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Eastern Caribbean cruises

Eastern Caribbean Loop via San Juan, Saint Thomas & Philipsburg

San Juan · Saint Thomas · Philipsburg · Antigua · Roseau

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

7 nights Bridgetown 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

San Juan · Saint Thomas · Philipsburg + more

Frequent changes of scenery across the itinerary.

Easy logistics

Round-trip from Bridgetown

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

Port experience

San Juan · 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

Crown Princess

Bridgetown → San Juan → Roseau → Bridgetown

Feb 5 · 7 nights

$1,286 oceanview · $184/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 $142/night, with most departures landing in the $118-$156/night band across 1 tracked sailing.

Typical price

$142/night

$994 total

Normal range

$118-$156/night

$823-$1,089 total

Lowest recent fare

$177/night

$1,238 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 · 5 port calls · 2 sea days · 5 countries

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

  1. 1

    Embark in Bridgetown

    Embarkation ports can vary by sailing

  2. 2

    San Juan

    Puerto Rico · Eastern Caribbean

  3. 3

    Saint Thomas

    Virgin Islands, U.S. · Eastern Caribbean

  4. 4

    Philipsburg

    Sint Maarten (Dutch part) · Eastern Caribbean

  5. 5

    Antigua

    Antigua and Barbuda · Eastern Caribbean

  6. 6

    Roseau

    Dominica · Southern Caribbean

  7. 7

    Disembark in Bridgetown

    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.