Relaxed pace
4 ports in 10 nights
Plenty of uninterrupted ship time.
Eastern Caribbean cruises
Eastern Caribbean Loop via Tortola & Saint Thomas
Tortola · Saint Thomas · San Juan · Puerto Plata
Balanced itinerary with more sea time than port-packed variants. Covers Virgin Islands, British, Virgin Islands, U.S., Puerto Rico, and Dominican Republic.
10 nights
Philadelphia
Eastern Caribbean
4 ports
6 sea days
What this trip feels like
Easygoing, familiar and ship-focused
6 sea days give you plenty of uninterrupted time onboard, while Tortola, Saint Thomas, and San Juan 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 · Saint Thomas · San Juan + more
Frequent changes of scenery across the itinerary.
Easy logistics
Round-trip from Philadelphia
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.
Best overall value
Norwegian Pearl
Philadelphia → Tortola → Puerto Plata → Philadelphia
Nov 28 · 10 nights
Good value
$799 inside · $80/night
13% below typical · 3-month lowAll departures
All upcoming departures
Compare all sailings for this itinerary.
Itinerary pricing
What this itinerary usually costs
Typical pricing runs around $96/night, with most departures landing in the $88-$126/night band across 4 tracked sailings.
Typical price
$96/night
$959 total
Normal range
$88-$126/night
$883-$1,261 total
Lowest recent fare
$80/night
$799 total
Comparison set
4 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
10 nights · 4 port calls · 6 sea days · 4 countries
4 port calls across Virgin Islands, British, Virgin Islands, U.S., Puerto Rico, Dominican Republic · Leans more toward sea time than a port-packed 10-night route.
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Embark in Philadelphia
Embarkation ports can vary by sailing
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Disembark in Philadelphia
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 + Antigua
Eastern Caribbean: Philipsburg, Antigua & Fort-de-France
11 nights · 13 ports · 0 sea days
+1 night +9 ports
Much more time ashore for only one extra night.
Compare this route →
From $1,049
More variety
Add Charlotte Amalie, Saint Thomas + Saint-Barthélemy
Eastern Caribbean: Charlotte Amalie, Saint Thomas, Saint-Barthélemy & Saint John's
12 nights · 7 ports · 7 countries
+2 nights +3 countries
A much broader Eastern Caribbean experience.
Compare this route →
From $2,640
Longer trip
Make it 21 nights
Eastern Caribbean: San Juan, Cruz Bay, Saint John & Castries
21 nights · 6 ports · 15 sea days
+11 nights +9 sea days
More time onboard without changing the trip's overall pace much.
Compare this route →
From $1,006