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 Castries, Little Bay & South Friars Bay
Castries · Little Bay · Antigua · South Friars Bay · Jost Van Dyke
Port-heavy Eastern Caribbean itinerary. Covers Saint Lucia, Montserrat, Antigua and Barbuda, Saint Kitts and Nevis, and more. Includes anchorage-style calls.
7–14 nights
Bridgetown
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
Castries · Little Bay · Antigua + more
Frequent changes of scenery across the itinerary.
Easy logistics
Round-trip from Bridgetown
No open-jaw flights or separate arrival and departure transfers.
Port experience
Castries · 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
Seabourn Ovation
Bridgetown → Castries → Jost Van Dyke → Philipsburg
Jan 9 · 7 nights
About average
$3,759 balcony · $537/night
Cheapest upcoming
Seabourn Ovation
Bridgetown → Castries → Jost Van Dyke → Philipsburg
Feb 26 · 7 nights
About average
$8,499 suite · $1,214/night
All departures
All upcoming departures
Compare all sailings for this itinerary.
Itinerary pricing
What this itinerary usually costs
Typical pricing runs around $616/night, with most departures landing in the $565-$671/night band across 6 tracked sailings.
Typical price
$616/night
$8,208 total
Normal range
$565-$671/night
$7,441-$9,049 total
Lowest recent fare
$537/night
$3,759 total
Comparison set
6 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 Saint Lucia, Montserrat, Antigua and Barbuda, Saint Kitts and Nevis · More port-intensive than many 7-night alternatives.
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Embark in Bridgetown
Embarkation ports can vary by sailing
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Disembark in Bridgetown or Philipsburg
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 Philipsburg + Fort-de-France
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