Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Bridgetown, Barbados: Econ from $309. – Mar-May (Including Spring Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Montego Bay, Jamaica: Biz from $915 Econ from $273. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Christiansted, U.S. Virgin Islands: Econ from $213. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Saint Thomas Island, U.S. Virgin Islands: Biz from $812 Econ from $183. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Willemstad, Curaçao: Econ from $421. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > San Juan, Puerto Rico: Econ from $104. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Oranjestad, Aruba: Biz from $1,053 Econ from $273. – Jan-Mar
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
BOS > Piarco, Trinidad and Tobago: Biz from $898 Econ from $194. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Kingston, Jamaica: Biz from $934 Econ from $260. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Montego Bay, Jamaica: Biz from $919 Econ from $282. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Willemstad, Curaçao: Econ from $354. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > George Town, Cayman Islands: Econ from $269. – 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.…
BOS > Saint Thomas Island, U.S. Virgin Islands: Econ from $184. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > San Juan, Puerto Rico: Econ from $87. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Simpson Bay, St. Maarten: Econ from $208. – 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.…
BOS > Montego Bay, Jamaica: Biz from $1063 Econ from $277. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Christiansted, U.S. Virgin Islands: Econ from $183. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Willemstad, Curaçao: Econ from $401. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Piarco, Trinidad and Tobago: Econ from $172. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Oranjestad, Aruba: Biz from $1053 Econ from $267. – Nov-Jan
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…
BOS > Bridgetown, Barbados: Econ from $319. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Saint Thomas Island, U.S. Virgin Islands: Econ from $194. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > George Town, Cayman Islands: Biz from $888 Econ from $249. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Nassau, The Bahamas: Biz from $679 Econ from $227. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > San Juan, Puerto Rico: Econ from $99. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Montego Bay, Jamaica: Biz from $904 Econ from $276. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Oranjestad, Aruba: Econ from $264. – Oct-Dec
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
BOS > St. John’s, Antigua And Barbuda: Econ from $292. – Dec-Feb
The first thing you’ll learn when going to Antigua is how to properly pronounce it. (The “u” is not pronounced,…
BOS > Bridgetown, Barbados: Econ from $285. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > San Juan, Puerto Rico: Econ from $110. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Willemstad, Curaçao: Econ from $405. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Punta Cana, Dominican Republic: Biz from $703 Econ from $266. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > George Town, Cayman Islands: Econ from $284. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Kingston, Jamaica: Biz from $1079 Econ from $284. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Montego Bay, Jamaica: Biz from $858 Econ from $277. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Simpson Bay, St. Maarten: Econ from $207. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Saint Thomas Island, U.S. Virgin Islands: Econ from $201. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Oranjestad, Aruba: Biz from $868 Econ from $268. – Oct-Dec
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
BOS > San Juan, Puerto Rico: Econ from $86. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…