The Ultimate Key West Date Guide

Key West date guide - the casa marina resort pier
Key West Date Guide - Mallory Square
Key West date guide - The Ernest Hemingway is a great local attraction

The historic town of Key West Florida is perfect for a romantic getaway with the love of your life. Key West offers a wide range of activities for any couple looking for a place to celebrate a honeymoon, anniversary, or even a simple getaway. To help you better plan your stay, our Key West date guide will ensure long lasting memories of this destination.

Where To Stay

The Kimpton Lighthouse Hotel is a boutique property located in the heart of downtown, and I would argue in one of the best locations in town. Specifically, the Kimpton Lighthouse is situated on Whitehead Street across from the Ernest Hemingway Home and Museum. This boutique hotel offers a lot when you stay here, and when you add in its extremely convenient location, it becomes a must-stay for when you visit Key West!

The Perry Hotel is located on Stock Island – just a few minutes from Key West. This property is truly special. The grounds are absolutely beautiful—with so much to do! If you’re looking for an island paradise with activities to keep you busy throughout your stay, look no further than the Perry Hotel.

The Casa Marina is a luxurious Waldorf Astoria Resort. This resort offers stunning views, exceptional service and stylish accommodations. With a large beach that is reserved exclusively for hotel guests, the Casa Marina is an elegant refuge for Key West travelers.

The Oceans Edge Resort and Marina is another spectacular gem on Stock Island. Life at Oceans Edge is always active if you choose it to be. The hotel offers a myriad of outdoor experiences from kayaks to paddle boarding to bike rentals to yoga classes. The property spans over 20 acres and offers six swimming pools and gorgeous views of the ocean and lush gardens. In short, the hotel offers all the reasons to come sample the fun in Key West!

What To Do

If you are planning to visit Key West with your significant other, it can sometimes be hard to find an activity that both of you will enjoy. Here are some of the most popular dates in Key West that I think everyone will love!

The Ernest Hemingway Home and Museum is the island’s #1 attraction and is definitely a must-see. The home is beautiful and rich with Key West history. You can take a guided tour and learn more about the property and the famous writer that once owned it, Ernest Hemingway. It sits on an acre of picturesque gardens with many cats roaming around – a lot of them being descendents of Hemingway’s own polydactyl cat.

All aboard! Hop on board the Key West Conch Train for an exciting tour of the island. The old-fashioned train ride will give you a great view of this tropical wonderland from a different perspective, and the local guide will tell you all about the history of the island, from its settlement by explorers to its rise as a popular tourist destination. The train stops at a number of attractions, so sit back and enjoy the ride, and don’t forget your camera!

The iconic and beautiful Key West Lighthouse is a lovable landmark in Key West. Visitors can climb the 88 steps to the top of the lighthouse, as well as walk the grounds and keeper’s quarters. Inside, you will find the belongings and photographs of past lighthouse keeper’s and their families. 

The Key West Butterfly and Nature Conservatory! Experience a unique and dramatic collection of exotic butterflies, birds, flowers, and trees in this magical paradise. Learn more about these beautiful creatures, and explore the gift shop and gallery.

The sunsets in Key West are truly something to see. One of the best places to watch the sunset is Mallory Square which is near Duval Street. Every night, you can watch street performers for the sunset celebration. Another great option is to reserve a sunset cruise with Sebago Watersports. They offer a few different experiences and activities, but they’re all sure to have an amazing view of the sunset.

Another great stop for Key West history, The Audubon House. Explore the stately home and beautiful gardens and get a glimpse of life in Key West during the late 19th century. You can also shop for beautiful artwork and collectables inside of the museum store.
Spend a day at the Dry Tortugas National Park. With its vibrant coral reefs, island wildlife, crystal blue water, and rich heritage, the Dry Tortugas will not disappoint! Tours provide travelers with spectacular opportunities to witness the abundant marine life as well as history and wildlife of this remote Florida destination.

Where To Eat

When it comes to vacationing, the hardest part for me is finding great spots to eat and drink. With so many options, it can be overwhelming deciding which restaurant or bar you should try out while visiting. We’ve curated a list of some of our local favorites.

Bagatelle is a beautiful gem that offers brunch seven days a week as well as two happy hours! If you still need convincing, their menu consists of an array of eggs benedict, lobster mac and cheese, fresh local fish,fine steaks, and so much more – yes, our mouths are watering too.

Bagatelle has a sister, and her name is First Flight. The restaurant/brewery’s building is very famous on it’s own for being the birthplace of Pan American World Airways. The brewery offers three original brews on tap, and the restaurant offers a delicious lunch and dinner menu with an inviting atmosphere.

Santiagos Bodega is an amazing tapas restaurant with a relaxed and eclectic atmosphere. Make sure to order the saganaki – you’ll thank me later.

If you are seeking a relaxing and laid back place to enjoy some great food while exploring Key West, you cannot go wrong by visiting Blue Heaven. You may have even heard of it, as it is quite famous for its welcoming outdoor dining experience – featuring neighborhood roosters and cats – as well as its amazing food.

Louies Backyard is a Key West restaurant that locals love and visitors flock to. It’s a waterfront dining destination with one of the best views in the town – a large outdoor patio, a sandy beach and a glittering ocean that spreads out before you.

When visiting Key West, Latitudes at Sunset Key Cottage is the perfect place to have an unforgettable dining experience, offering tantalizing views of the offshore waters of Key West along with an award-winning menu.

Key West is a magical place, rich in history and full of fun places to go. You and your significant other are sure to have a great time together. We hope that you take us up on some of the suggestions in our Key West date guide, and we would love to hear about your experiences! Planning more than just a weekend getaway? Contact us today to get started on planning your Key West wedding!


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