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7 Days of Adventure in Sarasota & The Keys

Before the first cold snap hits, we're already dreaming of winter adventures in Florida.

By: Sara Sheehy + Save to a List

The Sunshine State is a sought-after vacation destination for visitors from around the globe. Why? Because it’s so much more than theme parks and lazy days on the beach (though those are great, too). We recently took a deeper dive into wild Florida. The video below captures some of the highlights.

Looks pretty amazing, right? To inform your Florida adventure, check out this seven-day itinerary that includes hiking, kayaking, fossil-hunting, wakeboarding, jet skiing, plus some creature comforts (cozy hotels, upscale restaurants, and tasty beverages).

Day 1

3 PM: Arrive in Sarasota, Florida

Forget about connections. Dozens of cities have nonstop service into Sarasota Bradenton International Airport. Book your flight to land in the afternoon, so you have time to settle into your hotel and do a bit of exploring before dinner.

Lodging options abound in Sarasota, but check out the Homewood Suites by Hilton Sarasota Lakewood Ranch Hotel for easy access to Nathan Benderson Park, a favorite of rowing teams, paddlers, and cyclists. Drive two minutes to the park and watch the paddlers on the water while keeping an eye out for the park’s famous Dragon Boats. These colorful Chinese watercraft can hold 22 people and feature ornamental dragon heads on the tip of the boat fronts. Watch one go by or join in and take a class! Those who favor relaxation after a long flight will find it at the hotel’s outdoor pool.

When your stomach starts to growl, walk across the street to Ford’s Garage, your pit stop for prime beef burgers and other comfort food, and craft beers. Enjoy a milkshake or top off your day with a caramel apple cookie skillet! After dinner, you’re going to want to rest up; you have an action-packed day tomorrow.

Day 2

9 AM: Explore Myakka River State Park

Myakka, one of Florida’s oldest and largest state parks, has 39 miles of hiking trails and a 7-mile scenic drive through palm trees and along grassy marshes.

On the 4.4-mile Deep Hole Trail, a sinkhole is home to hundreds of alligators during the dry season. Get to the park when it opens to secure the required permit for this hike. There are only 30 per day and they can go fast -- especially if you’re visiting on the weekend.

Leave time in your schedule for an eco-boat tour on Upper Myakka Lake. Be sure to bring your camera and keep all your limbs safely aboard the boat! You’ll learn what makes Myakka unique among America’s freshwater lakes as you keep an eye out for alligators, 5-foot-tall sandhill cranes, and other wildlife.

After the boat tour, hop back in your car and make your way east to the town of Arcadia for lunch and an afternoon of paddling. For an authentic Mexican experience and friendly folks, eat at Azul Tequila.

1 PM: A Cattle Country Canoe and Fossil Hunt

Arcadia is a land of cowboys, cattle, citrus, and watermelon — not necessarily in that order. It’s also home to the Peace River, where the outfitter Canoe Outpost offers canoe rentals. Load up on one of their old-school blue buses and bounce down a dirt road to the paddling put-in.

Floating in a canoe along the Peace River’s cypress and live oak-lined banks is easy and relaxing. Stop at one of the sandy beaches along the way to comb for fossils and shark teeth, the remains of ancient marine animals that lived between 5-million and 26-million years ago.

6 PM: Dinner at Nancy’s BBQ

Back in Sarasota, Nancy’s BBQ is an upbeat, family-friendly restaurant that draws crowds for its house-smoked Boston butt and brisket that you can feast on at outdoor picnic tables.

Day 3

10 AM: Paddling at Nathan Benderson Park

You may be tired from yesterday's excursion, so sleep in a bit (and maybe order some room service pancakes) before this morning's paddle at Nathan Benderson Park. The park includes North America's top 2,000-meter sprint rowing course and regatta center. It also provides year-round recreational opportunities for people of all ages.

Rent a canoe, rowboat, kayak, or stand-up paddleboard and go for a spin around the 400-acre lake. The park also offers fishing, seven miles of walking and running trails, and bird-watching from the water.

Noon: Megalodon Shark Teeth Hunting

Before the hunt, you’d better eat. Walk a quarter-mile north from the hotel to JPAN Sushi & Grill at University Town Center for a bento box or sushi rolls.

The next stop is south to Venice, the Shark Tooth Capital of the World. No special equipment is required to hunt for shark teeth, but it’s much easier to sift and sort the sand with the proper tools. There are many shops in town that rent or sell specialized kits.

Stop in at Shark Frenzy for insight and tips about where to go. When you’re finished hunting, head back to the shop for a free identification session of the fossils you found. Many of the triangle-shaped teeth are smaller than an inch, while some are palm-sized! They’re often smooth from years of wear, but some have serrations from when they were used for gnashing up fish.

8 PM: Dinner and Drinks

In downtown Sarasota, start at 99 Bottles Taproom & Bottle Shop for rotating taps of craft beer and wines by the glass. Next, make your way to Duval’s (reservations recommended), voted best all-around restaurant and best seafood restaurant in Sarasota. Eat your fill of lobster mac & cheese and seafood bouillabaisse.

Day 4

7 AM: Drive to the Florida Keys

Up and at ’em, adventurer! It’s time to make your way south to the famous Florida Keys. The fastest route takes you inland past Fort Myers and Cape Coral, through the northern reaches of Big Cypress National Preserve, along the outskirts of Miami, and down the Keys until you reach the beach town of Marathon. This seaside town is a haven for boaters and anglers, and hosts the Florida Keys’ Fastest Stone Crab Claw Eaters contest!

1 PM: Local Eats and Wakeboarding

In Marathon, head to The Lagoon on Grassy Key for a locally sourced lunch at Bongo’s Café.

After eating, it’s time to hit the water. The onsite Keys Cable Park offers two cable-powered wakeboard courses. Staff tune each board to meet the needs of the rider’s experience level. These courses are great for learning how to wakeboard or sharpening your skills.

The Lagoon at Grassy Key also offers kiteboarding, foil boarding, sailing, paddleboarding, and kayaking. The staff knows everyone in town, so ask about booking an expert guide for spearfishing, fly-fishing, charter fishing, snorkeling, or free diving.

5 PM: Drinks, Dinner, and a Good Night’s Sleep

Head to your hotel to unpack and get spiffed up for a night on the town. Check out Faro Blanco Resort & Yacht Club for a boutique hotel experience right on Marathon’s marina. Snag a bayside room for views of the resort’s historic red-and-white lighthouse.

Those who want to dine at Il Postino will want to stay the night at Isla Bella Beach Resort. The restaurant, open to guests only, is known for its fresh pasta and ocean views. We recommend starting with an Isla Paloma cocktail and conch chowder, followed by blackened mahi. Buon appetito!

Day 5

9 AM: On to Key West

At the southern end of the Florida Keys lies the vibrant town of Key West. Notice the pastel houses and Cuban influences around every corner! Drop off your luggage at your hotel (we love The Perry for its nod to the city’s maritime heritage and views of the working waterfront) before making your way to Get Up and Go for a kayaking excursion like no other.

Ranked as one of America’s best kayaking tours by USA TODAY, Get Up and Go offers charters in clear kayaks that make it easy to see the ocean life beneath you. You’ll paddle alongside thick stands of mangroves through coastal saline water and beautiful shorebird sanctuaries. Keep an eye out for starfish, sea turtles, sea cucumbers, jellyfish, iguanas, pelicans, manatees, and dolphins. Wear something that you can get wet.

Noon: Lunch and Leisure

Grab a flight of beer and lunch at First Flight Island Restaurant & Brewery. Try house drafts like the Main Squeeze - Citrus Wheat or Havana Red - Amber Ale.

Then, wander around beautiful downtown Key West. Take a stroll down Duval Street and pay a small fare to hop on the 90-minute historical trolley tour. Maximize your time on the ride by stopping at art galleries, restaurants, and the Key West Aquarium. Or, head back to the hotel to spend the afternoon at one of their two waterfront pools. Maybe order an appetizer and take a nap? The world is your oyster.

6 PM: Sunset Tiki Cruise

“Why go bar hopping when you can hop on a bar?” is the motto of Cruisin’ Tikis Key West, a tour company that offers 90- to 150-minute cruises on their floating tiki boats. Each rental comes with a Coast Guard-trained captain, bottled water, sodas, and a cooler with ice. Bring your own adult beverages. Float on the calm waters of the Keys while taking in the world-class sunset and silhouettes of palm trees.

For dinner, check out Tiger Bar Exotic Eats & The Champagne Room. This fun international street food restaurant offers modern small-plate dining in the Tiger Bar. Go to the tropical pastel Champagne Room to peruse the boutique wine list and snack on artisanal hors d’oeuvres like parmesan fries and Peking duck spring rolls. Only 30 seats are available in the restaurant, so make a reservation to secure your spot.

Day 6

9 AM: All-day Watersport Adventure

Go big before you go home with a full-day experience at the Ultimate Adventure H2.0 Excursion with Fury Water Adventures. This all-inclusive package will introduce you to snorkeling on North America’s only barrier coral reef, parasailing, a jet ski tour, a banana boat ride, and the all-ages playground at Key West’s largest ocean water park.

Breakfast, lunch, and unlimited refreshments are included in the package. You’re going to need a lot of sustenance to get you through the day.

7 PM: One Last Sunset

Soak in one last Keys sunset while dining at LL's Test Kitchen inside the Stock Island Yacht Club. We recommend the royal red shrimp carbonara and Key West Conch chowder,

If you have energy left to spare, spend it exploring Key West’s nightlife. Go bar-hopping on Duval Street, take a Key West Ghost & Mysteries Tour, or catch a live show at the Smokin’ Tuna Saloon.

Day 7

8 AM: Homeward Bound

It’s time to make your way home via Key West International Airport or, for more flight options (but a 3+ hour drive), Miami International. If time allows before departing Key West, check out the exceptional breakfast at Blue Heaven, which serves Keys, Caribbean, and seafood specialties out of its distinctive blue building in the historic Bahama Village neighborhood.

If you’re anything like us, heading home tanned and maybe a little bit sore, you’ll be asking yourself: When can I come back? Luckily, Florida is full of beautiful, welcoming destinations to explore. Get the inside scoop from local pros with these trip recommendations:

Ultimate Insider’s Guide to Jacksonville

Adventures in Fort Lauderdale

A Tropical Adventure in Florida Keys!

Experiences to Remember in Beautiful Orlando, Florida

Fort Myers Insider’s Guide

Miami Insider’s Guide: Culture and Adventure Wrapped Into One For An Adventurous Spirit

Florida Panhandle Adventures!

Your Insiders Guide to Tampa Bay

Our 12 Favorite Beaches in Florida

20 Must-Do Adventures in Florida

5 Tips for Adventuring Responsibly in the Sunshine State

We want to acknowledge and thank the past, present, and future generations of all Native Nations and Indigenous Peoples whose ancestral lands we travel, explore, and play on. Always practice Leave No Trace ethics on your adventures and follow local regulations. Please explore responsibly!

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