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

Caribbean and Bahamas cruises from Philadelphia: winter round trips on Norwegian Pearl

This schedule has 19 Caribbean cruises and 6 Bahamas cruises from Philadelphia, all winter round trips on Norwegian Pearl. The Caribbean trips last 10 to 12 nights and most spend five days at sea. The 8-night Bahamas trips also call at Port Canaveral, Florida. On 3 November 2026 Caribbean fares started at $609 and Bahamas fares at $819 per person.

By Andrew Budai · Last checked · Rates and opening hours change, so confirm before you travel.

Every Caribbean and Bahamas cruise from Philadelphia on this schedule is a winter round trip on Norwegian Pearl. There are no one-way trips south and none shorter than 8 nights.

The schedule has 19 Caribbean sailings, from 28 November 2026 to 7 March 2028, and 6 to the Bahamas, from 12 February 2027 to 25 March 2028. On 3 November 2026 Caribbean fares ran from $609 to $1,919 and Bahamas fares from $819 to $1,049 per person, for the cheapest cabin listed with two sharing, taxes and port fees included. The table at the end of this guide lists the Caribbean sailings. The Bahamas page lists the Bahamas ones.

How long is a Caribbean cruise from Philadelphia?

Between 10 and 12 nights. Every one is a round trip, and most spend five days at sea, two or three going south and two or three coming back. That leaves four port days on a 10-night trip, five on an 11-night trip and six on a 12-night trip.

Pearl leaves Philadelphia at 4pm and is due back at 7am or 8am, according to the itineraries on sale. The departures fall on different days of the week, so check the day as well as the date. Our cruise length page compares every length on offer.

Which islands do Caribbean cruises from Philadelphia visit?

San Juan is on 19 of the 19 Caribbean sailings, and Puerto Plata in the Dominican Republic on 17. The 2026 to 2027 winter mostly pairs them with St. Thomas and Tortola in the Virgin Islands. Most of the 2027 to 2028 winter reaches further, to St. Maarten, Antigua, St. Lucia, Barbados or St. Kitts.

These are the itineraries on sale, with the ports in the order Pearl visits them.

LeavesNightsPorts, in orderDays at sea, going then coming back
28 November 2026, 23 January 2027, 20 February 2027, 26 February 202810Tortola, St. Thomas, San Juan, Puerto Plata3, 2
13 January 202710St. Thomas, Tortola, San Juan, Puerto Plata3, 2
8 December 2026, 2 February 2027, 2 March 2027, 7 March 202810Puerto Plata, San Juan, St. Thomas, Tortola2, 3
3 January 202710San Juan overnight, Tortola, St. Thomas2, 3
13 December 202710Puerto Plata, San Juan, St. Maarten, Antigua2, 3
23 December 202611St. Maarten, St. Thomas, Tortola, San Juan, Puerto Plata3, 2
28 March 202711Bermuda overnight, Tortola, St. Thomas, San Juan, Amber Cove1 each side of Bermuda, 2
27 November 202711Puerto Plata, San Juan, Antigua, St. Lucia, St. Maarten2, 3
23 December 202711St. Kitts, St. Lucia, Antigua, San Juan, Puerto Plata3, 2
27 January 202811Antigua, St. Lucia, St. Maarten, San Juan, Puerto Plata3, 2
7 February 202811St. Maarten, St. Lucia, Antigua, San Juan, Puerto Plata3, 2
3 January 202812St. Maarten, Barbados, St. Lucia, Antigua, San Juan, Puerto Plata3, 2
15 January 202812St. Maarten, St. Lucia, Barbados, Antigua, San Juan, Puerto Plata3, 2

The order changes the day. When San Juan comes late in the trip, Pearl is usually there from 7am to 3pm. On the trips that start with Puerto Plata, the ship reaches Puerto Plata at 11am or later and spends the next day in San Juan from about 10am to 6pm. The trip of 3 January 2027 is the only one with a night in San Juan, from 6pm on Wednesday to 6pm on Thursday.

What is the weather like at sea on a winter cruise from Philadelphia?

The sea days at each end cross the stretch of the Atlantic where NOAA says nor'easters form, within 100 miles of the coast between New Jersey and Georgia. NOAA says these storms are most common between September and April and most severe in winter, and that their gusts can top hurricane force.

The trip also starts and ends in a Philadelphia winter, so pack for both climates. Hurricanes are a smaller concern on these dates. The National Hurricane Center gives the Atlantic season as 1 June to 30 November, so only the departures of 28 November 2026 and 27 November 2027 leave inside it, in its last days.

Are there cruises from Philadelphia to the Bahamas?

Yes. Norwegian Pearl sails 6 8-night Bahamas round trips from Philadelphia, in February and March of 2027 and 2028. Each calls at two of Nassau, Grand Bahama and Great Stirrup Cay, and at Port Canaveral, Florida. Most also call at Jacksonville. The sailing of 20 March 2027 calls at Norfolk, Virginia, instead.

LeavesPorts, in orderDays at sea, going then coming back
Friday 12 February 2027Nassau, Grand Bahama, Port Canaveral, Jacksonville2, 1
Friday 12 March 2027Nassau, Great Stirrup Cay, Port Canaveral, Jacksonville2, 1
Saturday 20 March 2027Norfolk, Port Canaveral, Grand Bahama, Great Stirrup Cay1, 2
Friday 18 February 2028Jacksonville, Port Canaveral, Great Stirrup Cay, Grand Bahama1, 2
Friday 17 March 2028Jacksonville, Port Canaveral, Great Stirrup Cay, Grand Bahama1, 2
Saturday 25 March 2028Jacksonville, Port Canaveral, Great Stirrup Cay, Nassau1, 2

The 2027 trips reach the Bahamas first and stop in Florida on the way home. The 2028 trips do it the other way round. On 3 November 2026 the Bahamas trips started at $819 per person, or $102 a night, for the cheapest cabin listed with two sharing, taxes and port fees included.

What can you do at Port Canaveral and Jacksonville on a Bahamas cruise?

Port Canaveral's own page lists Jetty Park's beach, The Cove restaurants and the Kennedy Space Center Visitor Complex as nearby, and the Cocoa Beach Pier a short drive away, though it gives no distances. JAXPORT's cruise page names no sights near its terminal at 9810 August Drive in North Jacksonville.

How long you get depends on the year. These are the times on the itineraries on sale.

Port2027 Friday trips20 March 20272028 trips
Port CanaveralWednesday, 7am to 5:30pmTuesday, 8:30am to 9pmMonday or Tuesday, 9am to 9pm
JacksonvilleThursday, 7am to 1pmNo callSunday or Monday, 11am to 7pm

The Port Canaveral calls of 20 March 2027 and of 2028 last 12 hours or more, the longest stops on these trips. The 2027 Jacksonville calls last six.

What is Great Stirrup Cay?

Norwegian Cruise Line's private island in the Bahamas. Norwegian says a new pier lets you walk straight from the ship to the sand. Its page lists complimentary places to eat and the Great Life Lagoon pool, with swim-up bars, and offers cabanas for rent and Silver Cove villas as a private retreat.

It is on 5 of the 6 Bahamas sailings, and the trip of 12 February 2027 skips it for Grand Bahama. On the 2028 trips Pearl is there from about 10am to 6pm.

Which Caribbean cruise from Philadelphia also goes to Bermuda?

Only Norwegian Pearl's 11-night trip of 28 March 2027. It spends a night at Bermuda's Royal Naval Dockyard, from 10am on Tuesday to 1pm on Wednesday, then calls at Tortola, St. Thomas, San Juan and Amber Cove in the Dominican Republic before two days at sea home.

It has four days at sea, one fewer than the other Caribbean trips, and is back in Philadelphia at 8am on 8 April 2027. Our Bermuda guide explains getting around the island from Dockyard.

Do you need a passport for a Caribbean or Bahamas cruise from Philadelphia?

Not under U.S. rules, for a U.S. citizen on a round trip. CBP says closed-loop cruises, which start and end at the same U.S. port and stay in the Western Hemisphere, allow a government-issued photo ID with proof of citizenship such as a birth certificate. CBP also warns that the countries you visit may still ask for a passport.

CBP counts Puerto Rico and the U.S. Virgin Islands as part of the United States, so San Juan and St. Thomas are U.S. stops. The other islands on these trips are not on its list of U.S. territories: Tortola, the Dominican Republic, St. Maarten, Antigua, St. Lucia, Barbados, St. Kitts, the Bahamas and Bermuda.

If you had to leave the ship and fly home from one of them, CBP says U.S. citizens need a passport to enter the United States by air from the Caribbean, and the passport card is not accepted for international air travel. Our cruise documents guide explains which document covers which trip.

How much is a Caribbean cruise from Philadelphia?

On 3 November 2026 Caribbean fares ran from $609 to $1,919 per person, for the cheapest cabin listed with two sharing, taxes and port fees included. The lowest worked out at $61 a night, against $78 on the Bermuda trips. Fares move often, so check the sailing you want.

TripLowest fare on 3 November 2026Lowest per night
Caribbean, 10 nights$609$61
Caribbean, 11 nights$1,029$94
Caribbean, 12 nights$899$75
Bahamas, 8 nights$819$102

The sailings of 23 December 2026 and 23 December 2027 cover Christmas and New Year and are back on 3 January. Our holiday cruises page lists them with the other holiday dates.

The fare does not cover getting to the terminal: see our guides to cruise parking, the airport and hotels near the terminal. For the lowest fares on every route, see cheap cruises from Philadelphia, and the Caribbean page lists every Caribbean sailing with a link to each one.

When do Caribbean cruises leave Philadelphia?

From late November to late March, in both winters on this schedule, with the Bahamas trips in February and March. In between, Pearl sails to Bermuda from April and to Canada in September and October 2027, so there are no Caribbean departures in summer.

The first Caribbean departure on this schedule is 28 November 2026 and the last 7 March 2028. Our Philadelphia cruise season guide shows what leaves in each month, and the full schedule lists every sailing by date.

Sources

Cruises from Philadelphia to the Caribbean

From the schedule on this site, rebuilt every day.

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