St Kitts, or Anguilla ..sigh also Grand Cayman
 

HI there ~ planning a trip for late May leaving from Chicago.
Last year fell in love with Captiva Island in So FL but want to go someplace else. Captiva's beach was wonderful but the island got small quickly. We love FL but need new adventures.

Looking for....good walking beach, (some shells would be nice, ) the kind of beach you can walk to things on...breakfast, cocktail etc. Some nightlife...nothing to crazy ~ we just like to sit and listen to some music or something until at least 10 pm or so. Our days start with beach walks that turn into beach time, afternoons are for little adventures....hiking, finding local art, etc.
looking for good food, nothing fancy.....we like the locals places and prefer to not have to get dressed up to eat.
St Kitts (Timothy Beach resort) is one thought....beach bars look fun to me....my sweetie said " thats a bar?" when I showed him the picures....
Anguilla (Ku) looks wonderful
How do the islands compare? Anguilla is turning out to be more expensive.....

Grand Cayman (condo rental) also is another thought.
We stopped there during a cruise and I did not want to get back on the boat. Like that you can walk to a lot of things......

Am I correct that GC would be a different type of island experience that SK & Ang with GC being less of a true island experience? I am all for the remote island with funky beach bars but I think I might have to easy my sweetie into that!

Thanks for any help & clarity you can share! Sorry so long!

Have you considered Tortola, BVI?

You might want to read the later posts on the topic called "St. John vs. BVIs" to get some good tips would might want to look into about Tortola.

We sort of already have a trip in the future "out there" to the BVI's ~some friends of ours sail and want us to join them the next time they go so we are saving that.

Anguilla has superb restaurants, incredible white sand beaches, some fun night spots like Johnno's or the Pumphouse etc, many beach bars on Shoal Bay, easy excursion to Scilly Cay on Sunday for drinks, seafood, and music from the Happy Hits, never know when you'll see a celebrity -- sweet, helpful people -- the island itself is dry, arid, no sightseeing really, unless you take ferry over to St. Martin for the day -- St. Kitts dining is pretty good, low key beach bars, the island itself is more lush with better sightseeing (the fort, rain forest, mountain hikes, scenic train ride, batik factory), people are OK but reserved and less accustomed to giving the right level of service that tourists expect, take ferry boat over to Nevis for a day trip with "Killer Bee" cocktails at Sunshine's beach bar near the Four Seasons. Grand Cayman is a totally different experience, much more like going someplace in Florida.

Also, St. Kitts beaches are OK but not great, can't compare to Anguilla beaches.

A friend borrowed us her newly built house in Sanibel, and like you, we also fell in love with the Sanibel/Captiva area.
Cayman is full of people looking for the same kinds of things that you are. You could always head down there and rent a condo. Having been there already, you know it's a place you like.
Here's another thought. Nevis is a little further of a distance, BUT, it has fantastic dining, an interesting history, a good choice of places to stay, some local shops, and you can take the ferry over to St. Kitts and still get the experience of seeing that island.

I have been to GC twice. It is a wonderful island.

While it's not super adventurous [no jungle, waterfalls, cenotes, etc.] it does have it's own flair. The water is BEAUTIFUL the beaches are PRISTINE.

You can rent a car and snorkel from place to place; the snorkeling is INCREDIBLE.

You can swim with stingrays [go when there's NOT a cruise ship in town and with smaller charter group], you can look for star fish. There's a hiking trail, Mastic Trail.

The food is AMAZING. You are safe to explore to your heart's content or grab a book and sit. The people are friendly and warm.

It's definitely a place I'll go back to someday.

Trish

I have wondered if Anguilla would be too quiet for us. Loved Nevis and St. Kitts. 2 very different experiences. If you use the same taxi driver for your stay, as we do, they become your best and very informative friend! Nevis is quiet and peaceful whereas St. Kitts offers more to do and is more built up, so to speak, although not like Aruba. Food in both places is good and there are rainforest hikes on both islands. Beaches are good.
We like to split our time between Nevis and St. Kitts and begin our stay in Nevis to chill out and then hop to St. Kitts' Marriott. Although it is out of place on the island, we love the option of the casino at night and their lobby bar has very nice bartenders.

I will offer my vote for St.Kitts as it is a lush beautiful island with very friendly people but with a British influence.

It is steeped in history and lost to see and do...but also if you stay at Timothy Beach Resort you can be equally happy to sit on your beautiful patio looking at the Caribbean Sea, sunset, beach...you can stroll or even roll down to the beach bars...listen to music at a picnic table toes in the sand and eat GREAT food...or go to a more posh spot further down the beach.

Jump in a cab and go to a luxurious restuarant with a view of Nevis and high end food and wine list...

Stroll down the little road for Pizza and beverages...it is a wonderful island with beaches full of lovely shells but real sand not shells as can be found sometimes in Fla.

But it is not White Sandy beaches like beautiful Anquilla but in my experience it has a LOT more to offer than Anquilla...Just to prove our love of St.Kitts and Timothy Beach Resort we are returning this year for two weeks to stay in a condo with our three year old son and my parents will be in a condo next door (TBR) - we did this last year and it was an idylic trip...happy to offer any further suggestions!

St.KITTS and Timothy Beach Resort!!