New York to Willemstad, Curacao: 15 night trip. Flight Alone: $308. Dates we found this fare: Mon, Mar 12 to…
JFK > Pointe-à-Pitre: $178 round-trip
New York to Pointe-à-Pitre, Guadeloupe: 10 night trip. Flight Alone: $178. Dates we found this fare: Fri, Mar 09 to…
JFK > San Juan: $261 round-trip
New York to San Juan, Puerto Rico: 1 night trip. Flight Alone: $261. Dates we found this fare: Tue, Mar…
JFK > George Town: $318 round-trip [SOLD OUT]
New York to George Town, Cayman Islands: 1 night trip. Flight Alone: $318. Dates we found this fare: Thu, Jan…
EWR > Christiansted: $293 round-trip
Newark to Christiansted, U.S. Virgin Islands: 7 night trip. Flight Alone: $293. Dates we found this fare: Mon, Mar 05…
EWR > Bridgetown: $306 round-trip [SOLD OUT]
Newark to Bridgetown, Barbados: 8 night trip. Flight Alone: $306. Dates we found this fare: Mon, Feb 26 to Tue,…
EWR > Ponce: $279 round-trip [SOLD OUT]
Newark to Ponce, Puerto Rico: 5 night trip. Flight Alone: $279. Dates we found this fare: Sun, Jan 14 to…
JFK > St. John’s: $773 including 7 nights [SOLD OUT]
New York to St. John’s, Antigua and Barbuda: 7 night trip. Flight Alone: $270. Dates we found this fare: Mon,…
EWR > Providenciales: $310 round-trip
We’ll just miss each other… I’m going to Turks the week after this. Newark to Providenciales, Turks and Caicos Islands:…
EWR > Bridgetown: $306 round-trip [SOLD OUT]
Newark to Bridgetown, Barbados: 8 night trip. Flight Alone: $306. Dates we found this fare: Tue, Feb 27 to Wed,…
EWR > St. John’s: $274 round-trip
Newark to St. John’s, Antigua and Barbuda: 7 night trip. Flight Alone: $274. Dates we found this fare: Sun, Nov…
JFK > Hamilton: $708 including 4 nights
New York to Hamilton, Bermuda: 4 night trip. Flight Alone: $254. Dates we found this fare: Thu, Nov 16 to…
JFK > Pointe-à-Pitre: $385 including 4 nights
New York to Pointe-à-Pitre, Guadeloupe: 4 night trip. Flight Alone: $188. Dates we found this fare: Mon, Dec 04 to…
JFK > Aguadilla: $561 including 8 nights
Definitely check out alternate lodging links here. Not many package options. New York to Aguadilla, Puerto Rico: 8 night trip.…
JFK > Fort-de-France: $532 including 7 nights [SOLD OUT]
New York to Fort-de-France, Martinique: 7 night trip. Flight Alone: $188. Dates we found this fare: Thu, Jan 25 to…
EWR > Oranjestad: $605 including 6 nights
Aruba is one of my favorite destinations ever. Cheap, convenient to get to, and beautiful beaches. As soon as you…
EWR > Punta Cana: $486 including 6 nights
Newark to Punta Cana, Dominican Republic: 6 night trip. Flight Alone: $362. Dates we found this fare: Wed, Mar 14…
LGA > Simpson Bay: $518 including 5 nights
New York to Simpson Bay, Sint Maarten: 5 night trip. Flight Alone: $310. Dates we found this fare: Sun, Oct…
EWR > George Town: $309 round-trip
Newark to George Town, Cayman Islands: 8 night trip. Flight Alone: $309. Dates we found this fare: Sat, Nov 25…
EWR > St. John’s: $478 including 7 nights
Newark to St. John’s, Antigua and Barbuda: 7 night trip. Flight Alone: $258. Dates we found this fare: Sat, Oct…
JFK > Pointe-à-Pitre: $198 round-trip [SOLD OUT]
New York to Pointe-à-Pitre, Guadeloupe: 5 night trip. Flight Alone: $198. Dates we found this fare: Mon, Jan 29 to Sat,…
NYC > Crown Point: $395 round-trip
New York to Crown Point, Trinidad and Tobago Flight Alone: $395. Flight + basic hotel:Click for more details Flight plus…
NYC > Havana: $259 round-trip
New York to Havana, Cuba Flight Alone: $259. Flight + basic hotel:Click for more details Flight plus 4 & 5…
EWR > Havana: $191 round-trip
Newark to Havana, Cuba Flight Alone: $191. Flight + basic hotel:Click for more details Flight plus 4 & 5 star…
EWR > Providenciales: $274 round-trip
Newark to Providenciales, Turks and Caicos Islands Flight Alone: $274. Flight + basic hotel:Click for more details Flight plus 4…
Winter Break: LGA > US Virgin Islands: $331 round-trip [SOLD OUT]
New York to Saint Thomas Island, U.S. Virgin Islands plus 5 nights – Wed, Jan 03 to Mon,…
LGA > Turks and Caicos: $285 round-trip
You can also get a package for $530 including flight & 5 nights, but I’d advise poking around on AirBnb,…
Last-minute trip: JFK > Puerto Rico: $517 including flight & 7 nights
New York to San Juan, Puerto Rico plus 7 nights – Mon, Sep 18 to Mon, Sep 25.…
JFK > US Virgin Islands: $293 round-trip
New York to Christiansted, U.S. Virgin Islands plus 5 nights – Sat, Feb 03 to Thu, Feb 08.…
LGA > Turks and Caicos: $285 round-trip
New York to Providenciales, Turks and Caicos Islands plus 5 nights – Mon, Sep 18 to Sat, Sep…