Eastern Caribbean cruises

Eastern Caribbean Loop via Princess Cays, Puerto Plata & San Juan (Rare Variant)

⚓ Princess Cays · Puerto Plata · San Juan · Philipsburg · Saint Thomas

Balanced route with a steady mix of port days and sea days. Covers Bahamas, Dominican Republic, Puerto Rico, and Sint Maarten (Dutch part) and more. Includes private-island style stops.

☾9 nights Port Canaveral Eastern Caribbean 5 ports 4 sea days

Itinerary pricing

What this itinerary usually costs

Typical pricing runs around $139/night. with most departures landing in the $124-$149/night band. across 1 tracked sailings.

Typical price

$139/night

$1,248 total

Normal range

$124-$149/night

$1,113-$1,337 total

Lowest recent fare

Building history

$1,031 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.

All departures

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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.

March 2028
Cheapest
Median price/night
$120
1 sailing
Upcoming departures
13% below itinerary median
1 priced departures tracked

Route overview

How this route is built

Compare sailings →

9 nights · 5 port calls · 4 sea days · 5 countries

5 port calls across Bahamas, Dominican Republic, Puerto Rico, Sint Maarten (Dutch part) · Neither especially port-heavy nor sea-day heavy for this trip length.

  1. 1

    Embark in Port Canaveral

    Embarkation ports can vary by sailing

  2. 2

    Princess Cays

    Bahamas · Bahamas

    Private
  3. 3

    Puerto Plata

    Dominican Republic · Eastern Caribbean

  4. 4

    San Juan

    Puerto Rico · Eastern Caribbean

  5. 5

    Philipsburg

    Sint Maarten (Dutch part) · Eastern Caribbean

  6. 6

    Saint Thomas

    Virgin Islands, U.S. · Eastern Caribbean

  7. 7

    Disembark in Port Canaveral

    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.