That’s what I did in my 20ies. I’d freelance during winter with some cross country skiing tours in local woods thrown in. Then wrap up my projects in spring, spend the summer cycling and amateur racing and then start looking for new projects as season wrapped up. I didn’t have money for dance trips but I had a ton of great time on my bicycles and raced at relatively high amateur level.
Would I be happier working 3 months more and spending a couple weeks riding in fancy places with less stamina instead of riding a lot but locally all that time? I don’t think so.
There’s another legendary example in my circles. Dude bought a very nice car. Put on expensive wheels, installed engine tune and all that jazz. He was completely out of money, couldn’t go on any road trip for a while. His girlfriend wasn’t excited to adore the car sitting at the curb whole holiday.