Port-forward pace
5 ports in 7 nights
Most days put a destination at the center of the plan.
Eastern Caribbean cruises
Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Tortola & Cruz Bay, Saint John
Charlotte Amalie, Saint Thomas · Tortola · Cruz Bay, Saint John · Philipsburg · Roseau
Port-heavy Eastern Caribbean itinerary. Covers Virgin Islands, U.S., Virgin Islands, British, Sint Maarten (Dutch part), and Dominica.
7 nights
San Juan
Eastern Caribbean
5 ports
2 sea days
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.
Broad destination variety
Charlotte Amalie, Saint Thomas · Tortola · Cruz Bay, Saint John + 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.
All departures
All upcoming departures
Compare all sailings for this itinerary.
Itinerary pricing
What this itinerary usually costs
Typical pricing runs around $123/night, with most departures landing in the $97-$143/night band across 2 tracked sailings.
Typical price
$123/night
$864 total
Normal range
$97-$143/night
$678-$999 total
Lowest recent fare
Building history
$549 total
Comparison set
2 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
7 nights · 5 port calls · 2 sea days · 4 countries
5 port calls across Virgin Islands, U.S., Virgin Islands, British, Sint Maarten (Dutch part), Dominica · More port-intensive than many 7-night alternatives.
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Embark in San Juan
Embarkation ports can vary by sailing
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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.
More port time
Add Basseterre, Saint Kitts + Bridgetown
Eastern Caribbean: Philipsburg, Basseterre, Saint Kitts & Bridgetown
7 nights · 6 ports · 1 sea day
Same length +1 port
Much more time ashore without making the trip longer.
Compare this route →
From $949
More variety
Add Castries + Bridgetown
Eastern Caribbean: Philipsburg, Castries & Bridgetown
7 nights · 6 ports · 6 countries
Same length +2 countries
A much broader Eastern Caribbean experience.
Compare this route →
From $989
Longer trip
Make it 8 nights
Eastern Caribbean: Basseterre, Saint Kitts, Philipsburg & San Juan
8 nights · 4 ports · 4 sea days
+1 night +2 sea days
More time onboard without changing the trip's overall pace much.
Compare this route →
From $648