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Eastern Caribbean cruises

Eastern Caribbean Loop via Princess Cays, Saint Thomas & Cozumel

Princess Cays · Saint Thomas · Philipsburg · Miami · Princess Cays · Falmouth · Georgetown, Grand Cayman · Cozumel

Port-heavy Eastern Caribbean itinerary. Covers Bahamas, Virgin Islands, U.S., Sint Maarten (Dutch part), United States, and more. Includes private-island style stops.

7 nights Miami Eastern Caribbean 8 ports
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What this trip feels like

Active, varied and destination-focused

With 8 ports across 7 nights, this trip keeps the focus on time ashore. Expect more destination variety and a busier rhythm, with the ship serving as the link between port days.

Port-forward pace

8 ports in 7 nights

Most days put a destination at the center of the plan.

Broad destination variety

Princess Cays · Saint Thomas · Philipsburg + more

Frequent changes of scenery across the itinerary.

Easy logistics

Round-trip from Miami

No open-jaw flights or separate arrival and departure transfers.

Port experience

Princess Cays · Pick your date carefully

Cruise traffic varies substantially by date, so your specific port day can feel very different depending on when you visit.

Best for · Destination-led trips · Active days ashore · Travelers who prefer variety

Think twice if · You want long, uninterrupted stretches of time onboard

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.

Best overall value
Princess Cruises

Regal Princess

Miami → Princess Cays → Philipsburg → Miami

Feb 27 · 7 nights

$1,035 inside · $148/night

All departures

All upcoming departures

Compare all sailings for this itinerary.

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Itinerary pricing

What this itinerary usually costs

Typical pricing runs around $138/night, with most departures landing in the $130-$145/night band across 1 tracked sailing.

Typical price

$138/night

$965 total

Normal range

$130-$145/night

$910-$1,015 total

Lowest recent fare

$148/night

$1,035 total

Comparison set

1 sailings

Used for itinerary baseline

When should I go?

Not enough departures yet to identify a reliable cheaper season.

Route overview

How this route is built

Compare sailings →

7 nights · 8 port calls · 7 countries

8 port calls across Bahamas, Virgin Islands, U.S., Sint Maarten (Dutch part), United States · More port-intensive than many 7-night alternatives.

  1. 1

    Embark in Miami

    Embarkation ports can vary by sailing

  2. 2

    Princess Cays

    Bahamas · Bahamas

    Private
  3. 3

    Saint Thomas

    Virgin Islands, U.S. · Eastern Caribbean

  4. 4

    Philipsburg

    Sint Maarten (Dutch part) · Eastern Caribbean

  5. 5

    Miami

    United States · US East Coast

  6. 6

    Princess Cays

    Bahamas · Bahamas

    Private
  7. 7

    Falmouth

    Jamaica · Western Caribbean

  8. 8

    Georgetown, Grand Cayman

    Cayman Islands · Western Caribbean

  9. 9

    Cozumel

    Mexico · Western Caribbean

  10. 10

    Disembark in Miami

    Disembarkation ports can vary by sailing

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Render your Mapbox or Leaflet map here from the supplied route and port JSON.

Embark port
Disembark port
Port of call

Other routes to consider

Not quite the right itinerary? Compare routes that trade a little simplicity for more ports, different destinations, or a longer trip.

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.