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Eastern Caribbean cruises

Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg

Charlotte Amalie, Saint Thomas · Frederiksted, Saint Croix · Philipsburg · Saint John's · Roseau

Port-heavy Eastern Caribbean itinerary. Covers Virgin Islands, U.S., Sint Maarten (Dutch part), Antigua and Barbuda, and Dominica.

7 nights San Juan Eastern Caribbean 5 ports 2 sea days
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What this trip feels like

Active, varied and destination-focused

With 5 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

5 ports in 7 nights

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

Broad destination variety

Charlotte Amalie, Saint Thomas · Frederiksted, Saint Croix · Philipsburg + more

Frequent changes of scenery across the itinerary.

Easy logistics

Round-trip from San Juan

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

Port experience

Charlotte Amalie, Saint Thomas · 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
Royal Caribbean International

Rhapsody of the Seas

San Juan → Charlotte Amalie, Saint Thomas → Roseau → San Juan

Oct 31 · 7 nights

Good value

$529 inside · $76/night

13% below typical · 6-month low
Cheapest upcoming
Royal Caribbean International

Vision of the Seas

San Juan → Charlotte Amalie, Saint Thomas → Roseau → San Juan

Jan 24 · 7 nights

About average

$501 inside · $72/night

Best near-term option
Royal Caribbean International

Rhapsody of the Seas

San Juan → Charlotte Amalie, Saint Thomas → Roseau → San Juan

Dec 5 · 7 nights

Good value

$539 oceanview · $77/night

11% below typical · 30-day low
Currently priced high
Royal Caribbean International

Rhapsody of the Seas

San Juan → Charlotte Amalie, Saint Thomas → Roseau → San Juan

Jan 15 · 7 nights

About average

$756 inside · $108/night

All departures

All upcoming departures

Compare all sailings for this itinerary.

Showing 21 upcoming departures.

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Itinerary pricing

What this itinerary usually costs

Typical pricing runs around $89/night, with most departures landing in the $81-$103/night band across 21 tracked sailings.

Typical price

$89/night

$624 total

Normal range

$81-$103/night

$569-$724 total

Lowest recent fare

Building history

$464 total

Comparison set

21 sailings

Used for itinerary baseline

When should I go?

Prices are usually lowest in winter

December–February departures have historically offered the best value.

December is typically the most expensive time to sail this itinerary.

Typical price / night

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Best value
Dec–Feb ~$76–$101/night
Most expensive
December ~$101/night

Route overview

How this route is built

Compare sailings →

7 nights · 5 port calls · 2 sea days · 4 countries

5 port calls across Virgin Islands, U.S., Sint Maarten (Dutch part), Antigua and Barbuda, Dominica · More port-intensive than many 7-night alternatives.

  1. 1

    Embark in San Juan

    Embarkation ports can vary by sailing

  2. 2

    Charlotte Amalie, Saint Thomas

    Virgin Islands, U.S. · Eastern Caribbean

  3. 3

    Frederiksted, Saint Croix

    Virgin Islands, U.S. · Eastern Caribbean

  4. 4

    Philipsburg

    Sint Maarten (Dutch part) · Eastern Caribbean

  5. 5

    Saint John's

    Antigua and Barbuda · Eastern Caribbean

  6. 6

    Roseau

    Dominica · Southern Caribbean

  7. 7

    Disembark in San Juan

    Disembarkation ports can vary by sailing

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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.