The Ultimate Middle & Lower Florida Keys Must-Do List: Marathon, Big Pine and Key West

The Ultimate Middle & Lower Florida Keys Must-Do List: Marathon, Big Pine and Key West

Whether you’re in the mood to play, dine, party or chill, the middle and lower Florida Keys offer up an amazing mix of things to do. Tap into our list of recs to make the most of your trip.


boats on calm water at lighthouse Florida Keys Sombrero


Sombrero Lighthouse and National Marine Sanctuary with Starfish Snorkeling

Who doesn’t want to see one of the world’s most amazing barrier reefs and its indescribably colorful tropical fish and coral through a snorkeling mask? No exaggeration—that’s exactly what you’ll experience on a Starfish Marathon Snorkeling Tours Sombrero Reef Snorkeling Tour. On the what-you’ll-see underwater menu: parrotfish, trumpetfish, huge schools of grunts and snappers, and more feeding around the living coral. On the what-you’ll-likely spot-along-the-way menu: dolphins, turtles and stingrays. And these are just the beginning when you hit the water with The Starfish. You’ll reach the reef on a fully covered custom catamaran outfitted with showers and concessions, and receive all the snorkeling gear you need—nothing fancy ‘cause the reef (located in the Atlantic, 7 miles from Marathon shores) is only 2-30 feet deep. How cool is that?!


Castaway Waterfront Restaurant & Sushi Bar

It’s fine. You’ll be uttering a string of “S” words at Castaway Waterfront Restaurant & Sushi Bar, from Seafood, Steak, Sushi and Spirits to Super, ‘cause, well, it is. Offering both indoor and outdoor seating, Castaway goes from breakfast to lunch to happy hour to dinner—with 52 beers to boot.

Each meal’s menu is chock full of delicious-sounding items, including some really inventive dishes. Ever tried a Spicy Tuna Dog (charred hot dog topped with spicy tuna, avocado, panko, green onion, masago, spicy mayo and eel sauce)? Or an Elk Chop? How about a Crab Enchilada stuffed with colossal lump and claw blue crab meat and three cheeses? On top of those, there’s a hugely creative sushi menu (try the Spicy Wahoo Tower). The brave among you will want to wet their whistle with the Castaway Rum Punch, which, yep, packs quite a punch. Or if you prefer beer, they offer 52 of ‘em!


Wind Down:

Chiki Tiki Bar and Grille at Burdines Waterfront

The ultra-casual Chiki Tiki Bar and Grille is the ultimate wind-down spot; something you’ll confirm once you arrive at the working marina where it’s located, climb the flight of stairs to the thatched structure and look out over the protected harbor. Ooh and aah at the views of fishing boats, yachts and worn-and-weathered live-aboards, the busted-and-beaten drawbridge leading to Boot Key and mangroves in their full-blown natural state.

Speaking of full-blown: Feel the breeze waft over you and watch the wading birds as you sip on a cold beer or tropical cocktail on the deck. If you opt to sit indoors (where there are more tables and a bar), the wall-to-wall license plate decor inside will egg you on to your next destination (should you ever feel like moving again). Chow down on the Jamaican-style seared ChikiTiki Chicken bun sandwich or a Shrimp Burger.


Big Pine Key & Ramrod Key

palm tree on beach overlooking the ocean


Bahia Honda State Park

Sink your toes into the palm-lined beach sands at Bahia Honda State Park where vodka-clear waters and sunset views will make you forget to breathe. A disintegrating old railroad bridge stretches out in the distance. After you finish gasping, gaze at the wading birds in the park (great white herons, great blue herons, tricolored herons, great egrets, snowy egrets and white Ibis); watch shorebirds along the water’s edge (willets, sanderlings, ruddy turnstones, plovers and more); picnic; paddle in the ocean or Gulf; and snorkel.

You won’t believe the sea life you can see just a few hundred feet from shore, in water that’s only 4-6 feet deep. And no worries if you don’t have a kayak or snorkeling gear with you; you can rent them at the park.

Plain ole swimming is great, too, given how warm, translucent blue and shallow the water is. You’ll probably spot some dolphins, too. Psst: Tell all your followers you’re a dolphin whisperer.



Good Food Conspiracy

Good Food Conspiracy, a natural foods/juice bar eatery, is a must-visit for veg and health food-loving travelers. The earthy smells that greet you when you walk in instantly announce a host of delectable offerings made with homegrown, organic ingredients—fresh brewed coffee, fruit smoothies, fruit-and-vegetable squeezes, hummus, and both raw and cooked vegetarian and vegan concoctions ranging from soups and salads to sandwiches and desserts. But this is more than an eatery; it’s also a market where you can gather up medicinal teas and other remedies, dried fruits and nuts, vitamins, oils and lots of other healthy food staples for car and hotel room snacking.


Wind Down:

Boondocks Grille & Draft House (in Ramrod Key)

Ramrod Key boasts the largest tiki bar in the Keys, Boondocks Grille & Draft House, and it’s a perfect place to eat and be entertained, whatever your age. With its various cheesy macs (Maine Lobster Mac—yum!), house fries (Gouda Bacon Fries, Crabby Fries, etc.), grass-fed beef burgers (one for you, one for them, one for everybody) and various hand-crafted sandwiches, the sprawling open-air restaurant will make you want to stay put. Who can resist that menu, the thatch overhangs and the live music?

But you’ll def feel the powerful tug of playtime too. What’s calling? Lush and indulgent, caveman-themed mini golf—complete with a tropical garden setting, cascading waterfalls and frozen drinks and brews. Yep, a full bar awaits you at the end—celebrate your victory or just the sheer coolness of having played the southernmost golf course in the Keys.


Key West


How does this sound for a 6-hour play day? Sail, reef snorkel, parasail, jet ski, ride a banana boat and romp on Key West’s largest ocean water park (3,500 sq. ft. of connected inflatable water toys—from an Action Climbing Tower to an Aqua Slide to a Trampoline). On Fury Key West’s Ultimate Adventure you get all this and more—like, a state-of-the-art catamaran, great snorkel gear and instruction from pros, complimentary drinks and a gourmet breakfast and lunch.

During the snorkel portion, you’ll see angelfish, parrotfish, blue tangs and plenty of other colorful fish species. For the water sports part, the boat docks on its own floating platform island in the Gulf and takes it from there. Excited yet?


Blue Heaven (breakfast)

This divine outdoor dining spot is particularly renowned for its Sunday breakfast with its Insta-worthy, taste bud-tickling Key Lime pie—the meringue topping positively towers and you’ll wonder how it stays put. But Blue Heaven is also home to notable (roaming) chickens and cats, great live music and seriously delicious food that belies the place’s improvisational decor.

Pour over the menu of American and Caribbean dishes, then try the Miso Baked Eggplant Salad, Atlantic Sea Scallops Provençale, Jamaican Jerk Chicken or Macrobowl (a veg feast in a bowl).


Milagro Restaurant and Bar

Who’s up for some fresh seafood or some Mexican or pizza prepared by a five-time winner of the Master Chef’s Classic who’s also cooked for multiple dignitaries? If that sounds like your cup of cava, head over to Milagro Restaurant and Bar, which just moved from Big Pine Key, where it was a favorite, to Key West.

Treat yourself to some Wood Grilled Octopus served over Applewood Bacon  Polenta or the Wood Grilled Pesto Shrimp “Macaroni” (read: cavatelli) and Cheese. Open Table customers have rated these dishes their favs, but the Grace pizza (made with aged Gruyere cheese, carmelized onion and shiitake mushrooms) and Beef Shank Pozole (with white hominy, avocado, cabbage and pasilla chile broth) look mighty good, too.


Wind Down:

Better Than Sex

The name of this dessert bar speakeasy, Better Than Sex, pretty much says it all. Enjoy an intimate, candlelit atmosphere; curtained tables and delve into a titillating menu that balances sweet and savory items with wine and cocktails. Really good: the irreverent dessert names. Even better: the chocolate and caramel-rimmed wines. The best: sweets like Naughty By Nature and Peanut Butter Perversion (you’ll have to read the menu to see what we mean). Order several desserts and dare to share.