Port-forward pace
21 ports in 21 nights
Most days are port days.
Eastern Caribbean cruises
Eastern Caribbean Arc: Basseterre, Saint Kitts, Road Bay & Spanish Town
Basseterre, Saint Kitts · Road Bay · Spanish Town (Virgin Gorda) · Saint-Barthélemy · Philipsburg · Spanish Town (Virgin Gorda) · Saint-Barthélemy · Charlestown · Saint John's · Terre-de-Haut (Les Saintes) · Soufriere · Bridgetown · Kingstown · Port Elizabeth, Bequia · Mayreau Island · Union Island
Port-heavy Eastern Caribbean itinerary. Covers Saint Kitts and Nevis, Anguilla, Virgin Islands, British, Saint Barthélemy, and more.
21 nights
Philipsburg
Eastern Caribbean
21 ports
What this trip feels like
Port-intensive itinerary
Port-intensive itinerary with 21 port calls across 21 nights.
Broad destination variety
Basseterre, Saint Kitts · Road Bay · Spanish Town (Virgin Gorda) + more
Frequent port calls throughout the itinerary.
Route logistics
Sails from Philipsburg
Check the exact departure and arrival ports before arranging flights.
Port experience
Basseterre, Saint Kitts · 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
0 of 1 sailings with enough price history currently have favorable pricing. Median current fare is $1,014/night.
Median current fare
$1,014/night
$21,289 total
Lowest recent fare
$1,014/night
$21,289 total
Pricing signal
0 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
21 nights · 21 port calls · 10 countries
21 port calls across Saint Kitts and Nevis, Anguilla, Virgin Islands, British, Saint Barthélemy · More port-intensive than many 21-night alternatives.
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Embark in Philipsburg
Embarkation ports can vary by sailing
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Disembark in Bridgetown
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 variety
Add Rodney Bay + Curaçao
Eastern Caribbean: Rodney Bay, Curaçao & Oranjestad
0 nights · 16 ports · 14 countries
−21 nights +4 countries
A much broader Eastern Caribbean experience.
Compare this route →
From $14,198