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Travel destinations, beaches and attractions and things to do in Florida. Documented by RESIDENTS of Florida.

10 Best Small Towns in Florida for Shopping

Best Small Towns in Florida for Shopping

Florida is known for beaches, Disney, alligators and oranges. With millions of visitors annually, shopping is big too. Here are our 10 best small towns in Florida for shopping. Every major retailer in the country has locations in Florida, but the shopping fun and creativity is found in small towns. Want to know where the best small town shopping near me is? Follow along.

Shop owners in Florida’s small towns have to be creative, unique, and fun in order to compete with their nationally branded competitors. From the panhandle to the Keys, small towns draw people from the beaches and highways into quaint communities known for their eclectic shops. Add a few equally exceptional restaurants and you have a perfect day at one of the 10 best towns in Florida for shopping.

Here is our list that we are growing, so contact us if you have some small-town Florida shopping we haven’t found yet.

  • Mount Dora – North Central Florida

Mount Dora Shops
Choose your shopping destination in Mount Dora.

Many internet lists include Mount Dora as being historically quaint with great restaurants in a lakefront community. Few small towns have more locally owned unique shops. Downtown houses everything from clothing, home goods, crafts, sewing, and artwork from local artists. You can spend a day shopping and visit Pisces Rising for some very good food and drink with a view of Lake Dora. Some of the best shopping in Florida is in Mount Dora.

  • Lido Beach –  Central Florida, Along the Gulf

10 best small towns in Florida for shopping Lido beach st armands
St. Armand’s Circle is the center of Lido Key. The beach is just a block or two away.

Across a bridge from Sarasota, Florida is one of the more intriguing small-town Florida shopping opportunities. As you leave the bridge heading for the beach there is a circle called St. Armand’s Circle developed by John Ringling, the circus magnate. 

Populating the buildings around the circle are more than 140 upscale shops. You can’t consider Sarasota a small town in Florida, but once you cross the bridge you get that small town feel in Lido Beach. Some of the best shopping in Florida for clothing and shoes.

  • Vero Beach –  Central Florida, Atlantic Coast

Shopping Vero Beach
From scuba gear to shoes, you can find it shopping the streets of Vero Beach.

On the east side of Florida, almost halfway between Jacksonville and the Keys is the beach town of Vero Beach. This oceanfront town is loaded with shops and restaurants. From boutiques to trinkets, you can walk down Ocean Drive and choose the shopping experience that fits your budget. Don’t forget a quick dash into Kilwin’s for an ice cream cone!

  • Fernandina Beach – Amelia Island, Northeast Florida Coast

Amelia Island Beach
If you get tired of shopping in Fernandina Beach, the beaches on the east side of Amelia Island are worth the visit.

There aren’t many Florida small towns that combine historic importance with clever shops and antiques. Amelia Island is as far north as you can go in Florida. Fernandina Beach is on the west side of the island along the Amelia River. 

Shops and restaurants line Centre Street downtown. You can even find the oldest bar in Florida, The Palace Saloon. We should note that Fernandina Beach on Amelia Island is one of our top favorite destinations and they belong in our 10 best small towns in Florida for shopping.

  • Key West – The Florida Keys, As far south in Florida as you can go!

Key West Shopping
You won’t find a more unique set of shops than Duval Street in Key West – a whole mile of them!

Yes, we know. You are going to say that Key West is not a small town. We would agree that it doesn’t seem that way, but in fact, the latest census shows only 26,000 residents. Florida Keys best small town shopping in is Key West.

Duval Street, in Key West, is crowded with shoppers from around the world. They can peruse major clothing chains right alongside some of the strangest shops you can find. Key West is the essence of quaint small town shopping in Florida.

This mile-long street is packed with one-of-a-kind stores on both sides. If you get sore feet shopping, there are plenty of cafés and famous bars along the way. The Florida Keys and Key West are one of our favorite topics. There are plenty of shopping opportunities along the way if you are driving through the Keys.

things you need when flying
  • Dunedin – West Central Florida, Along the Gulf

Dunedin shops
The shops in Dunedin on Main Street are plentiful and colorful.

Just north of Clearwater, Florida is the small Florida town of Dunedin. This waterfront community supports a long list of stores along Main St. You can find an assortment of shops from handcrafted foods to locally made crafts mixed in with several breweries Dunedin is known for. You can even find a Celtic store highlighting gifts from Scotland where the name of the town originated.

  • Apalachicola – The Panhandle, Northwest, Florida

Apalachicola Florida
Oysters may not be the predominant economic resource anymore, but shoppers will like the quaint shops.

This small fishing community was once the oyster capital of Florida. Slowly poor water quality caused the community to re-invent itself from a focus on seafood to a tourist town with quaint shops and even a, supposedly, haunted hotel. 

There are still some remnants of the oyster harvests in Apalachicola, but most of the older buildings have been converted into shopping experiences for visitors. There are still plenty of restaurants offering fresh oysters during your shopping breaks.

  • Naples – Southwest, Florida

Naples in the 10 best small towns in Florida for shopping
If upscale shopping is not in your budget, Tin City and Riverwalk a couple blocks from downtown Naples is an option for shops and good restaurants.

Can you say upscale? This Gulf front town supports some of the most extravagant boutiques in the country. Naples has been the home to some of the country’s wealthiest families for decades. The shops downtown, up and down 5th Ave. and more on 3rd Street, could keep you and your pocketbook busy for a day or two. This excursion is the ultimate small town Florida shopping.

We recognize Naples seems larger than its 19,000 residents, but it is still a unique small town shopping experience city in Florida. You will find the best shopping in Florida for jewelry and shoes here.

  • Winter Garden – Central Florida

Winter Garden Florida Shopping
This is the intersection of Plant and Main Streets in Winter Garden. This is the place to start your day!

Just get downtown to the intersection of Plant and Main Streets. From there you can find quirky shops, boutiques and creative restaurants. A stroll in either direction will find a town a few miles removed from the Disney area that has rejuvenated the center of its community. Winter Garden has become a bedroom suburb for Orlando.

  • St. Augustine – Northeast Atlantic Coast

St. George Street St. Augustine
This is one of the premier shopping streets in Florida called St. George Street. You can wander the shops for hours.

We are certain St. Augustine is the most historic city in Florida. Evidence of the Spanish who founded the city is clearly displayed in the architecture. While visitors explore the history, they also spend hours on St. George Street just a few blocks off the downtown square. 

The street is blocked off from vehicle traffic so pedestrians can easily visit the shops and restaurants. Best shopping in Florida for gifts with a historic theme or that sweater for cool weather.

What Did We Miss in our list of 10 Best Small Towns in Florida for Shopping?

This is the list we created from our memorable visits to these venues. Most locations have other attractions near them that can be explored on Florida Travel Blog. We are certain there are other shopping gems around the state and encourage you to send us your favorite 10 small towns in Florida for shopping.

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