What do Tampa and Miami have in common? Besides some of the best Cuban Sandwiches in the Sunshine State, they are both anchor cities of Florida’s Highway 41. This iconic road, also known as the Tamiami Trail, takes travelers through a unique landscape and thousands of years of history.
Come on along as we hit “The Trail” to explore some of the top landmarks of southwest Florida.
Florida’s Everglades are more than just pythons, alligators, and swamp. In fact, the Everglades is not a swamp at all. This vast ecosystem is actually a very wide, slow-moving river. Years of development and drainage have shifted the flow of this precious resource, however, generations of activists have succeeded in preserving portions of the “River of Grass.”
Just 45 minutes from Naples, this 1.5 million (yes, million) acre preserve is the largest wilderness area east of the Mississippi River. This national park, established in 1934, protects the southern twenty percent of the original Everglades, now an endangered ecosystem.
The park’s Gulf Coast Visitor Center is one of three access points to the Park. Located in the aptly named Everglades City (815 Oyster Bar Lane), this humble outpost serves as the gateway to the Ten Thousand Islands mangrove system. If you aren’t traveling with your own boat, contact park rangers in advance to get recommendations for experienced boat captains, or kayak guides to take you through this region.
Start planning your visit to Everglades National Park here.
20200 Tamiami Trail, Naples
Stop to pay homage to the engineers and workers who made your road trip possible. Collier-Seminole State Park houses the last remaining Bay City Walking dredge used to build the Tamiami Trail. This ingenious piece of equipment was built in 1924 to safely simplify the process of creating a roadway through the wetlands of the Everglades.
This 7,721-acre state park offers a variety of activities for a great day trip. Stretch your legs along one of the trails, or take a guided eco tour. Canoe rentals are available, or drop your own kayak in at the Blackwater River launch.
To plan your Collier-Seminole State Park visit click here.
Arguably a hidden Florida gem, this region along the southwest coast, where the state seems to end, actually continues out into the Gulf. Made up of small islands and keys seemingly floating out in the Gulf and various bays, is connected by causeways and quiet back roads. Known as the Paradise, this unique region is home to some of southwest Florida’s top landmarks.
This laid-back island is the perfect spot to relax after your Everglades adventures. Stop for lunch at one of the charming, casual restaurants on the water or “in town.” Then allow some time to explore this historic, pioneer town, once the Collier County Seat. There’s are several interesting landmarks packed into Everglades City’s 1.2 miles.
A visit to the Museum of the Everglades (105 West Broadway), located in the historic Everglades Laundry building, provides an interesting overview of the area. High quality exhibits and brief videos about the area make this stop worthwhile. While admission is free, donations are encouraged.
For a unique and fun way to enjoy the scenery, join an airboat tour. There are several operators on the northern edge of the island, off Collier Avenue.
Insider Tip: If you’re visiting from October 15-May 15 you’re in stone crab season. Stop by one of the local crabbers to get fresh-from-the Gulf stonies.
You’ve come this far – may as well keep on going! Just south of Everglades City, down Copeland Drive, is the community of Chokoloskee (chuck-a-luss-kee). This island was home to members of the native Calusa tribe, and their ancestors before them, for nearly 2,000 years. Although European settlers began arriving in the 1870s, a causeway to the mainland was not built until 1956!
For a glimpse of old Florida life, visit Smallwood’s Store (at the end of Marnie Street). This historic trading post is till operated by descendants of Chokoloskee post master Ted Smallwood. The landmark structure now houses a museum and giftshop. Occasionally they will feature public events including book signings for authors with a Florida connection.
Insider Tip: There is a nominal fee to enter the museum. It is worth the price of admission to walk to the back of the building and check out the amazing view and feel the “natural air conditioning.” The building is elevated on stilts and is not ADA accessible.
Just three miles east of State Road 29 is one of the smallest, yet notable, of southwest Florida’s top landmarks. Here you will find the smallest post office building in the U.S.A. located at 38000 Tamiami Trail East. When the original 1920s post office burnt down in 1953, locals replaced it with an old storage shed which still stands today.
Stop by during collection hours to say hello to the post master, purchase stamps, or even a postcard (yes, people still do that!), or just grab a quick selfie. Give a call at 239-695-2099 for operating hours.
State Road 92 at Goodland Drive
A slight detour on to State Road 92 will take you south to the historic fishing village of Goodland. A quick tour of this laid-back 222-acre community offers a glimpse into simpler days. Be sure to go slow — traffic is light, and town cats and dogs often nap right in the middle of the sunny streets.
During summer many fishing charters and tours close-down. However, from October to June this is a great place to begin your fishing back water adventures. When back on land enjoy a meal at one of the long-time family restaurants (most close during summer).
It’s not all slow-going on Goodland. The sleepy town comes alive on Sundays (fall-spring) when hundreds of locals and visitors come to hang out at Stan’s Idle Hour bar & grill ( 221 Goodland Drive) with their landmark buzzards.
Get the goods on Goodland here.
Marco Island is an island of upscale shops and restaurants, high rise condos and beautiful mansions with manicured lawns. However, history is never far away in Florida. Nestled within this affluent community are two historic landmarks that tell the story of this land’s earliest occupants.
1831 Addison Court
Hope in the car or on your bike and head to this small natural area in the midst of million-dollar mansions. A short trail takes visitors through this elevated area, Otter Mound, the highest point on Marco Island. This area has been home to the indigenous Calusa Indians, and later the thriving Caxambas Village, a fishing camp, and a clam processing plant. Now, despite surrounding development, it is the habitat of protected gopher tortoises and burrowing owls (don’t be surprised if you see a friendly snake or two!).
Visitors can still see the shell walls Mr. Ernest Otter constructed around his mound property during the 1940s and 50s. Later owners worked with preservationists and archaeologists to protect the land for generations to come. For detailed directions and information on Otter Mound click here.
Highland Point at Blue Hill Creek Drive
Once known as Horr’s Island, for the retired Civil War Captain who homesteaded it, Key Marco is now an exclusive community. History lovers can request a visitor pass to enter the gated neighborhood (be prepared to show photo ID). Drive past grand homes that stand in what was a bustling town in the 19th Century. You will need to use your imagination to recreate the scene, as the only remnant of the bygone era are the ruins of Captain Horr’s former home.
The northern shores of the Paradise Coast are home to beautiful white sand beaches, and historic charm. This waterfront community has something for visitors of diverse interests and ages.
LGBT Insight: Naples annual Pride celebration takes place each June at Cambier Park in Downtown Naples. Learn more about this event and the Naples LGBT community here.
25 12th Avenue South
Explore the upscale shops and eateries of 12th Avenue South, then head west to the Naples Pier. Enjoy a stroll out on wooden pier that’s been a Naples landmark since 1889. There is no charge to visit the pier which was completely reconstructed in 2015 to extend 1,000 feet over the Gulf.
Enjoy watching the many anglers, or even join in the fishing fun with rental equipment available at the pier’s bait shop. If catching a sunset is more your style, the end of the pier is a perfect spot for it.
Insider Tip: Bring quarters or a credit card for the ample pay-to-park options within walking distance of the pier.
Join a walking tour of the Naples historic district with volunteer guides from the Naples Historical Society (137 12th Avenue South). Visit the charming Palm Cottage House Museum, built in 1895 and now Naples oldest remaining residence and iconic landmark.
Plant lovers will enjoy exploring the Norris Gardens at the Palm Cottage. Bring the family – visitors of all ages can participate in a variety of educational programs throughout the year. To plan your visit and to learn more about Naples History click here.
1200 5th Avenue South
On the east side of town, on the site of an old marina, assembled from sturdy historic structures, is the charming Tin City. Nestled along the waterfront, this laid-back complex has been home to locally-owned art studios and shops since the 1970s. There are also two waterfront restaurants where you can relax, enjoy a beverage, and take in views of boats on the Intracoastal.
3800 Corkscrew Road, Estero
Step into history at Koreshan State Historic Site along the Estero River. This remarkable time-capsule was established in 1894 by Cyrus Teed the founder of a the Koreshan religious sect.
Seeking a “New Jerusalem” for his 300 followers, he moved the group from the Midwest to the shores of the Estero River. Here, among the palms, and azaleas, the settlers built a village. Eleven of the original buildings, including a residences, a meeting hall, a blacksmith shop, and kitchen, still stand today.
In 1961, when their membership had gotten down to just four members, they donated the settlement to the State. Now visitors can explore freely, or with a park ranger, to learn how these pioneering Floridians made life work in the challenging southwest Florida environment (before air conditioning!).
To plan your visit to this fascinating landmark click here.
1215 Roberts Avenue, Immokalee
Not many people associate Florida with cattle. However, nearly half of Florida’s agricultural land is involved in the cattle industry!
Just 44 scenic miles east of Naples is Roberts Ranch in the historic community of Immokalee (Seminole for “my home”). This 13-acre ranch was settled by cattleman Robert Roberts in the late 1890s. Today, the longest-operating ranch in south Florida, is a great place for visitors to see what life was like for early Florida pioneers.
This family-friendly historic site contains fifteen of the original Roberts family buildings, including their home and barns. Exhibits and public programs bring history to life at this top southwest Florida landmark. Click here to plan your visit.
Fort Myers offers a look into Florida’s ancient past, as well as its role in shaping our modern world.
On the barrier island of Estero, at the edge of a residential neighborhood, sits the Historic Mound House and archaeological site. Take in beautiful views of the Intracoastal Waterway, sit and enjoy the breeze from under massive shade trees.
Learn about Florida’s past inside the Mound House Museum, with interactive exhibits for visitors of all ages.
Dig Deep into the area’s history by going inside an ancient Calusa Indian mound for a presentation on southwest Florida archaeology.
2350 McGregor Boulevard, Fort Myers
Explore the neighboring compounds of inventors Henry Ford and Thomas Edison. Imagine a day in the life of these two great inventors as you stroll the beautiful grounds, step into their homes, and visit their workshops. Learn about the advances the two made in technology and science amidst this tropical paradise.
Plant lovers will be amazed by the botanical gardens, including some plants that remain from Edison’s time and experiments. Car buffs will enjoy the historic car collection housed on site.
Insider Tip: There are a few different tour packages to choose from. Check out all the options to decide what’s best for you and your traveling companions.
112 Periwinkle Way, Sanibel
Sanibel Lighthouse has literally been serving as a one of southwest Florida’s top landmarks since 1884! This historic site is a perfect getaway from the bustle of the mainland. Visitors can admire the 98-foot tall lighthouse from the ground, but the exterior stairway to the top is not accessible.
The views from this park, which features swimming, great shelling, and a nice fishing pier, make it a worthwhile destination.
Insider Tip: Pay parking fills up quickly, especially on weekends. Arrive early to get a spot at this landmark beach. Start planning your visit here.
Pine Island Road from Veran’s Parkway to Little Pine Island
Head west to the laid-back fishing village of Matlacha (pronounced Mat-la-shay). This small sliver of Florida is home to a once-thriving fishing industry.
Matlacha is a now a haven for artisans and craftspeople. Be sure to check out some of the quaint and quirky shops that line the main drag in brightly painted vintage buildings.
Seafood lovers will appreciate the many restaurants offering truly fresh catches, including coveted pink shrimp and mullet caught just off the Gulf coast.
Visit Bat House Park (4445 Pine Island Road) around dusk for a chance to see the resident bats head out for dinner. The park is also a great spot for watching sunsets or fishing (bring your own equipment). Even the public restroom here is a landmark! The structure was repurposed from the Snook Inn restaurant that sat on the site for generations.
Learn more about this quaint community here.
1200 West Retta Esplanade, Punta Gorda
Once the location of packing houses for the region’s thriving fishing industry, now Fishermen’s Village serves-up delicious meals, drinks, and family-friendly entertainment. Come for the day, or stay for the week! The village combines historic buildings, with new a revamped marina, and vacation rental villas.
Nestled on the shore of the Peace River, visitors can relax and enjoy the ever changing view as boats go by and bridges glisten in the distance. To plan your time at Fishermen’s Village click here.
Take a break from the Interstates to visit the off-the-beaten path destinations. Don’t miss these sometimes overlooked top landmarks of southwest Florida.
Travelers in southwest Florida that follow this mantra will often find their journey is the destination. Click here to check out other great locations.
**Disclaimer: There is a good chance that this post contains affiliate or sponsor links. If you make a purchase through them, we may receive a small commission at no extra cost to you (for which we are extremely grateful).
Also, while we do our best to highlight LGBTQ-friendly destinations and businesses, info provided is based solely on personal experience and recommendations by community partners. We hope that nobody experiences discrimination or homophobia while visiting Florida and beyond, but we make no guarantees. Please inform us if you experience discrimination or homophobia while visiting any destination so we can make updates to our recommendations.
Jacqui May has a background in nonprofit project management and writing. She is currently a freelance consultant, Florida Supreme Court Certified Family Mediator, and writer. She enjoys working with diverse organizations to connect them with resources, and make a difference in the community. Jacqui is a straight ally and several of her close family and friends identify as lgbtq. She volunteers with organizations serving veterans, developmentally disabled adults, the homeless, and low-income community members. Originally from New York City, she is a long-time Floridian and has extensively explored the Sunshine State. Jacqui loves history and believes that everyone has a story worth listening to.
