Asklemmy

I've been to Jamaica and Dominican Republic.

Jamaica is beautiful and, in my experience, has more to offer if you're going off the resort. But for a lone traveller, especially the first time, I can't recommend it as the safer or more relaxing option, sadly.

DR felt a lot more touristy and the resort was much larger than the Jamaican one I stayed at. When I think typical beach vacation, this nails it. I would feel safe travelling there alone.

As for time of year I can't say. Both my visits were around July.

A quick stop over by Aruba would be pretty. I've also heard good things about Martinique. I haven't been to either myself yet. I heard that Aruba also has a huge Carnival celebration, so that season around February would be super fun.

Belize. Tiny country next to Mexico and Guatemala. I was there in August for scuba diving. Population under 200,000.

It's British Commonwealth so everyone speaks English; has Mayan ruins and extensive caves; it's next to the second largest reef system in the world and has fantastic scuba diving.

Seeing Arecibo is on my vague todo list... why? Because I'm the generation that grew up with golden eye.

I lived in Grenada for a couple of years. It's a chill, safe place. I had my family there and we always felt safe, as long as we kept an eye out for speeding buses when crossing the street. It certainly checks the boxes you specified. Night life is limited. I'm planning to go back for a vacation in February.

As I recall there is a time of year that gets very windy. I think that's in winter, but my memory is fuzzy. The internet says February is the windiest, and that matches some of my memories. In any case it's always warm. I wouldn't worry about rain. That's tapered off by December. If it does rain it's a warm rain, and it's likely to come in short showers so I don't think you'd be stuck inside all day.

If you want to be in walking distance to amenities I'd recommend staying near Grand Anse. You can also get public buses there. (They are actually vans.) There are resorts close to the airport, but in those places you'd be dependent on taxis to get away from the resort - which might be fine if you want to be somewhere quieter.

Thanks, everyone, for all the advice! I have to say, it's pretty friggin' cool to post a question like this and have so many people chime in :)

I'll keep you in the loop on where I end up, and what I end up doing!

If you're into aviation, definitely Sint Maarten because of its airport where planes land very close to the beach.

Well you could catch the West Indies vs Bangladesh Test match at Sabina park! Thats the first week of December.

Go to Cuba, have nice rum and food, and spend lots of money.

I want to put in a dime for Guadalupe. It's a beautiful island with all tropical trimmings. It's not as touristy as Bonaire or Cuba. Has awesome diving spots and the people were quite welcoming.

It helps of you speak a bit of French, though.

The st Kitts train!

I'll throw Grand Cayman on the list. Specifically, I'd recommend visiting Stingray City. Just a really neat experience to feed/pet stingrays while wading around on a sandbar.

St. Thomas and particularly Gladys Cafe, especially if you like hot sauce.

Mexico is a nice time, and you can get good deals on all inclusive places. In general, Cancun is more about partying and Playa del Carmen is more about chilling and/or shopping. My wife and I have been to The Reef 28 in Playa del Carmen twice which is adults only and all inclusive with access to their sister resorts nearby and it was a great time. If you book through them directly you can get a bundle that includes flight and transportation to and from the Cancun airport, and they'll work with you to get deals on snorkeling or whatever you wanna do. Just don't pay for anything in the airport, they're scams.

Most importantly, have the vacation that you want and have the time that you want. You can see the sights, do adventures, or loaf, and it's your call what you want to do with your vacation.