A Long Weekend in Key West

If you've only heard tales of Key West, the title of this article may conjure images of unrestricted debauchery and the inevitable hangover and jail time that often accompany it. The true story of Key West is actually quite different. While you'll surely encounter some questionable conduct on your visit, Key West is really a charming place with great restaurants, an electric nightlife, and beautiful beaches. Of course, the homes for sale in Key West are like nothing else. You may be surprised to learn that the demographics on Duval Street are weighted heavily toward the over-40 and way-over-40 crowds.

We've lived on Marco Island for over twelve years, and one of our favorite things to do has always been to take a long weekend in Key West. Even though Marco and Key West are only 85 miles apart, the contrast between the two could not be more dramatic. Key West is one of those places that you love to visit because you couldn't imagine living there.

That said, we can think of no place that has a charm quite like Key West. It has a relaxed atmosphere yet there's always plenty to do. Whether you're looking for some down-time, some culture, or a little overindulgence, your trip to the southernmost point in the continental United States is certain to deliver.

Below, we detail the various transportation options from Marco Island to Key West, and then take a look at all of the cool things to do, awesome places to eat, and appealing places to snooze that will make this weekend one to remember. Of course, we'll consider the differences between Marco Island and Key West real estate.

Have you been to Key West? Tell us about your experience in the comments.

Getting to Key West from Marco Island

There are several ways to get to Key West from Marco Island. Drive it, fly commercial, or charter a private flight in a little puddle jumper-the journey is always part of the fun.

Driving to Key West

The scenic route from Marco Island to Key West will drive you 240 miles through the beautiful Florida Keys via the Overseas Highway, popularly known as U.S. Route 1. The drive will take roughly about 5 hours, depending on the flow of the traffic, but you'll want to leave room for plenty of stops along the way to enjoy the awesome views and cool shops.

Some of the most beautiful scenery that Florida has can be found on the Overseas Highway. The crystal-clear waters on either side of the road, the roadside stops, and plenty of opportunities to stop and see wildlife make driving to Key West fun. Be sure to check out places like Islamorada, called the "Sport Fishing Capital of the World," or Bahia Honda State Park, offering some of the top beaches in the Keys. Driving gives you a chance to explore the Lower Keys before you arrive in Key West.

Flying from Southwest Florida International Airport - RSW

Other than driving, flying from Southwest Florida International Airport in Fort Myers gets you to Key West faster. Silver Airways flies directly into Key West International Airport. The flight takes roughly an hour. This is great if the five-hour drive each way will cut too much into your fun time.

When you arrive at Key West International Airport, you are just a few minutes from the central part of Old Town Key West and off to a great start. It will be easy to find a waiting taxi, ride share, or rental car at the airport, ready to take you to your hotel or destination. We always rent scooters in Key West. There is a safety aspect that you must consider, but the convenience is amazing. You can always find parking for your scooter and you can zoom from place to place quickly.

Private Charters from Naples or Marco Island

For the absolute fastest trip to Key West, private charter flights can be arranged from Naples Airport (APF) or Marco Island Executive Airport (MKY). Companies such as Air Key West fly directly to Key West. Private charters are not inexpensive but offer a level of comfort and convenience that's hard to beat. For $900, you can get five people to Key West in less than 45 minutes. You can avoid long lines and crowds at the airport and travel in your style at a time that suits you.

In addition, some charter companies offer scenic flights en route to let you appreciate the Florida coastline and the Keys from up in the air before landing in Key West.

Things to Do in Key West

Once you arrive in Key West, the laid-back-casual attitude and energy of this island is really special. This little island is stuffed with culture, history, adventure, and plenty of relaxation. So here are some things we recommend for an unforgettable weekend.

Duval Street

The main artery of Key West and the very center of nightlife, dining, and entertainment is Duval Street. It's a little like a mini Bourbon Street if you know New Orleans. This famous street has an eclectic mix of shops, art galleries, bars, and live music venues. You can stroll the local boutiques by day and enjoy the rowdy bar scene by night at famous places like Sloppy Joe's, made famous by Ernest Hemingway, or The Green Parrot, a local watering hole with live music and a laid-back vibe.

Mallory Square

No trip to Key West is complete without taking in the sunset at Mallory Square. A perfect Key West experience, locals and visitors gather to watch the sun dip into the horizon every evening. Street performers, food vendors, and local artists are all over the place. The atmosphere is great. Get down there early to claim your spot.

Ernest Hemingway Home and Museum

To the lovers of literature, Ernest Hemingway's Home and Museum is no ordinary Key West house. Ernest bought his house in Old Town Key West in 1931. The American writer lived there for over ten years. You get to tour the house, see Hemingway's writing studio, and learn something about his life on the island. Plus, the museum is home to more than 50 six-toed cats, descendants of Hemingway's pets, and are as much a part of the experience as the house itself.

Snorkeling, Diving, and Water Sports

The waters around Key West are among the clearest and warmest anywhere, making it perfect for water sports. Take a snorkeling or diving tour to explore the brilliant coral reefs teeming with marine life, or rent a kayak and paddle through the mangroves. Like Marco Island, Key West is a great place to jet ski or parasail around the island for spectacular views of the lower Florida Keys.

Tour Fort Zachary Taylor Historic State Park

Spend a day at Fort Zachary Taylor Historic State Park, home to one of the best beaches in Key West. The park also includes a Civil War-era fort you can tour with a guide and learn about the military history of Key West. You can lounge on the beach, snorkel in shallow waters, or picnic in the shade of trees during the afternoon. It's an awesome park.

Where to Stay in Key West

There are loads of options for accommodations here, which run the gamut from luxurious resorts to small, historic homes converted to quirky boutiques. Here's a small selection of options to consider:

The Southernmost Beach Resort

Located on the more subdued end of Duval Street, The Southernmost Beach Resort is a bit more high-end, offering oceanview rooms, direct access to a private beach, and plenty of swimming pools. It's ideal for those looking for a little tranquility yet it's within a short walking distance to the action on Duval Street.

La Concha Resort

La Concha is located on Duval Street, with action to both the north and south. You could say it's in the thick of it. A modern rebuilding of a historic building, La Concha has all the amenities you want in a top-tier hotel. It's only a few blocks from Sloppy Joes and one of my favorite breakfast restaurants on Earth, La Creperie.

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort is a boutique hotel right in the middle of Old Town, only steps from the waterfront. This hotel offers large rooms, tropical gardens, and three pools for both relaxation and convenience.

Old Town Manor

We just discovered this hotel this year. It is located less than a block from the prime part of Duval Street. Like many hotels in Key West, Old Town Manor is a historic home that has been converted. It has tons of personality and is super-convenient to everything you want to be close to in Key West. Oh, the price is good, too.

Dining and Drinks in Key West

The food in Key West is as tasty as the culture. Fresh seafood, Cuban food, and island-inspired flavors are on every menu. Here's where you'll want to go:

Blue Heaven  

A Key West icon, Blue Heaven, provides a unique vibe. Dine al fresco under the tropical trees while roosters strut around the courtyard. The eccentric decor and Caribbean-influenced cuisine are awesome. The breakfast should not be missed. The menu is filled with local specialties: lobster eggs benedict, conch fritters. No meal here would be complete without a slice of their popular Key Lime pie.

La Creperie

Directly across Petronia Street from Blue Heaven is my personal favorite breakfast restaurant on the island, La Creperie. I always get the #52 L’Amour de Baies, which is a soft crepe filled with berries and topped with crème anglaise (it's in the photo). Unbelievable! They serve a wide variety of tasty breakfasts, not only crepes.

Latitudes on Sunset Key

We only discovered Latitudes a couple of years ago. It's another place that we never miss on a Key West trip. Located on a private island of luxury cottages called Sunset Key, Latitudes has just about the best sunset view in town, along with fresh seafood, fine steaks, and some creative cocktails. I recommend going to lunch at Latitudes. Just call ahead for a reservation and the staff will tell you when to meet the boat for the eight-minute ride to Sunset Key. You'll catch the boat near the cruise ship dock.

Captain Tony's Saloon

As authentic as Key West can get, Captain Tony's Saloon is the original location of Sloppy Joe's Bar, this historic spot has been a favorite hangout of locals and visitors alike for decades. Inside, every inch of its walls is adorned with memorabilia. Ernest Hemingway hung out here. Cold beer and live music make this yet another must-see place.

The Homes of Key West

Key West is old - at least when compared to Marco Island. Whereas Marco Island didn't really begin to develop in earnest until the late 1960s, Key West was established in the early 1800s. Today, historical homes are some of the most popular luxury real estate in Key West - and they're not cheap. The island has the most expensive real estate in Florida. The historic cottages and mansions are a big part of Key West's popular vibe. If you're an architecture fan or history buff, we recommend you take a trolley tour of the island to soak it all in.

If you'd like to learn more about the Key West real estate market and Key West-style houses, visit buykeywest.com for great articles and all of the current listings on the MLS.

Conclusion

A weekend of fun and adventure, relaxation, and island charm is what you get on a weekend excursion from Marco Island to Key West. Whether taking in the scenic drive down through the Florida Keys, flying in for a quick getaway, or chartering a private flight, it is well worth your time. With endless activities, beautiful accommodations, and an incredible food scene, Key West has everything you need on a weekend getaway.