Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Ponce, Puerto Rico: Econ from $233. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Aguadilla, Puerto Rico: Biz from $695. Econ from $180. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Santo Domingo, Dominican Republic: Biz from $668. Econ from $287. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Punta Cana, Dominican Republic: Biz from $878. Econ from $265. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Kingston, Jamaica: Biz from $1039. Econ from $358. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > San Juan, Puerto Rico: Biz from $635. Econ from $180. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Montego Bay, Jamaica: Biz from $1126. Econ from $351. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Oranjestad, Aruba: Biz from $802. Econ from $287. – Dec-Feb
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
CLE > Aguadilla, Puerto Rico: Biz from $695. Econ from $222. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Christiansted, U.S. Virgin Islands: Biz from $889. Econ from $351. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Ponce, Puerto Rico: Econ from $180. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Simpson Bay, St. Maarten: Econ from $295. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Willemstad, Curaçao: Biz from $1160. Econ from $406. – Dec-Feb (Including MLK Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Saint Thomas Island, U.S. Virgin Islands: Biz from $933. Econ from $286. – Dec-Feb (Including Winter Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > San Juan, Puerto Rico: Biz from $778. Econ from $146. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Oranjestad, Aruba: Biz from $1029. Econ from $324. – Jan-Mar
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…
CLE > Kingston, Jamaica: Biz from $1034. Econ from $367. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Montego Bay, Jamaica: Biz from $937. Econ from $348. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Christiansted, U.S. Virgin Islands: Biz from $939. Econ from $312. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Santo Domingo, Dominican Republic: Biz from $722. Econ from $316. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Willemstad, Curaçao: Biz from $1194. Econ from $463. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Kralendijk, Caribbean Netherlands: Econ from $528. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Simpson Bay, St. Maarten: Biz from $797. Econ from $291. – Oct-Dec [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Georgetown, Guyana: Biz from $1209. Econ from $507. – Nov-Jan
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
CLE > Oranjestad, Aruba: Biz from $802. Econ from $312. – Oct-Dec [SOLD OUT]
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
CLE > George Town, Cayman Islands: Biz from $1292. Econ from $387. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Montego Bay, Jamaica: Biz from $1032. Econ from $326. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Saint Thomas Island, U.S. Virgin Islands: Econ from $292. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Punta Cana, Dominican Republic: Biz from $452. Econ from $262. – Oct-Dec [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Bridgetown, Barbados: Econ from $475. – Dec-Feb (Including MLK Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Ponce, Puerto Rico: Econ from $264. – Feb-Apr (Including Spring Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Willemstad, Curaçao: Biz from $1345. Econ from $383. – Nov-Jan (Including Thanksgiving) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Larnaca, Cyprus: Econ from $561. – Oct-Dec [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
CLE > San Juan, Puerto Rico: Biz from $730. Econ from $218. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Santo Domingo, Dominican Republic: Biz from $692. Econ from $337. – Oct-Dec [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Aguadilla, Puerto Rico: Biz from $695. Econ from $264. – Sep-Nov (Including Fall Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Vancouver, Canada: Econ from $196. – Oct-Dec [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
CLE > Simpson Bay, St. Maarten: Biz from $658. Econ from $358. – Oct-Dec [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Oranjestad, Aruba: Biz from $818. Econ from $338. – Oct-Dec [SOLD OUT]
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…