Kicking Off ‘The Florida Project‘

You can’t go from the Midwest to Florida in the winter – for any length of time – and not have people ask if you are getting ready to buy a place down here. We’ve been down here for 5 weeks now and that has brought us 35 days closer to coming up with a more permanent Snowbird plan.

We’ve really clicked with the Florida Winter Summerland vibe this year. Perhaps that shouldn’t have been a surprise since we’ve probably vacationed here 25x in the last thirty years. It’s long been our favorite place to go to and most of those trips have been in the winter months.

Related: Winter Summerland

Our extended Sunshine State stay this winter has gotten us to what we’re now labeling ‘The Florida Project’. Framing up an investment in a winter place of our own in Florida. It’s not something we will jump right into, but something we’ll probably work out over the next few years. Key parts of the puzzle will be where to we want to be, how many months we’ll use it, and if we’ll downsize our current house in MN.

Related: Downsizing Day Coming?

We didn’t build our FIRE plan with a second place in it, but it was always in the back of our minds. We started our FIRE lifestyle with a bit of a financial buffer and that’s only improved with the nice market returns the last few years. I’m sure we can get the numbers to work on a high-level, but we’ll have to put pen to paper to figure out all of the exact considerations.

Happy to hear / would appreciate any thinking that was helpful for anyone else at this stage of the Snowbirding process. Any good resources that helped you?

Image Credit: (c)

7 thoughts on “Kicking Off ‘The Florida Project‘

  1. I’m thinking it would be nice to just rent a place in Florida for the winter and keep my current residence. Climate Change is just going to trash Florida.

    Liked by 1 person

    1. We’ve been renting the last few years and it’s been great. I think Florida can adapt to climate change just fine. The rise in sea level over the last 140 years (9”) is just a fraction of the change from daily tides.


  2. Wish I could help, but we decided owning a second place was just too much of a headache and the math would just never quite worked for us. We’ve decided to stick with renting for extended periods. There are good reasons to want to own in Florida (weather, no state income tax, etc.), but the other costs were just too high in the places that we seriously considered buying (southern FL & the Keys). Between lost opportunity costs of actual ownership, HOAs, Insurance, and RE Taxes, it became difficult to justify it. The more I looked at it, the more us renting places seemed our better option. However, if you can locate a good vacation rental to offset some costs, maybe it won’t be quite as expensive. I looked at this as an alternative option (setting it up an LLC and running it as a rental business for most of the year…being a rental property owner already, it seemed a good possible fit for us), but I still couldn’t make it to work out. Even with all the tax breaks of a rental, the huge HOA fees and larger management fees still made it difficult to cost justify. So our own “Project Florida” (now over 6 years running) has become a more permanent rental situation for the foreseeable future. I’m glad we did, in hind sight, we found that we like changing up locations every now and then. So best of luck to you guys! I certainly don’t mean to put a damper on your project. You may find much better locations and opportunities than the ones we found. Either way, it’s a great problem to have!!! BTW, we just booked several weeks in the FL Keys for late next January. Now looking for a couple more weeks in late February to Early March (next year) for somewhere on the Gulf coast. Gotta’ love those Florida winters!

    Liked by 1 person

    1. We may come to that same conclusion when we look at all of the details. It’s certainly hard to carry the costs of a second place that sits idle most of the year. That’s why our ‘Florida Project’ will be a multi year project -everything needs to work out just right.

      Great that you are getting lined up for next winter. I would have thought it was too soon to be doing so. Are they booked cancelable in case something changes? Maybe I should get booking myself!


  3. Hi, we bought our cottage on a whim when the market crashed back in 2008-2009. We had a windfall (unexpected inheritance) and decided to invest in Florida real estate – a small 2 bedroom land-locked cottage 2 blocks to the beach. It totally did not pay out financially as we did not rent it when we were not there (watch for that in Florida – every town has different regulations!) … but it brought us a lot of joy. Hubby’s strong retirement wish was to permanently relocate to Florida in retirement. I opted for the snowbird approach, but then found I really did not like the back and forth! So we are making the move to be permanent here – and bought a new property with that in mind (and made back some financially on the cottage as prices in Florida recovered and are now going up again). I do know a few folks who rent the same condo down here every winter (not uncommon), another friend who rents someplace different every winter – she likes to check different places out.

    Our criteria for property was walking distance to a walkable beach, two+ car garage for toys, able to walk places for dinner, more residential than tourist, and for the last property – on the inter-coastal. Getting clear on beach access will be important….inland is much less expensive than near the beach.

    Good luck!

    Oh, I was in Gulfport this weekend. a friend & I did the garden our… yeah, in the rain.

    Liked by 1 person

    1. Yeah – the rain unfortunately put a damper on the Gulfport Garden Tour. We saw the flamingos around town, but were gone most of the day. Our cottage is a yellow bungalow right across Beach Blvd from the Library.

      If the market was low right now, I’d jump at buying sooner than later. It feels like it is at the high end of the cycle right now, although I know a lot of people are still moving to Florida. Will see what happens as the pandemic comes to an end. Do you have a boat that you want to be on one of the inland waterways?

      Liked by 1 person

      1. Oh my, I probably walked right past your bungalow – we parked at the library and walked to most of the sites. The gardens were lovely, even in the rain, and it was fun to see other houses as well.

        Although we are on the inter-coastal, we have a “corner lot” – not enough water access for a dock. But it has a natural beach – yes sand – that we can easily step down from the seawall onto. Since we are non-motor water people (kayak, SUP), this works great for us! You can see the water view on many of my posts these days – that’s one of the reasons for being on water!


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