Port-forward pace
5 ports in 7–14 nights
Most days put a destination at the center of the plan.
Eastern Caribbean cruises
Eastern Caribbean Loop via Saint Thomas, Philipsburg & Antigua
Saint Thomas · Philipsburg · Antigua · Castries · Bridgetown
Port-heavy Eastern Caribbean itinerary. Covers Virgin Islands, U.S., Sint Maarten (Dutch part), Antigua and Barbuda, Saint Lucia, and more.
7–14 nights
San Juan
Eastern Caribbean
5 ports
2 sea days
What this trip feels like
Active, varied and destination-focused
With 5 ports across 7–14 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 · 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 · 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 → Bridgetown → San Juan
Jan 24 · 7 nights
$788 oceanview · $113/night
Cheapest upcoming
Crown Princess
San Juan → Saint Thomas → Bridgetown → San Juan
Jan 10 · 7 nights
$738 inside · $105/night
All departures
All upcoming departures
Compare all sailings for this itinerary.
Showing 14 upcoming departures.
Itinerary pricing
What this itinerary usually costs
Typical pricing runs around $132/night, with most departures landing in the $109-$141/night band across 14 tracked sailings.
Typical price
$132/night
$930 total
Normal range
$109-$141/night
$763-$1,019 total
Lowest recent fare
$105/night
$738 total
Comparison set
14 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
7–14 nights · 5 port calls · 2 sea days · 5 countries
5 port calls across Virgin Islands, U.S., Sint Maarten (Dutch part), Antigua and Barbuda, Saint Lucia · 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 Fort-de-France + Roseau
Eastern Caribbean: Philipsburg, Antigua & Fort-de-France
0 nights · 13 ports · 0 sea days
−7 nights +8 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
+33 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
+26 nights +18 sea days
More time onboard without changing the trip's overall pace much.
Compare this route →
From $2,242