It's the height of hurricane season. Where ever you choose, do be aware, and consider trip/travel insurance.

Aruba, Bonaire and Curacao are considered out of the 'hurricane zone', but, they can be effected.

Since $1000.00 is more like a weekly budget for me, I'll let others advise you......

Best beach - Grace Bay on Turks & Caicos ( airport code PLS)
Look at the Somerset resort , www.thesomerset.com
Great dining, very laid back Island. Not adults only though.

I suggest you consider Bermuda. There are usually some "in the event of bad weather" guarantees offered and hurricanes generally give Bermuda a miss.
Resorts which should fit your criteria
Tucker's Point
Cambridge Beaches
Newstead
The Reefs.

Have a great trip!

Traveling to the Caribbean in mid to late September has it's own set of challenges. It's the height of Hurricane Season and many resorts are close so that may limit your choices. That said, it's a time of year when you won't experience any crowds no matter where you go so that's not an issue. It's also a time of year when few, if any families travel so it really won't be necessary to confine your search to "adults only" resorts. Lastly, $1,000/night is a generous budget so you won't have any trouble finding accommodations on any island.

If I were you, I'd select the island first, then pick the resort on the island that most closely fits your particular lifestyle. Aside from a few "private island" resorts you should be able to find a resort with the "WOW" factor you are seeking on just about every island. And, since every island has a different vibe you can choose one that you particularly like.

So, which islands should you put on your short list? Here's a summary of some of my favorites along with a few resort recommendations on each island (you'll have to check to see if any of the resorts are closed in September):

Anguilla - 35 spectacular white sand beaches and 80+ restaurants make this island a real gem. this quiet island is perfect for those looking to relax on a beautiful beach and have exceptional dining experiences. Check Out Cap Juluca, Viceroy or Cuisinart resorts.

St. John - an easy ferry ride from St. Thomas this island is 2/3's a National Park so you'll find very little "crowding". Check out Little Dix Bay for it's understated luxury and 7 private beaches.

Barbados - Very interesting island with an decidedly English heritage. Good mix of beaches and mountains. Check out Sandy Lane Resort - it's the best on the island.

St. Barth's - wonderful small island that some people describe as the Paris of the Caribbean. Excellent beaches, upscale European vibe with over 100 restaurants , many among the best in the Caribbean (this island is a gourmand's delight) and some of the most sophisticated fashion shopping in the Caribbean. Check out Eden Roc, Le Toiny, Guanahani or Isle de France.

Nevis - With its Old World Caribbean charm going to Nevis is like stepping back in time to a period when sugar was King and Nevis was the queen of the caribbean. This lush mountainous island offers attractive darker sand beaches, abundant rain forests and lots of old Sugar Plantation ruins to explore. Check out the Four seasons, Nisbet Plantation Beach Club or Montpelier Inn.

Virgin Gorda (BVI's) - hilly island with plenty of excellent golden sand beaches, very good off beach snorkeling and a decent amount of restaurants. For resorts look at Little Dix Bay, Biras creek or perhaps Bitter end yacht Club.

If the above don't suit you there are plenty more islands and resorts you can look at.

Even Curacao though we love it, been there 3 times, has a windy season from the end of August until mid-Oct. The winds are 15-25mph when they kick-up. Aruba always has the Divi wind of 14mph no matter when you go so it will be there in Sept. Bonaire has less wind normally but there is no "wow" places. On Cuacao the Kura Halanda is a very classy old style claas hotel with very good food. The new Hyatt is larger but is very lovely but would be quiet if it is after mid-Sept. Also under the Arches there are 4-5 good to very good resturands. The only resturant to pass on is the Portofino at the Marriott. There is a French restaurant that was still open on our last visit 2010, the Chef?owner was getting on in years, made an excellent meal in a small restaurnt called LaRousse. With a rental car, take th full extra $25 coverage for the locals can drive without concern for you, and if you want to snorkel go to the North End and there are a series of bays where the snarkeling along the boulders along the sides is good for the Caribbean. At Klein Kenipp look for a sign foi Capt. Goodlife and if you go there he will take you out snorkeling to places you cannot access from the beaches of the 6-7 bays. If you go at3 you can snorkel for 2-3 hours at 3 spots for about $25/person and if he had a catch you can have a very basic dinner of lobster and in an informal style for $35+/person as I recall.
I do not like Aruba because it is too busy thats why I have not givien much on it tough there areseveral lovely hotels there.

I agree with Roams Around....but if you really want to wow her, take her to Palm Islands in the Grenedines........

thanks for the replies...I’m thinking maybe this is going to be a 2 island trip- a few days in 2 of the these 4: Anguilla,St Barths, St Kitts & Nevis. They seem to be pretty close, within 25-35 miles, of each other. How hard is it to island hop? Of the 4 how would anyone rate them..1-2-3-4?
Again thanks!

Easy 45 minute ferry ride between St. Kitts & Nevis. Those islands are 2 1/2miles apart at their closest point but ferry is between Basseterre & Charlestown which are 9 miles apart. There's a car ferry that also takes passengers which goes between the narrowest points (15 minute trip) but it's a 30 minute taxi ride from the closest hotel so there's no appreciable time savings.

Anguilla (AXA) & St. Barts (SBH) are further apart and it's a little difficult to get between the two. You have to either fly (a bit costly) or, if by ferry, you first go to St. Martin (i.e. 20 minute ferry between AXA and SXM then a different 1 hour ferry between SXM and SBH). Note: The ferry from SXM to SBH crosses a some "open water" and the ride can be a bit rough and uncomfortable - the ferry's nickname is the Vomit Comet.

Hard to "rate" the islands as the are quite different. AXA has the best beaches, SBH has the best "european sophistication", NEV the best Old world Charm followed closely St. Kitts. Which one is best for you depends on what you are seeking.

I wouldn't plan a vacation to the Caribbean in September, unless you don't mind not having sunny nice weather.

thanks again for the inputs...
if september weather is iffy in the Caribbean, what are the best alternatives? Aruba, Belize, Mexico?

The further south you go the less chance that island (destination) has of being struck by a hurricane or tropical storm.

You should know that just because September is the height of hurricane season it doesn't mean there will be a major storm brewing while you are traveling and even if there was the odds of a particular storm striking any particular island during the week or so you are traveling are quite small. For instance there may be a major storm that affects the US Virgin Island and Puerto Rico while the weather in the rest of the Caribbean is having perfect weather.

So, to answer your question, Aruba (as well as Bonaire and Curacao) have a low risk of hurricanes, Belize and Mexico have a greater risk but it is still relatively small. To put things more in perspective the Gulf Coast of the US and the coastal areas between Florida and North Carolina have a greater risk of being struck by a hurricane than any given island in the Caribbean.

You can research the frequency (or lack of frequency) major tropical storms have affected any given Caribbean island at www.stormcarib.com - use the "Climatology" link and click through to "Hits & Misses", pick the island you are considering and you'll find a list (by date) of all the major tropical storms/hurricanes that have affected that p[articular island over the las 150 years. You'll be surprised to find out there are really not that many for any given one or two week period.

If you do decide top travel t the Caribbean in September consider purchasing Trip Interruption Insurance that includes "hurricane coverage).

Lastly, I wouldn't recommend going to anywhere in the Caribbean during mid-September - not because of the risk of hurricanes or bad weather (generally speaking if there's no hurricane brewing at the time you are traveling the weather is generally quite good at that time of year) but rather because may resorts/restaurants and tourist oriented attractions are closed or operating under reduced hours or with reduced staff - the overall experience is not going to be anywhere near what you'll find during other times of the year.

We used to travel to Mexico in August and September, but got so tired of watching the weather channel to see if our trip was going to be canceled or intrupted by storms. Plus, it's just to hot and humid that time of year.

Have been to Nassua in Sept. 2003. Hurricane Fabian was scheduled to hit the area, but turned and hit Bermuda instead. We got lots of rain from that.

Went to Aruba in Sept. 2006 and had a great time. Perfect weather. Not to hot or humid like Mexico and a nice tradewind breeze. I wouldn't hesitate to go back in Septemeber again. I've read over the last few years Aruba has been getting Tropical storm weather between October and December.

After the Labor Day weekend, is a good time to go. Prices and crowds drop significantly. I have never experienced anything closed or not operating during that time period, but we went to major tourist areas that are heavily populated, so that might make a difference. Smaller destinations/hotels might use that opportunity to take their vacation or renovate.

This past September, we did an Alaska Cruise and spent time in Seattle. We have the best weather, but I understand that we lucked out and was not typical, so you never know.

We had orginally planned to go to Barbados this August, but after research found it would probably be too crowded with family vacations and moved the date to November. Didn't see anything about weather being an issue for that Island in August/Sept. since it's also considered outside of the hurricane belt.

I agree, whatever destination you chose get the trip/hurricane insurance that you can cancel for any reason, not just if your hotel closes or your flight is canceled.

In Nov. 2005 we were scheduled for Cozumel and hurricane Wilma hit that area. We had the cancel for any reason insurance, so just canceled and re-booked to St. Lucia paying the difference in hotel prices. While everyone else was scrambling and waiting to see what happed with their flights and hotel in Mexico. Yes, it costs more, but it's so worth it if you have to use it.

After spending about a bizillion hours looking at all the options it looks like we're probably headed to the Turks and renting a villa on Grace Bay. I know Sept isnt the best time to go but it's when we both have some time off, also it's looks very easy to get to Turks via US Airways from the east coast. Anyone have experience/ thoughts about T&C?
Thanks

some outstanding villas for you & your wife on this site: http://www.tcvillas.com/ballyhoo_cottage/
the 1 bedroom cottages would work well for you, are in good location near turtle cove marina (6 restaurants, dive shop, car rental, tiny liquor store) with really good walkin snorkeling & well within your budget. any of the larger villas will be equally as nice. i've stayed in tcvillas & they are very well maintained, beautiful houses.
you will need to rent a rental car.

thanks virgina
the wife has been considering these, same website
http://www.tcvillas.com/cottages_at_grace_bay/
they do have some nice looking places but a 3-6 BR house is just a waste for the two of us, maybe later if we go back with the kids
car-we're going to get a jeep or maybe a couple of scooters if I can talk the wife into it

Late to the party but was coming on to say it's raining in Mexico too that time of year.