Port-forward pace
5 ports in 7 nights
Most days put a destination at the center of the plan.
Eastern Caribbean cruises
Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg
Charlotte Amalie, Saint Thomas · Frederiksted, Saint Croix · Philipsburg · Castries · Bridgetown
Port-heavy Eastern Caribbean itinerary. Covers Virgin Islands, U.S., Sint Maarten (Dutch part), Saint Lucia, and Barbados.
7 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 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
Charlotte Amalie, Saint Thomas · Frederiksted, Saint Croix · Philipsburg + 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
Charlotte Amalie, 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
Grandeur of the Seas
San Juan → Charlotte Amalie, Saint Thomas → Bridgetown → San Juan
Aug 21 · 7 nights
About average
$696 inside · $99/night
Cheapest upcoming
Grandeur of the Seas
San Juan → Charlotte Amalie, Saint Thomas → Bridgetown → San Juan
Sep 18 · 7 nights
About average
$680 oceanview · $97/night
All departures
All upcoming departures
Compare all sailings for this itinerary.
Showing 23 upcoming departures.
Itinerary pricing
What this itinerary usually costs
Typical pricing runs around $112/night, with most departures landing in the $105-$125/night band across 23 tracked sailings.
Typical price
$112/night
$787 total
Normal range
$105-$125/night
$732-$877 total
Lowest recent fare
Building history
$608 total
Comparison set
23 sailings
Used for itinerary baseline
When should I go?
Prices are usually lowest in fall
September–November departures have historically offered the best value.
July is typically the most expensive time to sail this itinerary.
Typical price / night
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- Best value
- Sep–Nov ~$93–$105/night
- Most expensive
- July ~$158/night
Route overview
How this route is built
7 nights · 5 port calls · 2 sea days · 4 countries
5 port calls across Virgin Islands, U.S., Sint Maarten (Dutch part), Saint Lucia, Barbados · 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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Render your Mapbox or Leaflet map here from the supplied route and port JSON.
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 Basseterre, Saint Kitts + Tortola
Eastern Caribbean: Philipsburg, Basseterre, Saint Kitts & Bridgetown
7 nights · 6 ports · 1 sea day
Same length +1 port
Much more time ashore without making the trip longer.
Compare this route →
From $949
More variety
Add Catalina Island + Fort-de-France
Eastern Caribbean: Catalina Island, Bridgetown & Fort-de-France
7 nights · 5 ports · 5 countries
Same length +1 country
A much broader Eastern Caribbean experience.
Compare this route →
From $568
Longer trip
Make it 9 nights
Eastern Caribbean: San Juan, Philipsburg & Charlotte Amalie, Saint Thomas
9 nights · 4 ports · 5 sea days
+2 nights +3 sea days
More time onboard without changing the trip's overall pace much.
Compare this route →
From $791