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Home to the best Southwest Florida offers for nature and history lovers, this Everglades vacation guide lists the best things to see and do in Everglades City, Chokoloskee, and Ochopee. These small towns located off Tamiami Trail, almost equidistant from the Miami and Naples International Airports, are worth exploring. Keep scrolling for all our recommendations!

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Everglades Vacation Guide featured by top US travel blogger, The Common Traveler: Image of white building with palm trees, City Hall in Everglades City, Florida, USA

Everglades Vacation:
Best Things to See and Do in Everglades City

As the former capital of Collier County, Everglades City enjoys some historic buildings. The “Stone Crab Capital of the World” deceptively appears as a sleepy fishing village. A taste of Old Florida, Everglades City, was the first town established in Collier County, back in 1923 when the capital moved to Naples in 1962. 

Appreciate the Beauty of City Hall

102 Copeland Avenue N./102 Broadway Avenue E

It formerly served as the Collier County Courthouse until the capital moved to Naples in 1962. Listed on the National Register of Historic Places, this two-story, classical-revival style building was built in 1926. Today it serves the local population as the City Hall with city services.

Admire the Everglades Community Church

101 S. Copeland Avenue

This beautiful church with the red door captivates the idea of a small community non-denominational house of worship. While the church was established in 1926 on land donated by Barron Collier, this building was not completed until 1940. 

Gateway to the Everglades and Ten Thousand Islands

Gulf Coast Visitors’ Center 

815 Oyster Bar Lane

The temporary building at this location replaces the one destroyed by Hurricane Irma in 2017, so don’t be deceived by its appearance. This non-descript building belies all the information available to explorers of the Everglades and the Ten Thousand Islands in particular. 

This national wildlife refuge, maintained under the U.S. Fish & Wildlife Service auspices, is home to unique species. Don’t miss a kayak exploration among the mangroves – the Refuge contains three different species. You may even spot manatees on your quest!

Paddle the Wilderness Waterway

Expert paddlers interested in a 99-mile trip through the Ten Thousand Islands’ natural beauty will want to sign up for this eight-day journey. Campsites are available on chickees (raised platforms) along the trail. This trip starts at the Gulf Coast Visitors Center and ends at Flamingo Everglades National Park. This is one of the best places in Florida to kayak.

PRO TIP: Don’t paddle against the tide unless you want to be completely miserable! Purchase a nautical and tide chart from NOAA or at the Gulf Coast Visitors Center.

Watch the Sunset From the Ernest Hamilton Observation Tower

875 Copeland Avenue

This wooden structure provides a platform 75-feet high in the middle of nowhere. Pay the $2 fee for a spectacular spot to watch the sunset.

Stay or Eat at The Rod & Gun Club

Located on the Barron River, Banker Barron Collier, for whom the county is named, bought this property in 1922. Hosting dignitaries such as Presidents Roosevelt, Truman, Hoover, and Nixon and celebrities, including actors ranging from Sean Connery, Sally Fields, and many more. The Club also served as the setting for “Just Cause” and “Gone Fishing.” 

Learn About Local History at the Museum of the Everglades

105 W. Broadway

Initially serving as a laundry facility that opened in 1927, the Museum of the Everglades celebrates this former county capital. The building is included on the National Register of Historic Places and restored to its original glory. 

Enjoy Delicious Stone Crabs

If you’re visiting the area from October 15 to May 15, you’ve got to try the stone crabs that have given this town its reputation as the Stone Crab Capital of the World. 

Attend the Everglades Seafood Festival

102 Copeland Avenue

Held annually the second weekend in February in the area in front of City Hall, this free event serves as a fundraiser for the community. The event features carnival rides, fabulous seafood, craft booths, and live music. If you’re in the area during February, come to have some fun and serve the community simultaneously.

Everglades Vacation Guide featured by top US travel blogger, The Common Traveler: . Image of red building - Smallwood Store in Chokoloskee, Florida

Everglades Vacation:
Best Things to See and Do in Chokoloskee

Connected to Everglades City by a bridge in 1956, Chokoloskee is a sleepy fishing town where the pace just slows. Chokoloskee makes a great home base for those who want to experience the best of small boat fishing, but it is worth a stop for the rest of us too.

Visit the Smallwood Store

360 Mamie Street

Located at what feels like the end of the road, because it is the southernmost point on Florida’s west coast, the Smallwood Store opened its doors in 1906. Listed on the National Register of Historic Places, the building currently houses a museum dedicated to preserving the history of this secluded area and its people. This trading post served as the heart of the community for the 10,000 Islands – a bar and community meeting place – and the local store where goods from Cuba and the local Seminole population were available for purchase. 

Fans of ghost stories will want to hear about the many incidents of spooky stories — though apparently, those beings preferred to do their shopping at night, making a daytime visit perfectly safe!

It has survived seven hurricanes – so let’s keep it going!

Chokoloskee Bay

Nature fans can enjoy paddling and fishing in this wide, ten-mile long bay. Bring your binoculars if you’re into spotting birds! Several providers can arrange boat tours. Not into fishing? Book a tour that takes you into the sunset to capture beautiful nature photographs.

Eat at Havana Cafe

191 Smallwood Drive

Featuring a Cuban-American menu, the Havana Cafe has been called one of the best-kept secrets of Southwest Florida. Serving breakfast, lunch, and dinner, the Havana Cafe draws on its access to fresh seafood while giving meals a Cuban twist of flavor. 

Everglades Vacation Guide featured by top US travel blogger, The Common Traveler: Image of the smallest post office in Ochopee, Florida, USA.

Everglades Vacation:
Best Things to See and Do in Ochopee

Beginning as a one-family tomato farm in the early 1920s, Ochopee is an easy stop while traveling the Miami-Napes corridor on Alligator Alley (US 41). 

Visit the Smallest Post Office

38000 Tamiami Trail East

Initially serving as the storage shed for irrigation pipes, this tiny building became the smallest active post office measuring 7ft x 8ft. It allows for only one postal worker at a time. Considering how often they’re asked to pose for photos, it is a good thing that the postal workers here have a sunny disposition (pun intended!). This location serves as the mail center for the Seminole and Miccosukee Indians within the neighboring three-county area.

PRO TIP: Buy a postcard and mail it to your friends from this unique location, including those who collect unusual postmarks.

Hunt for the Skunk Ape

Skunk Ape Research Headquarters

40904 Tamiami Trail East

What is a Skunk Ape? The Everglades’ very own Big Foot relative! The creature is named for its rotting smell, reminiscent of a skunk, resembling an orangutan or gorilla and walking on two legs. Created and headed by Dave Shealy, first encountering a Skunk Ape at the age of 10, Shealy studies what he estimates are about 7-9 Skunk Apes living in the area. While Shealy is hesitant to talk to visitors who may belittle his belief in these creatures, the Headquarters is a unique place to visit. Purchase a T-shirt to enlighten your friends with knowledge of these curious beings. 

Spot Alligators at Big Cypress National Preserve

33100 Tamiami Trail

The nation’s first national preserve is probably one of the best places for alligator watching in the area! The boardwalk at the Oasis visitor’s center is one of the best places to spot them. Rangers from the National Parks Service lead groups into less-accessible areas while teaching you about the region’s unique flora and fauna. Fun fact: The size of the preserve is bigger than the state of Rhode Island. Outdoor lovers will thoroughly enjoy exploring the Everglades from here. With eight campsites, you can even enjoy an outdoor experience here.

PRO TIP: Stop by the Oasis visitor’s center and pick up a map of hiking trails. 

Stop for lunch at Joanie’s Blue Crab Cafe

39395 Tamiami Trail East

If you’re looking for a taste of blue crab, a cold beer, and a great place to chill, Joanie’s is it. Don’t miss the crab cakes! The interior walls are decorated with customers’ items – fun to walk around and look at while waiting for your meal. Not hungry yet? Grab a beer, chill on the porch, or admire the decor. 

Discover the Everglades on Wooten’s Everglades Airboat Tours

32330 Tamiami Trail East

Wooten’s is a popular destination if you’ve been looking for either a land or airboat tour. Offering private airboat tours, Wooten’s is an excellent place to start your Everglades adventure.

Where to Stay During your Everglades Vacation

Most people drive through the Everglades, frequently electing to stay in Naples or other SW Florida towns, or Miami to the east. But if you’d like to spend the night and enjoy slow travel through the area to discover all it has to offer, consider these options:

Everglades City Motel – Everglades Adventure Inn – Everglades City:

Perfect for travelers trailing their boats, this motel offers its guests free bikes to explore the town and discounts to nearby businesses.

Ivey House Everglades Adventures Hotel – Everglades City:

This bed and breakfast offers amenities like a pool and free bikes for its guests. Located within walking distance of the Museum of the Everglades, the staff also hosts Everglades tours and has kayaks and canoes available for rent.

Everglades Chickee Cottage and Bungalow – Ochopee:

For those looking for an eco-friendly experience, book a night in one of these native-American built lodges. Best suited for the traveler who will be happy with more spartan accommodations, though free WiFi is provided.

Everglades Vacation Guide featured by top US travel blogger, The Common Traveler:  Image of tree stump on shores of Chokoloskee Bay, Florida, USA

Itinerary for Your Everglades Vacation

Coming from Naples (west coast), I would recommend hitting, in order: Ochopee, Chokoloskee, and Everglades City. The order remains the same if coming from Miami (east coast).

Travel east on US 41 (Tamiami Trail) as if going to Miami. If coming from Miami, you’ll hit Ochopee first and would need to complete the Ochopee stops in reverse order until arriving at SR 29.

In Ochopee (approximately 34 miles east of Naples), visit Wooten’s Everglades Airboats, the Big Cypress Swamp Welcome Center, and the post office (this spot is about 3 miles east of the intersection of US 41 and SR 29). Take a break at Joanie’s Blue Crab Cafe. Wind up your visit at the Skunk Ape Research Headquarters. Trace your route back on US 41 heading west.

At the intersection of SR 29, turn left and head towards Everglades City. Follow the road through Everglades City and the signs into Chokoloskie. 

In Chokoloskee, start at the end of the island by visiting the Smallwood Store and then working your way back. Enjoy a meal at Havana Cafe. Continue back to Everglades City.

In Everglades City, park near the City Hall and walk to admire and read the historic placards at the City Hall, the Everglades Community Hall, and the Museum of the Everglades. Watch the sunset from the Ernest Hamilton Observation Tower and eat dinner at the Rod & Gun Club.

Take SR 29 all the way to I-75 for the fastest route home.

This Everglades vacation guide makes a great day trip from Naples, Fort Myers, Marco Island, or Miami!

Looking for more Southwest Florida content? Check out these posts:

Happy travels!
Annick, The Common Traveler

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Everglades Vacation Guide featured by top US travel blogger, The Common Traveler. Everything you need to know to plan a day trip (or longer!) to Everglades City, Chokoloskee, and Ochopee: where to go, what to see, where to eat, as well as odd attractions in the area. #swfl #everglades #florida #evergladescity #ochopee #chokoloskee #naples #marcoisland #southwestflorida #10000islands