Eastern Caribbean Loop via Philipsburg, Saint Thomas & Tortola

Philadelphia → Philipsburg → Saint Thomas → Tortola → San Juan → Puerto Plata → Philadelphia

11 nights
Philadelphia
Eastern Caribbean
5 ports

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Embark and disembark port

Port of call

Port by port

11 nights · 5 port calls · 5 countries

Stop #1

Embark

Philadelphia

United States · US East Coast
Stop #2

Philipsburg

Sint Maarten (Dutch part) · Eastern Caribbean

Usually docks
Stop #3

Saint Thomas

Virgin Islands, U.S. · Eastern Caribbean

Usually docks
Stop #4

Tortola

Virgin Islands, British · Eastern Caribbean

Usually docks
Stop #5

San Juan

Puerto Rico · Eastern Caribbean

Usually docks
Stop #6

Puerto Plata

Dominican Republic · Eastern Caribbean

Usually docks
Stop #7

Disembark

Philadelphia

United States · US East Coast

What would you change about this trip?

Explore other routes with different ports, trip lengths, and departure ports.

Add Basseterre, Saint Kitts

Depart from New York instead · 1 night longer

Adds Saint Kitts and Nevis

Lowest fare is ~22% lower than this route

Puerto Plata, San Juan & Basseterre, Saint Kitts

4 upcoming departures From $93/night

Skip Philipsburg

1 night shorter

Lowest fare is ~48% lower than this route

Tortola & Saint Thomas

4 upcoming departures From $63/night

Pricing

1 of 1 sailings with enough price history currently have favorable pricing. Median current fare is $120/night.

Median current fare: $120/night; $1,319 total
Lowest recent fare: $120/night; $1,319 total
Sailings with good pricing: 1 of 1 favorable; Price history for 1 of 1 sailings
Comparison set: 1 sailings; Currently priced departures

Best departures

How these are chosen

Best overall value: the strongest value signal, a fare furthest below Jibhop's typical fare for the same cabin, among departures with enough price history.
Lowest fare: the lowest current starting fare among all listed departures. Cabin categories can differ between departures, so check the cabin shown.
Best near-term option: a below-typical fare on a departure within the next 90 days.
Currently priced high: a fare above its usual range in Jibhop's observations. Shown as a warning, not a recommendation.

Best overall value

Norwegian Pearl

Philadelphia → Philipsburg → Puerto Plata → Philadelphia

Dec 23, 2026 · 11 nights

$2,189 suite · $199/night

58% below typical · Price trending down

All departures

Each fare is the departure's lowest current fare; the cabin category can differ between departures. Observed fares, not guaranteed availability.

Dec 23, 2026

Norwegian Pearl • 11 nights • Philadelphia ↔

Book today

58% below typical

$1,319

$120/night

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