32 Essential Southwest Florida Experiences

Don't leave SWFL without checking these things off your bucket list. Each of these can be experienced in a day or less. Start planning!

1. Cape Romano Dome Home

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These alien looking buildings are a former residence being swallowed up by the Gulf of Mexico on Cape Romano. You can only get there by boat, but this guide can help you get there.

2. Naples Pier

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This iconic Naples landmark shows up in countless publications. Definitely not well hidden--thousands of tourists flock here every day. However, it's one of those things that you just have to stop by.

3. Naples Bay Water Shuttle

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It may not be your rich uncle's yacht, but the Naples Bay Water Shuttle is the best way to navigate downtown Naples and all of it's high-end areas. With stops at the City Dock, Bayfront, Tin City, and The Dock Restaurant, you'll quickly realize why so many rich people flock to Naples--and why you never will be able to. Did I mention it's only $5 to ride all day? Did I also mention they sell beer and wine onboard?

4. Downtown Ft. Myers Music Walk

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Downtown Ft. Myers is fast becoming a hotspot for culture, arts, and fun-seeking night owls alike. While all weekend nights are fun, the third Friday of every month brings out local music talent to bars, cafes, and street corners to showcase their skills. No matter what you're in to, you'll find something to tap your toes to.

5. Hickory Blvd

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Bonita Beach Road, Hickory Blvd, Estero Blvd, call it what you will. The ride from Doc's Beach House in Bonita Springs north to Ft. Myers Beach is a spectacular one. Luxurious beach front mansions lead to a series of bridges that give you a vantage point over some of the best beaches in the area.

6. Delnor Wiggins Pass State Park

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For my money ($8 to be precise), this is one of the best beaches in the country. Although the beach and the park can be crowded during peak times, it can also be blissfully empty during non peak times. Good fishing can be had at the pass, and few people are aware of the hard bottom reef in front of Parking Area 2. Add those to a all day beach bbq and that goes way beyond your typical beach day.

7. Corkscrew Swamp Sanctuary

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Spend an afternoon in the shadow of trees that started their lives before Ponce de Leon discovered "La Florida" (and was subsequently killed by the SWFL native Calusa Indians). Although they are no bristlecone pines, hanging with organisms more than 500 years old has a way of rearranging your perspective.

8. Sanibel

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Sanibel is world renowned for shelling, fishing, and other beach related activities. Locals, however, will tell you that everything is just a littler cooler on Sanibel--literally and figuratively. The laid back island lifestyle, stunning natural landscape, architecture, and white sand beach is unmatched by anything else around. Except, maybe, it's neighbor to the north.

9. Captiva

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For those looking to get REALLY far from the mainland, drive right through Sanibel and keep on going. The bridge at Blind Pass doesn't look like much, but it brings you to an ever smaller, more secluded, and possibly even more laid back island. Be sure to check out The Bubble Room when you're there.

10. Gulf Coast Town Center

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Shopping, movies, nightlife, and the buzz of a college campus combine to make Gulf Coast Town Center a one stop shop for many Southwest Floridians. GCTC provides a much needed nightlife boost to SWFL. Tapas, cigars, craft beer, martinis, or buckets of Bud Light can all be enjoyed (not necessarily in that order) before your mandatory late night hot dog.

11. Watson's Place

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20 miles from the nearest road and surrounded by dense Everglades brush, this day trip takes you deep into the wilderness to the former plantation of an alleged murderer killed by a mob of scared neighbors, Edgar Watson. It's definitely off the beaten path, so hire a guide or use this page to help plan your trip.

12. Keewaydin Canoe Races

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Keewaydin is one of the few places in Southwest Florida where you can pull up a boat and camp overnight. Located on a barrier island between South Naples and Marco Island, it's at least 3 miles from the nearest boat ramp. There is usually a crowd there on weekends, but by far the biggest party of the year is during the Canoe Races, the unofficial celebration of all of the tourists leaving. Don't expect to see any canoes racing, just lots of drunk people and cops coexisting.

13. Boca Grande Pass

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There's some debate as to what Florida's most popular gamefish is, but ask anybody in the spring lineup in Boca Grande Pass and the answer will be unanimous: tarpon. This world famous tarpon hotspot has boats lining up dozens deep to follow massive schools of massive fish around. It's not advisable to stroll up in your jon boat if you don't know what you're doing. Hire a guide and he/she will show you what all the fuss is about.

14. Gasparilla Island

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Gasparilla Island today has little trace of some of it's early inhabitants including Jose Gaspar, more commonly known as the pirate Gasparilla. Notably Southwest Florida historians would have you believe that the existence of Gasparilla the pirate was questionable at best, but it's way more fun to pretend that he did exist. Other actual pirates did exist and spent time on Gasparilla, but none with more fame. Pass the rum!

15. Dog Beach

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On a small island inside New Pass in Bonita Springs, dog lovers unite to let their furry friends run and play while they enjoy a classic SWFL sunset. Only at dog beach does this scene play itself out day after day, year after year. The small beach shrinks and grows with the tide, but the dogs don't seem to mind.

16. Mound Key

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Also in Estero Bay, Mound Key is the 2,000+ year old shell mound made over the previous millennium or two by the Calusa Indians. These original Southwest Floridians dominated from Tampa to the Everglades, and Mound Key was very likely their cultural center. Calusa means "fierce people", as evidenced by the mortal wound they inflicted on a gentleman by the name of Ponce de Leon. Perhaps you've heard of him.

17. Clam Pass

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At the southern end of North Naples is a hidden beach accessible only to those in the know. When you park your car in the lot, you won't see sand, chairs, or any other signs of the beach. In fact, you're still more than a half mile away. Half the fun, however, is the golf cart ride through the mangrove forest engulfed boardwalk. Upon reaching your destination, you're greeted with what you've been waiting for the whole time--a beautiful bar. Oh, there's a beach there too.

18. Everglades City

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The sleepy fishing village of Everglades City may have a sordid past, but the barely 200 permanent residents have the gateway to the Everglades in their backyard, so that pretty much forgives all of it. Plus, the Everglades Seafood Festival descends on Everglades City once a year as well, and plenty of seafood, beer, and country music make everything OK.

19. Smallwood's Store in Chokoloskee

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Ted Smallwood and his family have been in fixture in Southwest Florida for as long as Americans have. The stories that building holds has led to novels, history books, and many a campfire story. It's had its struggles to stay open over the last 150 years and is still facing opposition, so get there soon before it's too late.

20. Lover's Key

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Pirates Jack Rackham and Anne Bonnay ran away from their past in Ireland and sailed into the Caribbean and up the coast of Florida. They spent a few days honeymooning on a small barrier island on the southwest coast. Today, we call this place Lover's Key. Lover's Key features one of the most spectacular beaches anywhere in the US, great fishing in the passes to the north and the south, and even miles of hiking and paddling trails loaded with awesome stuff to see.

21. Great Calusa Blueway

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This 190 mile paddling trail is not exactly a day trip. If you've been on the water in SWFL, chances are you've crossed paths with it before. However, very few have seen it all. There's no need to go in order. Pick any section no matter how short or long, get a kayak, and paddle on through. You'll see something you like.

22. Peace River Camping Trip

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Florida's second longest river spans the width of the state and dumps out into Charlotte Harbor. The Peace River Canoe Outpost makes it easy if you don't have the necessary equipment. When not drifting leisurely down the river, try your hand at some fossil hunting. The river is loaded with ancient sharks teeth from prehistoric days when most of Florida was underwater.

23. Jane's Scenic Drive

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Flanked by cypress swamps on either side, Jane's Scenic Drive takes you through the heart of an ecosystem that almost disappeared from South Florida. Fakahatchee Strand State Preserve has helped keep this part of Florida natural and beautiful, and there is no easier way to appreciate it than to drive through the heart of it. Thanks, Jane.

24. Big Cypress National Preserve

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Turner River Road and Wagon Wheel Road inject you into a wide open expanse of saw grass and cypress swamp, giving you a glimpse of what SWFL looked like long before the modern era. The Turner River itself has a legendary mangrove tunnel for the intrepid paddler. Offroading, hunting, camping, hiking, and paddling are just a few of the highlights of this virtually untouched wilderness.

25. Matlacha

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When driving west from Cape Coral to Pine Island along Pine Island road, don't blink. If you do, you may miss Matlacha (Mat-la-shay) all together. This tiny island fishing village is known for its colorful buildings, laid back locals, and abundance of island lifestyle. Fresh fish is always in style.

26. Everglades Airboat Ride

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While the Everglades has thousands of unique features. In order to see a lot of them quickly, you need to be in an airboat. Boats and swamp buggies can get you to some places, but there's nothing quite like skating across the surface of the water and land down a river of grass. There are dozens of airboat tour companies, so do some research, but they aren't hard to find as you drive east on Tamiami Trail.

27. Key West Express

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The Florida Keys is an experience in itself, but when in Southwest Florida few people realize that we are closer to Key West than Miami is. The Key West Express capitalized on this fact and build a large high speed catamaran to take you from Fort Myers Beach or from Marco Island straight into port in Key West. The trip takes a little more than 3 hours, but there is a comfortable cabin with on onboard bar. It's not free, but compared to the cost of driving there, getting a hotel, and driving back, there's not a huge price difference--except, of course, you don't have to drive.

28. Seminole Casino Immokalee

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There's a little bit of everything on this list, so why not add a little blackjack, poker, and slots? Seminole Casino in Immokalee is the only place for 100 miles where you can get your casino fix, so if you're looking for some late night high stakes poker, head east.

29. Rookery Bay

Rookery Bay National Estuarine Research Reserve is one of the world's last remaining undisturbed estuaries. Although it covers a huge area, the Evironmental Learning Center is a good place to start getting your education. From there, you can get involved in a guided kayak tour or boat tour to see the abundant wildlife up close. Everything from fishing, hiking, paddling, boating, bird watching can be done year round.

30. Cayo Costa

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Cayo Costa is a barrier island between Pine Island Sound and the Gulf of Mexico. What sets Cayo Costa apart is exactly that--the fact that it is apart from the mainland and far from any highrises, or vacation homes. It is one of the very few remaining strips of unsettled and unspoiled coastline in Southwest Florida. The only access is by boat or ferry, further isolating it from tourists and locals alike. Camp sites and primitive cabins are available.

31. Stan's in Goodland

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People come from miles around to show up to Stan's, especially on Sundays. It's not just because you have to--Goodland is a pretty well isolated place, but more so because there is an unmatched atmosphere at Stan's most any day of the week. Goodland has a quiet old fishing village feel. Drive up, boat up, or take the golf cart, and definitely don't miss the Buzzard Lope or the Mullet Festival.

32. Imperial River

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While the Estero River, Spring Creek, Mullock Creek, and Hendry Creek all empty into the Estero Bay, the aptly named Imperial River offers a grande experience in a few different ways. Traveling from the easternmost passable part east of I-75, you can literally watch a Florida timeline unfold in front of you. From ancient cypress trees to small river shacks to multi-million dollar mansions, the river takes you from old Florida to new beforing dumping you into Fish Trap Bay on your way to the Gulf of Mexico.