Relaxed pace
8 ports in 21 nights
Plenty of uninterrupted ship time.
Eastern Caribbean cruises
Eastern Caribbean Arc: San José, Jost Van Dyke & Road Bay
San José · Jost Van Dyke · Sopers Hole · Jost Van Dyke · Spanish Town (Virgin Gorda) · Road Bay · Philipsburg · Funchal, Madeira
Balanced itinerary, with more sea days than similar routes. Covers Costa Rica, Virgin Islands, British, Anguilla, Sint Maarten (Dutch part), and more.
21 nights
Philipsburg
Eastern Caribbean
8 ports
12 sea days
What this trip feels like
Mostly ship-focused
Mostly ship-focused, with 12 sea days and only 8 port calls.
Broad destination variety
San José · Jost Van Dyke · Sopers Hole + more
Frequent port calls throughout the itinerary.
Route logistics
Sails from Philipsburg
Check the exact departure and arrival ports before arranging flights.
Port experience
San José · You'll usually have a long port day
Cruise calls here typically give passengers plenty of time between arrival and departure.
Best for · First-time cruisers · Ship-focused trips · Easy short getaways
Think twice if · You want a port-intensive Eastern Caribbean itinerary
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
Not enough price history yet for this itinerary.
Median current fare
$198/night
$4,168 total
Lowest recent fare
$198/night
$4,168 total
Pricing signal
Building history
Price history for 0 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 · 8 port calls · 12 sea days · 5 countries
8 port calls across Costa Rica, Virgin Islands, British, Anguilla, Sint Maarten (Dutch part) · More sea days than many 21-night alternatives.
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Embark in Philipsburg
Embarkation ports can vary by sailing
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Disembark in Lisbon
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 + Basseterre, Saint Kitts
Eastern Caribbean: Philipsburg, Basseterre, Saint Kitts & Roseau
21 nights · 14 ports · 7 sea days
Same length +6 ports
Much more time ashore without making the trip longer.
Compare this route →
From $2,089
More variety
Add Rodney Bay + Curaçao
Eastern Caribbean: Rodney Bay, Curaçao & Oranjestad
0 nights · 16 ports · 14 countries
−21 nights +9 countries
A much broader Eastern Caribbean experience.
Compare this route →
From $14,198