The Florida Keys are close enough to our city to make them an easy travel destination for Torontonians; but far enough from the cold weather to provide the perfect warm island retreat. The stretch of islands are connected to the mainland via an over-the-water highway, which is equally as scenic as it is convenient.
With easy, direct flights right into Miami, it makes escaping the Canadian cold and getting to the Florida Keys that much easier. Simply grab a rent-a-car at the Miami International airport and make the road trip a pit stop adventure, exploring the different Keys along the way.
To help you plan your Great Escape this winter, we’ve partnered with The Florida Keys’ Tourism Board and put together an easy 5-day itinerary to get you inspired to plan your adventure.
Day 1: Key Largo
Drive to Key Largo from Miami International Airport.
Key Largo Accommodations: Baker’s Cay Resort
Baker’s Cay is a 15-acre, 200-room resort, equipped with stunning rooms, two swimming pools with a waterfall grotto, a pool bar and food truck, alongside a winding nature trail lined with hidden beaches, a boat dock, and wellness salon. The beachside taco venue includes house-made hot sauces crafted from peppers grown in Chef’s rooftop garden, as well as over 100 tequilas and mezcals.
Mid-Morning/ Early Afternoon Activity: Sandbar Swim Trip with Islander Girl Tours
Islander Girl Tours is owned and operated by a mother/daughter duo who grew up in the Keys [DYK: local natives to the Keys are referred to as Conch]. The duo spend their days diving and snorkeling—and have made their passion their career by launching their tour company Islander Girl Tours. Let their knowledgeable captains take you to some of the healthiest and most pristine living coral reefs in the world. The sandbar swim trip takes you to a sandbar where you can enjoy complimentary drinks from your boat, hangout on the sandbar, and visit the floating food truck/boat for some delicious bites.
Afternoon/Evening Activity: Enjoy a pint at Florida Keys Brewing Co.
This brewery is a must for those who love to enjoy a pint and good vibes. The colourful aesthetic is filled with keyzie fun. Joining in on your night might be the owners’ cats who frequent the taproom and brewery! Located in Morada Way’s Arts and Cultural District, Florida Keys Brewing Co. opened in March 2015 and infuses their brews with local flavours such as Key limes, citrus, and local honey.
Dinner at Calusa at Baker’s Cay Resort
Back at Baker’s Cay, Calusa welcomes visitors for breakfast and dinner. This indoor/outdoor Creole-Caribbean restaurant hints at New Orleans flavours, while bringing in the fresh flavours of the Keys. Enjoy panoramic views of the crystalline blue waters of the Florida Bay and the most eloquent paint brushed sunsets.
Day 2: Key West
Head to Key West
Key West Accommodation: The Perry Hotel at Stock Island Marina Village
Inspired by the industrial nature from which Stock Island has developed, The Perry Hotel at Stock Island Marina blends smooth wood finishes with rustic metal details. This design references the area’s iconic maritime heritage, while adding an updated touch. Located beside a state-of-the-art 288-slip marina —the largest deep-water marina in the Florida Keys— this boutique hotel’s pool deck overlooks the working waterfront. With three dockside restaurants [Matt’s Stock Island Kitchen and Bar, The Salty Oyster Bar and Grill and Sloppy Joe’s Dockside] you’ll be able to indulge in American coastal comfort food and craft cocktails with an innovative twist. Though not directly located in Key West, the free shuttle service operates hourly and is a great, easy and efficient way to get into Key West’s main streets.
Afternoon Activity: Explore the beautiful streets of Key West, including Duval Street and Mallory Square
Sunset Celebration is a nightly “street carnival” at Mallory Square. Overlooking Key West Harbor, the celebration features arts and crafts exhibitors, street performers, food carts, psychics, musicians and entertainers. Crowds of visitors from around the world flock to the celebration each evening to observe the setting of the sun over the water [DYK: The Florida Keys are renowned for their sunsets]. Duval Street is stretches across the island, running from the Gulf of Mexico to the Atlantic Ocean. With restaurants, cafes, shops, and everything in between, this popular street is one of the most iconic destinations in the Florida Keys.
Dinner at Latitudes on Sunset Key
Perched on the exclusive island of Sunset Key, Latitudes is the perfect dinner spot if you’re looking for a scenic sunset meal with sweeping views of the Gulf of Mexico. You’ll need to make a reservation in advance—and ensure you buffer enough time to get there as you’ll need to take the Sunset Key’s charter boat over from the mainland. The innovative seasonal menu features local fish, fresh produce, and a variety of island classics, elevating the casual fare with a Caribbean flair.
Day 3: Key West
Cuban Coffee Queen Downtown
With Cuba only a matter of miles offshore from the keys, the Cuban influence can be seen across the island! Cuban Coffee Queen’s downtown stall is a quick and easy spot to grab a morning coffee, café con leche, or Cuban chocolate mocha before a morning activity. Breakfast favourites include the Key Wester and the pork roll on Cuban bread.
Morning Activity: Dolphin Watch & Snorkel Tour with Honest Eco
The Dolphin Watch tour with Honest Eco features SQUID—Key West’s first electric-powered charter boat. The boat is a lithium ion battery-powered hybrid with electric motors, perfect for four-hour dolphin watching and snorkeling tours. The boat burns only three gallons of diesel fuel per trip, equivalent to about one-quarter of a gallon of fossil fuel per guest. Enjoy watching wild dolphins as they play, sleep, hunt and mate in Key West’s tranquil, turquoise waters in an eco-friendly way.
Afternoon Activity: Ernest Hemingway Home and Museum
For 10 years, Ernest Hemingway called Key West his home. At his Whitehead Street property, guests will take a step back in time, visiting rooms and gardens where the Nobel Prize winner spent the most prolific period of his writing career. Notable features include the island’s first swimming pool and his second-story studio, where he wrote many of his classic works [DYK: Hemingway used Depression-era Key West as the locale for “To Have and Have Not” — his only novel set in the United States].
Evening Activity: Land’s End Sunset Sail with Sebago Key West
Sebago Watersports offers amazing catamaran and schooner sailing tours! One of the most iconic Key West adventures includes the champagne sail, which has you aboard the Marquesa, enjoying the world-famous Key West sunset over drinks, and passed canapés.
Dinner at Milagro Restaurant
Milagro Restaurant and Bar is hidden off the beaten path, just two blocks from the Southernmost Point and one block from world famous Duval Street. Run by a husband and wife duo, an award-winning Executive Chef Kevin Montoya and the General Manager Maggie Montoya, Milagro is a labor of love with deep ties to scratch-made food, art, and the community.
Day 4: Key West
Mid-Morning/ Early Afternoon Activity: Southernmost Food Tasting & Cultural Walking Tour
This 3-hour walking tour visits 6 locally owned establishments in the historic old town. Delicious and mouthwatering food tastings, enough for a hearty lunch, are served in ethnic eateries and specialty shops that are unique to the Florida Keys. Between tastings, participants will experience what life is like for a Conch through the stories of the passionate local guides, which share their knowledge of architectural gems, tropical flora, and exciting local attractions and restaurants.
Dinner at Matt’s Stock Island
Located at The Perry Hotel Key West, Matt’s serves “American coastal comfort food” with innovative twists. Some of the cool menu offerings include iced cold seafood presented in a fisherman’s tackle box. Overlooking a colourful marina, it’s no wonder that Matt’s the winner of OpenTable’s 2018 Diners’ Choice Award for best ambiance.
Day 5: Upper Keys
Head to the Upper Keys
Marathon Accommodation: Isla Bella Beach Resort
At the threshold of the iconic Seven Mile Bridge lies Isla Bella Beach Resort. Framed by a canopy of native plants and tropical greenery, this private oasis features 5 oceanfront pools, a marina, a spa, a state-of-the-art fitness centre, and a variety of games and activities, like bocce ball, giant chess, and biking. Multiple dining options including Mahina, a world-class Polynesian-inspired restaurant.
Tour the Turtle Hospital
Opened in 1986, the Turtle Hospital treats injured sea turtles and, when possible, returns them to the wild. Educational tours allows you to learn about these beautiful creatures before being introduce to the resident sea turtles. While on the tour, you’ll learn about the hospital’s curative programs for loggerhead, green, hawksbill and Kemp’s ridley turtles. The hospital is believed to be the world’s only state-licensed veterinary hospital dedicated solely to the treatment of sea turtles.
Take in the views from the Old Seven Mile Bridge
Located at Mile Marker 47
The Old Seven Mile Bridge, better known as “Old 7,” was built over a century ago as the centrepiece of Henry Flagler’s Florida Keys Over-Sea Railroad. In 1938 the bridge was converted for automobiles and in 1982 the Federal government built a new span paralleling the historic one. “Old 7” was then retired and became a fishing pier and walking area.
Dinner at Mahina at Isla Bella Beach Resort
Mahina is a Polynesian inspired restaurant at Isla Bella Beach Resort. Influenced by Executive Chef Pavy Keomaniboth’s birthplace of Hawaii, Mahina features a coastal culinary experience using local fresh ingredients and flavors native to his homeland and the Keys. Mahina, which means “Moon” in Hawaiian, symbolizes the full-circle transformation of the menu.
For more information on the Florida Keys and Key West, visit Fla-Keys.com.