Congrats on your tenth year.
Here are some places we have been and where we stayed.
Cancun, Mexico. www.solmelia.com, great 4-5 star hotel, with fabulous restaurants on property. We also took a day trip to the Mayan ruins at Tulum, and a sanctuary called Xel Ha, which had snorkeling, hiking trail, tube float route, wildlife, sea turtle nests, huge fish, a water bridge, and a cliff to jump off into the water. Tons to do for the day. The Mayan ruins were also beautiful.
We have also been to Bahamas, Paradise Island to the Atlantis Resort, it was huge and beautiful as well. It has a huge aquarium, a rope bridge, huge pods with marine life and some local markets and things to do and shopping right over the bridge on the other islands. www.atlantis.com
In the States; Destin, Florida is incredible. The beaches are white sand and the resorts there are fabulous. I have not been there in October so you may want to check the weather at that time of year. The Sand Destin is a great place to stay. www.sandestin.com
One place we did not enjoy was Jamaica. The locals were almost hostile to us and we were there with a large group of friends, it was not the safest feeling we ever had on vacation. We did not experience this in Mexico or the Bahamas. Also, no matter where you go, be sure to ask how far the hotel is from the airport. If your hotel is 1 hour or more from the airport, it can easily take you 3-4 hours to get there and back when you arrive or leave because the shuttles that pick you up from the aiport stop at every hotel along the way. We made that mistake in Jamaica and spent 4 hours on the shuttle on the way home, not fun on narrow roads in the heat.
Also, I think, (I may be wrong), but I think, October is in hurricane season, so be aware, the prices may be low for that reason.
Hope this helps.