THIS IS MY FIRST TIME-SO GO EASY ON ME!! MY FAMILY OF 4 (HUBBY,WIFE,14YR OLD AND 12YR OLD DAUGHTERS) WOULD LIKE TO GO TO THE CARIBBEAN IN JUNE OF 06. FLYING FROM CHICAGO WE WOULD LIKE TO SPEND ABOUT $4000 WE ARE NOT INTO HEAVY DRINKING AND PARTIES WE WOULD LIKE TO STAY AT A NICE CLEAN HOTEL ON THE OCEAN,WHERE THERE ARE WATER SPORTS AND ACTIVITIES FOR THE FAMILY- WE WERE THINKING ARUBA,BAHAMAS OR CAYMAN ISLANDS. WE WANT TO MAKE THIS A SPECIAL MEMORABLE TRIP ---HELP PLEASE

I suggest:
1. rent a condo on Seven Mile Beach in the Cayman Islands or
2. Surfside Hotel in Bermuda or
3. Mahlo Bay Resort in St. John.

Well, it would be hard to beat the Vistalmar in Aruba (http://www.arubavistalmar.com/files/vistalmarH.html). In low season when you'll be traveling, the Vistalmar charges about $650 for the week which includes a rental car - which you'll need since, while it's oceanside, it's not beachside so you'll need to drive to get to the best beaches. The rooms at the Vistamar are air conditioned with daily maid service and have full kitchens (so you can save a bit on the cost of dining out). The owners also stock the refrigerator with breakfast items for your first day so you don't need to go out shopping right away. I haven't stayed at the Vistalmar but it is highly rated on tripadvisor and Fodors. Hard to beat for these rates.

We went to Aruba with our family of four. Our kids were just a couple of years younger at the time, 10 and 11. They are 11 and 13 now. They had a blast in Aruba and on Palm Beach, there are watersports available in front of every hotel. We stayed at the Marriott. It is a very nice hotel. Dining on Aruba is excellent and you can drink water out of the bathroom faucet! No problems with the water. There are restaurants that are cheap and some that are expensive. The Holiday Inn is next door to the Marriott and has a great beach in front of it. I am not sure what the rooms are like. The lobby and such don't look like your typical old Holiday Inn. So, you may want to check it out online.
The water is very aqua green on the island and I can say it was a fun trip for us.
Go to aruba-bb.com for more infor on the island and on the timeshare rentals and hotels.
I have also thought of Grand Cayman for my family. It looks very nice. There is a courtyard by Marriott that is across the street from the beach. I believe they have an all inclusive feature there. Four airfares will suck up a lot of money to go to the caribbean so perhaps try to make a package deal out of it. Good luck

Cayamn air used 2 have direct flights to GCM from Chicago. Check Plantana condos not 2 pricy. They are on a good section of 7 mile. Not 2 far from the store. Villas of the Galleon might also need 2 be looked at. If u want budget property try the Sunshine Suites. 100 yds away from the beach but sometimes a good value. Such a good value we stayed thier 3 times in one summer.

Cayman Airways does have year round direct flights from Chicago O'Hare.

Condos are a great option for a family, but the 7MB condos tend to have no watersports or activities as part of the resort, due to the ease in that area of getting those things provided off property.

Some properties in Cayman do however have condos in a full service resort, shoot for those