How to Spend Two Days in Everglades City and Chokoloskee

The Wizarding World of Harry Potter was magical. Tailgating with Tampa Bay Buccaneer fans was intense. But the best part of traveling around Florida was exploring the Everglades. Late November was a great time to be there. The weather was perfect and nature was teeming.

As we groggily emerged from a dingy Tampa hotel on the Monday after the football game, the three hour drive to Everglades City seemed like such a burden. But, the closer we got to Everglades City, the more the busyness, noise, and grime of the city melted away.

The drive from Tampa down I-75 is a mix of ocean vistas and riparian greenery. The real trick to driving through rural Florida is finding a radio station that isn’t trying to bring you to Jesus.

It was just getting dark by the time we arrived at our Airbnb. Rebecca was an excellent host and had provided us with a map of places to eat in town, and some of the other local attractions. She had plenty of reading material on the geography, plants, and wildlife in the area, too.

We chose a place to eat within walking distance, Island Cafe. It was full of weird alligator knick knacks and Christian paraphernalia. Which is fine. To each their own. You do you. Live and let live. Etc.

But, for a couple of lesbians in a small town, the Biblical decor and the belligerent drunk and the alligator skins on the wall all felt just a bit unsettling. Their food wasn’t very good either, so I can confidently recommend that you don’t eat there.

Like Salt Spring Island, these towns in the Evergaldes are small, so if you give yourself two days, you can leave with the feeling of a full experience. In fact, you will probably be ready to get back to civilization by the end of day two. Still, this is a great destination if you are interested in wildlife, birds, geography, or history.

Here is my recommended two day itinerary for Everglades City and Chokoloskee:

Day One
There are two distinct types of geography in this area which can more or less be be boiled down to salt water and fresh water. Day one is all about the salty sea air, marine wildlife, and killer Cuban style food. I like to have a simple oatmeal breakfast when I am planning to do something active in the morning, so I haven’t included breakfast in the itinerary. If you are staying in Everglades City, the day starts with a short, scenic drive to Chokoloskee.

  1. Coffee stop at Havana Cafe. As far as I could tell, this restaurant is the only one in Chokoloskee. If you have a sweet tooth like me, try the cafe con leche. Take a peek at the menu while you wait for your coffee, and get excited about the delicious lunch you’ll have later. You’re going to have to earn it, though.
  2. Three hour 10,000 Islands kayaking tour. We went with Shurr Adventures because we liked their website, photography, and tour options. Call me shallow, but those things matter to me. We departed from the Smallwood Store, navigating through oyster reefs and into the 10,000 Islands and Everglades National Park. We saw dozens of different species of birds, heard a manatee call, had dolphins swimming and playing alongside our kayaks, and learned about mangrove trees. It was hands down the most interesting kayak tour I have ever been on, and our guide was friendly, knowledgeable, and fun.
    Navigating through the oyster reefs and into the sheltered waters of the 10,000 Islands. The islands cover a vast area, but the water is only about waist deep throughout most of it.
    This is a mangrove seed. It can bob around in the water for years before settling on a sandy area and planting roots. Quite a cleverly adapted tree.

    We encountered a pelican party. Our invite must have gotten lost in the mail.
  3. Head back to Havana Cafe for lunch. After so much hard work, you deserve a cuban sandwich. A really good cuban sandwich on fresh baked bread. And maybe a cold beer to go with that. I love to return to restaurants, cafes, or bars that captivate me and gives me that feeling of rest and reflection after adventure. This is one of those places for me.
  4. Visit the Historic Smallwood Store Museum and Tigertail Gift Shop. This place is weird, in a good way. Chokoloskee has an odd history, complete with an entire town colluding on the murder of a local tyrant, and the folks here tell the stories really well. Their website allows you to take a virtual tour of the store, which is also a museum.  The building is not huge, so you’ll have some down time afterwards. Plenty of time to head back to wherever you are staying and clean the salt and sand off your body.
  5. Dinner in Everglades City at Camellia Street Grill. Camellia Street Grill is also filled with weird junk and knick knacks, but made us feel safe right away with a sign next to their menu declaring “Everyone Welcome.” This place is really neat, and the food is incredible. I wish I had taken a few pictures here. Imagine old bouys everywhere, an airstream and retired VW bug out back, and wooden signs with phrases like “Kiss My Grits” all over the place. If you have room for dessert, give the key lime pie a taste. Remember, real key lime pie isn’t green.

Day Two
Today is going to look a lot like yesterday, but instead of marine habitat, you’ll be exploring a riparian (river) environment. I hope you don’t mind a bit of repetition. There aren’t a lot of dining options in Everglades City and Chokoloskee, so I recommend sticking with what’s good and eating at the same places.

  1. Get that coffee fix again at Havana Cafe. You’re going to want more of that sweet, milky, caffeinated nectar of the gods. I usually like to make my own breakfast when I travel, but if you’re hungry, grab breakfast here.
  2. Walk the length of the boat launch on the north side of Everglades City. This is a neat place to take a stroll, relax, and breathe in that yummy oxygenated forest air. If you’re interested in an airboat tour, you should be able to find one around here, too.
  3. Grab lunch at Camellia Street Grill. They open at noon, so head back here for lunch and try something else off the menu. Don’t waste time and dollars looking for a better lunch somewhere else. This place is legit.
  4. Three hour mangrove tunnels kayaking tour. This tour is going to be much different than the 10,000 Islands tour. This is where you get to learn about alligators. They are kind of like the bears of the water. Don’t bother them and they probably won’t bother you. This trip started on a very lazy river system, and we could see a couple of alligators from our launch point.
    Our first alligator sighting happened before we even put our kayaks in the water.

    The mangrove tunnels are the spaces under the branches of the mangrove trees, which join together from both sides of the river to make a canopy. Arachnophobes beware, these areas make great homes for spiders. Be brave, like Tiffany.

    Trying so hard not to be scared of the snakes and spiders we saw along the way.

    We weaved in and out of these maze-like channels until we arrived at a grassy wetland area teeming with all kinds of birds. Storks flying overhead, ibises and egrets wading off in the distance. And, my favourite, a pair of roseate spoonbills flying overhead as the sun began to set (click here to see what these goofy birds look like). It was incredible. I felt like I was in a tourism advertisement.

    This is the grassy wetland that marked our turnaround point.

    This was our halfway point, so we lingered for a few minutes, savouring a moment of perfect peace, then paddled back towards the launch point. As we approached our starting point, we realized we were encroaching upon a rook of birds settling down for the night. We slowly paddled backwards and watched as hundreds of birds, representing dozens of different species, landed on the safety of a small island, hoping the isolation and strength in numbers would protect them as they rested during the night hours.

  5. Dinner at Havana Cafe. I’m sorry. I know you are adventurous like me and want to try everything, but I can’t in good conscious recommend that you miss an opportunity to eat here again. And their dinner menu is different. It’s your last night, let’s make sure the food is good.

If you want bustling nightlife, a good party scene, shopping, or white sandy beaches, Everglades City and Chokoloskee are NOT for you. The pace is slow, the scenery is gorgeous, and two days is more than enough time to do it all.

Have you been to Everglades National Park? How about the Florida Keys? This part of the world is a hotbed for unique types of adventure. Let me know in the comments if I have missed anything, or if you have recommendations for other places like this to visit.

One response to “How to Spend Two Days in Everglades City and Chokoloskee”

  1. Kayaking in swamps is so underrated!!! It’s so peaceful, and some of the strangest sounds I’ve ever heard came out of the swamps when Rob and I went through one in Louisiana. The gators were mating apparently, and I don’t think there’s any slut-shaming in the gator community because they were loud and proud about it! *get it girls* Anyways, great article! I think maybe the next time we’re down there we’ll hit up the everglades (and this Havana cafe! Must’ve been good!)

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