We are spending this winter in Florida. Last year we worked remotely from Scottsdale, AZ for February and March. Shortly after we arrived back in Saint Paul, MN we had an early April snow storm. So, this year we extended our travels by four weeks; we are working remotely from January 12 – April 12. 

Our first vacation rental was in the community of Carillon, Florida between the towns of Panama City Beach and Rosemary Beach. It was a lovely, quiet, gated community with a bell tower that chimed and played songs at the top of every hour. Our house was very “Gone with the Wind” with two wrap-around verandas. The beach was at the end of our block and since the beach had a Southern exposure, we could watch both the beautiful sunrise and the amazing sunset. The towns along the coast: Rosemary Beach, Alys Beach, Seaside, and Grayton Beach were all adorable. There were some really good restaurants; although several restaurants were closed for renovations during January (their quietest month of the year.) While we were here, both of our children visited and I celebrated my birthday. It was a little chilly in January, but it was a great month and the community we stayed in was wonderful!

Our second vacation rental was in Naples Park, Florida. We were about a mile from Vanderbilt Beach and a mile from Tamiami Trail (Highway 41.) There was a Whole Foods nearby and an abundance of amazing restaurants within 15 minutes of our rental. This was big city beach living. The beaches were lined with large hotels and high-rise condos. Luckily, our house had a beautiful new pool with a hot tub and a tanning shelf in the backyard where we could forget we were in the city once in a while. We were always busy in Naples – our neighbors from Saint Paul have a winter home in Naples and my parents visited as well as my cousin and her husband (from Lauderhill, FL) and several Minnesota friends. We didn’t visit the beach very often here but we spent a lot of time in our pool, shopping, boating, drinking and eating out. Very fun!

Our third and final vacation rental is in Holmes Beach on Anna Maria Island. We are two blocks from the beach and walking distance from several locally owned shops, restaurants and bars. This town reminds me of a small lake town in Northern Minnesota. A lot of people get around the Northern part of the island on golf carts and beach bikes. We work during the days but once in a while we take a break to float in our little pool or take a walk on the beach. Everyone is very casual here… it’s a big night out if I put on make-up and I don’t remember the last time I saw John wear anything other than shorts. Sunsets on the beach are amazing and we rarely miss one. Around the second week in March we noticed an increase in traffic due to spring breakers. Since there is only one main road on the island and it can easily take 45 minutes to drive just a few miles, we agreed to utilize the free Island Trolley and Monkey Bus as much as possible. We’re really enjoying the slower pace of island living, but I must admit that I’m excited about stopping at our apartment in Chicago for a few days on our way home. Small town living is fun for a while, but I’m still a city girl at heart.

The three locations were very different and none of them are perfect, which is why we will continue our search for the next several years. Hopefully, after a few more years of travel and exploring, we’ll find a place we want to return to every winter. But until that time, we’re just grateful that we are able escape the cold and snow for a while.