Here are the parameters:
Five days - November 7 to 11
There are two of us
Departing from Calgary, Alberta
Would like to keep the cost below $2000 total flight, accommodations, food
We would prefer warm locales
We like active vacations - considering bringing our road bikes if it’s an appropriate location
We also like history/culture
Any suggestions?
Here in the Dominican Republic is where Christopher Columbus first landed. In fact there are two different places in this country that both make the claim that he first landed there. There is bachata music if you like to dance etc. It is very tropical and PM me and I’ll pick you up at the airport for a small fee. $40.00 hotels all over the island with pools etc…
Hm, I have not been to the DR yet, so it’s a possibility. What kind of adventure sports can you do there? How’s the SCUBA diving?
You can fly to Maui for under $600, but get a package deal that includes hotel and a rental car. Flight time is under 10 hours via Vancouver, which is less time than getting to the Caribbean.
Lahaina is beautiful and just about guaranteed to be sunny and warm. There is lots to do on the island.
Hurricane season doesn’t end until November 30 in the Caribbean. This is something you don’t have to worry about in Hawaii.
Good suggestion Mangosteen, but I probably should have mentioned that Hawaii is out. I go there a couple of times a year already, and am there in January anyways. 
NOLA is out as well - was there this past April and am going again next April.
Phoenix, Palm Springs or San Diego would be my initial recommendations. All are warm weather destinations on the western side of the US, and should be really nice in November.
In fact, I’m headed to Arizona in a few weeks (but to Sedona, because Phoenix is still in triple digits this time of year). It’s great for hiking, golf, tennis…
Bringing your bikes will probably add a few hundred bucks to your flight cost because they will be bulky. I’d rent them at my destination.
Hmmm…a 5 day vacation leaves only 3 days to relax assuming two days traveling. How long are you willing to spend flying to get to where you are going?
Fly down to southern US, rent an RV, drive around, sight see and find some trails for a few days and then go back home?
Some short cruise trip? It might not be that active but it may be all inclusive.
Think of an extreme activity you both always wanted to do and see if you can get it done?
I wouldn’t call San Diego warm in November. Could be low 70’s or high 60’s. The wind coming off the Pacific can make these temperatures quite cool. With ocean temperatures in the low 60’s, swimming at the beach will be cold.
Great suggestions, thanks folks!
I would prefer to keep time flying to a minimum - say 3 to 4 hours? I can probably fly out the evening of the 6th, so will have a full day on the 7th. I’m also able to fly home in the evening on the 11th and sacrifice sleep before work the next day.
I like the suggestion of driving around the Southern US. One suggestion from a friend was to fly in to Las Vegas, rent a car, and hit Zion, Moab and the Grand Canyon to hike and/or mountain bike. We could bring tents/sleeping bags and camp, or stay in cheap hotels. Looking at the map, total driving time for the route would be about 15 hours, at about 4 hours between locations (except LV to Zion is only a couple of hours). How will the weather be in November? Keep in mind we are from Canada, will likely have snow here when we leave, and find 90 degrees to be too hot.
What about Baja California?
Baja is an option for sure! I believe there is some good cycling in the area, correct? Where would we fly in? As for travel with bikes, we are luckily pretty loyal Westjet customers and get free bike transport with them, so no issue there.
It looks like Westjet flies (with connecting flights) to San Diego which is a few miles from the border or for Baja California Sur it flies to Loreto and Cabo San Lucas.