Newark to Providenciales, Turks and Caicos Islands: 5 night trip. Flight Options Flight Alone: $281. Dates we found this fare:…
JFK > Crown Point, Trinidad and Tobago: $803 including flight & 7 nights lodging [SOLD OUT]
New York to Crown Point, Trinidad and Tobago: 7 night trip. Flight Options Flight Alone: $406. Dates we found this…
EWR > Bridgetown, Barbados: $649 including flight & 9 nights lodging [SOLD OUT]
Newark to Bridgetown, Barbados: 9 night trip. Flight Options Flight Alone: $307. Dates we found this fare: Sun, Feb 25…
EWR > St. John’s, Antigua and Barbuda: $458 including flight & 4 nights lodging [SOLD OUT]
Newark to St. John’s, Antigua and Barbuda: 4 night trip. Flight Options Flight Alone: $300. Dates we found this fare:…
Spring Break: EWR > Aguadilla, Puerto Rico: $442 including flight & 4 nights lodging [SOLD OUT]
Newark to Aguadilla, Puerto Rico: 4 night trip. Flight Options Flight Alone: $203. Dates we found this fare: Wed, Mar…
LGA > Christiansted, U.S. Virgin Islands: $278 round-trip [SOLD OUT]
New York to Christiansted, U.S. Virgin Islands: 3 night trip. Flight Options Flight Alone: $278. Dates we found this fare:…
Spring Break: EWR > George Town, Cayman Islands: $747 including flight & 6 nights lodging [SOLD OUT]
Newark to George Town, Cayman Islands: 6 night trip. Flight Options Flight Alone: $321. Dates we found this fare: Tue,…
EWR > Providenciales, Turks and Caicos Islands: $267 round-trip [SOLD OUT]
Newark to Providenciales, Turks and Caicos Islands: 8 night trip. Flight Options Flight Alone: $267. Dates we found this fare:…
President’s Day Weekend: JFK > Kingston, Jamaica: $667 including flight & 3 nights lodging [SOLD OUT]
New York to Kingston, Jamaica: 3 night trip. Flight Options Flight Alone: $451. Dates we found this fare: Sat, Feb…
Spring Break: JFK > Bridgetown, Barbados: $488 including flight & 8 nights lodging [SOLD OUT]
New York to Bridgetown, Barbados: 8 night trip. Flight Options Flight Alone: $236. Dates we found this fare: Mon, Mar…
JFK > Grenada, Grenada: $819 including flight & 9 nights lodging
New York to Grenada, Grenada: 9 night trip. Flight Options Flight Alone: $344. Dates we found this fare: Wed, Apr…
JFK > St. John’s, Antigua and Barbuda: $862 including flight & 8 nights lodging [SOLD OUT]
New York to St. John’s, Antigua and Barbuda: 8 night trip. Flight Options Flight Alone: $299. Dates we found this…
Spring Break Trip: JFK > Pointe-à-Pitre, Guadeloupe: $684 including flight & 15 nights lodging [SOLD OUT]
New York to Pointe-à-Pitre, Guadeloupe: 15 night trip. Flight Options Flight Alone: $199. Dates we found this fare: Sun, Mar…
MLK Weekend Trip: JFK > Willemstad, Curaçao: $778 including flight & 5 nights lodging [SOLD OUT]
New York to Willemstad, Curaçao: 5 night trip. Flight Options Flight Alone: $320. Dates we found this fare: Mon, Jan…
JFK > Ponce, Puerto Rico: $202 round-trip [SOLD OUT]
New York to Ponce, Puerto Rico: 5 night trip. Flight Alone: $202. (Flexibility: 5/5) Dates we found this fare: Fri,…
JFK > Pointe-à-Pitre, Guadeloupe: $198 round-trip [SOLD OUT]
New York to Pointe-à-Pitre, Guadeloupe: 11 night trip. Flight Alone: $198. (Flexibility: 3/5) Dates we found this fare: Thu, Mar…
EWR > Providenciales: $226 round-trip [SOLD OUT]
Newark to Providenciales, Turks and Caicos Islands: 7 night trip. Flight Alone: $226. Dates we found this fare: Wed, Jan…
JFK > Ponce: $232 round-trip [SOLD OUT]
New York to Ponce, Puerto Rico: 4 night trip. Flight Alone: $232. Dates we found this fare: Wed, Jan 24…
JFK > Christiansted: $288 round-trip [SOLD OUT]
New York to Christiansted, U.S. Virgin Islands: 14 night trip. Flight Alone: $288. Dates we found this fare: Sat, Jan…
LGA > Bridgetown: $300 round-trip [SOLD OUT]
LGA isn’t an international airport, but this flight lays over in another US airport before leaving the country. New York…
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,…
JFK > Hamilton: $766 including 5 nights
New York to Hamilton, Bermuda: 5 night trip. Flight Alone: $264. Dates we found this fare: Tue, Dec 05 to…
JFK > Havana: $250 round-trip
New York to Havana, Cuba: 6 night trip. Flight Alone: $250. Dates we found this fare: Sat, Mar 24 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 > 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 > 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.…
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…
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…
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.…