Which resort? chic, luxury, carribean, all inclusive a plus
 

Working on an anniversary trip…..went to Jumby Bay for Honeymoon and just loved it, but would like to go somewhere different. Will be going in early October. Any suggestions? Would like a fairly easy transfer from airport to resort.

There are some very nice resorts in Bermuda that will have meal plans. The Reefs comes to mind. Excellent food and a recently renovated areas and many rooms. It is mostly adults and will have a breakfast and dinner plan. Water will still be warm and weather perfect.

The Caribbean has lots of luxury, chic hotels that are either AI or offer AI or other meals plans. Is there any more info to go on than just somewhere different?

You will be going during hurricane season. Aruba, Curacao, or Bonaire might be your best bet at that time of year.

Check out these - all are upscale resorts (Note: You are going in October so some may be "closed" for the season):

Caneel Bay, St. John
Little Dix Bay or Biras Creek, Virgin Gorda
Peter Island Resort, Peter Island (BVI's)
Cap Juluca or Viceroy, Anguilla
Eden Roc, St. Barth's
Sandy Lane, Barbados
Four Seasons, Nevis
Casa De Campo, Dominican Republic
Palm Island, Grenadines

I'd choose Spice Island in Grenada.

Do you have the option to travel to the Caribbean in another month?

I agree with Doug although I've also been to a few of the resorts on RoamsAround's list and can recommend those as well. My husband and I went to Spice Island (Grenada) a couple of years ago. They offer an all-inclusive option. It's a gorgeous property and we loved it and Grenada. It's probably one of the most well-run resorts I've ever been to.