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

IND > Oranjestad, Aruba: Econ from $420. – Nov-Jan
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…

IND > Nassau, The Bahamas: 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.…

IND > Saint Thomas Island, U.S. Virgin Islands: Biz from $945 Econ from $400. – 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 $1,051 Econ from $458. – Nov-Jan
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 $914 Econ from $430. – 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 $1,572 Econ from $618. – Feb-Apr
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 $1,212 Econ from $462. – 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 > Willemstad, Curaçao: Econ from $675. – 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 $548 Econ from $205. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Providenciales, Turks and Caicos Islands: Econ from $470. – Oct-Dec
Thinking of going to Turks & Caicos? I’ve written several posts about our visit here. * This is a “fare…

IND > Oranjestad, Aruba: Econ from $512. – Dec-Feb
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 $904 Econ from $400. – Nov-Jan
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 $894 Econ from $410. – 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, St. Maarten: Econ from $459. – Oct-Dec
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 $972 Econ from $442.- Dec-Feb
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 $998 Econ from $474. – 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 $1,316 Econ from $696. – Oct-Dec
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 $641 Econ from $198. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Willemstad, Curaçao: Econ from $673. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Oranjestad, Aruba: Econ from $472. – Feb-Apr (Including Spring Break)
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…

IND > Saint Thomas Island, U.S. Virgin Islands: Biz from $884 Econ from $360. – Nov-Jan
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 $870 Econ from $390. – 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, St. Maarten: Econ from $439. – Sep-Nov (Including Fall 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 $951 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.…

IND > Montego Bay, Jamaica: Biz from $1,010 Econ from $470. – Oct-Dec
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 $571 Econ from $167. – Sep-Nov (Including Fall 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 $826 Econ from $248. – Dec-Feb
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 $740 Econ from $400. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Oranjestad, Aruba: Econ from $423. – Oct-Dec
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…

IND > George Town, Cayman Islands: Biz from $956 Econ from $421. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Bridgetown, Barbados: Econ from $444. – Sep-Nov
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 $1,000 Econ from $490. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IND > Aguadilla, Puerto Rico: Biz from $706 Econ from $308. – Sep-Nov (Including Fall Break)
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 $1,433 Econ from $591. – Apr-Jun
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 $930 Econ from $450. – Jan-Mar
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 $622 Econ from $203. – Sep-Nov (Including Fall 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 $883 Econ from $294. – Nov-Jan
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 $931 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.…

IND > Nassau, The Bahamas: Biz from $690 Econ from $400. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…