I wouldn't plan on "walking to restaurants" on Anguilla - while 1 or 2 may be close to where you end up staying the majority of places are pretty spread out.

If you are smart and want to really explore the island and visit some or all of it's 35 beaches and dine at many different restaurants you'll really want to rent a car.

By the way, driving "in the left" is easy- speed limits are low and it takes less than 5 minutes to get comfortable.

Last point - taxis will get expensive 2 R/T's a day in a taxi will exceed the daily cost of a rental.

thanks for the mention & no kidding that. Mexico alone could take a lifetime to do right!

Hi ekscrunchy. I've been to some of the islands on your list and Anguilla and St. Martin are two islands we visit regularly.

You should look into Frangipani on Anguilla. It's on a great beach, usually fairly calm as it's a bit protected, and there are a few very good restaurants within walking distance with one of them being right in the hotel, Straw Hat. Driving on Anguilla is easy since there is relatively little traffic and there aren't that many roads. The roads have dramatically improved since we first started going there in the 1990's when even the main road was only partially paved. Now the main roads are paved and there are even a few traffic lights. I believe taxis are quite expensive. I don't think you need to rent a car for the entire time but you should definitely rent one for a few days to visit some of the other wonderful restaurants and beaches. The car rental companies will deliver a car to you at your hotel and then you can simply drop it off at the ferry dock or airport. It's easy to combine an Anguilla/St. Martin trip as there is a frequent public ferry between the two islands.

The French side of St. Martin can definitely feel very French. English is spoken everywhere but you definitely hear a lot of French. Orient Beach is one of my favorite beaches anywhere. It's very crowded in the morning until about 2:00 when the cruise ship passengers have to get back to their ships and then it's glorious. But the mornings are great for people watching. Orient Beach is probably not the best beach to actually swim. There are too many people and too much activity. There are better beaches for swimming on the French side.

My husband and I are just back from our second trip to Jamaica but the first time to Negril. The beach there is great. Mostly calm waters and there are quite a few small hotels along the waterfront and many local restaurants (the jerk sauce at Auntie's Restaurant was exquisite). The local crop vendors mostly just ask the males if they want to buy and the other vendors won't harass you if you say no thank you. I didn't find them overbearing. I'm with suze about the locals however. Not overly warm and fuzzy but I do love the food in Jamaica.

I love many things about Jamaica (from my limited 3 trips to Negril) and would love to return and venture out around the island. Love the music, food, scenery, weather, Rasta influences in attitude and cuisine, most of the local people once they get to know you a bit, the route taxi system, the shack restaurants. Negril definitely gives me that "Dorothy we're not in Kansas anymore" feeling. The craziest stuff can happen there, pretty much on a daily basis. I have more funny stories from a few trips to Negril, then from 30 trips to Puerto Vallarta.

No one responded to your question about Isles des Saintes, but it is my favorite stop in the Caribbean. ;-)

Oh, thanks so much! I read a recent article in the NYTimes and became intrigued. Is the food really not very good there? How about the swimming?

Have you considered Barbados? The beaches are calm and swimmable on the west coast (St James), turquoise colour with light sand beaches. There are many places for food, ranging from the Cliff to beach shacks. There is stuff to do off beach too, historical sites etc. It's a great intro island to the Caribbean, it is what you expect, palm trees and gorgeous beaches.

Antigua also have many swimmable beaches, eg Jolly Beach. It is said there are 365 beaches, one for each day of the year.

We went to Negril during March and found it a bit too cool for swimming, few degrees warmer and it would have been perfect. Based on that, I would head more south if I was travelling at that time of year again.

We did regret not visiting Les Saintes and Marie Galante whilst in Guadeloupe. Even though the food was not as great as I expected, I would go back to Guadeloupe and Martinique as they are so beautiful, have stunning beaches plus volcanos, rainforests etc.

I found these websites useful in planning my trip

http://www.antilles-info-tourisme.com/index-us.htm

http://www.express-des-iles.com/index.cfm?lng=en

Odin thank you for bringing up the geography issue. Like many people, I sort of assumed that the entire Caribbean was always warm and did not even consider that it would be warmer further south. I would be upset if I got there and felt too cool to swim in the sea, after all that is kind of the point of the entire exercise!

I've not thought about Barbados, or Antigua, but would be open to those if conditions are right with food and swimming...thank you again.

ekscrunchy - not in the Caribbean but an island off the coast of Mexico you may want to consider is Isla Mujeres. Easily reachable by ferry, it seems to have a lot of what you are looking for - pretty beach, lots of casual restaurants in town (walking distance from some of the hotels), beautiful scenery (especially on the southern part of the island (you can rent golf carts and drive around the small island). I'd wait until later March or April though.

Thanks, Tom. I've been to Isla Mujeres a few times and agree it is very nice but I'd like to explore someplace new this time. Never been to Holbox but, again, not for this trip..

ah ok ekscrunchy. let us know where you decide to go.

I personally think the Grand Case Beach Club is perfect for what you are seeking. I love the French side of St. Martin and the ramshackle village of Grand Case is a perfect mix of sea front restaurants with great food. While there are tourists for sure, it doesn't have the feeling of a big resort area. You can easily do day trips to Anguilla or St. Barth's (or both). Since St. Martin tends to get more European tourists, people do tend to dress up a bit more at night. Americans definitely prefer shorts and flip flops all day and all night. However, it's not stuffy or formal and there are places where you would feel very comfortable at night in shorts and flip flops (Calmos Cafe for example)

I personally like St. Martin better than Anguilla or St. Barth's but I've enjoyed those islands as well. Anguilla beaches have beautiful white sand and amazing turquoise water but it's so flat and scrubby and that is just not appealing to me after a while. Also, there is no real little town or villages where you can walk around and explore. That's a downside for me personally. The food was good but I don't think it had the range found in St. Martin.

St. Barth's is very hilly and has beautiful beaches but it's incredibly expensive. It's so French that you'll actually feel like you are in France. I enjoyed St. Barth's (I've been several times) but I prefer the French/Caribbean vibe of St. Martin when I'm visiting the caribbean.

I'm barefeet at the Calmos Café !

http://lecalmoscafe.com/

Would you consider St Croix?

We loved The Buccaneer:
http://www.thebuccaneer.com

Thanks, but not St.Croix. Too "Americanized" and I've been to USVI before. From what I'm reading here I should head further south for weather.

Barbados, Anguilla and St. Martin sound interesting. But Barbados does not get very good marks for food. I'm not looking for high-end fancy dining; I'm sure all the islands offer that. I want interesting food at least vaguely rooted in local traditions. Bad way to put it but I think you can get my drift.

<want interesting food at least vaguely rooted in local traditions>

I'm tellin ya, Jamaica ;-)

All the islands have cuisine rooted in local traditions, Barbados included. Locals have to eat. I don't know where the low marks for food come from. For a small island, it has a great number of places for cheap eats/beach shacks etc, around Oistins fish market & St Lawrence for instance.

We did not find St Croix to be "Americanized".