Cruise itinerary
14-Night Caribbean Cruise from Boston, Massachusetts
14 nights · Caribbean · 8 ports of call
14-night Caribbean cruise aboard Norwegian Breakaway, departing Boston, Massachusetts and calling at Saint Thomas, Castries, Saint George's, Willemstad, Oranjestad and Georgetown, Grand Cayman and 1 more.
- Free advisor
- No booking fees
- 10,000+ sailings
At a glance
- Cruise line
- Norwegian Cruise Line
- Duration
- 14 nights
- Region
- Caribbean · Americas · North America · South America
- Departs
- Boston, Massachusetts
- Returns
- New Orleans, Louisiana
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 Breakaway sailing, typically within 24 hours.
Where this voyage takes you
Day-by-day itinerary
- Day1
Boston, Massachusetts
Depart 16:00
A historic New England port city in Massachusetts, central to the American Revolution. Boston is known for the Freedom Trail linking colonial landmarks, the Italian North End, Fenway Park, and the cobbled streets of Beacon Hill.
- Freedom Trail
- Fenway Park
- North End
- Day2At sea
- Day3At sea
- Day4At sea
- Day5
Saint Thomas
Arrive 07:00 · Depart 14:00
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
- Day6
Castries
Arrive 10:00 · Depart 19:00
The capital of St. Lucia, tucked into a sheltered harbour on the island's northwest coast. Beyond the market town rise the rainforested interior and the iconic twin Piton peaks further south along the volcanic coastline.
- The Pitons
- Central market
- Pigeon Island
- Day7
Saint George's
Arrive 07:00 · Depart 15:00
The capital of Grenada in the eastern Caribbean, set around a horseshoe harbour ringed by red-roofed houses. Known as the Spice Isle for its nutmeg, the island offers Grand Anse beach, hillside Fort George and rainforest waterfalls inland.
- Grand Anse Beach
- Fort George
- Nutmeg plantations
- Day8At sea
- Day9
Willemstad
Arrive 07:00 · Depart 22:00
The capital of Curaçao in the southern Caribbean, with a UNESCO-listed centre of Dutch colonial architecture. Willemstad is known for the candy-coloured waterfront of Handelskade, the swinging Queen Emma pontoon bridge, and its floating market.
- Handelskade façades
- Queen Emma Bridge
- Floating Market
- Day10
Oranjestad
Arrive 07:00 · Depart 17:00
The capital of Aruba, set on the island's leeward south coast in the southern Caribbean. Oranjestad is known for its Dutch colonial façades along Wilhelminastraat, a free streetcar through downtown, and white-sand beaches like Eagle and Palm just north.
- Eagle Beach
- Palm Beach
- Dutch colonial centre
- Day11At sea
- Day12
Georgetown, Grand Cayman
Arrive 09:00 · Depart 19:00
Grand Cayman's capital and the main port of the Cayman Islands, set on the calm western shore. Cruise ships tender into the harbour beside Seven Mile Beach, with Stingray City sandbars and Caribbean reef diving a short boat ride away.
- Seven Mile Beach
- Stingray City
- Seven Mile reefs
- Day13At sea
- Day14At sea
- Day15
New Orleans, Louisiana
Arrive 07:00
Upcoming departures
- 8 Nov 2026
- 4 Apr 2027
Upcoming sailings of this itinerary — a NestCruise advisor confirms current availability and your fare.
14-Night Caribbean Cruise from Boston, Massachusetts FAQ
Which ports does this cruise visit?
This 14-night Caribbean cruise calls at Boston, Massachusetts, Saint Thomas, Castries, Saint George's, Willemstad, Oranjestad, Georgetown, Grand Cayman and New Orleans, Louisiana.
How many days are spent at sea?
7 days are spent at sea; the rest are in port.
Where does this cruise depart from?
It departs from Boston, Massachusetts and ends in New Orleans, Louisiana.
How long is this cruise?
14 nights aboard Norwegian Breakaway.
When does this itinerary sail?
Upcoming departures include 8 Nov 2026 and 4 Apr 2027. A NestCruise advisor can confirm current availability.