Winter Caribbean Cruises from New York City, 2027-2028
Norwegian Cruise Line sails 10 winter Caribbean cruises from New York City between November 2027 and March 2028: nine 11 to 12-day round trips on Norwegian Bliss and one 10-day one-way sailing to San Juan on Norwegian Prima. Norwegian Bliss's winter Caribbean itinerary from New York typically calls at St. Kitts, St. Maarten, Tortola, St. Thomas, Puerto Plata and San Juan.
Table of Contents
- Quick Facts
- Season Highlights
- Why Sail to the Caribbean from New York in Winter?
- Itinerary Breakdown
- Month-by-Month Winter Caribbean Cruise Calendar
- Ship Deployment
- Planning Tips
- How to Find the Best Deals
- Related Guides
- Frequently Asked Questions
Quick Facts
| Fact | Detail |
|---|---|
| Total Sailings | 10 Norwegian Cruise Line Caribbean sailings from New York, November 2027 - March 2028 |
| Departure Port | New York, New York (sailings typically depart the Manhattan Cruise Terminal; verify with your cruise line) |
| Ships | Norwegian Bliss (9 round-trips), Norwegian Prima (1 one-way) |
| Durations | Typically 11-12 days round-trip; one 10-day one-way |
| Season | Early November 2027 through early March 2028 |
| Popular Ports of Call | San Juan, St. Thomas, Philipsburg (St. Maarten), Tortola, Basseterre (St. Kitts), Puerto Plata |
| Typical Price Range | Approximately $177-222 per night for inside cabins for solo travelers at single occupancy on the 8 non-holiday Norwegian Bliss round-trips (subject to change, as of September 2026) |
Price ranges above are based on CabinSaver's fare tracking as of September 2026.
When it is 30 degrees in Midtown, a ship bound for St. Thomas is boarding about two miles from Times Square. For the winter 2027-2028 season, Norwegian Bliss anchors Norwegian Cruise Line's Caribbean program out of New York. No flights, no baggage claim: board in Manhattan in a coat, come back with a tan.
Find the best prices using our cruise deal finder or sign up for deal alerts to get notified when prices drop.
Season Highlights
Two ships carry NCL's winter Caribbean program from New York in 2027-2028:
- Norwegian Bliss runs the core schedule: nine round-trips between November 8, 2027 and March 6, 2028, nearly all 12 days. The repeating itinerary loops through the eastern Caribbean with calls at St. Kitts, St. Maarten, Tortola, St. Thomas, Puerto Plata, and San Juan, and includes a Christmas and New Year's holiday departure on December 22.
- Norwegian Prima opens the season on November 3, 2027 with a 10-day one-way sailing from New York to San Juan that folds in Bermuda, Barbados, Antigua, and other eastern Caribbean calls, a routing NCL does not repeat later in the winter.
Departures are spaced roughly every two to three weeks through the season, so there is typically a sailing to match a January thaw escape, a February school break, or an early-spring reset.
Why Sail to the Caribbean from New York in Winter?
The pitch is simple: the entire tri-state area can reach the ship by car, train, or subway. Sailings typically depart from the Manhattan Cruise Terminal on the West Side (verify your terminal with the cruise line before travel), which means no winter-storm flight cancellations standing between you and vacation, no checked-bag fees, and no burning the first day of your trip in an airport. For drive-to cruisers from New Jersey, Connecticut, Long Island, and the Hudson Valley, it is the lowest-friction way to get to the Caribbean in January.
The trade-off is a couple of cool sea days at each end as the ship transits the Atlantic seaboard, which is exactly why these itineraries run 11-12 days instead of a week: enough time to earn four to six full port days in the heart of the eastern Caribbean. Norwegian Bliss is well suited to those sea days, with an observation lounge, race track, and full indoor amenity deck for the stretch before the weather turns warm.
Itinerary Breakdown
Here is how Norwegian Cruise Line's 10 winter Caribbean sailings from New York compare by ship:
| Ship | Norwegian sailings | Length | Months sailed | Route |
|---|---|---|---|---|
| Norwegian Bliss | 9 | 11 to 12 days | Nov 2027-Mar 2028 | Round trip to St. Kitts, St. Maarten, Tortola, St. Thomas, Puerto Plata and San Juan |
| Norwegian Prima | 1 | 10 days | Nov 2027 | One-way to San Juan via Bermuda, Barbados and Antigua |
Norwegian Bliss: 12-Day Eastern Caribbean Round-Trip
The workhorse itinerary of the season sails round-trip from New York with calls at Basseterre (St. Kitts), Philipsburg (St. Maarten), Tortola (British Virgin Islands), St. Thomas (US Virgin Islands), Puerto Plata (Dominican Republic), and San Juan (Puerto Rico). Nine departures run between November 8, 2027 and March 6, 2028; the January 15 departure is a slightly shorter 11-day version that typically drops the St. Maarten call. Inside cabins on the 8 non-holiday departures typically ran approximately $177-222 per night for solo travelers at single occupancy (subject to change, as of September 2026), and Bliss also offers studio cabins for solo travelers.
Norwegian Prima: 10-Day One-Way to San Juan
Prima's November 3, 2027 sailing is the season's outlier: a one-way routing from New York to San Juan that calls at the Royal Naval Dockyard in Bermuda, then St. Kitts, Barbados, St. Maarten, Tortola, Antigua, and St. Thomas. It packs more ports into fewer days than the Bliss loop, with the trade-off of a return flight from San Juan. As a newer premium ship on a port-intensive one-way, it has shown higher per-night fares, with inside cabins ranging approximately $310-376 per night for solo travelers at single occupancy over the tracking window (subject to change, as of September 2026).
Month-by-Month Winter Caribbean Cruise Calendar
November 2027
The season opens with three departures. Norwegian Prima sails November 3 on the 10-day one-way to San Juan via Bermuda and the eastern Caribbean. Norwegian Bliss begins its round-trip rotation with 12-day departures on November 8 and November 28, the latter returning December 10 with the ship dressed for the holidays. As of September 2026, the November 28 sailing was the lower-priced of the two, at approximately $172 per night for inside cabins against approximately $202 on November 8, for solo travelers at single occupancy (subject to change).
Ships: Norwegian Prima, Norwegian Bliss. Destinations: Eastern Caribbean, Bermuda. Duration: 10-12 days.
December 2027
Norwegian Bliss sails December 10, returning December 22, then turns around the same day for the marquee holiday departure: December 22 to January 3, spending both Christmas and New Year's Eve in the Caribbean. Holiday-week fares typically run well above the winter norm: the December 22 sailing has shown inside cabins at approximately $314-346 per night versus approximately $177-222 on the non-holiday Bliss departures, for solo travelers at single occupancy (subject to change, as of September 2026).
Ships: Norwegian Bliss. Destinations: Eastern Caribbean. Duration: 12 days.
January 2028
January is the busiest month, with three Bliss departures: January 3 (12 days), January 15 (11 days, the compact version of the loop), and January 26 (12 days). These sailings depart in the coldest stretch of the New York winter, with inside cabins typically approximately $193-222 per night for solo travelers at single occupancy, above the late-November and December 10 departures at approximately $171-172 (subject to change, as of September 2026).
Ships: Norwegian Bliss. Destinations: Eastern Caribbean. Duration: 11-12 days.
February 2028
Norwegian Bliss sails once in February, departing February 7 and returning February 19. The single departure covers the Presidents' Day window on the back half of the itinerary, making it a natural fit for families working around the February school break.
Ships: Norwegian Bliss. Destinations: Eastern Caribbean. Duration: 12 days.
March 2028
The season closes with the March 6 departure, returning March 18. It is the last chance of the winter to reach the Caribbean from a New York pier before the ship moves on to its spring deployment, and it typically draws spring-break demand in the balcony and above categories.
Ships: Norwegian Bliss. Destinations: Eastern Caribbean. Duration: 12 days.
Ship Deployment
- Norwegian Bliss - November 2027 through March 2028, nine round-trips from New York on the 11-12 day eastern Caribbean loop; observation lounge, go-kart track, and studio cabins for solo travelers
- Norwegian Prima - November 3, 2027 only, 10-day one-way from New York to San Juan via Bermuda and the eastern Caribbean; NCL's Prima-class flagship experience on a port-heavy routing
Planning Tips
- Pack for two seasons. You will board and disembark in New York winter weather, with typically two to three cool sea days on each end. Layers for the first and last days, summer gear for the middle.
- Plan your route to the pier, not the airport. Sailings typically use the Manhattan Cruise Terminal on the West Side; confirm the terminal with your cruise line, and compare parking, ride share, and train-plus-taxi options in advance since terminal-area parking rates are typically significant for a 12-day sailing.
- Book the holiday sailing early if it is the one you want. The December 22 Christmas and New Year's departure is unique in the schedule and typically books ahead of the surrounding dates.
- Consider the January departures for the quietest ships and softest demand. Post-holiday sailings typically see the season's lowest occupancy pressure.
- Solo travelers: check Bliss studio cabins. Norwegian Bliss carries dedicated studio staterooms with their own lounge, a category few other Caribbean-from-New-York options offer.
- On the Prima one-way, book your San Juan return flight with buffer. Disembarkation timing can vary, so afternoon flights are the safer choice; verify disembarkation details with the cruise line.
How to Find the Best Deals on Winter Caribbean Cruises from New York
Norwegian Cruise Line pricing fluctuates based on demand, booking time, and availability. Here's how to time your booking:
- Book early - Promotional fares often available 12-18 months in advance
- Monitor price drops - Fares change weekly; set up deal alerts to track your preferred sailings
- Consider shoulder dates - Early November and late January departures offer lower demand than holiday and school-break windows
- Compare the same loop across months - Because Bliss repeats one itinerary all season, you can trade dates freely; inside cabins on the 8 non-holiday departures typically ran approximately $177-222 per night for solo travelers at single occupancy (subject to change, as of September 2026)
- Weigh the Prima one-way separately - More ports in fewer days, but add the cost and logistics of a return flight from San Juan
Our deal finder shows real-time pricing across all 10 departures, helping you compare fares for your preferred dates and destinations.
From a pre-Thanksgiving one-way through Bermuda to a March round-trip that outlasts the last nor'easter, the winter 2027-2028 season gives New York cruisers a Caribbean option in every month from November through March.
Ready to book? Check live pricing and availability for any of these sailings.
Data current as of September 2026, derived from CabinSaver's own cruise fare tracking. Always verify availability and details directly with the cruise line.
Related Guides
- 2027 NYC Cruises: Sailing from New York in Every Season - A full-year guide to Norwegian's 2027 cruises from New York, including the Bermuda season that follows these winter sailings.
- 2027 Caribbean Cruise Preview: Ships, Ports, and Sailing Calendar - The hub guide to Norwegian's 2027 Caribbean season, with every departure port, ship and month in one place.
- St. Thomas, Tortola, St. Maarten & San Juan: Norwegian's 2027 Eastern Caribbean Ports of Call - A closer look at the islands on the Norwegian Bliss loop from New York.
- 2027 San Juan Cruises: Prima and Viva in the Deep Caribbean - Where Norwegian Prima's November one-way from New York ends.
- 2027 Philadelphia Cruises: Bermuda, Caribbean and Canada on Norwegian Pearl - The other Northeast drive-to port with winter Caribbean round-trips.
Frequently Asked Questions
Which Norwegian ships sail from New York to the Caribbean in winter 2027-2028?
Norwegian Bliss operates nine round-trip Caribbean sailings from New York between November 2027 and March 2028, and Norwegian Prima adds a 10-day one-way sailing from New York to San Juan on November 3, 2027.
How many days is a winter Caribbean cruise from New York?
Most winter 2027-2028 Caribbean sailings from New York are 12-day round-trips on Norwegian Bliss. One January departure runs 11 days, and Norwegian Prima's November one-way to San Juan runs 10 days.
What ports does a winter Caribbean cruise from New York stop at?
The core Norwegian Bliss itinerary typically calls at Basseterre (St. Kitts), Philipsburg (St. Maarten), Tortola, St. Thomas, Puerto Plata (Dominican Republic), and San Juan (Puerto Rico). Norwegian Prima's one-way routing adds Bermuda, Barbados, and Antigua.
Can I cruise to the Caribbean from New York all year?
No. Norwegian Cruise Line sails to the Caribbean from New York primarily in the fall through early spring. In the winter 2027-2028 season, departures run from early November 2027 through early March 2028, with the ship deployed elsewhere in the warmer months.
Do holiday cruises from New York cost more?
Yes, typically. The December 22, 2027 Christmas and New Year's sailing on Norwegian Bliss has shown inside-cabin fares of approximately $314-346 per night for solo travelers at single occupancy, versus approximately $177-222 per night on the 8 non-holiday Norwegian Bliss winter departures (both subject to change, as of September 2026).