Port-forward pace
5 ports in 7 nights
Most days are port days.
Eastern Caribbean cruises
Eastern Caribbean Loop: Road Bay & Jost Van Dyke
Road Bay · Jost Van Dyke · Sopers Hole · Jost Van Dyke · Spanish Town (Virgin Gorda)
Port-heavy Eastern Caribbean itinerary. Covers Anguilla and Virgin Islands, British.
7 nights
Philipsburg
Eastern Caribbean
5 ports
2 sea days
What this trip feels like
Port-intensive itinerary
Port-intensive itinerary with 5 port calls across 7 nights.
Broad destination variety
Road Bay · Jost Van Dyke · Sopers Hole + more
Frequent port calls throughout the itinerary.
Easy logistics
Round-trip from Philipsburg
No open-jaw flights or separate arrival and departure transfers.
Port experience
Road Bay · 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
Not enough price history yet for this itinerary.
Median current fare
$520/night
$3,638 total
Lowest recent fare
$475/night
$3,323 total
Pricing signal
Building history
Price history for 0 of 3 sailings
Comparison set
3 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
7 nights · 5 port calls · 2 sea days · 2 countries
5 port calls across Anguilla, Virgin Islands, British · More port-intensive than many 7-night alternatives.
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Embark in Philipsburg
Embarkation ports can vary by sailing
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Disembark in 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 San Juan + South Friars Bay
Eastern Caribbean: San Juan, Jost Van Dyke & South Friars Bay
8 nights · 11 ports · 0 sea days
+1 night +6 ports
Much more time ashore for only one extra night.
Compare this route →
From $3,679
More variety
Add Grand Turk Island + San Juan
Eastern Caribbean: Grand Turk Island, San Juan & Saint Thomas
7 nights · 9 ports · 8 countries
Same length +6 countries
A much broader Eastern Caribbean experience.
Compare this route →
From $449
Longer trip
Make it 8 nights
Eastern Caribbean: South Friars Bay, Little Bay & Rodney Bay
8 nights · 3 ports · 5 sea days
+1 night +3 sea days
More time at sea.
Compare this route →
From $4,798