Please help me choose an island for February.
 

My husband and I are planning a trip for February. We are limited to 5 days, 4 nights. We will be flying out of Chicago. Nonstop flights are limited to San Juan, Montego Bay, and Punta Cana. Honestly we aren't thrilled about any of the 3. We could also connect but don't want to spend entire days travelling. We want to snorkel, walk and relax on a beautiful Caribbean beach, do some exploring/sightseeing, have good food and drinks. Not big partiers. Our hotel budget is probably about $250 a night. I appreciate any suggestions/advice from you experienced travellers of the Caribbean!!

You could fly into Montego Bay and take a 90 minute bus ride into Negril, my favorite tropical destination. Beautiful beach for walking, relaxing vibe, good food and drink. The water was a little choppy when we were there so I cannot comment on snorkeling. For exploring/sightseeing and good food and drink, I recommend San Juan. Unfortunately, I cannot recommend where to stay but I loved the Old San Juan area. Never been to DR. There's nothing nonstop to Grand Cayman? Sounds like it would suit all your needs except sightseeing. I think most of the sights are underwater!

From San Juan you can get very cheap & short (less than an hour) flights to either St Thomas or St. Martin, which are two of my favorite Islands for great beaches, snorkeling and sightseeing. I would stay a night in San Juan,(Isla Verde has some beautiful beaches, and is very close to the airport) Old San Juan has some great sightseeing and shopping) then fly to St Thomas in the morning spend all day and spend the night and try to get a night flight back the next day and spend your last day and one more night in San Juan. I live in Detroit and it is not easy to get a non stop flight to San Juan. I wish we could! Instead we do Cruises but you really need 7 days to enjoy a cruise. You should definitely try that out sometime!! I've been to Jamaica and I would not go out of my way to go back! People are rude, there was alot of drugs (you could smell it in the air on the beaches) and there are definitely alot of Land-sharks watch your money if you go there)I would also recommend Nassau Bahamas, we went there in Sept. on a cruise and we were pleasantly surprised how beautiful the beaches were. The water was as beautiful as any other Caribbean island we have been to.

Grand Cayman sounds like it would be perfect for you. It has great snorkeling, many food options and Seven Mile Beach. There are 2 non-stop flights per week from Chicago on Cayman Airways in the winter.

Your budget is just perfect for a Jamaican vacation at an all inclusive resorts. I must admit that on public beaches some locals like to harass the tourist but all this is eliminated when you stay at an all inclusive hotel. Fly into Montego Bay and stay at Ocho Rios, Montego Bay or Negril. There are many all inclusive resorts that are available at this price.