Eastern Caribbean cruises

Eastern Caribbean Loop via Key West, Celebration Key & San Juan (Rare Variant)

⚓ Key West · Celebration Key · San Juan · Saint Thomas · Basseterre, Saint Kitts · Philipsburg · Frederiksted, Saint Croix · Ocho Rios

Balanced route with a steady mix of port days and sea days. Covers United States, Bahamas, Puerto Rico, and Virgin Islands, U.S. and more. Includes private-island style stops.

☾14 nights Galveston Eastern Caribbean 8 ports 6 sea days

Itinerary pricing

What this itinerary usually costs

Typical pricing runs around $92/night. with most departures landing in the $86-$98/night band. across 1 tracked sailings.

Typical price

$92/night

$1,285 total

Normal range

$86-$98/night

$1,204-$1,378 total

Lowest recent fare

$100/night

$1,405 total

Comparison set

1 sailings

Used for itinerary baseline

Best departures

Best upcoming sailings

Start here. These departures surface first because they combine stronger pricing, useful timing, or a notable warning signal for this itinerary.

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When should I go?

Scan monthly pricing to see which departure windows tend to look stronger or weaker for this itinerary.

October 2027
Cheapest
Median price/night
$100
1 sailing
Upcoming departures
9% above itinerary median
1 priced departures tracked

Route overview

How this route is built

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14 nights · 8 port calls · 6 sea days · 7 countries

8 port calls across United States, Bahamas, Puerto Rico, Virgin Islands, U.S. · Neither especially port-heavy nor sea-day heavy for this trip length.

  1. 1

    Embark in Galveston

    Embarkation ports can vary by sailing

  2. 2

    Key West

    United States · US East Coast

  3. 3

    Celebration Key

    Bahamas · Bahamas

    Private
  4. 4

    San Juan

    Puerto Rico · Eastern Caribbean

  5. 5

    Saint Thomas

    Virgin Islands, U.S. · Eastern Caribbean

  6. 6

    Basseterre, Saint Kitts

    Saint Kitts and Nevis · Eastern Caribbean

  7. 7

    Philipsburg

    Sint Maarten (Dutch part) · Eastern Caribbean

  8. 8

    Frederiksted, Saint Croix

    Virgin Islands, U.S. · Eastern Caribbean

  9. 9

    Ocho Rios

    Jamaica · Western Caribbean

  10. 10

    Disembark in Galveston

    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.