Laid-back Key West

My Guide & Bucket List

Key West and all of it’s laid-back island vibes make it the perfect getaway! It’s been the location of our last two Annual Girl’s Trips and it plays host to more bachelor and bachelorette parties than you can shake a stick at. The famed Duval Street is the smaller, cleaner, beach-ier Bourbon Street and a welcoming party scene when you live an hour away from the real Bourbon Street like we do. Key West is easy. Everything you want to do is close by and most of it’s within walking distance which I think is perfect when you’re dealing with a group and looking to party. Packing’s easy too! All you need is a swimsuit, some short dresses, t-shirts + shorts, and flip flops. It’s hot and there’s never a need to get dressed up in the Keys making it easy to stuff everything in a backpack and avoid those baggage fees on your Spirit flight!

There’s no other place quite like it and I’m sending lots of good vibes to the Conchs who are in the midst of recovering from devastating Hurricane Irma which hit just one week after we last visited. If you’d like to donate, your tourism dollars may be the best donation you can give or you can simply donate to any of these charities:

  • Florida Disaster Fund was established to help Florida communities respond and recover during times of disaster. One hundred percent of the proceeds go toward disaster-related relief. Donations are tax deductible. Click here to donate or text the word DISASTER to 20222 to make a onetime donation of $10.
  • The Hurricane Irma Community Recovery Fund supports grassroots Florida organizations which are helping the most vulnerable communities recover.
    Donate here.
  • Dogs and cats housed at shelters by the Humane Society of Greater Miami are accepting monetary donations to help give the pets a comfortable place to live while they wait for a loving human to take them to their fur-ever home. To make a donation visit

How to get there:

It’s cheaper for us to fly into Fort Lauderdale which is just north of Miami so we typically rent a car from the airport and get a room for the night at the Hollywood Beach & Suites (a super cute hostel) so we can eat at the Taco Beach Shack. Amazing tacos & $2 PBR’s anyone?! It’s also easy access to Hollywood Beach and there’s a Greek bar across the street – Taverna Opa – or you can check out Bonny & Read’s for beachfront drinks and pub grub.

Hollywood Beach & Suites

Other options include flying into Miami or spending more to fly directly into Key West – but you’ll miss out on the Keys road trip!

Our Favorite Stops on the Florida Keys Road Trip:

The road trip takes about four hours straight thru but can take much longer depending on what stops you make. (Or if it’s Labor Day it could take you 8 hours… 😬)

Sundowner’swith a porch overlooking the water in Key Largo and our personal favorite Key Lime Pie in all of the Florida Keys you’ve got to stop here! We also love their Fried Green Olives with fig jam. P.S. Be sure to try their sea salt scrub in the bathroom which is available for purchase.

Sundowner’s Key Lime Pie

Islamorada Beer Company quick stop right on Highway 1 to grab a flight of local brews. Friendly staff + bar games.

Keys Fisherieshome of the legendary Lobster Rueben in Marathon.

Turtle Hospital – We still haven’t timed it quite right to be able to reserve a spot on the 90 minute tour of this sea turtle hospital and rehabilitation facility which includes a presentation on sea turtles, a behind the scenes look at the facility and a chance to feed the permanent residents! Call (305) 743-2552 to make a reservation. Tours typically run daily from 9:00 – 4:00pm every hour on the hour.

Where to Stay:

So far we’ve rented the Sea Breeze condo through Key West Vacation Rentals and the Casa Bella condo through AirBNB which had a rooftop pool. Both came with free parking and were located steps from Duval. The Circle K is right there too so we could grab drinks for the pool and groceries. We stayed on the quieter southern end of Duval because the end closer to Mallory Square was sold out by the time we booked but it’s not too difficult to walk from one end of Duval to the other. The addition of readily available Uber’s and Lyft’s in 2017 makes things even easier.

Breakfast & Brunch:

Cuban Coffee Queen – to grab a Cuban con Leche (Cuban espresso with steamed milk) and pan cubano (toasted Cuban bread) that you can dunk in said coffee and to get a picture in front of the Key West postcard.

Image result for cuban coffee queen
Photo Credit: Key West Historic Seaport

5 Brother’s Grocery & Sandwich Shop – another spot to get your Cuban coffee fix. They also have a mouthwatering Cuban sandwich.

Blue Heaven – an iconic stop on any Key West trip. Go for brunch and try the Lobster Benedict and their insanely tall Key Lime Pie if you love meringue. You’ll have a great time waiting for your table exploring the eclectic courtyard.

Le Petit Pari – a cute little morning spot for french fare like crepes and croissants.

Pepe’s Cafe & Steakhouse – A Cuban fisherman opened Pepe’s in 1909 making it the oldest eatery in the Keys. It’s a local’s place but visitors have caught on. Their motto, “A fairly good place, for quite a long while.” Grab a good-old-fashioned breakfast like their chipped beef on toast.

Glazed Donuts – Insta-worthy donuts.

Lunch & Dinner:

Half Shell Raw Bar – for your fill of local seafood like stone crab and Key West Pinks.

The Schooner Wharf Bar Laid-back local’s spot with lawn chairs and a Tiki vibe overlooking the Historic Seaport making it the perfect spot to catch the sunset plus live music, fresh seafood and a vast selection of tropical cocktails. We loved their Mahi Mahi and Drunken Shrimp. Bonus: you can take the shells from the shrimp and feed them to the tarpon from the pier!

El Siboney – the spot for traditional Cuban home cooking.

B.O.’s Fish Wagon – This driftwood shack looks like it’s about to fall over but it’s a staple in Key West for fresh fish sandwiches, conch fritters and fast food like burgers. Cash Only.

Santiago’s Bodega – tapas bar with generous portions plus House specialty Sangria all served in an inviting atmosphere.

Kojin Noodle Bar – When you’re hungover and need some Ramen in your life this New York style hole-in-the-wall will hit the spot.

Garbo’s Grill – Visit this Airstream turned food truck featured on Diner’s, Drive-In’s and Dives to try their fish tacos, burritos, hot dogs & burgers.

Onlywood Pizzeria Trattoria – for authentic Italian pizza.

Night Life:

The Porch & The Otherside Be sure to check out the bars located on the first floor of the famed Porter Mansion (Caroline’s is on the side facing Duval). The Porch has an eclectic vibe and an excellent selection of beer. We tried the Crazy Lady Honey Blonde Ale on the bartender’s recommendation and loved it! The Other Side is a more upscale cocktail bar where we had a delicious Hemmingway Daiquiri because when in Rome. They prepare all of their cocktails with the freshest ingredients and finest spirits. You can bring your drinks out to the courtyard if the bars are too packed or you fancy some fresh air.

Brief history lesson: the real original Sloppy Joe’s was in Havana, and no longer exists. Some believe “Sloppy Joe” Russel’s bar was the inspiration for a bar Hemmingway called “Freddy’s” in his Key West novel To Have and Have Not.

Sloppy Joe’sfor when you wanna get Sloppy! A must do on any Key West trip.

As the story goes, “Sloppy Joe” Russell abruptly moved half a block from the current location of Captain Tony’s Saloon (see below) to the current Sloppy Joe’s location in 1937, upset that his landlord had raised the rent $6 a month. His patrons helped him move out — at midnight. Since he owned the bar thought to be “Freddy’s” he claims to be home of the Original Sloppy Joe’s of Hemmingway fame even though the location changed.

Sloppy Joe’s

Captain Tony’s Saloon The other maybe more original, Original Sloppy Joe’s. From 1933 to 1937, “Sloppy Joe” Russell ran a bar out of this former city morgue where Captain Tony’s is now located. Captain Tony’s has a ton of history and embodies the laid-back bohemian paradise of Key West. Captain Tony himself is a former mayor, the inspiration for the Jimmy Buffett song “Last Mango in Paris” and a Key West original in his own right who still frequents the bar at 80 something years old. I just think since it’s less commercialized and it’s the original location it’s “more original” but regardless both bars are worth checking out.

The Green Parrot – Open in various iterations (a grocery store, then a bar) since 1890, the Parrot attracts an “old salty dog” crowd of locals and fishermen, with a smattering of tourists lucky to have found the much-beloved dive spot.

If you’re looking for a wine bar try Vino’s on Duval or check out Point 5 located on the second floor of a gorgeous old home above Nine One Five.

Vino’s on Duval

Mary Ellen’s Bar – This place is tucked off of Duval Street but had a great crowd in the late afternoon when we passed by. Try their famous Jameson Frozen Irish Coffee. They also specialize in grilled cheese!

Smallest Bar to grab a Rum Punch served in a fresh pineapple and try to get a seat at one of the 3 barstools.

Rick’s for when you wanna dance the night away.


Garden of Eden – if you wanna get naked. For real. This clothing optional bar is located on the third floor of the The Bull and Whistle Bar.

If you’d like to take your pub crawl to the next level check out my Bar Golf Scorecard: Key West Bar Golf. It’s sure to get you Sloppy and should probably be broken up into two nights πŸ™‚

Late Night Eats:

Mr. Z’s – fresh made stromboli, signature cheesesteak, pizza by the slice or by the pie.

Sandy’s Cafe – hole-in-the-wall sandwich joint located inside a laundromat. Grab a Cuban Mix.

Things to Do (besides eat and drink!):

Beaches – Don’t come to Key West for the beaches because they’re not the long stretches of white sand you picture when you think of Florida but if you want to get some Sand and Sea in here are your options:

  • Southernmost Beach – It’s a small beach but you can hit up the cafe for a Key Lime Colada and take a dip in the ocean. Chair rentals are available through the hotel and you can also wait in line to snap your obligatory photo in front the iconic Southernmost Point Buoy.
  • Smather’s BeachThis man made beach has a much larger stretch of sand, chair rentals and volleyball courts. Plenty of water sports rentals too. The waters can be a little rocky though and seaweed washes up on shore.
  • Higgs Beach – At this dog friendly beach there are plenty of palm trees and volleyball courts but same deal with Smather’s… the water is a little rocky and seaweed washes up on the shore. You can grab drinks and a meal at Salute! on the Beach.
    Higg’s Beach
  • Fort Zachary Taylor – blessed with a well-maintained, sandy beach with chairs, umbrellas and watersports equipment for rent. Completed in 1866, the fort played important roles in the Civil War and Spanish-American War, and visitors can tour the National Historic Landmark every day at noon. This 54-acre state park is also home to several nature trails, a stunning coral reef for snorkelers, picnic tables and a beachfront cafΓ©. The three-story fort once held the largest collection of Civil War cannons in the U.S. (many of which are still there). Admission to the park is $2.50 when walking or biking and $6.50 per car. Stop by the Eco-Discovery Center, it’s free! Just a step away from Fort Zachary Taylor State Park, you’ll find their star Living Reef exhibit, which includes a 2,500-gallon reef tank teeming with colorful living corals and tropical fish.

Excursions – Jet Ski, Snorkel, Scuba Dive, Wine Cruise, Para-sail… look at what’s on offer through Danger Charters or Fury Cat. We did the Rum and Reggae Sunset & Snorkel Cruise with Fury which was kind of a bust due to the jellyfish but not their fault. Just bad conditions due to recent storms. The crew was great and the rum punch was actually tasty and strong. Overall it was nice to be out on the water for a few hours. We’ll try our luck with the jet skis next time!

Fury Charters – Rum & Reggae Snorkel & Sunset Cruise

Hemmingway’s Home – For $14 cash you can take a 30 minute tour of the home of famed American Writer and Key West legend Ernest Hemmingway. You’ll also get to visit with the six-toed cats that call the property home.

Key West CemeteryIt might sound like a strange place to go but with saucy epitaphs like “I Told You I Was Sick” and “At Least I Know Where He’s Sleeping Tonight” this cemetery makes a great place to take a morning stroll with your Cuban coffee before the sun hits it in the afternoon. The tombs are above ground (like in Nola) since the rocky soil made digging down impossible. Grab a map at the main entrance or check out the online brochure that details some of the more fascinating plots.

Take a Day Trip to Dry Tortugas National Park – an archipelago about 70 miles offshore. The 100-square mile park is mostly open water with seven small islands. Accessible only by boat or seaplane, the park is known the world over as the home of magnificent Fort Jefferson, picturesque blue waters, superlative coral reefs and marine life, and the vast assortment of bird life that frequent the area.

Key West also has plenty of tours… ghost tours, food tours, walking history tours, or sightseeing on the Conch Tour Train. You’re sure to find something that interests you!

Let me know of any favorite restaurants, bars or activities that I’m missing in Key West or if you have any suggestions on a new location for next year’s Girl’s Trip!

Kim Live Signature


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