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Help picking the perfect for us resort

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I am looking for your expert advice on helping pick the perfect for us Jamaican resort for our 17th anniversary

About us
We are in our 40s
Budget of $2200(including airfare) give or take a few $$$
AI resort

I 'think' Ive narrowed down our destination to Jamaica-Montego Bay or Negril areas(T&C keeps popping its head up though)

I'm more of an R&R type of girl,powdery sand ,beach lounging with fruity drink in my hands,low key,low maintenance,love visiting with locals,meeting new people and I'm decisionally challenged :-)

My husband while low key and a whole lot more reserved in the people department will not be content sitting in a beach lounger with a fruity drink in hand for seven days. He doesn't need to go go go either but would like some choice in activities.

I'm more sand and surf, he's more cliff/rain forest/deep sea fishing,caves, cool historical stuff.... adventurous, ok he's adventurous

I'd like to try snorkeling but I'm not sure I'm coordinated enough and I'm serious :-) my husband would love it.

I think since this is our first trip to the Caribbean that an AI will be the way to go for us.
We are looking for a comfortable AI resort,with a variety of decent food options,good drinks and some activities during the day/evening.I don't need to party into the wee hours but I don't want lights out at 10pm either. The AI doesn't have to be huge or extreme LUX, Im looking for clean, and if I can get an oceanfront room with patio close to the beach at a less expensive AI resort, I'll take it.

In the past 3 years I have buried my Mom,Dad,Grandmother and 2 close friends, so when I say I'm coming for the view,the sound of the ocean and to live on "Island time" I'm serious.

Transfers I'm a little confused about this, will we need to hire a local company,also customs and the airport what can we expect(Never traveled outside of the US) Tips/Advice?

I read somewhere on here about a boat excursion that was like 2-3hrs off resort with apps and drinks for around $20-30,not even sure if it was for Jamaica. Help if it is, I'd like to include that.

Is there a good site/travel agency that you like that allows payment plans or should I just book now with CC (Booking with payment plan options websites) I've been checking bookit.com

I'm looking at traveling March 14-20 from Tulsa,Ok. I know this is spring break season and while I like children, there is a reason I'm leaving my 3 teens at home. I don't need an adults only AI the option of an adult only area is appealing.

I read someones trip report here on Negril and the Grand Pineapple(she even found her relatives while on Vacation) they split their time between GP and then moved to the cliffs, I remember going AHHH the View AHHH the beach Ahhh.... I think that one trip report via her blog sold me on Negril.

I have read,read and re-read this forum looked at so many resorts that they are all running together now and I can't remember what was what!

So I thought I'd come here, tell you a little about ourselves and have you help me pick the place for us because the "Decisionally Challenged" part of me isn't making choosing a resort very easy.

Thank you so much for your help and advice

Georgie

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