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Where to Find That Vintage, “Old Florida” Feeling

by Andrew Selby | Updated: January 29, 2025

small-town-florida

One of the first things people learn when moving to Florida is that all of the most popular tourist destinations actually do a pretty bad job of demonstrating the laid back lifestyle that Florida used to be known for.

Hence the birth of the “Old Florida” concept.

Back before tourism was such a big business, Florida was known for a slower pace of life with small towns and family owned shoppes and restaurants. But that Old Florida tradition still lives on today, you just have to know where to look for it.

Here are some of our favorite destinations that offer the perfect version of that Old Florida experience!

Follow the Sun to Dunedin

Located west of Tampa and just north of Clearwater, Dunedin offers residents the perfect hybrid lifestyle that allows them to be close to the big city action, but also far enough removed that they can find some peace and quiet as well.

As one of the oldest cities along the West Coast of Florida, there is a fantastic amount of history that exists here, and more to come as the locals are continually improving their quality of life with world-class dining options.

Like many of the small coastal towns in Florida, Dunedin has its share of unique shops full of interesting items. As you stroll through the area, you can always find something interesting at The Spice & Tea Exchange, and The Celtic Shop of Dunedin.

Whether you are looking to grab some BBQ from The Dunedin Smokehouse, enjoy fresh seafood from Lucky Lobster, or sip on a pint and order a bite to eat at Clear Sky Draught Haus, your inner foodie can’t help but appreciate the variety and quality it will find in Dunedin.

Valencia Ridge, the all-new community in the greater Tampa area, offers contemporary home designs and world-class amenities for the ultimate 55+ luxury living. Nothing compares to the incredible 55+ lifestyle, as the world-class clubhouse will feature multiple pools, pickleball and tennis courts, fitness center, restaurant and bar, sports lounge, social hall and much more. 

Get More Information About Valencia Ridge

Laid Back Beachfront Living – New Smyrna Beach


The Old Florida experience is definitely alive and well in beautifully laid-back New Smyrna Beach located along the Atlantic Coast of Central Florida. Located about an hour east of Orlando and just south of Daytona Beach, New Smyrna offers residents close proximity to the bigger Florida cities without all of the hustle and bustle.

Most of the things to do in New Smyrna revolve around the 13 miles of beaches that are known for having some of the best surfing in all of Florida. There is also a thriving local art community with tons of local artists selling their work in little shops right along the beach.

In addition to the lure of the surf bum lifestyle, New Smyrna also boasts a rich history. You might want to spend a few hours checking out their Sugar Mill Ruins that will really take you back in time.

When it comes to food, it’s all about the casual eateries in New Smyrna Beach. Local operations like The Breakers sell food right along the beach. Then there are the awesome pulled pork nachos at Yellow Dog Eats Kitchen & Bar. Don’t worry, collared shirts and ties aren’t required for great food at either of these spots!

The Island Paradise – Cedar Key

Gulf Sunset


Small, quiet, and located right on the Gulf of Mexico, the island of Cedar Key represents everything that you think of when you hear the term “Old Florida.”

One of the coolest things to do while you are in Cedar Key is to tour the island by plane with Marvin Franks. Marvin will take you up in his white and blue 1950 Cessna 170A and give you a 20 minute tour that is full of absolutely breathtaking views of the entire island and surrounding areas.

When you get hungry on an island in the Gulf of Mexico, seafood is going to be on the menu just about everywhere you go. Places like Tony’s Seafood Restaurant, Big Deck Raw Bar, and Steamers Clam Bar & Grill are all located right on the island and all serve fantastic tasting seafood in a casual environment.

If you find yourself in this area, be sure to go check out the Villages of Citrus Hills:

The Villages of Citrus Hills, Citrus Hills, FL

Located less than an hour from The Villages, the Villages of Citrus Hills is a Florida Retirement Community with single-family homes and maintenance-free villas that have been built with today’s demanding retiree in mind. But what makes the promise of Florida Retirement in the Villages of Citrus Hills truly come together for today’s new breed of active adult retiree is its extraordinary collection of world-class community country club amenities and extensive social activities. Villages of Citrus Hills offers a variety of home styles and neighborhoods to choose from.

Get the Citrus Hills Brochure

Upscale Old Florida Charm – Fernandina Beach

On the east coast of northern Florida is where you will find Amelia Island. And on Amelia Island is where you will find the fabulous beach town of Fernandina Beach.

This is one of the more upscale towns in our Old Florida collection, so if you are looking for an option that has a few excellent golf destinations, this is the choice for you. In addition to all of the excellent golf courses, there are also tons of boutique shops where local artists are able to sell their creations.

If you’re looking to grab a casual bite to eat in Fernandina Beach, one of the most unique options is Timoti’s Seafood Shack. This is a super-casual spot with picnic table dining and take-out containers, but the food quality is unbelievable.

For a more formal option that still won’t break your budget, getting tapas from Espana is always a fun option. Just about everything on the menu here is absolutely fantastic. And since it’s all tapas, you can order a few different choices and try them all!

And for a bit of history, don't forget to hit the oldest bar in Florida, The Palace Saloon (pictured above). If nothing else, at least visit their website and scroll down and read about the history of it, it's pretty cool!

If you find yourself in this area, be sure to check out Del Webb Wildlight:

Experience a new level of retirement living at Del Webb Wildlight. This distinctive active adult community is located 20 minutes away from downtown Fernandina, Amelia Island beaches, and downtown Jacksonville. Del Webb Wildlight provides unique opportunities centered around signature resort-style amenities hosted by a full-time lifestyle director to ensure you stay active.

Learn More About Del Webb Wildlight

The Gateway to the Keys – Key Largo

As the very first option along that famous stretch of islands known as the Florida Keys, Key Largo offers the perfect combination of close proximity to the mainland with a laid-back island vibe. Much like many of the islands further south into the Caribbean, life moves just a little bit slower in the Keys.

Lounging around for most of the day is the optimal way to pass the time in Key Largo. But if you do feel the need to be active, it also happens to be one of the best scuba diving locations in the entire world. There are literally dozens of ancient shipwrecks to explore throughout the Keys.

With its perfect location almost as far south as you can get without leaving the country, restaurants in Key Largo definitely have a bias towards local seafood. Some of the best spots in town include Key Largo Fisheries, Mrs. Mac’s Kitchen, and The Fish House.

Cresswind Palm Beach at Westlake is a 55+ community offering resort-style amenities, including Club Cresswind with pools, fitness facilities, arts studios, and sports courts. Located between Wellington and Palm Beach Gardens, residents enjoy easy access to beaches, shopping, and West Palm Beach attractions. Kolter Homes offers 12 floorplans designed for active adults.

Get More Information About Cresswind Palm Beach at Westlake

Over to you…

Know a great place to experience that “old Florida” feeling? Let us know in the comments down below!

Reader Interactions

Comments

  1. Mark Greenwald says

    February 15, 2025 at 7:43 am

    Let’s not forget Dunnellon. With the Withlacoochee & Rainbow Rivers flowing by, you can’t help but slow down a bit to admire your surroundings.

    Reply
  2. Mark L. Johnson says

    January 29, 2025 at 2:21 pm

    We enjoy downtown Bonita Springs for a lot of the aforementioned reasons. It’s on old US 41, halfway between Naples and Fort Myers.

    Reply
  3. George Cole says

    September 22, 2023 at 9:13 am

    The Fanlew community in Jefferson represents the true North Florida history.

    Reply
  4. Joan M Cartwright says

    April 29, 2023 at 8:23 am

    Yankee Town is old Florida at its best!

    Reply
  5. Nikki says

    January 20, 2023 at 12:12 pm

    High Springs and Micanopy are cool small Florida towns too.

    Reply
  6. Deborah Huckeba says

    January 19, 2023 at 10:22 pm

    Apalachicola still has an old Florida vibe. Very much off the beaten track. Only Highway 98 in and out., and we do have moss on oaks, river and beaches.

    Reply
    • Dorothy Scoggins says

      May 1, 2023 at 1:47 pm

      Deborah you are so right! My husband and I have spent years following the coastlines around Florida, as well as crisscrossing the state, all of the Keys and the Panhandle towns. The first time we saw Apalachicola area, we were both blown away. YES, IT IS OLD FLORIDA. We loved it,. and planned to come back to that area. Sadly, I lost my husband before we made our move. Apalachicola remains my favorite.

      Reply
  7. Linda Ward says

    January 18, 2023 at 5:22 pm

    Homasassa Springs is Old Florida at its best. Don’t miss the fresh shrimp at The Freezer on the riverfront.

    Reply
  8. Jim T says

    August 23, 2022 at 2:38 pm

    Check out Crystal River and Inglis ,Yankee town area where Elvis filmed follow that dream.
    You will be transported back in time to a more peaceful historic Florida that time has forgotten !

    Reply
  9. Bernadette Penfield says

    June 26, 2022 at 8:12 pm

    Floral City, Inverness and Crystal River. All have an old Florida vibe!

    Reply
  10. Michael West says

    June 26, 2022 at 2:01 pm

    You can have all the moss on my oak trees…in Bartow.

    Reply
  11. Jason Kersey says

    May 6, 2022 at 9:53 am

    Matlacha and Pine Island west of Cape Coral

    Reply
  12. Sharon Burstein says

    January 16, 2022 at 3:33 pm

    Boca Grande is quintessential Old Florida at its best. Nicely styled old world laid back feel with well dressed understated crowd.

    Reply
  13. JR says

    August 16, 2021 at 1:39 pm

    I’ve stayed in Cocoa Beach when there were only two motels there, 60 years ago. You could drive and park on the beach. There was no such thing as parking meters to pay to park to go to the beach……..That was old Florida.

    Reply
  14. Charles Dailey says

    August 16, 2021 at 1:14 pm

    Old Florida waterfront living is what I’m looking for for a seasonal rental

    Reply
  15. James Buxton says

    August 16, 2021 at 12:02 pm

    I would definitely add Mount Dora & Cassadaga just because of it’s funky paranormal vibe.

    Reply
  16. Michael Schumacher says

    August 16, 2021 at 11:40 am

    What about Bokeelia?

    Reply
  17. Dancerdee57 says

    August 15, 2021 at 1:18 pm

    Stuart, Venice, Mount Dora to name a few more.

    Reply
  18. Jodi Pearson says

    August 14, 2021 at 8:36 pm

    These are wonderful recommendations. I’m wondering if there are any towns in Florida left that still have Moss hanging from the trees. I want to live somewhere where there’s Moss hanging on the trees!

    Reply
    • Charles Craig says

      August 17, 2021 at 9:48 am

      I believe we saw those trees when we visited Dunedin. Hadn’t seen anything like that before.

      Reply
    • Dale says

      June 26, 2022 at 5:43 pm

      Floral city still does It reminds me of the movie The Headless Horseman

      Reply
    • Louise says

      June 30, 2022 at 8:26 pm

      St. Augustine is where the tree moss is plentiful.

      Reply
      • Danielle says

        April 29, 2023 at 9:43 am

        Amelia island has beautiful trees with hanging moss

        Reply
    • Allison says

      January 29, 2023 at 10:16 am

      Micanopy and any towns around Gainesville

      Reply
    • Mark Greenwald says

      February 15, 2025 at 7:39 am

      Many of the state and county roads in Marion County are lined with stately oaks with Spanish Moss hanging from them. State Route 200 near the Marion/Citrus County line is a great example, especially as you pass by the Ross Prairie Preserve.

      Reply
  19. Steve says

    August 14, 2021 at 4:08 pm

    Bagdad Fl is much more “old Florida” than anything in the article!

    Reply
  20. Lisa Cross says

    August 14, 2021 at 3:24 pm

    Winter Garden was such a nice place to visit. Walking on the street, browsing in the shops and eating at local eateries.

    Reply
  21. Edward McGowan says

    August 14, 2021 at 1:13 pm

    Palm Coast, Florida looks nice.

    Reply
  22. Scott says

    August 14, 2021 at 12:10 pm

    Clearwater used to be that way back in the 1960’s. I was born in Tampa and my Godparents lived on the beach in Clearwater. I miss going to their house.

    Reply
    • Jerry Horn says

      June 13, 2022 at 10:13 am

      “Used to be” is right. My Grandparents retired to Largo in the sixties after deciding that the west coast of Florida was less crowded than the east coast. Pinellas County in the sixties was a developing area. I lived with my Grandparents from 1968-1971, graduating from Largo HS and St Petersburg Jr College. It was a wonderful place to live at that time.

      When I returned for my 50th high school reunion in 2019, I found the Clearwater/Largo area to be a much different place than I remembered. It was still nice, but the laid back ambience was gone.

      Reply
    • bob says

      April 29, 2023 at 9:26 am

      all of florida used to be like that in the 60s and 70s even south beach miami they rolled the sidewalks up when the sun went down.

      Reply
  23. Joan Adh says

    August 14, 2021 at 11:49 am

    This is what I’ve been looking for. Thank you so much for featuring this appealing option. While I love all inclusive areas, as they are beautiful, I long for that old Florida appeal.

    Reply
  24. Jim says

    August 14, 2021 at 10:01 am

    Stuart, Florida

    Reply
  25. Laraine says

    August 14, 2021 at 9:45 am

    Arcadia Florida is also very old Florida the town main Street has antique shops , an old fashioned ice cream Parlor and the old theater turned museum is fun to check out.

    Reply
  26. USA says

    August 14, 2021 at 9:11 am

    Do you want to see real old Florida go to Quincy Florida rich in history just north of Tallahassee Garson County

    Reply
  27. Roy Smith says

    August 14, 2021 at 9:11 am

    Cedar Key is a marvellous place, used to ride my motorcycle there every winter several times, affordable living and certainly less hustle and bustle.

    Reply
    • Mark Greenwald says

      February 15, 2025 at 7:42 am

      Love that place. They’ve had a rough couple of years from the storms….but they’re coming back. Fortunately, we’re only an hour away so we’ll go over periodically, if only to support the local businesses.

      Reply
  28. Marcia says

    August 14, 2021 at 8:59 am

    Anna Maria Island.

    Reply
    • Teresa Amin says

      January 18, 2023 at 5:47 pm

      And Cortez near Anna Maria Island. One of the last fishing villages left in FL.

      Reply
  29. Dawn says

    August 14, 2021 at 8:29 am

    Venice Fl!

    Reply
    • DancerDee57 says

      August 15, 2021 at 1:16 pm

      Love Venice! We were there yesterday!

      Reply
    • Paul says

      August 16, 2021 at 5:15 pm

      Englewood also

      Reply
  30. Margie says

    July 27, 2021 at 10:27 am

    Welaka is really old Florida! For now

    Reply
  31. Frederick P. Ahrens says

    May 24, 2021 at 6:24 am

    You forgot Brooksville, FL

    Reply
  32. Constance Dickerson says

    June 3, 2018 at 12:31 pm

    Though I certainly understand the appeal of beach communities, there is certainly a vibrant old Florida feel in communities like Lake Placid. Give us a look sometime. It has fishing, hiking, boating, good restaurants and affordable living.

    Reply

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