Key West’s Coconut Beach Resort has a lot going for it. Not only does this highly rated property (it averages a 4.5 out of 5 rating on Google) boast its own small beach with superb views over the Atlantic, something of a rarity here, but it is also handily located close to Duval Street, Key West’s liveliest area. This meant that exploring this funky island town on foot was going to be a breeze as pretty much everything to see and do here is either on or close to Duval and, therefore, within walking distance of our resort.

Better still, our home for our first-ever week in this tropical paradise was located at the very bottom end of the 1¼-mile long Duval Street, the city’s main drag, meaning we were on the “quiet” side of the island. All of the action we’d heard about? Well, that was at the opposite end of Duval, which meant a surprisingly relaxed and peaceful stay… until we wanted some of that action for ourselves.

The Southernmost Point Of The Continental US

Car parked (we didn’t need it for the whole week we were here) and luggage unpacked, we headed first to one of the most photographed spots on the island: The Southernmost Point of the Continental U.S.A. Considered Key West’s ultimate selfie spot, this iconic landmark is located at the corner of South Street and Whitehead Street, a 10-minute walk from our resort and just a couple of minutes away from Duval.

This large red, black, and yellow buoy lives up to its word and marks the southernmost tip of the contiguous United States. Just 90 miles from Cuba, this symbolic reminder of the region’s proximity to the Caribbean was erected in 1983 and has been a bucket-list item for visitors ever since.

Tips & Tactics: Expect a lineup to grab a photo, so arrive early to beat the crowds. And as good as a selfie can be, ask an obliging fellow tourist to take the photo for you.

The Key West Butterfly And Nature Conservatory

From this Key West landmark, you’re just a block from Duval’s most southerly attraction: The Key West Butterfly and Nature Conservatory. Here you’ll literally be surrounded by hundreds of free-flying butterflies from around the world, all housed in lush, climate-controlled gardens concealed in glass.

As well as the 60 species of butterflies, a variety of exotic free-flying birds, including some native to the Florida Keys, can also be viewed, along with some flamingos. Handy displays provide details of these colorful creatures, and the butterflies do occasionally land on visitors, so have your camera ready. It’s certainly a great place to get up close to these amazing creatures, an experience that’s enhanced by the attraction’s many flowering plants.

Tips & Tactics: The conservatory has an excellent gift shop with artwork from a variety of local artists who’ve managed to capture these colorful creatures perfectly. Take one home as a memento to brighten your walls.

Key Lime Pie And Cuban Cigars

As we walked up Duval Street, we were able to quickly cross another couple of items off our bucket list: key lime pie. While countless souvenir-style shops claiming to sell the “best” version of this Key West staple are everywhere along Duval, we found our very own sweet spot at La Grignote, just three minutes from the Butterfly Conservatory. This French-inspired café has its own take on this iconic dessert using local, somewhat tart Key limes to give it the famous tangy taste. Mouthwatering and so much better than the mass-produced touristy versions, we tried further up Duval.

Authentic Cuban cigars were next on our list of “must buys” in Key West, and again, we didn’t have to go far to find them. Duval is lined with souvenir shops selling everything from t-shirts dedicated to Jimmy Buffet’s Margaritaville to key lime pie-flavored cigars. While we tried a few of these novelty cigars, we wanted something authentic to take home… the real thing. And in Key West, authentic “sticks” go back a long way, with the art of crafting hand-rolled cigars a tradition passed down from generation to generation of Cubans.

Our search for the perfect Cuban cigar led us to the Rodriguez Cigar Factory at the top end of Duval. Established in 1984, you can not only buy first-rate Cuban cigars here but can also embark on a fascinating tour that reveals the full process of manufacturing these delightful indulgences.

Tips & Tactics: Another great café/bakery in Key West is Frenchie’s Café, just a few minutes walk from Duval along United Street. Run by expats from France, they get our vote for Key West’s best breakfast and the freshest croissants. And while they no longer have a store in Key West, the Original Key West Cigar Factory, established in 1968 and the Keys’ oldest cigar company, sells its premium stogies online.

The Hemingway Home and Museum

Not quite mid-way along Duval Street (and a block to the west) is The Ernest Hemingway Home and Museum. Located in Key West’s “Old Town” area, this historic property was Hemingway’s residence from 1931 to 1939 and is where he penned some of his most famous works, including To Have and Have Not. Built in 1851, this elegant Spanish Colonial-style home has been meticulously preserved and features original furnishings and personal artifacts from the life of one of America’s greatest writers.

Guided tours are included with admission. And be sure to ask about the attraction’s famous colony of six-toed cats. Descendants of Hemingway’s beloved pet, Snowball, these friendly felines pretty much have the run of the property.

Tips & Tactics: This must-visit museum only sells tickets at the entrance (not in advance), so lineups can be a little long at times. Arrive early or later in the afternoon an hour or so prior to closing at 5 pm. Be sure to spend time wandering the gardens, as there are plenty of quiet corners to really appreciate the setting… and those six-toed felines.

Mallory Square and Key West’s Famous Sunset Celebration

No visit to Key West is complete without an evening visit to Mallory Square. Located at the north end of Duval, it’s here you’ll partake in another bucket list must-do: the Sunset Celebration. Set overlooking the Gulf of Mexico, this nightly event has been happening for over 50 years and is so magical an experience you’ll want to attend it at least a couple of times during your Key West getaway. As the sun begins to dip into the Gulf, crowds gather along the waterfront, creating a lively atmosphere filled with street performers, local artists, food vendors… and plenty of anticipation.

Watching the sunset here certainly feels like being part of something special as the sky transforms into brilliant shades of orange, pink, and purple, casting a golden glow over the enthralled onlookers. We did it twice: on our first and again on our last night, and both times, we were enthralled by the sheer enthusiasm of the crowds as the day drew to a close, and a night of fun on Duval Street’s north end lay ahead of us.

Duval Street’s Intoxicating Nightlife

As daylight disappears and evening takes over, Duval Street (especially its north end) really kicks into gear. While great restaurants like Pinchers and Blackfin Bistro serve first-rate seafood dishes for seated guests, our favorite spot was the legendary DJ’s Clam Shack. And don’t be deceived by its humble exterior (it really does look like a shack!). Here, you’ll be able to grab delicious seafood staples like conch fritters, lobster rolls, and, of course, clams, all served up with delicious dressings and all with little fanfare. If you time it right, you’ll be able to grab a table at the back, but these tend to go fast. Failing that, grab your food and eat as you wander.

Then, of course, there’s the drinking. Key West is known as a place to party, and partying, of course, usually involves drinking. While there’s not a noticeable police presence (they’re discrete, but there), local bylaws do prohibit carrying open alcohol containers, so keep your drinking to the bars and clubs that line Duval. And there’s no shortage of options. From the Margaritaville Restaurant, inspired by the legendary Jimmy Buffet’s favorite tipple, to the awesome Abbey cocktail lounge, you’ll never run out of watering holes here.

Tips & Tactics: While sit-down meals are plentiful, you’ll want to book ahead as the best of them fill up fast (you’ll be lucky to get a spot as a walk-in). We discovered early on that some of the best bars don’t serve food so weren’t averse to letting patrons bring their DJ Clam Shack or Blue Heaven seafood dinners onto the patio in order to wash it all down with a cocktail… or two. Just be sure to ask first.

The Final Word

Since that first trip to wonderful Key West, my wife and I have visited the self-proclaimed “Conch Republic” three times, each one as memorable as the first. On that first visit, we drove, and the excitement of traveling the spectacular Overseas Highway from Miami still echoes and is only matched by the sheer pleasure of spending time in Key West. And while we did (and still do) walk everywhere when we got there, you don’t have to.

In addition to the tour buses, the city operates a free Duval Loop service that runs buses all day from the Atlantic side of town up to the Gulf, with plenty of stops in between. Also, numerous golf cart and scooter rental companies are available, offering an easy-to-park and easy-to-drive alternative to cars, public transit, or walking.

And don’t feel you have to see everything in Key West in a day or even a week. There’s no end of fun things to do here, and after four visits, we still haven’t seen and done everything (a ferry ride and a visit to Dry Tortugas National Park is the big bucket list item still to do). However you get there, however you get around, and however you choose to have fun, I guarantee your Key West journey will be unforgettable.