Are you open to staying at a private villa, or do you need to be at a resort?

Doesn't much matter. If its not a resort, we would need easy access to fine dining. We are both picky eaters, I cant eat anything spicy, so we will stay away from carribean only places. Also, if not a resort, would like at least some amentities, A/C (or screens to keep bugs out), and a tv and a phone.

I am curious to see what other people say because I don't think any one island checks all of those boxes. We have enjoyed St. John, Virgin Gorda, and St. Kitts/Nevis -- but all of those places aren't strong on nightlife.

The casino/nightlife really doesn't have to be there. As long as we can maybe take a daytrip to an island that has that. We have been married for 6 years and never had a honeymoon, so I am trying to give it to her now that I can. We are not that big on Nightlife, but it would be nice to stay out late some nights.

Can you find properties on the beach at St. John's? Are the beaches packed? Is there any nightlife? Hiking?

St. John (no s) has Caneel Bay, which is a beautiful resort but may be out of your price range if the $5000 includes airfare. I'm also not sure if they have TVs. Lot of hiking (2/3 of the island is a national park) and many beautiful beaches, of which only one or two are crowded on a regular basis. Check out the recent trip report on this site. Estate Lindholm is also an option there.
On nevis, check out Nisbet Plantation and the Four Seasons.
BTW, May is a great time to go the Caribbean.
On Virgin Gorda, check out Mango Bay. But again, it is a QUIET island.

St.John is not going to have much nightlife.

There are only a handful of Islands with Casinos. It's difficult to find peace and quite and casinos. They generally do not go hand in hand.

Look at Puerto Rico and Culebra

Ok, take a casino out of the mix. Is there something that fits the bill then?

St John and Virgin Gorda would be my choices based on your criteria. Beaches on ST John will be more crowded than VG. But there is a better selection of restaurants in St John than VG. Check out little dix on VG.
I would also recommend Harbor island in the bahamas but that will not meet your hiking criteria but will meet you quiet/restaurants criteria. Same with Anguilla - amazing beaches, amazing restaurants, expensive, no hiking.

I would say Aruba, but the food, jewelry, and clothing there is quite exspensive as almost everything is shipped to the island from far away. I actually think Grand Bahama Island is a great, cheap place for a nice vacation. The island is very quiet as the most popular tourist destination in the Bahamas is Atlantis in Nassau and the beaches there are very nice. Also, the shops and restaurants are very cheap as the get most of their stuff comes from the US and that is only 60 miles away. Have fun!

Thank you for all your responses so far. Virgin Gorda looked really good for awhile there. The only problem with Virgin Gorda is there is no nightlife whatsoever.

We are NOT looking for a party central area like Cancun and such, just a nice place to go dancing or have a drink and have some people around. I guess the closest thing I can think of offhand is the movie Couples Retreat ( I know its based in Bora Bora which is way to expensive). It had the quiet room on the ocean so we can have peace and quiet and listen to the waves, but also some pretty exciting nightlife if we so choosed.

Hiking and exploring the Island is still a must have. And just the quiet place to sleep is a must have. A place that is on the beach is perfect where we are like 20 steps or so from the beachfront, and we can walk out and be at peace without a million people around us. Also, my wife doesn't want to cook at all. That means every meal prepared or brought in, which is another reason why Mango Bay doesn't work for us.

I know I am asking for alot, but hopefully there is a place out there that can give this to us.

If I could merge Mango Bay sleeping area on an island with more of an upbeat tone with beautiful hiking and exploration, I would be in heaven.

A few years ago my husband and I went to Grenada and had a wonderful time. We hiked (hired a great guide who took us on two trips) to two waterfalls, went to the cocoa and spice plantations. We split our time on the island between a hotel on Grand Anse and at La Sargesse which is secluded. I loved it as we went to sleep maybe 50 feet off the protected cove, and lounged on the quiet beach during the day. There is only one dining room with wonderful choices. You can take a taxi to a nearby resort if you like. I would definitely go back there. There is also walking around the old section of St. Georges which was quite interesting. We took the public bus from Grand Anse a few times just to get a feel of everything and felt very safe doing that. We tend to like trips like this which are more adventurous rather than "cookie-cutter". Hope that helps; have fun.

We took our kids to St Thomas, St John and Barbados. The best of these three for hiking, secluded beaches and scenery is St John - without a doubt. You can camp in eco-huts if you want to be in nature and enjoy a more indepth experience of the National Park. One reason St John is so beautiful is that most of it is a National Park and the fantastic beaches like Trunk Bay are part of the Park. There are tasteful bars off many of the beaches that don't have a hedonistic Spring Break atmosphere. Cruz Bay has some restaurants and at least one place for music and dance, but it's a small place. There is an underwater snorkel trail at Trunk Bay and it's wonderful for beginners. Many of the other beaches are just as beautiful, the water is calm and clear; however, I am under the impression that different weather conditions and time of year can affect the water.
We just returned from Barbados and there was a better night life there. Oistin's Fish Fry on Friday night was fun, but I have 3 kids so we only stayed out until bedtime. St Lawerence Gap has several nice restaurants and many mediocre ones. We stayed at a fantastic resort on Dover Beach called Ocean Two Resort and Residences. We had a very affordable two bedroom suite. We had a fully loaded kitchen, two baths with large glass shower stalls, a jacuzzi and two balconies. It was new, clean and well designed and the service was remarkable. There was a roof top pool for adults and a beautiful pool for kids by the beach and bar. The only draw back was the water which was too rough to swim in, beautiful to look at and wade in - but it was dangerous. Thankfully the resort posted flags so one knew when it was safe. I'm told that the water is calm there later in the summer and I was aware that the west coast was better for swimming. We rented a car and visited several other beaches so we did find a placid pool to dip into. Barbados would be a better choice for nightlife, horse races, wildlife refuge and botanical gardens, and we enjoyed more local food there than what was available in the USVI. I will go back to St John because it is so beautiful, and I loved the water, but I don't know if I'll go back to Barbados. It's all about the water for me and we had a great experience at Trunk Bay, Cinnamon Bay and Magen's Beach on St Thomas, and while Carlisle Bay outside Bridgetown Barbados was calm and clear, it wasn't in the same ball park.

Based on your criteria I would suggest Anguilla or Babados. Both have plenty of beautiful beaches, and based on the time of the year, it should not be crowded at all. Now if you want complete solitude on a beach then you most likely will give up the night life.

Both of these islands are well developed and have the most sophisiticated cuisine in the caribbean.

I would highly recommend renting a villa. We've been to many islands and always stayed at a villa. Most places have Satellite TV, Wifi, and often with a private pool as well. Homeaway.com is a good place to look.

In terms of hiking Barbados might have a more varied terrain than Anguilla.

Hi Matthew,
If it is peace and quiet and relaxation you are looking for, I suggest the paradise island of Aruba. Not Palm Beach Aruba which is pretty lively with activities going on but on beautiful, serene Eagle Beach. (There is the Alhambra Casino and Alhambra Shopping Bazaar across from Eagle Beach within walking distance).The dining is exquisite and the island offers you much to do in the daytime as well as many night time activities. There are no waterfalls in Aruba except for the man made ones by the pool areas in some resorts. There is hiking, biking, kayaking, golfing,shopping, snorkeling, jeep tours, Atlantis Submarine excursions,and romantic sunset sailing if you choose. There are Piano bars,Martini Lounges, Magic shows,party boats,liqud dancing fireworks at the Paseo Herencia Plaza, casino nightlife and lots more. There is plenty of shopping to do,local festivals to attend and museums to see in the town of Oranjestad which can be reached by taking the public bus on Eagle beach for about $2.30 roundtrip. Once you visit Aruba I'm sure you will want to return..... as my husband and I do year after year.
Good luck and enjoy your vacation wherever you go!

http://www.arubahotelsbeaches.com/aruba-sightseeing-tours.html
http://www.arubahotelsbeaches.com/aruba-hotels.html
http://www.arubahotelsbeaches.com/aruba-night-life.html

How about a boutique hotel in Playa del Carmen off of 5th Avenue. You can get quite beach front rooms and then about a 15 - 20 minute walk to 5th Avenue in Playa del Carmen. Tons of restuarants, bars, shopping and entertainment.

Look at Las Palapas, Mahekal Beach Resort, Le Reve, Maroma Resort, and Petit Lafitte

Closest thing I can think of that gives you some of the seclusion beach front your looking for and nightlife within a reasonable distance. Tons of things to see and do off property including eco tours, Mayan Ruins, eco parks, hiking.

Check this site for accomendations:

http://www.locogringo.com/dynamic/lodging.cfm?start=1&page_no=1&area=Playa%20del%20Carmen&type=Hotel%2FResort

Check this site for things to see and do:

http://www.playadelcarmentours.com/

I would recommend looking at Anguilla-quiet, secluded beaches, great food all there. Beach bars for music and dancing also there. It is relatively flat, but there are still areas to hike and it is easy to explore. You could go to Anguilla specific forums to discuss hiking. Also, easy and inexpensive to take a day trip to St Martin/St Maarten for shopping and casino