We liked Grand Cayman. We took direct flights from Dulles and rented a condo on 7 mile beach that was walkable to restaurants and a shopping center. We rented a car to tour around the island. It was really nice but maybe a lot of work with 3 kids. We only had 1 kid at the time but if I went back, I’d look into a resort instead.

Next year, we’re trying an all inclusive for the first time, in Cancun. I think it will be more of a break for me than a vacation rental.

We’ve also gone on a cruise and got to see a few different islands. Would you be interested in that? It was great. No cooking or cleaning. There was a kids club if your kids will go and paid babysitting for the under 3s. One kid only went for a few hours when there was an activity he wanted to do and we sent my 2yo to babysitting at the same time and went to a show. It was also fun wandering around the ship with them and going to beautiful beaches in port.

Nowhere near Venezuela. We love Aruba but it’s off the list right now.

We took my 2 and 4 year old to Orient Bay in St Martin last month. Incredibly easy trip; everything is walkable in the main village (grocery store, cafes, ice cream, 7-10 restaurants) and we hit a different beach club every day. Stayed in an Airbnb with washer/dryer and ate in the backyard every day. Was super easy, and relatively inexpensive. Rented a car from a local company and they picked us up and dropped us off right at the terminal. We used the car very sparingly but was nice to have. Most places take USD = EURO so that helps as well.

Florida and Puerto Rico