Port-forward pace
11 ports in 8 nights
Most days put a destination at the center of the plan.
Eastern Caribbean cruises
Eastern Caribbean Loop via Philipsburg, Terre-de-Haut & Road Bay
Philipsburg · Terre-de-Haut (Les Saintes) · Saint George's · Castries · Puerto Plata · Miami · Charlotte Amalie, Saint Thomas · Road Bay · Saint-Pierre · Basseterre, Saint Kitts · Philipsburg
Port-heavy Eastern Caribbean itinerary. Covers Sint Maarten (Dutch part), Guadeloupe, Grenada, Saint Lucia, and more.
8 nights
San Juan
Eastern Caribbean
11 ports
What this trip feels like
Active, varied and destination-focused
With 11 ports across 8 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
Philipsburg · Terre-de-Haut (Les Saintes) · Saint George's + more
Frequent changes of scenery across the itinerary.
Route logistics
Sails from San Juan
Check the exact departure and arrival ports before arranging flights.
Port experience
Philipsburg · 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 $737/night, with most departures landing in the $696-$773/night band across 2 tracked sailings.
Typical price
$737/night
$8,846 total
Normal range
$696-$773/night
$8,351-$9,270 total
Lowest recent fare
$640/night
$5,120 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
8 nights · 11 port calls · 10 countries
11 port calls across Sint Maarten (Dutch part), Guadeloupe, Grenada, Saint Lucia · More port-intensive than many 8-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 Miami
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.
No meaningfully different nearby routes are ready to compare yet.