Port-forward pace
10 ports in 14 nights
Most days are port days.
Eastern Caribbean cruises
Eastern Caribbean Arc: Tortola, Basseterre, Saint Kitts & Road Bay
San Juan → Road Town → Basseterre, Saint Kitts → Saint-Barthélemy → Road Bay → Miami → Providenciales → Puerto Plata → La Romana → Jost Van Dyke → Saint-Barthélemy → San Juan
Port-heavy Eastern Caribbean itinerary. Covers United Kingdom, Saint Kitts and Nevis, Saint Barthélemy, Anguilla, and more.
14 nights
San Juan
Eastern Caribbean
10 ports
2 sea days
What this trip feels like
Port-intensive itinerary
Port-intensive itinerary with 10 port calls across 14 nights.
Broad destination variety
Road Town · Basseterre, Saint Kitts · Saint-Barthélemy + more
Frequent port calls throughout the itinerary.
Easy logistics
Round-trip from San Juan
No open-jaw flights or separate arrival and departure transfers.
Port experience
Road Town · 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
1 of 1 sailings with enough price history currently have favorable pricing. Median current fare is $651/night.
Median current fare
$651/night
$9,120 total
Lowest recent fare
$651/night
$9,120 total
Pricing signal
1 of 1 favorable
Price history for 1 of 1 sailings
Comparison set
1 sailings
Currently priced departures
When should I go?
Not enough departures yet to identify a reliable cheaper season.
Route overview
How this route is built
14 nights · 10 port calls · 2 sea days · 8 countries
10 port calls across United Kingdom, Saint Kitts and Nevis, Saint Barthélemy, Anguilla · More port-intensive than many 14-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 Rodney Bay + Little Bay
Eastern Caribbean: Rodney Bay, Little Bay & Saint John's
14 nights · 11 ports · 3 sea days
Same length +1 port
Much more time ashore without making the trip longer.
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From $5,679
More variety
Add Rodney Bay + Curaçao
Eastern Caribbean: Rodney Bay, Curaçao & Oranjestad
0 nights · 16 ports · 14 countries
−14 nights +6 countries
A much broader Eastern Caribbean experience.
Compare this route →
From $14,198
Longer trip
Make it 21 nights
Eastern Caribbean: Half Moon Cay, Falmouth & Georgetown, Grand Cayman
21 nights · 14 ports · 7 sea days
+7 nights +5 sea days
More time at sea.
Compare this route →
From $2,049