We have been to many islands due to numerous cruises. We also spent a week on St Kitts and St Maartin. Looking for an island that:

is easy to fly to from Boston(dont want to take 2 planes and a ferry)

a unique property on the beach(no Marriot, Westins or Ritz)where we can walk to beach bars and restaurants

We are thinking Grand Cayman, St Thomas, Anguilla...and we continue to think. Please help

Maybe Harbour Island (outer Bahamas) - only about 3 miles long, so you can walk , or take golf cart.

See about Boston to Ft. Lauderdale to ELH (Eleuthera).

If you decide to go to Harbour Isle, its a very short water taxi over there.
(like maybe 5 minutes from ELH)

out of your choices,
I would skip St. Thomas (due to crowds, cruise ships, etc)

However, if you go from Boston to FLL then to N. Eleuthera you still have to take a cab to the water then a water taxi to Harbour Island- does not take a long, long time but it is certainly the "two planes and a ferry" DeeLo said she did not want.
What about Great Exuma? I know you said "no Marriott, Westins or Ritz" but you really might want to take a look at the website for the Four Seasons on Great Exuma. I have not been to Anguilla, although it sounds wonderful, but I am pretty sure you are still looking at two planes and a ferry to get there.

I really enjoyed Grand Cayman and you gotta love how easy it is to get to. We only stayed at the Westin and Ritz so can't help you with unique properties.

If you don't have to be on 7 mile beach there are many other options. It's a beautiful island. You could rent a car [it's easy to drive around there].

St Thomas was 'ok' but we loved spending a day on St John. You might look into staying there. You ferry from StT. I couldn't get good air travel. We're in Indiana and most everywhere takes a big chunk of our day to get to, which doesn't work when you only have 6 days.

Good luck. Looking forward to your responses.

USAir is launching non-stop service from Boston to Cayman in the next week or so, but even if you go via Miami, it is pretty eay, as we are only just over 1 hour from Miami).

OP wants "a unique property on the beach(no Marriot, Westins or Ritz)where we can walk to beach bars and restaurants".... can't answer, as I run a resort in Cayman..but there are a few options in that category

a couple of possibilities -
- on st. thomas look at www.secretharbourvi.com on east end near red hook and ferry to st. john for day trips, coki world, etc.
- on grand cayman you could check www.thereef.com - on the northeast end, in a quieter area of the island, about 45 mins to 7mile beach.
both are condo style resorts directly on the beach, privately owned mid-size resorts.

or you might enjoy provo in turks and caicos. AA has 3 1/2 hr non-stop. lots of cool places directly on stunning grace bay beach. you could look at: turks and caicos club, grace bay club or sibonne. loads of other options but these are each pretty unique.

I would avoid 2 of the 3 you mentioned: St. Thomas and Grand Cayman. I find them generic and less remarkable. I like Anguilla, Eleuthera, and Saba(although Saba is very unique and not beachy). St. Barts is stunning and so is St. John. I haven't been to the Grenadines and or Tortola or St. Croix but those sound appealing as well.

My very first choice would be Anguilla. It is our favorite island of all time. However, you will either have ferry over from St. Martin or fly a smaller plane over from there. It's not at all a hassle, but you said you didn't want to do that. Talk about great beaches and food. Anguilla's got it.
Cayman would be my second choice. Their main three hotels are Marriot, Ritz, Westin and Hyatt-another thing you said you didn't want. But, you could stay in a very nice condo on seven mile beach, and have the luxury of being on the beach and being within walking distance of MANY good restaurants. It should be a non-stop for you. The people on Cayman and Anguilla are great.

STT is ok for a day visit but would for sure stay on Gorgeous STJ or visit Beautiful Anguilla! Good Luck

If you truly want all the things you mentioned, (Direct flight, beachfront, walkable to bars & restaurants,) I believe Grand Cayman fits the bill.

Seven mile beach is actually about 5.5 miles, but who's counting? The southern & middle sections tend to be busier with more resorts & hotels, but this also puts you in the heart of the action for restaurants & beach bars. The northern end on 7MB is more spread out, more quiet, but you'll want to rent a car to get to the restaurants. This would be a very quick drive away.

Condos are a very popular choice on GC, and there are many different choices. A great site that show all the resorts and where they are located on 7MB is: www.caymanvacations.com

We've been to GC twice, and the flights are easy, and leaving from Boston in the early am, we are usually snorkeling by 3pm.

Have you looked into Tortola in the BVIs. No Westins...great place to explore. Roads are a little crazy to drive but what I loved about it was the dramatic landscape, unbelievable beaches and every beach had someone cooking up fresh fish and mixing rum punch. For us, these lovely islanders made it easy to spend the entire day on the beach. And we explored a different beach every day. We traveled from Boston and it was simple. I think you can get cheaper flights into St. Thomas and take a ferry but we flew into the Beef Isand airport.

We rented a house around brewers bay beach but if I was to go back I'd get an ocean front room at Sebastian's or a room at the sugar mill hotel or, although the rooms don't look fantastic, the resort on long beach...that beach is stunning. I'm not sure I'd call any of them upscale but certainly unique.

If you ever make it there, smugglers cove beach was my favorite although the husband liked josiahs bay beach best...opposite ends of the island

We are actually heading to eleuthera this may so I'm looking forward to that!

GiveMeSun-
Thanks for the helpful info on Tortola. We had booked a trip a few years ago until a major hurricane shook OUR world here so we cancelled. Do you remember Apple Bay by any chance? The house I had rented was called Sugar Apple-you could pay a daily fee for privileges at Long Bay Beach Resort (pool, fitness center, etc.)-I wonder in case I want to try again for the same place. Also- did you by any chance go to the little island (forget its name) that has the Pusser's Resort? My daughter has been twice lately with owners of a house on Great Camanoe and said that the Pusser's was "Mom's kind of place" (small, remote, etc.)
Also, where are you staying in Eleuthera in May? We are going in mid April for the first time (although we had been many times to out islands in the Bahamas).
Thanks for your reply!

I'm glad you are considering Grand Cayman, because it is really an amazing place.

harbourheightscayman.com offers a very affordable, relaxing vacation at the Grand Cayman Islands. It is not very big, so you don't have to worry about crowds and the staff is amazing.

They also offer many different activities and is located on the Seven Mile Beach. You really should considering taking a trip there.

One of our favorite beach vacations(out of 17 years going to the Caribbean) was Anguilla.

We stayed at Shoal Bay Villas(sbvillas.ai) and had a balcony right on, and I do mean right on the sand. The beach and water were perfect, and the restaurants outstanding. "Ku" right next to SB also looked very nice.

Seven Mile Beach on Grand Cayman was also fabulous, but very, very busy--lots of Marriott's and Hyatt's, etc.

On Shoal Bay West there are several beach bars and restaurants, but of the small variety not huge hotels.

One of our favorite restaurants on Anguilla was "Zara's" and was walkable down the beach from SBV

Sorry to say that you do have to take a ferry or small plane from St. Martin, but it is worth the effort.

We also stayed at Secret Harbor in St. Thomas. Outstanding sunsets, and snorkeling. It's on a bay by itself, so no big hotels and pretty quiet.

Caneel Bay, St. John might be another one to look at. Quiet, great beaches and snorkeling, and lots of good restaurants, but you would probably need a car.

We were in the same position this year--easy to get to, etc. We're going to try Grace Bay, Turks and Caicos. We hope it's as good as Anguilla(the reviews do compare the two). We're staying at "Ocean Club West". Good luck!

USVI and BVI sound like good choices for you. We really enjoyed Caneel Bay, and sailed through the BVI, very unique islands and many interesting people. Check out the Bitter End Yacht Club and Little Dix.

My first thought was that your criteria are at odds with themselves. To me, Grand Cayman, St. T all mean Marriots, Hyatts and Westins. Then I happened to think about Grand Cayman's East End. Take a look at The Reef hotel http://www.thereef.com

maybe you have already made your decision, but i just returned from a week on grand cayman. had not been there in 15 yrs., its just as nice as ever.

many more choices for condos on 7 mile beach & lots of restaurants. we stayed at The Avalon, it is north of the Ritz on 7 mile beach. all of the condo properties are pricey, but really nice! you can walk to many places or just sit on private beach & stare at the water. i have a great name for private snorkel/fishing trips & also for jet skis delivered right to your beach.

I do remember Apple Bay and thought it was nice as well. I think it is near Sebastians, which had a fantastic breakfast! I like the idea of using long bay beach resort amenities and that is very close to smugglers cove beach, which I mentioned was my favorite

I didn't get to the island where pussers place was although I went to the their place in the marina for a rum punch. For anyone on their way to Tortola, you must go to The Dove in Roadtown for dinner. Start the evening off with their Champagne happy hour, Champagne cocktails were $2. The food was the best I've had on vacation and there was something so wonderful about sitting on the deck under a mango tree strung with lights.

We are going to be staying at The Cove on Eleuthera this year and looking forward to it. How about you?

Give Me Sun,
Thanks for your reply. I will print your tips and put them in my BVI file to remember for later.
In Eleuthera we are renting a house in North Palmetto Point called Romantic Bungalow. We have rented villas in other locations and enjoy the space and privacy. The Cove looks very nice. Please let me know how you like it. We will probably try to go by there or at least have dinner one night. Have a great trip!