Hello everyone! I know there's been a ton of these posts, but of course everyone's criteria are slightly different. And the more I search these forums to find the Caribbean island that would best suit us, the more I seem to have created a fantasy in my head that doesn't exist. What we're looking for:

* A town we can walk around. We will not do an all-inclusive resort, we love to explore too much. Ideally, we'd love to stay in a small town with a lovely hotel/villa/AirB&B, and then walk down to the beach or to lunch/dinner. Walking is a plus, we're not wild about driving a ton. Public transportation or bicycles would also be a plus.

* Local life. We're not interested in American chain restaurants or shops.

* Avoiding huge crowds. We don't mind other tourists or some people watching, but we're not going to Cancun for a reason.

* Gorgeous scenery. Of course. A few spots for land hiking are a plus.

* Nightlife - Casinos & wild parties aren't really our thing. Live music, theatre, or a quiet wine bar or brewery is more our speed.

Any suggestions?

Thanks!

Oh, we'll be going in August, so hopefully that will help the crowds

The problem with your "Fantasy Island" is you are looking for a secluded place that has everything you want within walking distance. Quite frankly, that doesn't really exist. To paraphrase the line from the movie FIELD OF DREAM "...If you build it they will come..." which equates to the more "things" you want within walking distance the more crowded it will be. Most islands in the Caribbean don't really have "small towns". Instead they have one or two "towns" where you'll find most of the local businesses (not necessarily tourist oriented places) and lots of tiny "villages" each with a few houses and a convenience store or two. Points of interest, restaurants, etc. are usually scattered around the islands. Public transportation generally consists of independently owned mini-vans that drive along the main roads picking up and dropping off locals going to/from work or the local markets. Bicycles are not always a practical means of transportation due to mountainous terrane, narrow twisty potholed filled roads and lack of sidewalks or bike lanes not to mention high temperatures and humidity.

All this really means is that if you avoid the larger islands and are willing to make some concessions on "walkability" you can find many islands that will come close to what you are seeking.

Look at many of the Bahamas Out-islands (Long Island, Harbour Island, Cat Island come to mind). Also look at Nevis, Dominica (don't confuse this island with the Dominican Republic) and Anguilla. You won't find any large All inclusive, chain restaurants or crowds on any of those islands.

Excellent, that's really quite a big help! I knew this was the place to ask, as I'm really quite naive about the Caribbean. If I don't worry about bicycling or public transportation, or even too much about some crowds... just want a non-inclusive hotel/villa, beach, and restaurants in walking distance... does that make it easier?

The flights to Anguilla are bit expensive at the moment, although it does seem to fit the bill. Any other recommendations?

Look at rental villas/condos in the Frigate Bay area of St. Kitts - all will be within walking distance of both Atlantic and Caribbean side beaches and more than a dozens restaurants and beach bars (as well as a few other shops). Another plus is the Frigate Bay area is rather flat so bicycling is possible (but not wise when venturing outside the area). The only slight drawback is the Marriott Resort is also in the same area some you are likely to encounter some "spillover" of tourists staying at that resort but in August that shouldn't be of major concern. You WILL NEED transportation (not bikes) to visit other beaches and most of the major points of interest around the island.

Nevis is another island which comes very close to your requirements (no All Inclusive on the island although some resorts do offer meal plans) however, you'll have to make a concession for "walkable restaurants" as most are spread out around the island. Best to have a rental car as bicycling not recommended as primary means of transportation and "local mini-van buses" are few and far between in the evenings. Exception is if you stay at very upscale Four seasons Resorts which has several on site restaurants and is within walking distance of about 5 beach restaurants/bars.

If you don't mind the hustle and bustle of a more crowded island look ataxy of the small boutique hotels in the Grand Case area of St. Martin. The beach there is nice, the town is lovely with 10 to 12 restaurants and a score of interesting shops all within walking distance of the hotels.

Lastly, check out Harbor Island in the Bahamas. It may be exactly what you are seeking. Quaint town with plenty of restaurants, 3 1/2 miles of nearly empty pink sand beaches, large variety of rental villas and cottages, quaint B&B's and a few small resorts (NO All Inclusive). Best of all Golf Carts are the preferred mode of transportation.

I agree that there are conflicts in your request list. Small places without a lot of tourists aren't likely to be featuring theaters and wine bars!


<just want a non-inclusive hotel/villa, beach, and restaurants in walking distance>

Sure that's easier here's two examples of places I know of in Negril:
https://tensingpen.com/
http://www.charelanegril.com/site/

The first one is on "the Cliffs" the second on the 7-mile beach. No need for a car you can walk or use the "route taxi" (shared) system to get up and down the road along the coast. Plenty of interesting small local restaurants you can walk to. It's 90 mins from the Montego Bay airport (shared shuttles available).

It might be cheaper to fly to St Martin and take a ferry to Anguilla, rather than fly to Anguilla. There are more flight options to SXM.

Ah, I was not aware of the ferry to Anguilla. I'll also check out Harbor Island. Thank you all for the replies.

Oh boy, I completely "missed" the reference to theaters, wine bars and breweries - none of which are prevalent in the Caribbean.

You'll find resorts/restaurants that will, on occasion, offer a "Rum Tasting" cocktail hour and/or perhaps a special dinner with "wine parings" but wine bars and bars with a huge selection of "micro-brewed beers" are not the norm. FYI - outside of a few mega All Inclusive or very high end resorts you may find the selection of beers is rather limited to a few local brews and and something like Heineken, Guinness and Carona.

On those islands that have breweries they are places that bottle the local beers and are not usually open to to public and mici-breweries are as rare as hens teeth. You'll probably find a restaurant or two on most islands that have a fairly extensive wine list and perhaps offer occasional wine tastings, the concept of a "wine bar" outside of a mega-resort isn't something that is found on the smaller more remote islands you seem to be seeking.

Likewise "theater" is just not something that you find on most islands. At best, you might encounter an amateur production put on by high school students or the local drama club as a fund raiser for some local charity. Such production is more likely to be done in during the winter months and certainly not in August when few people are on the island.

Live music on the other hand can be found on jus about every island - not necessarily every night but certainly enough times for most tourists to get a taste of of the local various of "Music".

I most often vacation in Puerto Vallarta Mexico. Honestly it has more of your wish list than anywhere I've been in the Caribbean.

A town to walk around, a few wine bars and microbreweries, several theaters, tons of live music, gorgeous scenery. Of course there are other tourists there along with a large resident local population. It ain't Cancun.

As to the theater & wine bars, obviously I'm showing my naïveté and unfamiliarity with the area. Basically, casinos & spring break bars are generally not our scene. But that's even a minor point... mostly we want a place with hotels/villas (not inclusive resorts), local restaurants, and a natural beauty & good beaches to read/swim at. Ultimately, the other things I mentioned hardly matter.

And thanks for the Puerto Vallarta tip!

I'm not sure how swimming in the sea is in Puerto Vallarta, but doubt it will match Anguilla where the beaches are stunning and easy to swim in, Grand Case has everything, a lovely swimming beach and restaurants in walking distance, you can take trips to Anguilla and St Barths for a change of scenery.
Anguilla as many islands have Sunday BBQs on the beach with music.

Of course ocean swimming on the Pacific Coast of Mexico is nothing as nice as the fine waters of the Caribbean. Just pull up photos to see the differences. But the beaches are scenic and certainly nice enough to <read/swim at> and the rest of the city fits more of the request than where I've been in the Caribbean.

I don't know of any place that fits everything on their wish list.

Since I happen to spend my own vacations most often in PV, when they talked about wine bars, live music, theater, etc. it came to mind. Because Vallarta has that on offer and I personally have never seen those in the Caribbean (but I've only been to USVI, Jamaica, and Dominican Republic).

Personally, I don't think Anguilla is for you. (Don't get me wrong it's one of my favorites)

But no hiking, no real town, no walking around, dinners are by car

Sounds like you would like Ambergris Cay in Belize, Roatan in Honduras, placencia in Belize

Back to the request about activities like:

<live music, theatre, or a quiet wine bar or brewery>

You need cities of a certain size to support this kind of local &/or tourist aimed activities. It is unlikely to find them in a "small town".

No casinos or spring break bars are easy enough to avoid.

As are "resorts" generally speaking easy to avoid. Just don't stay at one there are fairly universally some alternative of independent hotels, apartment rentals, etc.

Harbour island in the Bahama out island or Elbow Cay also in the Bahama out islands. The latter is probably a bit more 'crowded' than the prior. The prior has a more upscale feel. I would recommend you look at each more closely to see if they would meet your above listed criteria. If you are looking for more quiet then yes you need to go to places where a car rental is required.

The first place I thought of when I read your post was Hopetown on Elbow Cay (mnag beat me to it!) -- which then makes me think also of New Plymouth on Green Turtle Cay. Both are in the Abacos (Bahamas Out Islands).

Limited tourism (though probably the most among the Out Islands, though that is a low bar); compact islands easy to explore by golf cart, on foot, or by rental boat. No large resorts, but a handful of small, intimate inns and lots of rental villas and cottages. Amazing beaches. All of your basic needs met within a short distance of where you're staying -- even live music on occasion from your local rake-n-scrape artist (though no theaters or wine bars). No chains or franchises.

As an added bonus, Hopetown offers its candy striped lighthouse, allegedly one of the most photographed sights in the Bahamas. And if you rent a boat, you can island hop to other islands, some of which are uninhabited.

Harbour Island (a small island off Eleuthera) is a more upscale version of the Abacos, but you'll have similar pastel-painted cottages and creamy/pink beaches.

Go to St John. Stay in Cruz Bay at either Gallows Point or Grande Bay if you want to walk to town/dinner/bars. Take open-air taxis to other beaches/hikes.

Beautiful island.