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!

We've only been to Grand Cayman on your list. We loved it. We rented a condo on 7 mile beach and the beach wasn't crowded at all. We were walking distance to a shopping center where there were restaurants and shops.

We rented a car and did some exploring at different beaches and visited the turtle farm. It was relaxing and safe.

Anonymous wrote:

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.

We didn’t have that experience at all fwiw.

We did not have that experience either and we drove all over the island.

OP, take a look at Dorado Beach Ritz Carlton. It includes a free water slide and everyone gets a bike when you check in.
We enjoyed our stay here and also touring around the island.

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.

We didn’t have that experience at all fwiw.

OP here, thank you! This is all great info.

Anonymous wrote:The ones I've visited from your list:

Cayman: PROS: really beautiful beach; safe to explore; easy with kids; resorts close to airport; US-style grocery store; great options for condos and villas; fantastic snorkeling and scuba diving; good restaurants. CONS: kind of bland and Americanized, the beaches by the big resort hotels get very crowded.

Puerto Rico: I've only been to Dorado Beach, and the Ritz there may be the nicest resort I've ever visited. I would like to get back there and explore the other parts of the island.

Barbados: surprisingly excellent restaurants and excellent hospitality; lively nightlife, if that interests you; fun and safe to explore; feels like a "real" country and not just a nice place for Americans to go on resort vacations. The beaches vary---on one side of the island they are very rough and not swimmable (although stunningly beautiful), while on the other side they are calm with clear water.

Other islands I liked were Eleuthera and Harbour Island in the Bahamas. They require an extra flight to get to, but are worth it if you want a more low-key vibe and perhaps the most beautiful beaches I've ever visited----sugary sand (often with pink hues) and the clearest stunningly-blue water you can imagine. I also really enjoyed Anguilla---lovely beaches, low-key vibe, foodie-level dining. Virgin Gorda was also really nice, although I think that and the other British Virgin Islands are best explored by boat and not by spending your entire stay on one of the islands.

I didn't really care for Turks & Caicos. It's very similar to Grand Cayman in a lot of ways (similarly lovely beaches and very Americanized), but it felt a lot more crowded. This may be because we stayed at a resort and did not rent a condo like we did in Cayman, but I just prefer Cayman to it in general. If you do go, make dinner reservations well in advance of your trip.

I did not like Jamaica at all. We stayed at Round Hill, which was nice enough, but there were safety issues leaving the resort and we felt kind of stuck there. At night, our villa literally had armed guards and a guard dog.

Agree with this assessment of GC, which we love and have been traveling to for more than 20 years. But it’s a place to go sit on the beach (or snorkel/scuba); it’s not a place for exploring.

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.

I went to Curacao in 2008 with DH and a 10 month old. I don't recommend bringing a baby or toddler. It was meh--I recall sand flies which were not pleasant.

I am sure I missed some of the best parts of the island because I have heard good things from others.

Those are some great options. Note that PR is probably the easiest to get to (in terms of number of nonstop flights).

We went to Grenada about 5 years ago with a toddler and two sets of grandparents. It was beautiful. We stayed at air bb and explored the island by car. It was fun visiting different beaches, which were beautiful with clear water and you could snorkel off beach. We also hiked and visited a cocoa plantation and rum distillery. It was very green which appealed to us. Lots to do. Reminded us of St. Lucia without the pitons. Highly recommend!

OP here, thank you! This is all really helpful information.

I enjoyed Curaçao. We spent a week there; one half in a hotel in Willemstad, and one half in a resort in West Punt. We rented a car to get between the two places (they were close though— like maybe 60-90 minutes at most between them? Maybe even less.)

The whole country was clean, safe, walkable (in Willemstad, though we did walk out around the resort and found a couple of good eating places). A lot of good food too! Oh and absolutely great diving and/or snorkeling, swimming, and boat activities.

Overall, I’d recommend it. And I have spent time in other Caribbean destinations and didn’t enjoy them (Bahamas for instance— just completely overrun with cruise ships).

Anonymous wrote:Looking into a Caribbean trip at some point, family with middle school age boy. Would like a mix of nice beaches and things to do (places to walk around, either nature or town). I've done some searching around and landed on Grand Cayman, Puerto Rico, Grenada, Barbados, and Curacao. I'm curious of others' experiences with these islands and/or if there are other islands I should add for consideration?

We've been to Puerto Rico and Curacao.

Puerto Rico: Beautiful beaches in Puerto Rico, numerous things to see (El Yunque National Forest, Old San Juan, and many others), safe, great food, easy to drive, several options in terms of hotels and resorts, and direct flight from D.C. area.

Curacao: Beautiful beaches and safe. However, our adolescent children thought it was too quiet and not as lively as Puerto Rico.

The ones I've visited from your list:

Cayman: PROS: really beautiful beach; safe to explore; easy with kids; resorts close to airport; US-style grocery store; great options for condos and villas; fantastic snorkeling and scuba diving; good restaurants. CONS: kind of bland and Americanized, the beaches by the big resort hotels get very crowded.

Puerto Rico: I've only been to Dorado Beach, and the Ritz there may be the nicest resort I've ever visited. I would like to get back there and explore the other parts of the island.

Barbados: surprisingly excellent restaurants and excellent hospitality; lively nightlife, if that interests you; fun and safe to explore; feels like a "real" country and not just a nice place for Americans to go on resort vacations. The beaches vary---on one side of the island they are very rough and not swimmable (although stunningly beautiful), while on the other side they are calm with clear water.

Other islands I liked were Eleuthera and Harbour Island in the Bahamas. They require an extra flight to get to, but are worth it if you want a more low-key vibe and perhaps the most beautiful beaches I've ever visited----sugary sand (often with pink hues) and the clearest stunningly-blue water you can imagine. I also really enjoyed Anguilla---lovely beaches, low-key vibe, foodie-level dining. Virgin Gorda was also really nice, although I think that and the other British Virgin Islands are best explored by boat and not by spending your entire stay on one of the islands.

I didn't really care for Turks & Caicos. It's very similar to Grand Cayman in a lot of ways (similarly lovely beaches and very Americanized), but it felt a lot more crowded. This may be because we stayed at a resort and did not rent a condo like we did in Cayman, but I just prefer Cayman to it in general. If you do go, make dinner reservations well in advance of your trip.

I did not like Jamaica at all. We stayed at Round Hill, which was nice enough, but there were safety issues leaving the resort and we felt kind of stuck there. At night, our villa literally had armed guards and a guard dog.

Looking into a Caribbean trip at some point, family with middle school age boy. Would like a mix of nice beaches and things to do (places to walk around, either nature or town). I've done some searching around and landed on Grand Cayman, Puerto Rico, Grenada, Barbados, and Curacao. I'm curious of others' experiences with these islands and/or if there are other islands I should add for consideration?