Does anyone have any opinions concerning spending the Holiday season in Jamaica or an island in the Eastern Caribbean? Any suggestions?

Literary 100,000's of people travel to the Caribbean for the "Holiday Season" every year and a great many of them will choose Jamaica as their destination. Some will be first time visitors and many will be repeat visitors. There will be solo travelers, couples and families. It's the busiest time of the year for tourism in the Caribbean so resorts/hotels tend to be fully booked so best to make your plans as early as possible. Some resorts/hotels have minimum stay requirements during the Christmas/New Years holidays. Expect to see the highest room rates of the year. Likewise, airfares tend to be high during holiday periods - there's a limited number of flights to any given destination so, here again, make reservations as soon as possible.

What exactly are your concerns and what kind of suggestions do you need? It would help if you gave more info about yourself and any travel companions, where you are traveling from, when, exactly you plan to travel, how long a trip, what type of budget in terms of actual dollars you have for airfare, accommodations, food, excursions, etc. and what you'd like to see/do while on your trip.

If it is for this Christmas, I would think it is too late to book anything, usually Christmas gets booked up many months in advance.

If you are talking this year . . . Start planning for next year.

Besides that your questions such as they are are totally unanswerable. This year or next? Budget (very important) ? How many days do you have? Where are you traveling from and are you willing to take multiple flights? Family holiday or romantic couple's getaway? Resort or rent a house or condo? What sorts of activities do you want?

But definitely - when and budget . . .

For Jamaica... I love Negril. 90-minutes by shuttle from the Montego Bay airport. Gorgeous 7-mile beach or the Cliffs.

Yes there are parts of Jamaica where I would have "concerns" but Negril is not one of them.

Jamaica is very expensive when it comes to walks, food and excursions

Depends where you go and where you stay. Negril is most definitely not "very expensive". If you eat local-style you can get great meals for around $5usd.