Looking for high end first trip to Caribbean
 

I would like to take my wife to a Caribbean trip of 7 to 10 days duration in Feb 2015. We are veteran travelers but have never been to the Caribbean. We are looking for a change from our normal Hawaii trips. Our requirements are: nice scenery (not flat), Nice 4 or 5 star hotel on a great beach, prefer adults-only if possible, can be all-inclusive but doesn't have to be, short distance (5 miles or so) to a small town that would have some good dining/nightlife options. We prefer to not eat all of our dinners at our hotel. Would like an island that is fairly easy to get to, maybe a few hours from Houston or the East coast. Our budget is in the $8,000 to $10,000 range depending on whether we can use miles for airfare. What islands and/or hotels would you recommend? I am currently overwhelmed by the many options and would like to narrow my search based on these criteria. Thanks.

Caneel Bay St John

Look at:

Caneel Bay, St. John
Little Dix Bay, Virgin Gorda
Cap Juluca or Viceroy, Anguilla
Four Seasons, Nevis

thank you, I have heard of those. Will check out.

Also look at Spice Island Resort in Grenada. It's a beautiful, very well-run property on a gorgeous beach with very good food. It will also be nice and warm in Grenada in February since it's pretty far south.

If you go to Caneel during February school vacation, I am willing to bet there will be a lot of families with children. We were there a few days before Thanksgiving a few years ago and the difference from the week before to the few days before Thanksgiving was major with the number of young children. Also, while I loved Caneel, it's not really an upscale resort. It's spread out on a few stunning beaches but the accommodations may be a little disappointing if you are looking for your typical 4-5 star setting. You definitely go to Caneel for the beaches and snorkeling right off the beach rather than for the rooms.

Grand Cayman & Barbados have upscale resorts and lots of restaurants that you can dine at outside of the hotel. Cobblers Cove in Barbados is beautiful, it is a Relais & Chateaux hotel, think English country house in the Caribbean. They have a great restaurant. Scenerywise, Barbados is prettier than Grand Cayman. St Barts only has upscale hotels but requires a bit more effort to get to.

St. Maarten also has great restaurant options, nightlife and beaches. A luxury all inclusive there you may consider researching Sonesta Great Bay Beach resort , its all inclusive and close to Phillipsburg town.

Following this Barbados is wonderful when it comes to luxury and food and so is Anguilla.

If you're going to consider Anguilla, you should also look at Provo in Turks and Caicos. Provo is an easy 3 hour non-stop flight from NYC on Jetblue. The main beach, GRACE BAY, has consistently been voted one of the top beaches in the world.

There are excellent dining options, but not much nightlife. In fact, not much of a town. Life really centers around the beach and water activities.

Many of the resorts are condo-style, with full kitchens so that you don't have to eat every meal off-property. A few that I'd highly recommend, very luxurious are: The Venetian, West Bay Club, Grace Bay Club, Regent Grand, and, for more of a total hotel type experience: Seven Stars.

We fell in love with Antigua, I have stayed at many different hotels there. Many do all inclusive if you choose.

Blue Waters was heavenly, the Cove Suites on a bluff were gorgeous.

Galley Bay is incredible with beachfront suites and small cottages with their own plunge pool in the gardens. Loved it there!

Carlisle Bay was luxury all around with the best views of Antigua farms, rolling hills and a beautiful beach.

Hermitage Bay has cliffside gorgeous rooms with a plunge pool or directly on the beach. A very beautiful setting for honeymooners.

Sandals before the insanity started with the addition. Not really interested in going back to this particular place but that was our first intro to Antigua and we have returned half a dozen times simply because we love the island and the people and the upscale choices. Tons of great places to eat simple lunches and amazing dinners.

I would also recommend Jumby Bay which is on its own island a few minutes off shore. Pure luxury, but some people complain of being bored.

Oh and the Regent Palms in Turks and Caicos, which doesn't really fit the type of island you seek, but will boggle your mind as to the beaches, amazing restaurants and ease of getting around. Many four and five star resorts to choose from.

I didn't think Anguilla fit the type of island the OP is seeking, but if they are going to consider it, might as well look at Provo!
Both islands are flat and scrubby, but have great beaches, esp. Turks!

I vote for Virgin Gorda

After 20+ islands Grace Bay, Turks & Caicos is the one we return to time and again.
It has everything on your list except one thing---it is flat, but the lovely high end properties, restaurants, and that magnificent beach make up for that.

You have traveled to Hawaii, and that has the scenery for sure, but for us it was just way too commercial.

St. John might fit the bill for scenery, but a bit more laid back. We love it, but it doesn't have the luxury you are seeking.

Barbados also has some outstanding properties on the gorgeous West side beach, a bit more scenery but nothing like Hawaii.

So, you get the drift. I don't think you'll find scenery like Hawaii anywhere in the Carib. but the amazing beaches & water will far surpass that Hawaiian experience.

Anguilla, St. Bart's---now those also have high end luxury but are hard to get to.

So, for us it's Turks & Caicos hands down.

Have fun researching and it will be interesting to see where you chose to go.