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November 2026 December 2026 January 2027 February 2027 March 2027 April 2027

Destination

Caribbean cruises from Philadelphia

Winter round trips of 10 to 12 nights on Norwegian Pearl, from November to March. Most call at San Juan, Puerto Plata, St. Thomas and Tortola. The longer ones add St. Maarten, Antigua, St. Lucia or Barbados. Expect two or three days at sea each way before and after the islands.

Our Caribbean and Bahamas guide covers the winter round trips, which islands each one visits and how many sea days to expect.

There are 19 such sailings on the board, running 10 to 12 nights, operated by Norwegian Cruise Line aboard Norwegian Pearl. The lowest recorded starting fare is $609 per person, on the Tue, Dec 8, 2026 departure.

Ports of call

San Juan (Puerto Rico)19 Puerto Plata (Dominican Republic)17 Tortola (British Virgin Islands)12 St. Thomas (U.S. Virgin Islands)12 Philipsburg (St. Maarten)7 St. John's (Antigua)7 St. Lucia6 Bridgetown (Barbados)2 Royal Naval Dockyard (Bermuda)1 Amber Cove (Dominican Republic)1 Basseterre (St. Kitts)1
Schedule last updated · 19 departures listed · Dates can change. Verify with the cruise line before booking.

Your Caribbean options

All routes

The 19 departures below run 3 different routes, cheapest per night first.

Distinct itineraries available, cheapest per night first
ItineraryNightsFrom
10-Night Caribbean

Calls at Tortola (British Virgin Islands) · St. Thomas (U.S. Virgin Islands) · San Juan (Puerto Rico) · Puerto Plata (Dominican Republic)

Next on Sat, Nov 28, 2026

10$609$61 a night
12-Night Caribbean

Calls at Philipsburg (St. Maarten) · Bridgetown (Barbados) · St. Lucia · St. John's (Antigua) · San Juan (Puerto Rico) · Puerto Plata (Dominican Republic)

Next on Mon, Jan 3, 2028

12$899$75 a night
11-Night Caribbean

Calls at Philipsburg (St. Maarten) · St. Thomas (U.S. Virgin Islands) · Tortola (British Virgin Islands) · San Juan (Puerto Rico) · Puerto Plata (Dominican Republic)

Next on Wed, Dec 23, 2026

11$1,029$94 a night

Starting fares per person, for the cheapest cabin listed, with taxes and port fees included, checked . Fares change often, so check the current price before you book.

Every departure by date

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By month

November 2026 1 December 2026 2 January 2027 3 February 2027 2 March 2027 2 November 2027 1 December 2027 2 January 2028 3 February 2028 2 March 2028 1

Other destinations from Philadelphia

Bermuda 49 sailings · from $549 Bahamas 6 sailings · from $819 Canada and New England 7 sailings · from $1,279 Europe and transatlantic 1 sailing · from $1,269

Starting fares per person, for the cheapest cabin listed, with taxes and port fees included, checked . Fares change often, so check the current price before you book.

Caribbean from Philadelphia: questions

How many Caribbean cruises leave Philadelphia?
19 Caribbean cruises leave Philadelphia, across 10 months, on 1 ship from Norwegian Cruise Line.

How long are Caribbean cruises from Philadelphia?
From 10 to 12 nights. The most common length is 10 nights, on 11 of the 19 sailings.

Which ports do Caribbean cruises from Philadelphia call at?
The ports these 19 sailings call at most are San Juan (19 sailings), Puerto Plata (17 sailings), Tortola (12 sailings), St. Thomas (12 sailings), and Philipsburg (7 sailings). Each sailing's own ports are in the list on this page.