Palm Heights, Ritz, Westin, or Kimpton Grand Cayman.

Fairmont El San Juan in PR

The Sanctuary at Kiawah SC. Spa, biking, trails, and beach.

I’d avoid South Beach because it’s crowded and loud. I prefer a quiet beach.

Ritz St. Thomas is quiet.

I love cruises. Get a balcony and you can hear the ocean at night. Free room service. Spa on board. Find a quiet place to chill. Entertainment if you want it.

I'm going on a long weekend trip to the Caribbean with a friend. Am spending way less than that and am really excited about it. It should be relaxing and beautiful. There's also enough hiking, snorkeling available to keep us busy.

Look into some of the islands. There are direct flights to some (Aruba, Turks/Caicos, PR), while others may require a connection.

Go stay at an adults only hotel in Miami Beach. Eg, graystone, or if you’re up for a hostel vibe, the freehand. Warm breezes, great food, excellent Cuban coffee, and floating in the gentle waves.

Anonymous wrote:

Anonymous wrote:Go to the Retreat Costa Rica. It’s the perfect place to relax.

https://www.theretreatcostarica.com/

Limited direct flights to Costa Rica from DC.

OP again. This looks lovely. Went to Costa Rica last year. It was not a direct flight. Must fly direct non stop. Will look.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:San Juan. Beautiful long walking trails circling Old Town. Easy flight. Great food.

Any recommendations for where to stay? Ocean front?

Condado if you want to be right on the beach. Old San Juan if you want to be a little closer to other action (bars, etc).

Both are a short Uber ride from the airport. There are direct flights to San Juan from all 3 airpots around here. Southwest, JetBlue, and United. Easy trip.

If you're looking for some "cabana boy" attention, some other places in the region may be better for that purpose.

Ugh. I’m a novice. What is cabana boy attention? In intrigued.

Anonymous wrote:Grand Cayman

OP again/I love grand cayman. Also love Turks and Caicos.

Anonymous wrote:

Anonymous wrote:San Juan. Beautiful long walking trails circling Old Town. Easy flight. Great food.

Any recommendations for where to stay? Ocean front?

Condado if you want to be right on the beach. Old San Juan if you want to be a little closer to other action (bars, etc).

Both are a short Uber ride from the airport. There are direct flights to San Juan from all 3 airpots around here. Southwest, JetBlue, and United. Easy trip.

If you're looking for some "cabana boy" attention, some other places in the region may be better for that purpose.

Anonymous wrote:Go to the Retreat Costa Rica. It’s the perfect place to relax.

https://www.theretreatcostarica.com/

Limited direct flights to Costa Rica from DC.

Anonymous wrote:Montego Bay, an all inclusive, adults only, close to the airport.

I need to be close to the ocean. Is the airport close?

Go to the Retreat Costa Rica. It’s the perfect place to relax.

https://www.theretreatcostarica.com/

Clearwater beach/tampa. San Juan is a great suggestion. NYC. Orlando - a nice hotel and a day at Disney.

Grand Cayman