Which island to go to in January/February
 

My best friend and I are trying to plan a trip towards the end of January to celebrate her 40th birthday. We have been to Mexico, Aruba, and the Dominican Republic. We are from Boston and are trying to escape the miserable New England winter so we want temps around 80 +. It will only be for 5 days, 4 nights. Looking for an all-inclusive resort where we can just drink, eat, swim and relax. We are also both single, so it would be nice to go to an island that isn’t strictly honeymooners. Does anyone have any islands to recommend?

Any Caribbean island from Puerto Rico and south will have average daytime temperatures in the low-to-mid 80's F during January.

Unfortunately you've been to several Caribbean destinations that are noted for having an abundance of All Inclusives but I'll list them anyway in case you want to return:

Dominican Republic
Aruba
Cancun
Cozumel
Playa del Carmen

You'll also find a good number of All Inclusives on Jamaica and to a lesser extent Antigua and St. Lucia.

There are a few upscale resorts in the BVI's that offer "Meal Plans" but they are not true "All Inclusives".

The Marriott on St. Kitts offers an "All Inclusive Option" but it is mainly just food & drink and does not include on & off resort activities.

If you are willing to pass on "All Inclusive" you can visit just about any island.

What part of Mexico have you been to already? Surely not the entire country? I ask because they offer so many All-Inclusive resorts, more so than many of the Caribbean islands.

Negril Jamaica is one place I'm familiar with that sort of fits this request.