Port-forward pace
11 ports in 5–14 nights
Most days put a destination at the center of the plan.
Eastern Caribbean cruises
Eastern Caribbean Loop via Saint Thomas, Basseterre, Saint Kitts & Roseau
Saint Thomas · Basseterre, Saint Kitts · Roseau · Saint George's · Bridgetown · San Juan · Saint Thomas · Philipsburg · Antigua · Castries · Bridgetown
Port-heavy Eastern Caribbean itinerary. Covers Virgin Islands, U.S., Saint Kitts and Nevis, Dominica, Grenada, and more.
5–14 nights
San Juan
Eastern Caribbean
11 ports
What this trip feels like
Active, varied and destination-focused
With 11 ports across 5–14 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
Saint Thomas · Basseterre, Saint Kitts · Roseau + 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
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
Crown Princess
San Juan → Saint Thomas → Castries → San Juan
Feb 14 · 14 nights
$1,559 inside · $111/night
Cheapest upcoming
Crown Princess
San Juan → Saint Thomas → Saint George's → Bridgetown
Jan 3 · 5 nights
$893 oceanview · $179/night
All departures
All upcoming departures
Compare all sailings for this itinerary.
Itinerary pricing
What this itinerary usually costs
Typical pricing runs around $142/night, with most departures landing in the $116-$156/night band across 5 tracked sailings.
Typical price
$142/night
$994 total
Normal range
$116-$156/night
$809-$1,089 total
Lowest recent fare
$171/night
$857 total
Comparison set
5 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
5–14 nights · 11 port calls · 9 countries
11 port calls across Virgin Islands, U.S., Saint Kitts and Nevis, Dominica, Grenada · More port-intensive than many 5-night alternatives.
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Embark in San Juan
Embarkation ports can vary by sailing
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Disembark in San Juan or 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.
More port time
Add Fort-de-France + Half Moon Cay
Eastern Caribbean: Philipsburg, Antigua & Fort-de-France
0 nights · 13 ports · 0 sea days
−5 nights +2 ports
Much more time ashore in a shorter trip.
Compare this route →
From $1,749
More variety
Add Ketchikan + Juneau
Eastern Caribbean: Ketchikan, Juneau & Victoria
40 nights · 18 ports · 12 countries
+35 nights +3 countries
A much broader Eastern Caribbean experience.
Compare this route →
From $3,016
Longer trip
Make it 33 nights
Eastern Caribbean: Los Angeles, Cabo San Lucas & Puerto Quetzal
33 nights · 13 ports · 20 sea days
+28 nights +20 sea days
More time onboard without changing the trip's overall pace much.
Compare this route →
From $2,242