Eastern Caribbean cruises

Eastern Caribbean Loop via Great Stirrup Cay & Saint Thomas (Private Island Focus)

⚓ Great Stirrup Cay · Saint Thomas · Tortola · Puerto Plata

Balanced route with a steady mix of port days and sea days. Covers Bahamas, Virgin Islands, U.S., Virgin Islands, British, and Dominican Republic. Includes private-island style stops.

☾7 nights Miami Eastern Caribbean 4 ports 3 sea days

Itinerary pricing

What this itinerary usually costs

Typical pricing runs around $147/night. with most departures landing in the $127-$164/night band. across 3 tracked sailings.

Typical price

$147/night

$1,029 total

Normal range

$127-$164/night

$889-$1,149 total

Lowest recent fare

Building history

$959 total

Comparison set

3 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

All upcoming departures

Compare all sailings for this itinerary.

When should I go?

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

November 2027
Median price/night
$177
1 sailing
Upcoming departures
20% above itinerary median
1 priced departures tracked
January 2028
Cheapest
Median price/night
$173
1 sailing
Upcoming departures
20% above itinerary median
1 priced departures tracked
February 2028
Priciest
Median price/night
$186
1 sailing
Upcoming departures
15% above itinerary median
1 priced departures tracked

Route overview

How this route is built

Compare sailings →

7 nights · 4 port calls · 3 sea days · 4 countries

4 port calls across Bahamas, Virgin Islands, U.S., Virgin Islands, British, Dominican Republic · 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

    Great Stirrup Cay

    Bahamas · Bahamas

    Private
  3. 3

    Saint Thomas

    Virgin Islands, U.S. · Eastern Caribbean

  4. 4

    Tortola

    Virgin Islands, British · Eastern Caribbean

  5. 5

    Puerto Plata

    Dominican Republic · Eastern Caribbean

  6. 6

    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.