via Providenciales, Puerto Plata & Road Bay (Port-Heavy)

⚓ Providenciales · Puerto Plata · La Romana · Jost Van Dyke · Saint-Barthélemy · San Juan · Road Bay · Saint John's · Frederiksted, Saint Croix · Catalina Island · Puerto Plata

Port-heavy Eastern Caribbean itinerary. Covers Turks and Caicos Islands, Dominican Republic, Virgin Islands, British, and Saint Barthélemy and more.

☾14 nights Miami Eastern Caribbean 11 ports 3 sea days

Itinerary pricing

What this itinerary usually costs

Typical pricing runs around $675/night. with most departures landing in the $579-$752/night band. across 1 tracked sailings.

Typical price

$675/night

$9,450 total

Normal range

$579-$752/night

$8,100-$10,521 total

Lowest recent fare

Building history

$7,770 total

Comparison set

1 sailings

Used for itinerary baseline

Best departures

Best upcoming sailings

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When should I go?

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November 2026
Cheapest
Median price/night
$666
1 sailing
Upcoming departures
Typical value
1 priced departures tracked

Route overview

How this route is built

Compare sailings →

14 nights · 11 port calls · 3 sea days · 8 countries

11 port calls across Turks and Caicos Islands, Dominican Republic, Virgin Islands, British, Saint Barthélemy · More port-intensive than many 14-night alternatives.

  1. 1

    Embark in Miami

    Embarkation ports can vary by sailing

  2. 2

    Providenciales

    Turks and Caicos Islands · Eastern Caribbean

  3. 3

    Puerto Plata

    Dominican Republic · Eastern Caribbean

  4. 4

    La Romana

    Dominican Republic · Eastern Caribbean

  5. 5

    Jost Van Dyke

    Virgin Islands, British · Eastern Caribbean

  6. 6

    Saint-Barthélemy

    Saint Barthélemy · Eastern Caribbean

  7. 7

    San Juan

    Puerto Rico · Eastern Caribbean

  8. 8

    Road Bay

    Anguilla · Eastern Caribbean

  9. 9

    Saint John's

    Antigua and Barbuda · Eastern Caribbean

  10. 10

    Frederiksted, Saint Croix

    Virgin Islands, U.S. · Eastern Caribbean

  11. 11

    Catalina Island

    Dominican Republic · Eastern Caribbean

  12. 12

    Puerto Plata

    Dominican Republic · Eastern Caribbean

  13. 13

    Disembark in Miami

    Disembarkation ports can vary by sailing

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Embark port
Disembark port
Port of call

Alternatives

Compare nearby alternatives

Nearby options in the same planning set, with price and trip-shape tradeoffs called out so you can compare without restarting your search.

FAQ

What’s the best month to sail this itinerary?

It depends on weather and crowd levels. Use the sailing list to compare dates and prioritize port days with comfortable conditions.

Are these sailings all the same route?

They can be close but not identical. Look for differences in port order, arrival times, and sea day placement.

How should I choose between two similar sailings?

Compare: (1) ship, (2) port day timing, (3) number of sea days, (4) price vs cabin value, and (5) flight convenience.