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Key West: The Ultimate Happy Hour Guide & Tour

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Key West: Where the sun kisses the sea, history dances in the streets, and every sunset paints a masterpiece in the sky. A tropical symphony of colour, charm, and endless possibilities.
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Jody Joseph
Simply Wanderfull

Table of Contents

Cheers to 24 happy hours in Key West! This vibrant, bohemian laid back tropical paradise where every hour feels like a celebration and the sun-kissed streets come alive with music, roosters and fun times. 

Let’s take off on this spirited journey through the vibrant streets of Key West. Turn on this Jimmy Buffett Playlist make yourself a delicious Frozen Margarita or get yourself a slice of Key Lime Pie and keep on reading! Trust me this will get into the vibe of Key West quickly!

From the iconic Duval Street to the charming streets and waterfront spots, Key West boasts a plethora of bars and restaurants to chose from. My article will cover some great places to stay, yummy food, tasty cocktails, key lime pie, Jimmy Buffett some roosters, a conch tour and so much more! 

For more of a deep dive into some Key West history check out this book called Key West: A Smuggler’s Tale.

Having parrot head parents and visiting Key West many times in my life; together we came up with this great Happy Hour guide for some great first hand information on planning a visit to Key West!

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Key West Camping Old Family Photo: 1992
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Parrot Head Parents
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Jimmy Buffett Concert

Key West Information:

Here is some basic information on Key West!

  • Southernmost City: Key West is the southernmost city in the continental United States, situated at the tip of the Florida Keys archipelago. Key West is located approximately 129 miles southwest of Miami, Florida. The most common route to travel from Miami to Key West is along the Overseas Highway (U.S. Route 1), which connects the mainland to the Florida Keys and the route to where all your troubles melt away.
  • Tropical Paradise: On average, Key West experiences around 250 to 260 sunny days per year making it an ideal destination for those seeking sun and relaxation.

  • Small But Mighty: Key West is approximately 4 miles long and about 1 mile wide at its widest point. The island is relatively small, and its compact size makes it easy to explore by foot, bicycle, or other forms of transportation. 

  • Historic Charm: Immerse yourself in history with attractions like the Ernest Hemingway Home, Truman Little White House, and Fort Zachary Taylor Historic State Park.

  • Vibrant Duval Street: Experience the lively atmosphere of Duval Street, known for its vibrant nightlife, diverse shops, and a variety of restaurants.

  • Water Adventures: Explore the crystal-clear waters surrounding Key West through activities such as snorkeling, diving, fishing, and boat tours, offering a rich marine life experience.

For more in-depth travel information check out The New Key West Bucket List: 100 Off Beat Adventures in the Southernmost City.  

 
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Sloppy Joe's Bar, Key West

Getting To Key West

Getting to Key West may take a bit of pre-planning. You can drive, fly or take a boat!

Drive: The most scenic way to get to Key West would be by car from Miami, Florida. The drive is approximately 129 miles and takes approximately 3-4 hours depending on traffic. Winding through a series of interconnected islands including the beautiful Key Islamorada, this iconic highway offers breathtaking views of turquoise waters and lush landscapes. If you are not in a hurry, grab a bite to eat along the way at Marker 88 or Robbies of Islamorada . A great mid-way stop to Key West offering cold drinks and delicious food! For a beautiful overnight stay check out the Checca Lodge in Islamorada. It is located right on the water with some great fishing, fine dining and beautiful accommodations. 

Another notable stop would be the Seven Mile Bridge. An iconic engineering marvel, the Seven Mile Bridge provides stunning views of the turquoise waters. Stop at the Old Seven Mile Bridge for a leisurely walk or bike ride. You may remember the Seven Mile Bridge in the movie True Lies. A 1994 action-comedy film directed by James Cameron and stars Arnold Schwarzenegger and Jamie Lee Curtis.

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Marker 88
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Seven Mile Bridge

Boat: Taking a boat is a quick and great way to get to Key West if you are already visiting other parts of Florida. 

The Key West Express offers service to Key West from Fort Myers, and Marco Island. The trip takes approximately 3-3.5 hours and you avoid all that nasty Miami traffic! We have taken the Key West Express twice now and can say it was very convenient and less stressful way to get to Key West!

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Key West Express
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Key West Express Fun

Plane: Although Key West is a very small airport they do have direct flights from major cities such as: New York, Boston, Fort Lauderdale, Miami, Charlotte, Atlanta, Chicago and more. 

Some of the major airlines that currently fly to Key West are: American Airlines, Delta Airlines, United, Jet Blue and Silver Airlines.

The airport is right in Key West and not far from all of the attractions.

TIP: For my travel planning I love to use Kayak for car rentals, airfare and hotel pricing.

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Where To Stay:

Key West has plenty of accommodations for such a small island! From hotels, and inns to bed & breakfasts to house boat stays, airbnb’s and camping! They really cover it all! Check out a full list at the official Key West Tourism page. I will note a few great places here that you may want to consider.

Luxury Hotels:

Inns & B&B:

Camping:

  • Boyd’s Campground Located on Stock Island and close to Key West has some cool campsites right on the water!

Houseboat Rental:

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The Simonton
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Casa Marina Waldorf Astoria

The Ultimate Key West Happy Hour guide:

Key West has many bars and restaurants to choose from and too many to count! Here is a list of some of the notable places to visit while you are in Key West.

Blue Heaven: Tucked  away on a quaint side street is the Blue Heaven Al fresco dining outdoors, featuring live music, cold drinks, the BEST Key Lime Pie and great food!

The Saint: This bar offers a unique happy hour from 4:17-7:17 pm with 30% off drinks and an assortment of $10 plates.

Martin’s: Known for its quality tapas and signature martinis, with 50% off on these items during happy hour from 4-6 pm.

Schooner Wharf Bar is a notable mention. This open-air, waterfront bar offers two daily happy hours, one from 8 AM to noon and another from 5 to 7 PM. Known for its friendly atmosphere, live music, and nautical-themed decor, it’s a popular spot for enjoying cold drinks and delicious food like Peel & Eat Shrimp and Conch Fritters, all while overlooking the marina. 

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Schooner Wharf Bar

The Bull & Whistle Bar: Featuring 3 separate bars on 3 floors. Located on Duval and Caroline a Key West gem! Local musicians play each night.

The Green Parrot: The only food here is the free popcorn which is always flowing. The very best time to come here is on Fridays for “soundcheck”. The featured band does a set from 5-7 pm and it’s a party not to be missed. Discounted drinks are everyday 4-5:30 pm. 

La Te Da’s: The Terrace bar is a great place to people watch with a cold beverage in hand! So Much Fun! Jimmy Buffett even sings about La Te Da’s in a song!

 

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Tiki House Bar
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Captain Tony's Saloon

Captain Tony’s:  Favourite watering hole for many celebrities from Jimmy Buffett to Ernest Hemingway. Originally built in 1851 and is a must stop on your Happy Hour Tour.

Old Town Mexican Cafe
All-week, 4pm-6pm 1/2 price apps, wine, beer, and well drinks

Happy Hour Stops On Google Maps!

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Sloppy. Joe's Bar
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Schooner Wharf Bar

The Hogs Breath Saloon is located at the corner of Front and Duval streets entertaining guests for 20+ years with live musical talent from local to national levels. Stop by to catch the awesome live music. Grab a cold beer in, and don’t forget to pick up a Hog’s Breath T-shirt in their store. Check out the menu and see who will be playing the music lineup.

The Iconic Sloppy Joe’s Bar: is a Key West institution that has been around since Prohibition was repealed in 1933. The bar has seen its share of famous patrons, including Ernest Hemingway, and has a laid-back, down-to-earth atmosphere that has kept people coming back for generations. And YES they do offer Sloppy Joe’s on the menu! A Key West Favourite!

Louie’s Backyard: American & Caribbean Flare in a spectacular ocean front setting with fine dining. Magical panoramic views of the Atlantic Ocean await you at the Upper Deck at Louie’s. Fine wines by the glass or bottle are served as a perfect compliment to the small plates of focaccia, carpaccio, oven-fresh gourmet pizzas and more. Open 5-10pm, Tuesday through Saturday. A local and visitor favourite for over 25 years.

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Louie's Backyard
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Hog's Breath Saloon

Santiago’s Bodega: Tapas and Happy Hour from 3pm to 6pm 

Southernmost Beach Café: 4pm to 6pm

The Roost: Noon-6 pm. Nibbles and well $6 drinks 

The Saint
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Alonzo's Oyster Bar

Roostica: Stock Island here’s a $5 small plate menu with bruschetta, wood-fired wings, sausage  and meatball sliders, and a 1-topping mini-pizza. The happy hour bar menu includes $7 wine, $4  well and beers for $4 and $3, draft and domestic respectively and runs from 4-6 pm. 

Ram’s Head: Basic bar food, peel n’ eat shrimp which is a good deal at 50% off for any app. Table or bar  seating is available and it’s one of the cheaper places in town especially if you’re a beer drinker;  $4 draft or domestic bottles and $2 off any wine or liquor. Happy Hour: 4-6 pm 

Martins: The signature martinis, well drinks, and all the tapas are 50% off. Yes, you read that right. So  hurry over there when you get into town for one of the best happy hours in Key West. Happy  hour runs from 4-6 pm. 

Grand Cafe: What a great way to sample the fine dining menu with appetizers that are 50% off. Beer, wine,  and all cocktails are also half-price. This is one of the more upscale best happy hours in Key  West 4-7 pm. 

 

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Roostica, Stock Island
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Martin's

Galleon Sunset Tiki Bar : There’s no food happening here so you’re coming strictly to get hydrated. There’s actually two  happy hours. If you want to get an early start, check out the 2 for 1 Bloody Mary’s 10am-Noon,  Mon-Sat. Sunset happy hour is 4-7 pm with 2 for 1 rocks margaritas and well drinks. 

Boat House Bar and Grill : While you can get the requisite conch fritters, many of the small plates are not run-of-the-mill  bar food. Think lobster tempura, bbq ribs, coconut shrimp, baby lamb chops. Pretty nice  especially since the food, well drinks, beer, and wine are half-price. HH: 4-6 pm 

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Latitudes Sunset Key
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Captain Tony's Saloon

Alonzo’s Oyster Bar: There’s no guesswork here because there’s actually a happy hour small plate and bar menu. As  the name implies, there’s a raw bar offering $2 raw oysters on happy hour. This isn’t gourmet  food but decent-portioned bar food and a $4 well drink or glass of wine is a steal in Key West. 

Latitudes on Sunset Key: If you celebrating something special consider Latitudes. A special romantic setting and fine dining. Latitudes is considered one of the BEST restaurants in Key West.

The Smallest Bar in Key West:  72 square feet and the size of a jail cell this quirky little Happy Hour stop is worth a mention. Located near Mallory Square.

Two Friends Patio:  This is a great choice for breakfast and Mimosa’s! Get. yourself a piece of Key Lime Pie. here, its absolutely delicious! I also have a great recipe for tiny Key Lime Pie Tarts that tastes a lot like their key lime pie.

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Smallest Bar Key West
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Two Friends Patio

Key West Happy Hour Guide Brochure

Things to do in Key West

Key West offers so many great things to do! Here are a few recommendations that I can offer:

  • Conch Tour Train: The Conch tour is a great way to get acquainted with Key West and you. can take advantage of the hop on hop off option to explore each of the areas throughout Key West. It is also great if you just want to hear a little history of the area and get off your feet for a bit! There are 2 tours. One that is focused on the main Duval Street and surrounding area or the second tour takes you around the entire island. Both tours are fantastic!
  • All-Day Watersport Adventure: If you have time and love being on the water check out this tour! It offers a full day of Jet Ski, Snorkel, Waterpark, Kayaks, Lunch & More! We took this tour for my 40th.  birthday and had an incredible day! Definitely worth the money. There are many companies that operate in Key West for water sports, sunset sails and other water activities. For more information check out: Sunset Water Sports Key West or Fury Key West.
  • Jimmy Buffett Tour: Jimmy Buffett and Key West go hand-in-hand. Take a walking tour around Key West and visit some of Jimmy Buffet’s stomping grounds. Visit the place where he played his first gig, the home of the famous Cheeseburger in Paradise, to his favourite watering holes and discover the inspiration behind some of his greatest hits!
  • Rent Some Bikes: Taking a bike ride around Key West is my most favourite thing to do in Key West! It is a great way to see the island and you can take stops for some cold beverages and keep on moving! Check out Eaton Bikes or Fury Bikes for more information on bike rentals.
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Jimmy Buffett Recording Studio
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Sunset Water Sports

Southern Most Point: Visit the Southernmost point in the Continental United States of America. Symbolized with a buoy and a great photo opportunity.

Ernest Hemingway House:  Ernest Hemingway a famous writer and lover of cats! Visit his beautifully maintained estate and museum.

Sunset Celebration: Each night there is a celebration of the sun arts festival that takes place at the pier and the end of Duval Street. Here you will find street performers, delectable foods, tarot card readings, and keepsakes. 

Parades, Festivals and More: Key West loves a parade and a festival! There are always so many events occurring throughout the year! Most notable is the Fantasy Festival, the Key West Pride Festival, Hemingway Days and More. For the complete schedule of events check out the Key West Tourism page.

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Southernmost Point
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Sunset Celebration Key West

Key West Butterfly and Nature Conservatory: A tropical paradise housing thousands of butterflies, exotic birds, and vibrant flora in a glass-enclosed habitat.

Dry Tortugas National Park: Accessible by ferry or seaplane, this remote national park features Fort Jefferson, pristine beaches, and incredible coral reefs for snorkeling.

Key West Aquarium: Experience interactive exhibits showcasing marine life native to the Florida Keys, including sharks, sea turtles, and stingrays.

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Key West can get very busy with tourists especially in the peak season. You may want to check out Stock Island! Nestled just northeast of Key West, Stock Island is a hidden gem that captivates visitors with its authentic charm and diverse offerings.

Known for its maritime heritage and thriving arts community, Stock Island provides a refreshing escape from the bustling streets of Key West.

Travelers can explore its working waterfront, where vibrant shrimp boats and fishing charters dock, creating a picturesque scene. The island boasts a burgeoning culinary scene, with waterfront restaurants serving up fresh seafood and local flavors.

With marinas, nature trails, and a laid-back atmosphere, Stock Island offers a delightful retreat for those looking to experience the genuine character of the Florida Keys while remaining in close proximity to the vibrant energy of Key West.

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Stock Island

cheers to key west!

I hope that you found this article to be helpful and that you get a chance to visit Key West! It is definitely a place to add to your travel bucket list! Download my Key West Happy Hour Guide for an easy way to see all the great restaurants and pubs of Key West from the palm of your hand!

I would love to hear from you! Do you have questions? Have you been to Key West and want to add some other great places that may have been missed? Drop me a line below!

I really appreciate you taking the time to read my blog article and I hope that Key West brings you great memories also. I am so grateful to have visited Key West with my family and friends throughout the years. I can’t wait to make many more memories on this beautiful island paradise! Cheers to Key West!

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14 thoughts on “Key West: The Ultimate Happy Hour Guide & Tour”

  1. Awesome read and yes such a beautiful place. And does anyone remember the brownie lady at the celebration of the sun back in the 90’s.

  2. “Key West: The Ultimate Happy Hour Guide & Tour is an absolute gem for anyone seeking the perfect blend of relaxation and revelry. This guide unveils the hidden treasures of this vibrant island, leading you to the best happy hour spots where you can savor the laid-back atmosphere and sip on refreshing concoctions. With its expert recommendations and insider tips, this guide transforms your visit into an unforgettable adventure, ensuring every sunset in Key West is accompanied by a cheers-worthy moment.”

  3. You have certainly captured the essence of Key West. Having travel there for over 30 years on an annual pilgrimage it is our go to place for good times. Great memories and lots of sunshine Jody. Congratulations on another fantastic article.

  4. I absolutely love Key West. I haven’t visited for over a decade but now I really want to go back after reading your delightful article. The only thing missing was a photo of a Hemingway cat. They are adorable.

  5. I really loved Key West (it’s been a while) especially driving there over all the bridges from Miami was such fun. And of course, we visited the Hemingway Museum. Don’t care too much for his writing but acknowledge he is a literary great- of course we came for the cats!

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