I know this is probably a frequent question, but I've been spending alot of time researching this topic to no avail. I was hoping I could get some advice for the perfect island to visit based on my wife and I's preferences.

I love Hawaii. I have been to Oahu 4 times and Maui once. We travel from Dallas/Fort Worth and I can usually get a good deal by using a free flight with miles, and a flight/hotel combination for 7 nights through Orbitz. I would like to keep the fligh/hotel combination for 7 nights for 1 person to around 2k-2.5k. In Oahu, we usually stay at the Waikiki Parc hotel in the heart of Waikiki. We rent a car for the entire trip so we can explore the island during the day. In Maui, we stayed at a condo, the Aston Mahana.

I also have been to Cancun once and Riviera Maya once. We stayed at Iberostar Grand in the Riviera Maya and loved it.

Preferences:

Nice hotel with facilities and an ocean view (don't mind staying at a condo like the one we stayed at in Maui either - cooking a few nights there to save $)
Beach palapas (I know this is anal - I don't need a tan, I'm already brown)
Safey/Easy driving to explore the island
Great Food - both local eats and fine dining
Nice Bars/Lounges - live music, etc.

That's it really it. We just like to relax, eat, drink, and enjoy the beach. We don't even care for the activities and all of that. We loved the all inclusive at Iberostar Grand, but I'm looking for something where I can get more of a variety and get out of the hotel.

From the research I have done so far, St. John, Anguilla, and Aruba sound good, but they are expensive. Any other suggestions? If you need more info just let me know.

There's really nothing I've seen in the Caribbean that is like Hawaii. They are just so entirely different. The only islands I know personally are Jamaica and Domican Republic which I enjoyed very much but neither really fit what you seek.

Our first experience with the Caribbean was at Grand Cayman, we took our two teenagers. We liked it so much we returned 3 times. We all liked it for its vibe, laid back, lots of dining options and grocery stores. It also has a lot of condos that are beachfront. Stayed close to Rum Point and also on 7 mile beach. Liked them both for different reasons. You have to go to Sting Ray Island, yes, it is the touristy thing to do and was reluctant at first but glad I went there. Snorkel at Cemetery Reef and take a drive around the island.

I am looking for a new place to go this year and cannot seem to find that same kind of feel. If anyone can reciprocate I would appreciate it. I think condos beachfront are the way to go and do not like to stay in hotel chains.

Doesn't really sound like St John. You might want to read my trip report on St John just a little lower on this page.

betterbidding.com

Westin Resort bidding priceline.com St. John

resorty non AI maho.org vrbo.com decent condo options there.

Really nothing like crowded touristy Oahu though.

St Thomas Marriott Frenchmans Reef

www.puntacana.com Hard Rock Hotel new there of Excellence

great AI lots of action great beaches.

luxurylink.com great values

For summer out of the storm belt Grand Hyatt Aruba

at Palm/Eagle beach is very nice.

Might also consider branching out to the Big Island

konaweb.com Hapuna Prince for me a couple of years ago

was great got $1k air package including car on priceline.com

Great hawaiian vibe volcanoes rain forests beaches

simply awesome.... LOTS less rain/storms summer

fall than Carib

gazzerk,

which beachfront condo did you stay at in the Cayman islands? Are rental cars expensive?

Grand Cayman is great. We stayed at the Marriott there, but there are many choices in condos. I think in GC, condo is the way to go. (Have read here about Plantana and Villas of the Galleon as nice condos on a good stretch of beach).

We also liked Aruba. It is not a pretty island, but we rented a jeep and went around without any problems. It is very desert like. The resorts are lush and very beautiful. There are many variety of resorts/timeshare condos to choose from. My friends stayed on Eagle beach in a condo called the Divi Divi. It was very nice and less crazy than the Marriott. The Marriott was great for us because we have teens and there is lots of action and watersports. Her area in Aruba was quieter and the beach was larger.
Food on both islands is great. I think GC was more expensive in food choices, but I liked both islands and would return to either. I think both are great beach vacations. Aruba has a better weather chance for being all sun all the time. It is just generally drier. I have been twice and it never rained there.
I think anywhere in the caribbean will be expensive unless you do an all inclusive somewhere. We also liked the big island of hawaii if you haven't tried that one. The Hilton resort there is huge. The Marriott next door is large too, but a little quieter. (we collect hilton and marriott points for trips )

I didn't find Jamaica (Negril) expensive at all. But, we didn't stay at resorts.

We also stayed at very reasonably priced, and nice small hotel/resorts on Nevis and St. Kitts.

Our next trip is Curacao and Bonaire, got a one bedroom unit on Curacao, including a car, for about US$165.00 a night.