Eastern Caribbean cruises

Eastern Caribbean Loop via San Juan, Saint-Barthélemy & Philipsburg (Rare Variant)

⚓ San Juan · Saint-Barthélemy · Philipsburg · Frederiksted, Saint Croix · La Romana · Nassau

Balanced route with a steady mix of port days and sea days. Covers Puerto Rico, Saint Barthélemy, Sint Maarten (Dutch part), and Virgin Islands, U.S. and more.

☾10 nights Miami Eastern Caribbean 6 ports 4 sea days

Itinerary pricing

What this itinerary usually costs

Typical pricing runs around $564/night. with most departures landing in the $476-$707/night band. across 1 tracked sailings.

Typical price

$564/night

$5,644 total

Normal range

$476-$707/night

$4,762-$7,066 total

Lowest recent fare

Building history

$7,225 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.

November 2026
Cheapest
Median price/night
$726
1 sailing
Upcoming departures
29% above itinerary median
1 priced departures tracked

Route overview

How this route is built

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10 nights · 6 port calls · 4 sea days · 6 countries

6 port calls across Puerto Rico, Saint Barthélemy, Sint Maarten (Dutch part), Virgin Islands, U.S. · Neither especially port-heavy nor sea-day heavy for this trip length.

  1. 1

    Embark in Miami

    Embarkation ports can vary by sailing

  2. 2

    San Juan

    Puerto Rico · Eastern Caribbean

  3. 3

    Saint-Barthélemy

    Saint Barthélemy · Eastern Caribbean

  4. 4

    Philipsburg

    Sint Maarten (Dutch part) · Eastern Caribbean

  5. 5

    Frederiksted, Saint Croix

    Virgin Islands, U.S. · Eastern Caribbean

  6. 6

    La Romana

    Dominican Republic · Eastern Caribbean

  7. 7

    Nassau

    Bahamas · Bahamas

  8. 8

    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.