Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > San Juan, Puerto Rico: Biz from $395 Econ from $111. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > George Town, Cayman Islands: Biz from $826 Econ from $508. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Montego Bay, Jamaica: Biz from $354 Econ from $354. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Port Au Prince, Haiti: Econ from $279. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Punta Cana, Dominican Republic: Biz from $795 Econ from $313. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Christiansted, U.S. Virgin Islands: Biz from $689 Econ from $319. – 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.…

IND > Santo Domingo, Dominican Republic: Biz from $866 Econ from $303. – Jan-Mar (Including President’s Day Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Oranjestad, Aruba: Biz from $818 Econ from $286. – Jan-Mar
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…

IND > Saint Thomas Island, U.S. Virgin Islands: Biz from $669 Econ from $191. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Montego Bay, Jamaica: Biz from $848 Econ from $324. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Kingston, Jamaica: Biz from $775 Econ from $379. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > San Juan, Puerto Rico: Biz from $613 Econ from $116. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Kralendijk, Caribbean Netherlands: Biz from $807 Econ from $489. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Christiansted, U.S. Virgin Islands: Biz from $661 Econ from $262. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Santo Domingo, Dominican Republic: Biz from $828 Econ from $263. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Simpson Bay, Sint Maarten: Biz from $802 Econ from $353. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Montego Bay, Jamaica: Biz from $763 Econ from $291. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Port Au Prince, Haiti: Econ from $257. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Oranjestad, Aruba: Biz from $696 Econ from $378. – Feb-Apr (Including Spring Break)
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…

IND > Piarco, Trinidad and Tobago: Biz from $850 Econ from $399. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Punta Cana, Dominican Republic: Biz from $684 Econ from $366. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Christiansted, U.S. Virgin Islands: Biz from $630 Econ from $262. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Kingston, Jamaica: Biz from $789 Econ from $399. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Saint Thomas Island, U.S. Virgin Islands: Biz from $582 Econ from $152. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > San Juan, Puerto Rico: Biz from $570 Econ from $75. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Kralendijk, Caribbean Netherlands: Biz from $766 Econ from $448. – 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.…

IND > George Town, Cayman Islands: Biz from $768 Econ from $467. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Montego Bay, Jamaica: Biz from $700 Econ from $293. – Jan-Mar (Including President’s Day Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Santo Domingo, Dominican Republic: Econ from $317. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Oranjestad, Aruba: Biz from $696 Econ from $348. – Jan-Mar
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…

IND > Kingston, Jamaica: Biz from $852 Econ from $343. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Kralendijk, Caribbean Netherlands: Biz from $766 Econ from $448. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Nassau, The Bahamas: Biz from $781 Econ from $360. – Nov-Jan (Including Winter Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Saint Thomas Island, U.S. Virgin Islands: Biz from $685 Econ from $178. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > San Juan, Puerto Rico: Biz from $668 Econ from $77. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Port Au Prince, Haiti: Biz from $869 Econ from $252. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > George Town, Cayman Islands: Biz from $827 Econ from $467. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Montego Bay, Jamaica: Biz from $891 Econ from $285. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Santo Domingo, Dominican Republic: Biz from $900 Econ from $286. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…