Anonymous wrote:

Anonymous wrote:Went to Curacao in March with 8 yo boy and had an absolute blast. We rented a car and found there were actually so many different things to do other than the beach, though we did spend a significant amount of time at the beach because the snorkeling was that good. Highly recommend. We took Amtrak to NYC on a Friday afternoon, spent the night at the TWA Hotel connected to the JetBlue terminal at JFK and then flew direct the next morning. It was a neat little add on and extremely easy the next morning.

This is a great tip! Did you stay overnight in NY on your return too?

Yes, we flew back the following Saturday but rather than stay at the TWA, we stayed within walking distance of Penn Station so that Sunday morning we could just walk over and hop the train back.

Anonymous wrote:Went to Curacao in March with 8 yo boy and had an absolute blast. We rented a car and found there were actually so many different things to do other than the beach, though we did spend a significant amount of time at the beach because the snorkeling was that good. Highly recommend. We took Amtrak to NYC on a Friday afternoon, spent the night at the TWA Hotel connected to the JetBlue terminal at JFK and then flew direct the next morning. It was a neat little add on and extremely easy the next morning.

This is a great tip! Did you stay overnight in NY on your return too?

Went to Curacao in March with 8 yo boy and had an absolute blast. We rented a car and found there were actually so many different things to do other than the beach, though we did spend a significant amount of time at the beach because the snorkeling was that good. Highly recommend. We took Amtrak to NYC on a Friday afternoon, spent the night at the TWA Hotel connected to the JetBlue terminal at JFK and then flew direct the next morning. It was a neat little add on and extremely easy the next morning.

PR fits your bill. We recently took our boys (10 and 7) to PR (their first time; my third) and they had a great time. Highlights include hiking in the rainforest, walking around Old San Juan, and lots of beach time. OSJ is so beautiful I can never get tired of it. The boys loved exploring both forts there, flying kites outside El Morro, and eating paletas (sooo good). Very easy to get there from the DMV.

I also love Curacao. Went there years ago before kids. Great beaches for snorkeling. Wonderful food. That's pretty much all DH and I did when we were there. Can't wait to take the boys there as they'll love the snorkeling experience. The only drawback is the lack of direct flight.

Anonymous wrote:Grand Cayman. Don't stay on/around 7 Mile Beach. Rent a car, stay on the other side of the island (at least part of the time), and explore beaches and restaurants. And the caves -- but don't expect them to feel cool like caverns around here; in GC it's hotter in the caves. Worth it though!

Agree that the heart of Seven Mile Beach is super-busy and not where I’d choose to stay. But we stay in West Bay, which is just north of Seven Mile Beach, and it’s lovely: quiet, beautiful, easily accessible. Same beautiful beach, far fewer people; it’s virtually all condos rather than resorts.

Grand Cayman I've only done on a cruise stop, and we decided to go to a rum tasting. Everyone we traveled with went to Seven Mile Beach and unanimously declared it the most beautiful beach they'd ever visited, so joke's on us!

PR: I've done a trip to Rincon in the west and Vieques in the east, both times with a few days' stay in San Juan. I think this is a really good pick for variety - the bioluminescent bays are amazing and there's a rainforest to explore as well. The beaches in Vieques were lovely, but there wasn't too much to do there otherwise.

Curacao: for variety of beaches it's hard to beat this one. The island is very easy to navigate, the people are wonderful, and if you like snorkeling this is the winner. The food was also significantly better than PR. Getting in and out is a bit more difficult (I personally detest international layovers in Miami) but not anything too daunting.

I haven't been to the others. Have fun!

If you end up going to Puerto Rico, do the segway tour of Old San Juan. So much fun!

If you’re going in the second half of summer. Aruba and Curaçao have a major advantage of being out of the hurricane belt. The hurricane season starts earlier every year. We liked Aruba well enough — nice beaches, nice restaurants, decent snorkeling. Felt safe getting off the resort. The island has no natural water source so it is not much for history.

Puerto Rico has a major advantage in being close, no customs, and the historical stuff is amazing. I thought El Yunque was just okay but old San Juan was extremely cool as was the old Spanish fort El Moro. We stayed with the Wyndham Rio Mar whuch is very popular with families, if the resort previously recommended is outside your price range.

If you are Costco members, they always have good deals on resorts throughout the Caribbean.

My vote is for Dorado Beach Ritz. There are lots of options in terms of trips, and it's an easy peasy flight. You could have a relaxing time at the resort and visit El Yunque. It's easy to get a car and drive, or you could hire a driver/guide who knows the island.

The food is excellent and there's plenty of adventure!

There is also great music in Puerto Rico, so if that's on your list, you can check it out!

The resort beaches are really beautiful and chill unless you're there right during high season.

Have a great time wherever you end up going... and don't forget your sunscreen and travel insurance.

Aruba is clean. Easy to get around by bus or car. Interesting culture. Not a ton to do but nice beaches.

LOVE Curacao and spend a month there every year, but it's quiet. Also enjoy Grand Cayman, which I think would be most appealing in your situation. Not a fan of Barbados (bugs and infrastructure). Never been to PR.

NP here. I’ve been to all the places mentioned so far. I would also add Bonaire and Aruba. They are clean, safe and well-developed.

OP here, I really appreciate all these responses! If anyone else has perspectives on these, or alternatives to consider, I still welcome them.

+1 for Puerto Rico. I think PR is underrated. It's far better than the likes of DR, grand Cayman etc

Anonymous wrote:Only been to Puerto Rico of that list but found it really depressing. Seeing the level of poverty and overall run-down nature of it and knowing it was part of the US wasn't a nice "vacation vibe". Yes that sounds insensitive I guess but I also don't go vacation in the poorest section of Appalachia. Our resort was nice and I enjoyed San Juan - the rest of it was just sad.

As someone who grew up in an extremely wealthy family in a poor country in West Africa I think Americans have the luxury of living without seeing poverty. In my country we don't really have exclusive neighborhoods so the poor and rich alike mingle on a daily basis. But I def see your point, that's not something you are used to and it can be a culture shock.

I think the US does an amazing job hiding it's poor.