We are planning a quick weekend (4-night) getaway to celebrate our 20th anniversary, and are looking at our options in the Caribbean for a trip in two weeks, end of Septermber.

We are not looking for a large hotel, but rather a small getaway located oceanfront....the smaller and more romantic the better.

We are considering options in Bermuda, St. Martin, and Barbados:

- Bermuda, and possibly staying at the 9-beaches or Surfside Beach hotel
- St. Maarten, at the Hotel L’Esplanade or Grand Case Beach Resort
- and Barbados, at the Little Arches or Crane.

All of the above hotel recommendations gathered from Tripadvisor.

Looking to enjoy the beaches, not the night life. We are weighing the cons of the possible negative weather in Bermuda, with the pros of the easy flight (from EWR/NYC).

This will be our first trip to the Caribbeans, and we would really appreciate the help and guidance of your more experienced travelers to pick the right Island and recommended hotel !

Thanks

Can only help with your Barbados options. Little Arches is a delightful little boutique hotel across the street (a cul de sac quiet street) from a fabulous beach. The restaurant at Little Arches is also very good, and you would be in close proximity to the famous Oistins Fish Fry, which gets particularly lively and entertaining on a Friday night. And the fish is not all fried, in fact, most is grilled ( look for Fish Net) and it's not all fish.
The Crane is very nice but a much much larger establishment. Great location, couple onsite restaurants, an art gallery has just opened on the premises, and there are a few shops.
You may also want to look at Silver Point - located on a fab beach that attracts windsurfers and kitesurfers from around the world, but sea suitable for strong swimmers. The sea does tend to be very calm in September, generally.
The House is also a very elegant intimate hotel, but located on the busier west coast of the island.
Weather in September is generally hot, with clear horizons, clear sea (great for snorkeling/scuba diving), calm sea.
Today is a typical September day - hot & clear, slight breeze, flat & clear sea. Spectacular!

As far as Bermuda goes, the weather is typically still fine this time of year - it's hot and sunny today and should remain like this for several more weeks. I wouldn't put weather on your list of things to worry about.
Surfside is built on the cliffs way above the oceanfront. I'm not sure about beach access from the property, but even if there is, you're talking about quite a hike back up to the hotel. I'd email the property and check on that if I were you. I don't really see 9 Beaches as anniversary-romantic. It's about as close to family-style, laid-back as Bermuda gets. The cabins have weatherproof-canvas walls, like permanent tents. If you can handle the price tag, I think of Cambridge Beaches, Pompano and The Reefs when I think of small, romantic and beach-front.

Thanks all - taking some of the advice and heading to Bermuda - the simplicity of the commute (2-hour flight) one out.

We are also going to give the 9-Beaches resort a try. I know we'll have less (a lot less) luxury than some of the others, but we are the camping type and for us....at this point in type...there is an appeal to going "camping" Bermuda style.

We're hoping your weather outlook holds true txgirlinbda, and we will report back.

20 down - 20 to go!

Congrats and hope you have a great trip!

Congratulations and enjoy your trip. We celebrated our 10yr anniv at Bermuda a couple years back. It is a beautiful island. Do try to spend a day at St George's parish. We thought it was very cute/romatic and we had a lot of fun walking around the place.