Never been before; Any suggestions?

Ocho Rios or Montego Bay in Jamaica is an active place to go. Was going to take my son this year but funds flew out of my hands. ATV's, horseback riding, Dunn's River Falls, tubing, kayaking, zipline, Rose Hall Great House, Rick's Cafe, golfing, dolphins... you can sign up for any of those tours and you won't be alone (and they pick you up). You can check out Tripadvisor to see what A/I hotel you like. We were going to stay at Riu Ocho Rios. You should stay at least 4/5 days to be able to see sights and really enjoy and not be rushed.

first i must assume your dates are a mistype. dec 31 to dec 2 gives you one day. not even time to unpack.
as well many resorts require min 1 week stay during the xmas holidays. some require 2 week stay. i think there may be some flexabiliy for this year though as vacation bookings are down due to economy.
my suggestion is to fly to cancun. air canada has nonstop but price is almost $900. usair has a 1stop for $450.
all flt info & pricing i found on kayak.com you may be able to find better rates.
there are tons of all-inclusives in every price and size range to choose from. sports avail: tennis/golf, fishing deep sea and bone, horseback, atv jungle tours, excellent diving & snorkeling & explore cenotes and caves. nature - take a kayak tour in the sian ka'an biosphere. also there are 2 eco marine parks - xel-ha and xcaret. you can't get more historical than tours of maya ruins - coba, tulum or chichen itza. loads of fun duty free shopping in playa del carman - i'd look for an ai near playa. gives you a central location for all activities.
you can do all of these on your own or go with ai or other tour group.
for excellent info on all activities & many resorts look at locogringo.com
re safety. i went with a girlfriend and her 80 yr old mom. we rented a villa, drove around on our own and never felt unsafe. we did not venture out at night very often, however, except to go to dinner and home.
there is a dolphin eccounter in xel-ha.
ai perk is that you can go to bed & son can continue to party into the night without leaving resort property.

WestJet is offering nonstop service to Barbados which would be an easy visit for 5-7 days and probably cheaper than Air Canada depending on your chosen dates. There's are museums - Arlington House, George Washington House, Barbados Museum, Codrington College, Nidhe Israel Museum & Synagogue, various plantation houses that offer guided tours - Nicholas Abbey, Sunbury House, Tyrol Cot. There are several all inclusives - Almond Casuarina, Almond Beach Village, Mango Bay Beach Club, Amaryllis and a host of others.
Regarding safety - common sense rules - don't go wandering into quiet places (day or night), be aware of your surroundings, don't carry valuables with you or all your money/credit cards, etc etc etc.
You may find the following links helpful:

http://www.destinationcaribbean.net/index.php?option=com_accommodations&Itemid=153&countryid=19&parentid=19

http://www.destinationcaribbean.net/index.php?option=com_content&task=blogsection&id=5&Itemid=37&countryid=19&parentid=19

http://www.destinationcaribbean.net/index.php?option=com_content&task=blogcategory&id=134&Itemid=173&countryid=7&parentid=7

http://www.destinationcaribbean.net/index.php?option=com_content&task=blogcategory&id=131&Itemid=170

Hope that helps.

If it's your first time to the Caribbean, visiting an island such as the Turks & Caicos or Aruba where English is the first language can sometimes help you feel more comfortable. While these islands aren't known as much for their historical significance as some others with UNESCO World Heritage sites and what not, you'll get an awesome beach / watersports experience at either. (The architecture in Aruba has a Dutch flavor which is fun as well.) Both are easily accessible from Toronto. Here are a few hotels you may want to check out...let me know if you have any questions!

Turks & Caicos
Ocean Club Resorts
The Tuscany

Aruba
Hyatt Regency Aruba

Check out all inclusive packages for caribbean resorts (some including airfare) on www.cheapcaribbean.com; some are very heavily discounted. You might be better with one of these packages since truly you are buying airfare quite late for travel during the time period you mentioned.

Whether you go with a package or buy air separate, you'll have more options at reasonable prices after Jan 2 or so.

You both might like Riviera Maya in the Yucatan. I've been to many of the islands and prefer the fine white sand beaches of the Yucatan, which go on for miles and miles, as well as calm waters due to barrier islands. There is also history (Mayan ruins), big expanses of natural environment, great snorkeling, reliable weather that time of year.

We have been to many of the islands and Cancun/Mexico. Now in our early 50's. Love Cancun but it is not the islands. But it is the most reasonable in food and flights. Peso/dollar exchange best in a decade. Love Aruba but not any culture. Felt like g in southern U.S. I would recommend Barbados because English speaking and very Carribean. Try Mango Hotel/all inclusive or the Hilton on the south end of island. We love the diverness of this island.

If you choose Jamaica, I would look at Negril. because it's smaller I think it's more manageable for a first timer than some of the other spots on the island (and does have some all-inclusives).