Road Trip to the Florida Keys

The beach at the Moorings Village in Islamorada

The beach at the Moorings Village in Islamorada

While Miami tends to get the most attention, one place in the Sunshine State we think shouldn’t be overlooked is the Keys. The best way get there is to rent yourself a car (we suggest a convertible — trust us, you’ll want to drive with the top down) and take the scenic drive on the highway that sits above the ocean connecting the small islands that make up the Florida Keys.

Although you could drive straight from Miami to Key West along the Overseas Highway in about three-and-a-half to four hours (if traffic is good), opt to make overnight stops to enjoy some of the destinations and sights along the way.  

The first island you’ll want to hit en route is Key Largo. It’s very close to the Everglades, making it an ideal destination for kayaking and bird-watching. Locals consider it to be the Diving Capital of the World, thanks to the Key Largo National Marine Sanctuary and the John Pennekamp Coral Reef State Park, both which are protected from coral collection and spearfishing. Aside from the stunning underwater life there are ship wrecks, and even the famed Statue of Christ of the Abyss, which can be seen both by diving and snorkelling.

Photography courtesy Kona Kai Resort

Photography courtesy Kona Kai Resort

When it comes time to book yourself into a hotel, we suggest the Kona Kai Resort and Gallery.  It’s a charming boutique-sized resort, tucked away from the highway and is surrounded by lush tropical gardens. Literally steps from the ocean, you can watch the sunset on the dock while sipping a glass of wine, or from the nearby hot tub. The amenities we enjoyed included the complimentary Wi-fi, the use of kayaks and paddleboat ocean-side, and the bottled water and fresh fruit poolside. Because there are only 11 rooms, it’s a very laidback atmosphere — that and the beachfront hammocks, cozy rooms and adults-only guest policy, make for a very relaxing place to rest your head.

Sifca House at the Moorings Village

Sifca House at the Moorings Village

After you’ve dived and explored Key Largo, your next stop needs to be Islamorada, if only to stay at the gorgeous property of The Moorings Village. Built on what was once a coconut plantation, the property is 18-acres, and offers 18 cottages and homes, ranging from one-bedroom to three. Each cottage has a unique style and layout, all spread out just far enough away from one another that it feels very private. Every cottage offers a fully-equipped kitchen, TV, often a washer and dryer and lovely veranda. Onsite you’ll find a tennis court, outdoor pool, fitness centre and spa. Most cottages are only a minute or so away from the ocean, some even featuring ocean-views. It’s incredibly relaxing to take a book or lay on the beach watching the sailboats and kayaks float by. Take note, the beach itself is lovely, but not the best for swimming.

When dinner-time hits make a reservation at Pierre’s Restaurant, literally across the street (well, highway) from the resort. Surrounded by palms trees and set beach-side, the plantation-style house serves guests on not one but two floors. The main floor and veranda serves more casual fare and apres-dinner drinks, while the second floor offers a fine dining French menu. Opt to dine outside on the veranda where you’ll get stunning sunset views and hear the crashing waves of the ocean. While the cuisine is primarily French, many other worldly influences are notable. We were impressed with the variety of seafood as well as the local catches on the menu like the Florida Keys Snapper and Hogfish. The wine menu is also extensive.

After rejuvintating in Islamorda, you can hop back on the highway and head down to Key West. For those who want more on-water adventure, we suggest taking a tour with Big Pine Kayak Adventures in Big Pine Key just north of Key West. Naturalist Bill Keough has been leading kayak enthusiasts for years through the waters. You can rent a kayak and go on your own, but we suggest a guide to get a more indepth experience.

islandcityhouse_optYou’ll know you’ve hit the streets of Key West once you see the palm-lined streets, Gingerbread-style homes and the bustling harbour front. Check into the quaint Island City House Hotel, a bed and breakfast within walking distance of many of the areas highlights including Ernest Hemingway’s House, Mallory Square and Duval Street.

The hotel is composed of three different houses: the Arch House, the Island City House and the Cigar House all which share walkways surrounded by lush vegetation. In the morning you can enjoy a complimentary continental breakfast, which was regularly replenished both mornings we were there and included your standard items like fresh fruit, pastries, breads and of course fresh coffee, tea and juice.

The rooms in the Island City House which we stayed were quaint, and were an old Victorian meets Southern style, and also fully equipped with a kitchen. If you have tons of luggage you might need to ask for assistance, as some of the rooms are up a couple flights of stairs (no elevator). When it comes to things to do, Key West has tons to offer from biking and swimming to historic sites and a vibrant nightlife. Stay tuned for our next post on all of the highlights you won’t want to miss.

Island City House Hotel (
411 William St., Key West, Florida, 33040. 1-(800)-634-8230.

Kona Kai Resort and Gallery (
97802 Overseas Highway, Key Largo, Florida, 33037. 1-(800)-365-7829.

The Moorings Village (
123 Beach Rd., Islamorada, Florida, 33036. 1-(305)-664-4708.