This will not be happening this winter, but leaving this thread for the future, as Cabo seems like a good location due to easy access from the US (especially w/ Southwest, and potential for Companion pass use).
In my research, I found all-inclusive resorts for ~$115 USD/night, including everything (lodging, all food, alcohol, etc.) right on the beach. Seems fun.
I balked at first when a friend of mine wanted to celebrate her 50th birthday at an all-inclusive resort in Punta Cana a few years back. I ended up booking it anyways because my friend currently lives abroad and I though it would be a nice way to get together. She invited about 10-15 people. I knew she would be upset if I didn't go.
At the last minute, the resort cut the price down even after we paid. I think she also got a bulk rate for the group. I keep expense notes for all trips and everything else for that matter. Well all-in-all I paid $637 for four nights. That comes out to $157 per night. It would have been cheaper if someone had shared the room with me, but everyone else had someone to room with so I got a very nice (but cheapest option) solo room.
Yes, it was expensive but the food was truly amazing. All three meals in a day were large buffets with high quality food. We all stayed together in one location on the beach. I'm not a cruise fan, but the all-inclusive was better than I thought it would be, and it was the right setting to keep everyone together on focusing on my friend's milestone bday.
Would I have planned this trip on my own? Probably not. But I know my friend really appreciated that I went.
I also bookended the trip with some solo travel to the capital and stayed in a hostel and then a trip to Chicago.
With some travel hacking, I spent a total of $1600 for everything for 12 days (a few in the capital, a few in Punta Cana, a few in Chicago). It probably would have been cheaper had I not stayed in an all-inclusive, but it all averaged out well.
