Cruise itinerary
11-Night Caribbean Cruise from Philadelphia, Pennsylvania
11 nights · Caribbean · 6 ports of call
11-night Caribbean cruise aboard Norwegian Pearl, departing Philadelphia, Pennsylvania and calling at Philipsburg, Saint Thomas, Road Town, Tortola, San Juan (Puerto Rico) and Puerto Plata.
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At a glance
- Ship
- Norwegian Pearl
- Cruise line
- Norwegian Cruise Line
- Duration
- 11 nights
- Region
- Caribbean · Americas · North America · South America
- Departs
- Philadelphia, Pennsylvania
- Returns
- Philadelphia, Pennsylvania
How NestCruise works:we're advisor-led, not a booking engine. No fares are listed and there are no booking fees — tell an advisor your dates and party and they price your exact Norwegian Pearl sailing, typically within 24 hours.
Where this voyage takes you
Day-by-day itinerary
- Day1
Philadelphia, Pennsylvania
Depart 16:00
- Day2At sea
- Day3At sea
- Day4At sea
- Day5
Philipsburg
Arrive 07:00 · Depart 18:00
The Dutch-side capital of St. Maarten, set behind the long curve of Great Bay. Front Street is wall-to-wall duty-free; a short water taxi or drive reaches the French side's Marigot market and the famous low-flying jets over Maho Beach.
- Great Bay Beach
- Front Street duty-free
- Maho Beach plane-spotting
- Day6
Saint Thomas
Arrive 07:00 · Depart 18:00
An island in the U.S. Virgin Islands known for its deep harbour at Charlotte Amalie and its red-roofed hillsides. It offers duty-free shopping along the waterfront, the beach at Magens Bay, and a short ferry hop to quieter St. John.
- Magens Bay
- Charlotte Amalie
- Ferry to St. John
- Day7
Road Town, Tortola
Arrive 07:00 · Depart 18:00
The capital of Tortola in the British Virgin Islands, set on a harbour ringed by green hills. It is the main yachting base of the archipelago, with sheltered beaches, a small botanic garden, and ferries out to the surrounding cays.
- Cane Garden Bay
- Botanic Gardens
- Yacht harbour
- Day8
San Juan (Puerto Rico)
Arrive 07:00 · Depart 15:00
The capital of Puerto Rico and a major Caribbean homeport. Old San Juan's pastel colonial streets sit behind the massive El Morro and San Cristóbal forts, with rum distilleries and the beaches of Condado close to the cruise piers.
- Old San Juan
- El Morro fort
- Condado beaches
- Day9
Puerto Plata
Arrive 07:00 · Depart 15:00
A port on the north coast of the Dominican Republic, backed by the flat-topped Mount Isabel de Torres. A cable car climbs to its summit, the old town keeps a district of gingerbread Victorian houses, and amber and rum are local specialities.
- Mount Isabel cable car
- Amber Museum
- Victorian houses
- Day10At sea
- Day11At sea
- Day12
Philadelphia, Pennsylvania
Arrive 08:00
Upcoming departures
- 23 Dec 2026
Upcoming sailings of this itinerary — a NestCruise advisor confirms current availability and your fare.
11-Night Caribbean Cruise from Philadelphia, Pennsylvania FAQ
Which ports does this cruise visit?
This 11-night Caribbean cruise calls at Philadelphia, Pennsylvania, Philipsburg, Saint Thomas, Road Town, Tortola, San Juan (Puerto Rico) and Puerto Plata.
How many days are spent at sea?
5 days are spent at sea; the rest are in port.
Where does this cruise depart from?
It is a round-trip sailing from Philadelphia, Pennsylvania.
How long is this cruise?
11 nights aboard Norwegian Pearl.
When does this itinerary sail?
Upcoming departures include 23 Dec 2026. A NestCruise advisor can confirm current availability.