Relaxed pace
5 ports in 14 nights
Plenty of uninterrupted ship time.
Eastern Caribbean cruises
Eastern Caribbean Loop via Saint Thomas, Philipsburg & Antigua
Saint Thomas · Philipsburg · Antigua · Bridgetown · Castries
Balanced itinerary with more sea time than port-packed variants. Covers Virgin Islands, U.S., Sint Maarten (Dutch part), Antigua and Barbuda, Barbados, and more.
14 nights
San Juan
Eastern Caribbean
5 ports
9 sea days
What this trip feels like
Easygoing, familiar and ship-focused
9 sea days give you plenty of uninterrupted time onboard, while Saint Thomas, Philipsburg, and Antigua provide the trip's main day ashore. You're choosing this route for an easy break with minimal logistics, not destination variety.
Broad destination variety
Saint Thomas · Philipsburg · Antigua + 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 · First-time cruisers · Ship-focused trips · Easy short getaways
Think twice if · You want a port-intensive Eastern Caribbean itinerary
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 $128/night, with most departures landing in the $87-$191/night band across 2 tracked sailings.
Typical price
$128/night
$1,343 total
Normal range
$87-$191/night
$914-$2,000 total
Lowest recent fare
$128/night
$897 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
14 nights · 5 port calls · 9 sea days · 5 countries
5 port calls across Virgin Islands, U.S., Sint Maarten (Dutch part), Antigua and Barbuda, Barbados · Leans more toward sea time than a port-packed 14-night route.
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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 Kingstown + Saint George
Eastern Caribbean: Kingstown, Saint George & Fort-de-France
14 nights · 11 ports · 3 sea days
Same length +6 ports
Much more time ashore without making the trip longer.
Compare this route →
From $1,662
More variety
Add Ketchikan + Juneau
Eastern Caribbean: Ketchikan, Juneau & Victoria
40 nights · 18 ports · 12 countries
+26 nights +7 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
+19 nights +11 sea days
More time onboard without changing the trip's overall pace much.
Compare this route →
From $2,242