There are some places that you visit and you know that you’ll be back again and again (and again). For us, Key West is one of those places. It is a quick flight (or a 7 hour drive) from where we live and no matter how long we are visiting, it feels like a vacation. When planning a trip somewhere new, I am guilty of scouring the internet for tips, pinning places, reading reviews, and working myself into a frenzy. With that in mind, I wanted to create a list for like-minded travelers to reference of places that we love, in a place that we enjoy time and time again.

Where to Stay

Kimpton Fitch Lodge: This boutique hotel near Duval Street offers a luxurious retreat. They offer a welcome drink, including their own branded beer made by the nearby Waterfront Brewery, and include a nightly reception of drinks and snacks. The hotel is walkable to everything and also includes use of their bicycles. The rooms are small but super cute, spread out across multiple buildings. The hotel also has a nice pool area, surrounded by lush landscaping. This hotel is perfect for a family reunion or getaway.

Heron House: Hidden in lush gardens, Heron House provides an adults only escape in Key West. The property is close to Duvall Street but far enough away that you don’t hear any of the craziness. The rooms are spread throughout several historic homes and surround the pool, which has plenty of lounge seating. Above the pool there is a clothing optional sunning area, if you are trying to get rid of any tan lines. The rooms are spacious and include a wet bar and fridge, and the room rate includes a nice breakfast. This hotel is a great option for a romantic stay in Key West.

NYAH Key West: This unique spot is both a hostel and a traditional hotel. It encourages mingling with fellow travelers, featuring customizable rooms with bunks, as well as rooms with multiple rooms that you can book as a group. The hotel has a nice pool area, with three pools and a jacuzzi on offer. There is a daily resort fee of $34.95 and it covers breakfast, towel use, WiFi, and coffee all day. This is the hotel to stay at with a bachelorette, or friend group.

Airbnb: Airbnb offer a diverse range of accommodations, from cozy cottages to waterfront villas. We’ve utilized Airbnb in Key West several time when we’ve stayed for longer periods. They are all over the island and can be found in many price points.

Camping: There are a few campgrounds close to Key West but we’ve only stayed at one: the KOA on Sugarloaf Key. Depending on traffic, it is about a 20-30 minute drive into Key West from the campground. They have tent camping and RV spaces. They have a restaurant, bar, pool, and beach access. We tent camped here with friends and the experience is one of my Key West highlights.

Where to Eat

Two Friends Patio: A few years ago, some of my family members sailed from Oregon to Florida. They stayed in Key West for a while and kept telling us about this restaurant with an amazing happy hour and live music that all of the live-aboard sailors loved. We gave in on our next visit and haven’t looked back. The happy hour is unbelievable, with 1lb of Key West Pink Shrimp for $9.99 and delicious tropical cocktails. David loves it so much that on our last brief visit (2 days), we went twice.

Blue Heaven: An institution in Key West. There will be a line for breakfast, it will be worth it to dine amidst roosters with live music in a quirky garden setting.

Santiago’s Bodega: A funky beachy town isn’t the first place that I would associate with a tapas restaurant but Santiago’s does it right. We had several bartenders around the island recommend this spot and it did not disappoint. This is the perfect brunch of dinner spot to visit if you’ve had your fill of pink shrimp and conch fritters elsewhere.

A&B Lobster House: Another institution, this is restaurant offers a delightful oceanfront dining experience, serving up the freshest lobster and seafood dishes in a charming historic setting that captures the essence of Key West’s culinary and maritime traditions. This is a great spot for an upscale date night on the island.

Pepe’s Cafe: This beloved restaurant has been serving up delectable American and seafood classics since 1909, making it the oldest family-owned restaurant in Florida. This is often our first stop for breakfast when we take an early flight into Key West.

Mary Ellen’s: A quintessential Key West hangout that not only serves mouthwatering grilled cheese sandwiches but also offers a lively atmosphere with nightly activities like trivia, spelling bees, and vibrator races (yes, you read that correctly), making it a must-visit spot for those seeking delicious comfort food and entertainment in the heart of the Conch Republic.

Where to Drink

Tiki House: This tropical oasis is our regular haunt in Key West– as the name suggests, they make killer tiki drinks and visitors can learn the art of mixology at their engaging tiki drink making classes.

Irish Kevin’s: A lively pub that keeps the party going with live music (featuring drunken sing-alongs), a selection of 15 draft beers, and a must-try signature drink, the Green Gator, ensuring an unforgettable night (or day) of Irish hospitality and entertainment in the heart of Duval Street.

The Retro Room: If you are looking for gaming and entertainment haven in Key West, this spot fits the bill! It has an impressive beer selection to complement the vast array of arcade games, video games, and board games. When the summer rain hits, we like to grab a beer and board game and wait it out here.

Smallest Bar: The ideal pitstop for a refreshing drink during your Duval Crawl, a cozy (read: room for 3 people, including the bartender) and unique watering hole experience.

Schooner Wharf Bar: Located in the heart of the docks, Schooner Wharf Bar is a beloved waterfront gem where you can enjoy lively live music, strong libations, and the whimsical sight of free-roaming chickens; it’s also the perfect spot for an early morning breakfast before embarking on a boat trip.

Breweries: The craft beer scene in Key West can be experienced first had at The Waterfront Brewery and First Flight Isnad Restaurant and Brewery. The Waterfront Brewery, perched on the harbor (near Schooner Wharf Bar), offers a perfect blend of delectable brews and scenic views, with an extensive menu of house made beer to cater to every palate. First Flight Brewery, steeped in aviation history, allows visitors to savor craft beer in a historical setting, offering a flight of flavors accompanied by the fascinating story of the first transcontinental flight. I prefer to grab a beer at Waterfront but the food at First Flight shouldn’t be missed.

Distilleries: Not to lose it’s identify as a tropical cocktail town, Key West has two rum distilleries. Rum enthusiasts can embark on a flavorful journey at Papa’s Pilar and First Legal Rum distilleries. Papa’s Pilar, inspired by Hemingway’s adventurous spirit, welcomes visitors to explore their distillery with informative tours and tastings in a nautical-themed tasting room. First Legal Rum, the first legal rum distillery in Key West, offers an educational experience with tours that delve into the distillation process and tastings in their atmospheric tasting room, making both distilleries a perfect destination for those seeking a taste of the island’s rich rum-making heritage and its storied past.

Honorable Mentions: Captain Tony’s Saloon and the Hog’s Breath Saloon are two of the most iconic bars in Key West. If it is your first time visiting the island, these are two must stop destinations. On our most recent trip, we got caught in a rainstorm and discovered the Key West Fresh Squeezed Mimosa Bar. As the name suggests, the juices are pressed there and combined with a very generous pour of sparkling wine. The “bar” is a cart on Duval Street but don’t let that deter you from the best walking pick-me-up on the island!

What to Do

Sunset Boat Tours: Catching a sunset in Key West is a must-do and doing so from the water is even more magical. There are lots of companies to choose from, including lively party boats that offer music and a festive atmosphere or more serene sailboats for a tranquil and romantic experience. We have sailed on the Schooner Appledore several times and it has always been wonderful, with light Hors d’oeuvres and an open bar to enjoy while savoring the breathtaking sunset over the Gulf of Mexico.

Snorkeling Tours: Snorkeling tours provide an incredible opportunity to witness the vibrant marine life in crystal-clear waters. Key West’s coral reef, while breathtaking, is unfortunately endangered, underscoring the importance of responsible tourism. Companies like Sebago Watersports offer morning and afternoon 3-hour snorkeling tours, which not only allow you to marvel at the mesmerizing aquatic world but also include complimentary beer, wine, and soft drinks on the return trip to the port, ensuring a truly memorable and eco-conscious experience.

Ghost Tours: I highly recommended doing a ghost tour in any city that you visit that offers them. The tours offer a captivating and entertaining way to explore the city after dark, I especially like to book a tour on my first night in a new town, just to try and get the lay of the land. In Key West, tours not only provide a unique after-dark perspective on the island but also some of them incorporate a pub crawl aspect, making for a delightfully eerie and engaging way to discover the island’s spectral history while enjoying its vibrant nightlife scene. We’ve done a few in town and recommend both the Robert the Doll Experience and Key West Haunted Pub Crawl and Ghost Tour.

Kayak: Exploring the pristine waters of Key West from the seat of a kayak is an unforgettable adventure, and Lazy Dog Adventures is a top choice for this experience. They offer guided tours where you can paddle through the enchanting mangroves, providing a chance to spot a mesmerizing array of marine life, from nurse sharks and jellyfish to the gentle giants of the sea, manatees, and playful dolphins. For the more independent traveler, Lazy Dog Adventures also provides hourly kayak rentals, allowing you to create your own path.

Butterfly Garden: In need of a calm day after a night on Duval? The Key West Butterfly & Nature Conservatory is a tranquil oasis where you can wander amidst lush vegetation and be enchanted by the vibrant fluttering colors of countless butterflies in a serene tropical setting. They also have flamingos, other tropical birds, and an area to watch butterflies emerge from their cocoons.

Southernmost Point: Marked by a large buoy that represents the southernmost point of the continental United States. Visitors often line up for photos beside the buoy and the colorful marker displaying the distance to Cuba. To beat the crowds, it’s advisable to arrive early in the morning, as this popular attraction tends to get busier as the day goes on, making the sunrise hours the perfect time for a peaceful photo op.

Hemingway Home: This historic gem that once served as the home of the legendary American author, Ernest Hemingway. The house itself, with its charming Spanish colonial architecture, is steeped in literary history, and it was here that Hemingway wrote some of his most famous works. One of the most unique aspects of the Hemingway Home is its famous population of polydactyl cats, descendants of Hemingway’s own cat, Snow White. These cats, known for their extra toes, freely roam the property and are considered good luck charms by many visitors. The lush gardens of the Hemingway House also house a serene cat cemetery, where some of the beloved feline residents are laid to rest. It’s a fascinating and picturesque destination for literature and cat enthusiasts alike, offering a glimpse into the personal life of one of America’s greatest writers.

Mallory Square Sunset Celebration: The sunset celebration at Mallory Square in Key West is a daily spectacle that draws both locals and tourists. As the sun dips below the horizon, the square comes alive with a vibrant array of street performers, ranging from magicians and jugglers to musicians and artists. To secure a prime spot for this dazzling event, it’s advisable to arrive at least an hour before sunset, ensuring you have a front-row seat to the dazzling display of colors in the sky and the lively entertainment on the ground.

Key West Aquarium: This small aquarium is a quaint place to beat the rain and enjoy peeping some sea life. They have rescued sea turtles in the main exhibition hall that are always fun to watch. The aquarium is close to Mallory Square and the cruise terminal.

Where to Shop

90 Miles to Cuba: We love a good thrift shop and this place delivers with local goodies from tropical clothes, to books on local history, to a quirky selection of nautical jewelry.

Key West Island Books: On any trip, I make sure to bookmark a book store to visit. This charming store is off of Duval and is the perfect respite for a bookworm looking for a replacement book when they’ve already chewed through their vacation books.

Tucker’s Provisions: A great boutique for clothing shopping for everyone in the family. They carry unique pieces and a few things are proudly adorned with their signature rooster.

Key West Spice Company: A flavor-packed paradise for food enthusiasts, offering a delightful array of artisanal seasonings and spice blends that capture the essence of Key West.

Kino Sandals: This iconic shop captures the essence of Key West’s relaxed and fashionable atmosphere, making it a delightful place to find the perfect footwear to complement your beachy attire. They offer handcrafted, high-quality leather sandals (among other items), each a testament to timeless craftsmanship.

Kermit’s Pie Shop: A delightful taste of the Florida Keys, serving up the iconic Key Lime Pie, whose history is deeply rooted in the rich culinary traditions of Key West, making it a must-try treat for visitors seeking a slice of the island’s culinary heritage. Tip: If you forget to grab a pie in town, the airport has some to-go!

How to Get to Key West

By Air: Flying to Key West is a convenient way to reach the island paradise, with Key West International Airport (EYW) located just a few miles from the popular tourist areas, ensuring a quick and hassle-free transition from the airport to your vacation destination. This convenient airport not only saves time but also allows travelers to start enjoying the beauty and charm of Key West without delay.

Driving: Driving to Key West is a scenic adventure, with the Overseas Highway offering breathtaking ocean views and multiple craft breweries to stop and savor local beer along the way. Keep an eye out for the miniature Key Deer, an endangered species found on Big Pine Key, and make sure to drive carefully to protect these unique and adorable creatures.

Boat from Ft. Myers: While we have never taken the Key West Express, I’ve heard nothing but good things about this mode of transportation to the island. The ferry has food and a full bar– a great way to get the vacation vibes going!

Best Time of Year to Go

The best time to visit Key West is during the winter months, from November to April, when pleasant weather and a lively event calendar await. If you prefer a quieter and more budget-friendly experience, consider the shoulder seasons of May to June or September to October when the crowds thin out, and prices become more affordable. Keep in mind that May-October is Hurricane season in Florida and you should expect a bit of daily rain.

For us, any time of year is great to visit Key West– you get to the tropical island feel without having to bring your passport and there is always something exciting to see, eat, and drink.