Destination
Caribbean and Florida cruises from Boston
One-way voyages in October and November, when ships leave New England for the winter. They end in Fort Lauderdale, San Juan or New Orleans, so the flight home is part of the plan. The schedule we track has no Caribbean or Bahamas round trips from Boston.
Our Caribbean guide covers why these sailings are one-way in autumn, and how to plan the flight home.
There are 6 such sailings on the board, running 9 to 17 nights, operated by Norwegian Cruise Line, Celebrity Cruises, Windstar Cruises, and Royal Caribbean International aboard Norwegian Breakaway, Celebrity Silhouette, Celebrity Summit, Star Pride, and Jewel of the Seas. The lowest recorded starting fare is $839 per person, on the Sun, Nov 8, 2026 departure.
Ports of call
Your Caribbean and Florida options
All routesThe 6 departures below run 6 different routes, cheapest per night first.
| Itinerary | Ship | Nights | Departures | From |
|---|---|---|---|---|
| 14-Night Southern Caribbean Calls at St. Thomas (U.S. Virgin Islands) · St. Lucia · Grenada · Curaçao · Aruba · Grand Cayman (Cayman Islands) Ends in New Orleans (Louisiana) Next on Sun, Nov 8, 2026 | Norwegian Breakaway | 14 | 1 | $839$60 a night |
| 10-Night Boston To Fort Lauderdale Calls at Aruba · Curaçao · Bonaire Ends in Fort Lauderdale (Florida) Next on Sat, Oct 16, 2027 | Celebrity Silhouette, Jewel of the Seas | 10 | 2 | $913$91 a night |
| 9-Night Boston To San Juan Calls at Puerto Plata (Dominican Republic) · Samana (Dominican Republic) · St. Thomas (U.S. Virgin Islands) · St. John's (Antigua) · Tortola (British Virgin Islands) Ends in San Juan (Puerto Rico) Next on Wed, Oct 20, 2027 | Celebrity Summit | 9 | 1 | $904$100 a night |
| 17-Night Caribbean Calls at Hamilton (Bermuda) · St. George's (Bermuda) · Hamilton (Bermuda) · St. George's (Bermuda) · Gustavia (St. Barts) · Virgin Gorda (British Virgin Islands) · San Juan (Puerto Rico) · St. John (U.S. Virgin Islands) · Basseterre (St. Kitts) · Gustavia (St. Barts) · Philipsburg (St. Maarten) · Jost Van Dyke (British Virgin Islands) · Virgin Gorda (British Virgin Islands) Ends in San Juan (Puerto Rico) Next on Fri, Oct 22, 2027 | Star Pride | 17 | 1 | $6,040$355 a night |
| 10-Night Caribbean Calls at Hamilton (Bermuda) · St. George's (Bermuda) · Gustavia (St. Barts) · Virgin Gorda (British Virgin Islands) Ends in San Juan (Puerto Rico) Next on Fri, Oct 22, 2027 | Star Pride | 10 | 1 | $4,477$448 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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| Departs | Ship | Line | Nights | Itinerary & ports | From |
|---|---|---|---|---|---|
Sun, Nov 8, 2026 ends Sun, Nov 22, 2026 | Norwegian Breakaway | Norwegian Cruise Line | 14 | 14-Night Southern Caribbean Calls at St. Thomas (U.S. Virgin Islands) · St. Lucia · Grenada · Curaçao · Aruba · Grand Cayman (Cayman Islands) Ends in New Orleans (Louisiana) | Lowest fare shown |
Sat, Oct 16, 2027 ends Tue, Oct 26, 2027 | Celebrity Silhouette | Celebrity Cruises | 10 | 10-Night Boston To Fort Lauderdale Calls at Aruba · Curaçao · Bonaire Ends in Fort Lauderdale (Florida) | |
Wed, Oct 20, 2027 ends Fri, Oct 29, 2027 | Celebrity Summit | Celebrity Cruises | 9 | 9-Night Boston To San Juan Calls at Puerto Plata (Dominican Republic) · Samana (Dominican Republic) · St. Thomas (U.S. Virgin Islands) · St. John's (Antigua) · Tortola (British Virgin Islands) Ends in San Juan (Puerto Rico) | |
Fri, Oct 22, 2027 ends Mon, Nov 1, 2027 | Star Pride | Windstar Cruises | 10 | 10-Night Caribbean Calls at Hamilton (Bermuda) · St. George's (Bermuda) · Gustavia (St. Barts) · Virgin Gorda (British Virgin Islands) Ends in San Juan (Puerto Rico) | |
Fri, Oct 22, 2027 ends Mon, Nov 8, 2027 | Star Pride | Windstar Cruises | 17 | 17-Night Caribbean Calls at Hamilton (Bermuda) · St. George's (Bermuda) · Hamilton (Bermuda) · St. George's (Bermuda) · Gustavia (St. Barts) · Virgin Gorda (British Virgin Islands) · San Juan (Puerto Rico) · St. John (U.S. Virgin Islands) · Basseterre (St. Kitts) · Gustavia (St. Barts) · Philipsburg (St. Maarten) · Jost Van Dyke (British Virgin Islands) · Virgin Gorda (British Virgin Islands) Ends in San Juan (Puerto Rico) | |
Fri, Oct 20, 2028 ends Mon, Oct 30, 2028 | Jewel of the Seas | Royal Caribbean International | 10 | 10-Night Boston To Fort Lauderdale Calls at Royal Naval Dockyard (Bermuda) · Aruba · Curaçao Ends in Fort Lauderdale (Florida) Only one of our two sources lists it |
- NOV8
Sunday · 14 nights
14-Night Southern Caribbean
Norwegian Breakaway · Norwegian Cruise Line
Calls at St. Thomas (U.S. Virgin Islands) · St. Lucia · Grenada · Curaçao · Aruba · Grand Cayman (Cayman Islands)
Ends in New Orleans (Louisiana)
Ends Sun, Nov 22, 2026 in New Orleans
Lowest fare shown
- OCT16
Saturday · 10 nights
10-Night Boston To Fort Lauderdale
Celebrity Silhouette · Celebrity Cruises
Calls at Aruba · Curaçao · Bonaire
Ends in Fort Lauderdale (Florida)
Ends Tue, Oct 26, 2027 in Fort Lauderdale
- OCT20
Wednesday · 9 nights
9-Night Boston To San Juan
Celebrity Summit · Celebrity Cruises
Calls at Puerto Plata (Dominican Republic) · Samana (Dominican Republic) · St. Thomas (U.S. Virgin Islands) · St. John's (Antigua) · Tortola (British Virgin Islands)
Ends in San Juan (Puerto Rico)
Ends Fri, Oct 29, 2027 in San Juan
- OCT22
Friday · 10 nights
10-Night Caribbean
Calls at Hamilton (Bermuda) · St. George's (Bermuda) · Gustavia (St. Barts) · Virgin Gorda (British Virgin Islands)
Ends in San Juan (Puerto Rico)
Ends Mon, Nov 1, 2027 in San Juan
- OCT22
Friday · 17 nights
17-Night Caribbean
Calls at Hamilton (Bermuda) · St. George's (Bermuda) · Hamilton (Bermuda) · St. George's (Bermuda) · Gustavia (St. Barts) · Virgin Gorda (British Virgin Islands) · San Juan (Puerto Rico) · St. John (U.S. Virgin Islands) · Basseterre (St. Kitts) · Gustavia (St. Barts) · Philipsburg (St. Maarten) · Jost Van Dyke (British Virgin Islands) · Virgin Gorda (British Virgin Islands)
Ends in San Juan (Puerto Rico)
Ends Mon, Nov 8, 2027 in San Juan
- OCT20
Friday · 10 nights
10-Night Boston To Fort Lauderdale
Jewel of the Seas · Royal Caribbean International
Calls at Royal Naval Dockyard (Bermuda) · Aruba · Curaçao
Ends in Fort Lauderdale (Florida)
Only one of our two sources lists it
Ends Mon, Oct 30, 2028 in Fort Lauderdale
By month
Other destinations from Boston
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.
