Relaxed pace
5 ports in 14 nights
Plenty of uninterrupted ship time.
Eastern Caribbean cruises
Eastern Caribbean Loop via Tortola, South Friars Bay & Les Trois-Îlets
Tortola · South Friars Bay · Les Trois-Îlets · Port Elizabeth, New Jersey · Saint George's
Balanced itinerary with more sea time than port-packed variants. Covers Virgin Islands, British, Saint Kitts and Nevis, Martinique, United States, and more. Includes anchorage-style calls.
14 nights
Philipsburg
Eastern Caribbean
5 ports
9 sea days
What this trip feels like
Easygoing, familiar and ship-focused
9 sea days give you plenty of uninterrupted time onboard, while Tortola, South Friars Bay, and Les Trois-Îlets provide the trip's main day ashore. You're choosing this route for an easy break with minimal logistics, not destination variety.
Broad destination variety
Tortola · South Friars Bay · Les Trois-Îlets + more
Frequent changes of scenery across the itinerary.
Easy logistics
Round-trip from Philipsburg
No open-jaw flights or separate arrival and departure transfers.
Port experience
Tortola · 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 · 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
Typical pricing runs around $613/night, with most departures landing in the $558-$657/night band across 3 tracked sailings.
Typical price
$613/night
$8,584 total
Normal range
$558-$657/night
$7,818-$9,199 total
Lowest recent fare
Building history
$6,714 total
Comparison set
3 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
14 nights · 5 port calls · 9 sea days · 5 countries
5 port calls across Virgin Islands, British, Saint Kitts and Nevis, Martinique, United States · Leans more toward sea time than a port-packed 14-night route.
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Disembark in Philipsburg
Disembarkation ports can vary by sailing
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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 Kingstown + Saint George
Eastern Caribbean: Kingstown, Saint George & Fort-de-France
14 nights · 11 ports · 3 sea days
Same length +6 ports
Much more time ashore without making the trip longer.
Compare this route →
From $1,662
More variety
Add Ketchikan + Juneau
Eastern Caribbean: Ketchikan, Juneau & Victoria
40 nights · 18 ports · 12 countries
+26 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
+19 nights +11 sea days
More time onboard without changing the trip's overall pace much.
Compare this route →
From $2,242