5 Small Towns To Visit in Florida
Floridaโs reputation as a sun-soaked vacation destination is hard to beat! We feel the best small towns in Florida offer ‘beach fun’ along with other attractions, and historic sights and are often great to walk around, so you’re not driving around all the time.
Big resorts have their attractions but maybe you’re looking for a quieter, smaller town like St Augustine, Amelia Island, or Islamorada.
As Floridians, we have the luxury of spending time exploring Florida’s small towns. And what’s fantastic is that we’re discovering time and again that many of these make a perfect Florida vacation.ย
To help you decide which small towns might suit you, read on. We have also created some Florida Itinerary Ideas at the end and hope these are useful to you.
Florida’s Unique Small Towns
Our small town Florida destinations span from the north, at the Georgia state border to the tip of the USA mainland and over to the south west Florida coastline.
Whether you are looking for tucked away beaches, remote islands to kayak around, snorkeling trips on beautiful coral reefs or fishing in world class waters, thereโs a small town Florida destination waiting for you!
Getting to Florida
There are 131 airports in Florida! Twenty of these have an International designation so youโre going to have choices on where to fly into. We show the nearest airport to each of our small towns below.
Generally, flying into the bigger hubs is cheaper. The big 4 – Orlando, Miami, Fort Lauderdale and Tampa offer more frequent flight schedules from around the globe.
Donโt overlook growing regional airports like Sarasota (Sunshine Coast, south of Tampa), Melbourne (East Coast), Southwest Florida International (Fort Myers) and Jacksonville (North Florida) to name a few. Often lower cost airlines fly into these making tickets cheaper (eg. Allegiant to Fort Myers, TUI to Melbourne).
Also bear in mind that driving around Florida is very straightforward. It’s about a 3rd of the size of Spain and just above the average size of US states (22nd). Highways connect all our routes until you head onto islands but isn’t that the point – leaving hustle bustle behind for a few days ๐
Best time to travel to Florida
Is there a best time to visit Florida? Well, we think it depends on what you want to do or perhaps avoid ๐
December to May
Winter Months. Dec-Feb. Although many โsnowbirdsโ flock to Florida from colder US/Canadian states during November to Easter, it isnโt going to be super hot this time of year. But it’s fantastic for getting outside and cycling, playing sports and enjoying warm days on the beach. Markets and festivals abound in small towns around the state.
Spring (Mar-May) – March is Spring Break peak time in Florida so unless youโre here to party, we suggest coming before or after. The weather is warm, the days getting longer and the weather is beautiful. If youโre a baseball fan, you can come watch MLB teams training in many cities and small towns like Fort Myers and Sarasota.
June to November
Summer. June-August Itโs hot and sticky, although typically daily rain showers cool things off. Personally itโs not our favourite time to live in Florida but this means you can often find good deals on hotels. Florida schools break end of May and return mid August, so expect more local tourism during these times.
Autumn/Fall. September – November Another great time to visit although it is peak hurricane season. But donโt let that put you off. The weather is warm, the fishing can be better when the waters cool a little and thereโs a lot of outdoor festivals and concerts as well as sporting events to enjoy.
Check Where and When to find specific climate information by month for our Fabulous Small Town Florida Destinations.
St Augustine
Why Visit St Augustine, Florida?
Many of us believe we won’t find much โhistoryโ in Florida! BUT St Augustine will debunk this myth within a couple of hours of arriving! Quite incredibly, St Augustine is the longest continually inhabited European-founded city in the United States โ often termed the “Nationโs Oldest City.”
Stroll beautiful pedestrian friendly streets spilling over with an eclectic mix of quirky history, serious history and modern living. Combine this with never-ending views over the water, a wide range of quality places to stay and eat at, and you have a perfect Florida small town destination.
While there is a touristy fun side to St Augustine (think Ripleyโs, Ghost Tours, Fountain of Youth, Pirate shows etc) look beyond this and you will find a deeper local culture that is enticing to get immersed into.
Seek out side streets oozing with stories of the past, relax on nearby stunning beaches, explore a number of excellent museums and find local produce beautiful served in well-run restaurants!
Getting to St Augustine
The small town of St Augustine is about 50 miles south from Jacksonville International Airport and around a 2 hour drive (100 odd miles) from Orlando airport. If youโre in Daytona itโs about an hourโs drive.
From Orlando, you can take the main (& very busy) main I-4 interstate route and connect into I-95 (also busy). If youโre looking for a more relaxing drive then joining State Road 50 to connect to I-95.
There isnโt any direct public transport from either airport to St Augustine but if youโre looking for a partial bus service Greyhound does have some services from the airport hubs.
If you are driving, treat yourselves to a first stop en route at the beautiful New Smyrna Beach which is often deserted despite being a national historic landmark with its iconic lighthouse at 175 feet!
Where to Stay in St Augustine
Our vote is to stay in the heart of the town! We have booked different types of accommodation during our visits and loved them all. Check out downtown hotels like the St. Augustine Hilton Hotel which we stayed in during our first visit. These often include more amenities like a gym, swimming pool and inclusive breakfasts.
Alternatively if you want to be closer to the water, choose a hotel along the coast. Some are right on the beach side, others just across the road. The further back hotels are often cheaper but still offer great sea views on upper floors!
Finally, there are a number of wonderful traditional Inns in St Augustine historic city center. They are beautifully maintained properties full of character and with great service. and include hearty breakfasts. We enjoyed a stay at The Cedar House Inn in St Augustine’s historic district. For a first visit this is a perfect location as it’s so easy to walk out in the evenings for dinner vs. having to drive.
๐TPOP Tip:
Book accommodation that has private parking on site if you are driving. Overnight spots in the city centre is time-consuming, expensive and at busy times like a combative sport!
Check out Bed and Breakfast Inns of Old St Augustine for a full list of independently owned properties.
Fun things to do in St Augustine
1. Start by taking a free walking tour. A local guide will get you into the historic back streets and help you learn about lives from centuries back. A good email contact for booking a walking tour is freetourstaugustine@gmail.com.
Go in the morning! Its a beautiful stroll as the sunlight sparkles. If you love taking photos, you’re going to be in your element! Free walks are also a great way to get your bearings, check out restaurants and shops that you might want to return to later in your stay!
2. If youโd rather not walk or this isn’t possible for you, take the Old Town Trolley Tours St Augustine. It’s great fun and runs all day long with 20+ stops. You will see stops sign-posted all along the route like the one in the photo below. A full loop is around 70 minutes. Tip: Take the trolly if visiting in the summer when it can be a little hot to walk around for hours without overhead shade!
3. Explore Castillo de San Marcos, an important historical Fort, and now a national park. Itโs open daily except for US ThanksGiving and Christmas Day. If you have a national parks pass (US) then itโs free!
Itโs not a massive sprawl but is perfectly positioned next to the water and from upper sea walls, you get amazing views. This is a hands on experience and younger kids will love it too! Quite fascinating to learn that this fort was one of 9 built on this exact site, the first one back in 1565!
And the St Augustine Fun Continues..
4. Refresh at the town’s Distillery. After all this walking you may be quite thirsty, so pop into the St Augustine Distillery.
Focused on transforming Florida grown produce into a variety of vodka, gin, rum and bourbon, they offer a free (45 min) tour and samples. Always good to support a local business we say ๐
If you prefer wine, then head to the San Sebastiaฬn Winery in town, open daily from 10am-6pm.
5. Hike up the Lighthouse. To get to the top of St Augustine Lighthouse will take 219 steps but it is so worth it. On your way you will see a few exhibits and there is also a keepers house to check out. Itโs also open at night for a Ghost Tour!
6. Photograph Magnolia Avenue! You will pass this on your tours but we suggest going back early in the morning when itโs quieter to walk this absolutely gorgeous canopy street.
There are a couple of cafes here where you can enjoy breakfast! While you’re here, you can visit Ponce de Leon’s Fountain of Youth Archaeological Park which dates back to the 1500s. The spring purported to be the Fountain of Youth can be found in the park so go and splash your face – what harm can it do?
St Augustine Beaches And Rooftop Bars
7. Head to a rooftop bar or restaurant where you can sip as the sun sets! We enjoyed a cocktail at River & Fort. Also check out Harryโs which offers New Orleans style of food or Castillo within the Renaissance Hotel.
8. Soak up Florida’s rays at St Augustine Beaches which offer over 40 miles of options for getting near the water. You can simply park up and soak up the rays, bring the pup to some and even pack a picnic and come by horseback. Use the Augustine Florida Beach Guide to decide which ones work for you!
2024 Events to Check Out
March – Celtic Music & Heritage Festival
May – St Augustine Food and Wine Festival
September – Sing Out Loud Festival. A free music festival that spans the month at many different venues.
November- end January Night of Lights Show. Imagine being surrounded by 3 million tiny lights illuminating the town during the holiday season!
Amelia Island
Why Vacation in St Amelia Island
To leave mainland hustle bustle behind and embrace fresh ocean air and gentle breezes as you walk along deserted beaches. Coming to Amelia Island is perfect if you’re looking for a relaxed, laid back small town with a very walkable Victorian style architectural historic center.
Also known as the Isle of 8 Flags, resulting from different bygone ruling countries, Amelia island has excellent independent restaurants. This stunning island also claims fame with the oldest bar in the USA. It’s a memorable destination for 2-3 days for couples with a romantic feel, especially as the sun sets. Families too will love the wild beaches and open spaces to run around and well just have fun hanging out together.
Getting to Amelia Island
Itโs very easy to combine a stay in Augustine with Amelia Island as the drive is only around 90 minutes between the two if you take the interstate I-95.
Otherwise, check out prices to fly into Jacksonville (the nearest airport). From here youโre only a 30 minutes drive away. Itโs possible to pre-book an Uber or taxi over to the island because once youโre there you donโt really need a car if you’re staying downtown. That said, Iโd recommend it for the flexibility to get around and see things beyond the historic center if your stay is more than a night or two.
Where to Stay on Amelia Island
For a small island there is a remarkable range of accommodation choices. We stayed at The Fairbanks House in the historic district which is a great location with ample parking. The front veranda is perfect for a leisurely breakfast and cocktail hour.
If you dream of being right on the beach in a resort with ocean views then the Ritz Carlton or Omni both offer incredible ‘resort’ facilities and are bookable through Booking.com. You might check their sites directly too for low season ‘specials’.
Fun Things to Do on Amelia Island
1. Take a boat ride to Georgia. Cross over the state line into Georgia or sail into sunset on a dinner cruise from downtown. Once aboard, look out to the sandy banks to spot wild horses on the beach in Cumberland Island (in Georgia). Itโs about a 3 hour tour. Head down to the marina to find out times and prices. If you have a special occasion, Amelia Adventures can organize private boat trips for all occasions.
2. Go horse-riding on Fernandina Beach at sunrise. We booked this for our stay with Happy Trails Horses who were friendly and helpful. Annoyingly we had to cancel due to bad weather (horses donโt like sand blowing into their eyes either but weโre set to go next visit). Also check out the gopher tortoises around the sand dunes. They are so entertaining to watch from the walkways around the beach.
Things to Do Around Town
3. Sample happy hour at Floridaโs oldest bar. The Palace Saloon was reportedly the last bar to close when prohibition was declared. Afterwards, enjoy dinner at one of the excellent restaurants all within walking distance of historic district inns and hotels. We enjoyed The Patio Amelia Island for lunch and would recommend Espana Restaurant or Arte Pizza but there are plenty to choose from.
4. Visit 1,400 acre Fort Clinch State Park. This is where you will find both history from civil war times as well as nature to explore. Open daily from 8-5pm (check seasonal hours), itโs a wonderful place to hike and picnic. Kids will love searching for sharks teeth!
5. Check out Artrageous Artwalk held on the second Saturday of each month. Local galleries come together to showcase a range of styles and it reflects a deep love of art across the island. You can also sign up for a range of art classes or experiences at the Island Art Association.
2024 Events to Check Out
Eat shrimp, celebrate shrimp and generally have a good time!
If you miss the festival you can still learn about the history of the island. As a leader in boat building, the Amelia Island region became the heart of US shrimping in times past. The locally built Amelia Island Shrimp Museum was created to preserve this important local part of Floridian history and is worth a short visit.
Held at the Omni Resort and now in its 8th year, chefs come together to challenge themselves in a range of cook-offs culminating in a final on the Saturday. Live Music, food and beach memories for all the family.
October – Foodies Culinary Weekend
Calling all Foodies. Book yourself this unique culinary 3 night weekend event at the historic Addison on Amelia Island Inn on the beach. Experience the best this region has to offer in cuisine with market tours, food boards and lots of great food all included in the total price of your stay.
Indialantic (Space Coast)
Why Vacation in Indialantic (Space Coast)
With over 70 miles of dune edged sandy beaches, you can simply look up and almost weekly now, spot a rocket launch! Being on the Atlantic, this is also a great surfing spot in Florida. Hang out in the fun filled Cocoa Beach resort just south of Port Canaveral.
From Port Canaveral, you can board a short cruise to The Bahamas, Caribbean and beyond.
And, include a โbucket listโ adventure to the Kennedy Space Center on Cape Canaveral. This is a full day for all ages and fascinating to reflect on how far our space adventures have come over the past decades.
Getting to Indialantic
Indialantic is less than 1 hourโs drive (35 miles) from Orlando. Being the theme park hub of the USA, Orlanda benefits from countless daily flights from around the world.
You can also fly in directly to Melbourne International Airport from the UK with TUI. Within the US, there are non-stop flights currently (2024) from Atlanta (Delta) and Charlotte (American) as well as Allegiant from Pittsburgh and Avelo from Connecticut.
Where to Stay in Indialantic
Where to Stay? Beach resorts dot the beach fronts and as always tend to be pricer. We stayed at the Raddisson most recently but honestly found it to be a bit dated. If youโre coming to see a rocket launch, then you might prefer to stay nearer to the Launch site. The Kennedy Space Center page has all the hotel recommendations you will need, including options at Cocoa Beach and Port Canaveral.
Fun Things to Do in Indialantic
Be an astronaut for a day! The Kennedy Space Center needs no introduction. Itโs a full on fun packed day out and even then you probably wonโt see it all. If you are planing to see a launch, download Space Launch Now App and you will be in the know down to the hour, minute and second as to when the next one is.
Take a surf lesson. The Atlantic Ocean brings some good wave action to this coast and so where better to give it a go.
Chill on Cocoa Beach which is the hub of beach life on the coast line with ample options for renting your beach gear, grabbing lunch and refreshments.
Canaveral National Seashore. For nature lovers who prefer a quieter beach option, head to this oasis of Florida seaside.
You will need to pay to drive your car into this pristine area ($25 for 7 days of access). But itโs worth it as youโre close to special events like nesting turtles and rocket launches! There are absolutely no facilities so if you need it, bring it with you!
Spend a few hours at Archie Carr National Wildlife Refuge in Melbourne which is loved by loggerhead turtles. Its less crowded beaches are the most important nesting site in the USA for our turtle friends.
2025 Events to Check Out
August – The Space Coast Wing Battle at Wickham Park, Melbourne is as advertised. Burgers, fun and live music but here you get to taste burgers and then vote for the overall winner.
June – Viera Country Fest 2024 is a day of country music and a relatively new event. 2024 will be its 3rd year.
Kennedy Space Center offers daily events from meeting an astronaut to โ1st launch eventsโ. Having seen a launch in person, in 2023, itโs an incredible experience.
Islamorada, Florida Keys
Why Visit Islamorada
100 miles long, with 42 bridges and over 1500 islands, the Florida Keys is a paradise for marine life. Sparkling warm water, abundance of sea life, snorkeling and diving, sports fishing, endless biking, kayaking and SUP adventures to name but a few choices.
The islands are a stunningly beautiful string of pearls, offering a culture and way of life that is quite different from the mainland of the USA. At the end of the chain you are actually closer to Cuba than Miami.
The most southern town is Key West which effortlessly fuses its southern neighborโs culture with that of mainland southern USA charms. But don’t overlook Islamorada which is an oasis mid way down the keys and one of our favourites Florida small town destinations year after year!
Getting to Islamorada
To get to Islamorada from Miami airport, take Highway 1 and keep going south for just under 80 miles! Itโs a single highway with enforced speed limits, so pack your patience and just relax and enjoy the journey. If you keep going for just under 82 miles south of Islamorada you will hit Key West, the most Southern City in continental USA.
Islamorada has a renowned reputation as the world capital of sports fishing but look beyond โtight linesโ fishing culture and you’ll discover a โkick backโ coastal destination! From Key West, you can discover more remote islands like Dry Tortugas (although you will need to get there by boat or fly!) and book this adventure well in advance.
Key Largo and Islamorada are famed for sport fishing and beach edge resorts! Key Largo (an hour or so from Miami) boasts an underwater sea park and great reputation for diving. Along the route, you can discover some great National Parks too.
Where to Stay in Islamorada
If you want to splurge for a few days, head to the stunning Cheeca Lodge in Islamorada.
If you’re traveling as larger groups where you want more shared social time, opt for VBRO/Air B&B options. There’s plenty. But for a romantic getaway, I donโt think you canโt beat a waterfront resort anywhere in the keys.
Do shop around using Booking.com or Expedia.com for best prices. Also contact hotels directly as you might be able to get a better deal this way. We’ve increasingly found that resort hotels are adding โresort feesโ that can really jack up your total price!
For me, location is more important. If youโre on a tighter budget, think about whether you will actually use all a resort’s facilities. Some of the more ‘traditional’ Keys hotels and inns are actually great value and often in prime locations. Walk the beach vs heading to a hotel gym ๐
Fun Things to Do Islamorada
Go deep sea fishing! Head to Bud and Maryโs on Islamorada and with their decades of experience they will set you up. Or a few miles away in Key Largo, here is the Google Maps Link to Captain Bennie of Play Baby Charters.
We have booked trips with both and highly recommend them. Head out to the deeper waters to find that big catch. You can even eat your daily catch! Bring your prize from the day back to many of the restaurants and/or resorts and they will grill it up for you for dinner.
Dive or snorkel in John Pennekamp Coral Reef State Park, on Key Largo, which contains large living coral formations. It is the first undersea park in the USA.
Book a day trip from Key West to Dry Tortugas National Park on the Freedom Ferry that departs from Key West around 7.30am daily . If you want to camp here overnight, you need to plan 9-12 months ahead and reserve your spot. It is a 70 mile journey (each way) and takes around 2 1/2 hours. All the details can be found in the Key West Tours website.
Cycle part of or all of the Overseas Heritage Trail – 90 miles that crosses over island bridges and has a 20 mile trail around Key Largo.
Relax by the water or try kayaking, SUP, swimming in the warm waters of the Gulf of Mexico.
2024 Events to Check Out
There are a number of fishing tournaments and sailing regattas in Key Largo, Islamorada and across the Florida Keys islands which are fun offshore and on the beach!
If you are a fan of country music and are planning a trip in September, maybe keep going to Key West. It’s Always 5 O’Clock in Key West.
Captiva Island
Why Vacation in Captiva?
The island of Captiva is tucked away off the mainland 3 miles from Fort Myers and adjacent to Sanibel Island. This region was hit hard by Hurricane Ian in 2022, and rebuilding continues apace.
These islands remain a beautiful part of West Florida & USA and are a little undiscovered (for now!). Captiva and Sanibel are where to come for a laid-back, quieter Florida small town trip, where you can walk less busy beaches and go shelling to your heartโs content.
Walk a few paces and you can sit with a sundowner and just let nature do the rest! There’s miles of cycling trails through nature preserves if you want more energetic pursuits.
Getting to Captiva
Southwest Florida (Fort Myers) is the nearest airport with a pretty good network of services from around the US. From here, it is about a 1 hour drive to Captiva across the Sanibel Causeway. Fort Myers has a good summary of airport transfer options if you don’t plan to rent a car.
A Fun Fact to note if you’re checking out Captiva on the map. North Captiva is separated from Captiva (due to a hurricane years ago) and is only accessible by boat. But that’s the fun of being here!
If youโre coming from overseas, look for connections into Fort Myers. Otherwise fly either to Miami or Tampa and drive here. Itโs 160 miles from Miami and 126 miles from Tampa.
Where to Stay in Captiva
We suggest you check out Captiva-Sanibel local chamber of commerce site for options from rentals to hotels.
This community of around 20-25 houses share a pool, tennis court and from here itโs an easy access to the mini town center. Back on the mainland, you have more choices including resorts like the Sanibel Marriott which are great for families with plenty of facilities, like 4 swimming pools, for the kiddies.
Fun Things to Do in Captiva
1. Toes in the Sand Sunsets. Experience a fiery red west coast sunset on a secluded beach. Or just watch the sun float up as you sip that morning coffee with water lapping gently around your feet.
2. Go shelling at Bowman Beach. The coastline here is so productive with beautiful shells that it is a dream for those of us who enjoy strolling along the beach and picking them up. Use this Captiva Shelling Guide for tips on where to go and what to look for. Just remember not to collect anything still living!
3. Visit Edison Ford Estates. Head into Fort Myers and visit the 20 acres that makes up Edison Ford Winter Estates From a fascinating laboratory collection to the family summer houses, there is plenty to enjoy for an afternoon at this National Historic Site which has welcomed visitors since 1947. This area also has plenty of restaurants to enjoy around the River Walk afterwards.
Stay Active in Captiva
4. Hire a fishing charter. After youโve caught your quota, tie up and have lunch at a local restaurant. Often dolphins and turtles will be swimming around you! Capt Jimmy of Sanibel Captiva Fishing comes with the best of recommendations with decades of knowledge about the best fishing spots around the bays of these captivating islands.
5. Cycle from Captiva to Sanibel through JN Ding Darling State Park. Open daily (9am-4pm) but note some parts are closed Fridays. This is a paradise for bird lovers with over 200 species to look out for, including White Pelicans. It’s also a great space to kayak around protected mangroves with routes for all levels. (Check opening hours as post hurricane work is ongoing within the reserve).
6. Eat dinner while you soak in sunsets and/or ocean views. The Mucky Duck Pub is perfect for sundowners and has ample indoor seating but pre-book as it’s deservedly popular.
Crows Nest Steakhouse Restaurant boasts sunset views from an elevated position within the Shipyard Restaurant at โTween Waters Island Resort. The Green Flash Restaurant has been upgraded and offers a lunch and dinner menu, as well as hosting bigger celebrations including weddings.
2025 Events to Check Out
Events here tend to be local and advertised via the local chamber of commerce or in hotels, local businesses or on-line. As the islands rapidly recover more infrastructure, more events will return.
We like to think coming here is more a choice for nature and hidden beaches rather than lots of entertainment. Local restaurants like the Mucky Duck or Crows Nest will often have local bands playing.
Small Town Florida Itineraries
There are so many itinerary options to blend visiting Florida’s unique small towns with global heavyweight vacation spots. These are a few ideas to get your creative travel planning going.
Miami | Islamorada
Fly to Miami
2-3 nights South Beach
Hire a car and drive south
2-3 nights in Key Largo or Islamorada
Return to Miami for final night
Tampa | Captiva | Fort Myers
Fly to Tampa/ St Peterburg.
3-4 nights Tampa or St Peterburg
Drive south to Fort Myers
3-4 nights on Captiva Island
Note: Fly directly to Fort Myers and do the trip in reverse
Orlando | Indialantic | St Augustine or Amelia Island
Fly to Orlando
2-3 nights in Kissimmee ( Disney)
3 nights – Hire a car and drive to Melbourne or Cocoa Beach.
Drive to Space Coast (visit Nasa & a launch!) then carry on to St Augustine or Amelia Island (or both!)
2 nights St Augustine/Amelia Island
Wrap Up – Exploring Florida’s Small Towns
Every one of Florida’s small towns are unique with personalities that offer experiences beyond mass tourism. Other great destinations near where we live and that we always love to spend time in are:
Sarasota is a small town on Florida’s west coast where we hang out for most of the year. It’s the gateway to the white beaches of Siesta Key and known for its arts, museums, food and restaurants.
A fabulous guide to a day out, drive the coastal route from Siesta Key (Sarasota) to Anna Maria Island.
Living most of the year on Siesta Key, Florida we know what kids love when visiting Florida’s award winning beach island. Use our Affordable Things to Do with Kids on Siesta Key, Florida and take out the stress of planing their next stay.
We hope this post inspires ideas for venturing beyond big tourist cities in Florida and helps you discover new favourite beaches and sunset spots!
