The majority of all inclusives will be found in Mexico, Jamaica and the DR.

Look at the Ibersotars, El Dorados, Royal Hideaway, Ellexance and Secrets resorts in Mexcio.

Look at Couples, Sandals, Iberostar, the Jewell, and Secrets in Jamaica.

Look at the Excellance and Majestic in the DR.

Antigua- Blue Waters, Galley Bay, Sandals, Jumby Bay, St. James Club

Barbados - Turtle Beach, Mango Bay, Sugar Cane Club

St. Lucia - Rendezvous, Sandals, Jade Mountain

St. Vincent - Palm Island Resort

Here's a list of AI's in the Caribbean:

http://www.caribbeanallinclusive.com/caribbean_all_inclusive_resorts.cfm

Here's a list of AI's in Mexico:

http://www.mexicoallinclusive.com/mexico_all-inclusive_resorts.cfm

Factor in that September is prime hurricane season, so trip/hurricane insurance is essential. Make sure you get the policy so that you can cancel for any reason and not just if your flight is canceled or hotel is closed. It costs more, but it's worth it.

High end AIs
Antigua - Hermitage Bay, Carlisle Bay, Curtain Bluff, Blue Waters and Galley Bay.
Barbados - many high end hotels but not all AI, some offer meal plans, eg Sandpiper, Coral Reef Club, Cobblers Cove. Best location is the west coast for calm Caribbean sea.
St Lucia - Jade Mountain, recently renovated Sugar Beach, Anse Chastanet
Grenada - Calabash Hotel, Spice Island Beach

It does seem like September might just be too risky to travel to that area. However, what are people's thoughts on Iberostar Grand Baravo Hotel in DR.

I do not like Jamaica and have done tons in Mexico so looking for something new and different.

The Iberostars in Mexico and Jamaica get really good reviews. I am not a fan of the DR. I like to be more adventurous on vacation and there really isn't all that much do there.

If you really want to go in September, you might look at Aruba, Curacao, Barbados, St. Lucia, Grenadines and Grenada. More outside of the hurricane belt, but still no real guarentee.

There are not really any good AI's in Curacao and not recommended in Aruba as there are tons of really great dining choices and bars.

If you really want an upscale AI, I would go with Barbados, Grenada or the Grenadines.

Isn't DR also at risk from hurricanes in September? Haiti is on the same island and it gets hit often.

I've been to the Caribbean almost always in the hurricane season, for the past 25+ years, so far lucky but there will always be a first time.

Aruba, Curacao, Tobago, Barbados are outside the hurricane belt but still feel the effects of a hurricane. St Lucia has got hit in recent years and Grenada was also hit a few years back. However my last visit to Grenada was during September and we had no issues at all, there is no way to foretell. Last year we planned to go to Grand Bahama in October but had to postpone due to hurricanes.