My family is looking into visiting Jamaica, will be our first time there. My question is: which side shall we visit: Kingston side or Montego Bay? The plan is to stay there about a week. We would like to do 2 or max 3 tours (of top attractions of Jamaica, don’t know which one yet, have not started reading about Jamaica). Then spend most of time playing at the beach. Just want a relexing time, no rushing around seeing everything.

There is direct flight from Chicago O’Hare to Montego Bay, a plus for going there. If we go to Kingston, then one stop at Montego Bay.

MoBay. Almost all the beaches that people go for are on the north and west coasts, which is why MoBay is the tourist airport. The Treasure Beach area (Sandals Whitehouse, lots of other places) are on the south coast, but quite a ways from Kingston.

Kingston is pretty exotic to visit, but it's probably not what you're looking for as an intro to Jamaica. East Queen Street (Road?), while interesting, is a long way from Ocho Rios!

I loved Kingston when there for work several years ago, even though a few people were literally trying to kill us (long story, US cop at the time on a homicide investigation). The Halfway Tree area is cool... still, not exactly vacation paradise for a first timer family.

Don't get me wrong, I love everything about Jamaica, and I've seen a hell of a lot of it, far from the tourists. Great, wonderful people.

I just returned from Mo Bay and I would definitely recommend that over Kingston.
Kingston is not really the place you want to stay, although we did stay 2 nights in the mountains above Kingston at the Starlight Chalet.
If you are a little adventurous..getting there is NOT easy..Starlight Chalet...5000 feet up..is awesome.
Mo Bay though has many more choices to offer you.

Without knowing more about what more you're looking for in a vacation, my first instinct is to tell you MoBay and to then head over to Negril.

BUT flying into Kingston would put you closer to the Parish of Portland, town of Port Antonio, which is the lushest, most beautiful corner of Jamaica. It's where Jamaicans go for vacation on the island and it's a place where I've longed to go for some time.

When you visit MoBay you can find lots of activities to keep you busy. From visiting Rose Hall or river rafting, the possibilities are endless. Jamaica is a spectacular island with lots of sun and breathtaking natural beauty. There are many fabulous resorts in MoBay and I would go back in a second.

Montego Bay. We stayed at the Beaches resort in Ocho Rios and flew into Mo Bay. Really pretty and I felt it was a little safer.

Definately MoBay for first time vacation. Ocho Rios and Negril are more accesible from Montego Bay. Also there are really no beaches in Kingston.

Personally, I have spent way more time in Kingston than MoBay, but I was there for work, not fun. Kingston is the business center and Capital of Jamaica, not really a tourist locale. There are plenty of fun things to see and do in Kingston, but for family fun it's MoBay.

Have fun.