Budget is each or for both? That can limit everything, as it's peak season.

You find it all. Definitely not secluded beaches yet go out and night and mingle, the 2 don't coexist.

Most islands won't have colonial architecture or major history unless you go to a large island or mainland central America.

You're not going to find long isolated beaches and waterfalls and forests, unless you're in a mainland country.

The closest on your list is Tulum, but keep in mind it gets crowded, but seems to meet everything else.

Others to consider, Roatan, Ambregris Cay in Belize, maybe Costa Rica. Theyll be the cheapest, and have historical sites and possible Forrest hikes.

Most of the .Caribbean is out for multiple reasons, including budget. (islands are smaller, you can find waterfalls with no beaches, secluded beaches but no mingling, etc)

Thank you for your response! Budget is per person and can be stretched! And yes, I know it's a tall order and we're of course, expecting to compromise on all of our wants but are so curious to see what Fodorites can tell us that we wouldn't find on our own.

Right now, leaning towards Vieques--cheap, non-resort, history, pristine beaches, luminescent bay!!--check. What is missing?

Viesques might work fr you, especially since you can combine with Puerto Rico, which offsets what Viesques has.

What it's missing, is the crowds, the mingling, nightlife, waterfalls, live music and dance. But puerto Rico has that, so you can easily combine.

Is this for this December/January or next? If it were not for budget, maybe flights/accessibility from NY and perhaps language, I would suggest the French islands Martinique and/or Guadeloupe. They would fulfil most requirements, they have holiday rental accommodation called gites and the owner lives nearby, music & food is probably some of the best in the Caribbean, there is nightlife around certain towns (eg Trois Illets Martinique), lots of beaches, some crowded and some not, with different kinds of sand, some light some dark sand.

Stories, well that might be an issue with language but plenty of the islanders esp younger people speak English. There is alot of local history, ruins and plantation houses to visit. Most of the Caribbean islands have ruins or colonial architecture in varying amounts.

St Pierre in Martinique is the most fascinating city with fantastic fruit market. Guadeloupe has a national park which is UNESCO recognised and covers a large part of the island, with many hiking trails, waterfalls, volcano etc and the Jacques Cousteau Underwater reserve.

But, with the budget you have it would be impossible, and these islands seem to be out of alot of American's comfort zone anyway, these are rustic islands without much luxury but with benefits of being part of France (food, supermarkets, good condition of roads, good standard of living etc). These islands might be more suitable for experienced travellers.

Grenada might also fit the bill, there are beaches which are not crowded for example the stunning La Sagesse, the capital St Georges is one of the loveliest, the north of the island is secluded and there is hiking in the centre of the island.