The Keys to Key West

Name a better combination than the sun and the sand and a book in your hand. I don’t think you can! I’m most relaxed when I’m at the beach. The sound of the waves crashing while I casually sip on a strawberry daiquiri? The dream. Which is why I’ve pieced together the ultimate Key West itinerary for book lovers who thrive at the beach and enjoy a side of key lime pie on a stick. You can spread this list out across multiple days for a casual vibe, or if you’re ambitious, cram everything into one. The choice is yours, but I promise you’ll have a great time.

Snorkel Along the Reef

Obviously our first stop involves surf and sand. What kind of Key West itinerary wouldn’t start with you lathering on sunscreen first thing in the morning and heading out to sea? A shitty one, frankly. But this isn’t a shitty itinerary, no. I’m taking good care of you over here, which is why your first stop of the day is the Opal Key Marina for morning snorkeling. I highly recommend booking through Fury. They have a ton of times available, they offer discounts and deals, and their staff was knowledgeable and safe while also fun as hell. We booked a 3-hour excursion that left mid-morning so that we could sleep in, but they had both earlier and later options available. If snorkeling isn’t your vibe, they also offer sunset catamaran cruises, jet skis, parasailing, and a host of other water sport fun.

Hemingway House

When I tell you the Hemingway House is a haven for readers and tourists alike, I’m not exaggerating. This is one of the most stunning properties I’ve ever visited. Located in the heart of Key West, guests can tour Ernest Hemingway’s former home and grounds. The house was built in 1851 by a skilled marine architect and salvager named Asa Tift. It follows a French Colonial style and features 18-inch-thick limestone walls that provide protection during tropical storms and hurricanes. The site’s elevation of 16 feet above sea level makes it one of the highest points on the island.

During his time at the Hemingway House, Ernest penned some of his best-received works, including:

• Green Hills of Africa
• Short stories like “The Snows of Kilimanjaro” and “The Short Happy Life of Francis Macomber”
• Novels such as To Have and Have Not and Islands in the Stream

After Hemingway’s divorce and passing, the house became a private museum in 1964. It was designated a National Historic Landmark in 1968, where it remains a popular tourist attraction for literary and architectural lovers. If you get the chance to stop by, I highly recommend it.

Lunch at Moondog Cafe

I hope you’re hungry, because we skipped breakfast (since you can’t swim for 30 minutes after eating) in favor of a big lunch. Moondog Cafe was one of my favorite meals on the island. The seating area is a quaint little cottage, yet it’s lively with a ridiculous delicious menu. We ordered the Caesar salad, the shrimp tempura salad, and the gyro pizza. When I tell you I still dream about their wasabi soy dressing, I’m not exaggerating. Moondog’s also has a great bakery, so if we hadn’t been in such a rush to get to the marina, I highly recommend stopping for breakfast.

Island Books

You know if I’m traveling, I’m seeking out then recommending independent bookstores. This Key West itinerary could specialize in just independent bookstores if I tried hard enough. Instead I’ll focus on two. Island Books was one of my stops, and it’s worth adding to your itinerary. Centrally located in Old Town Key West, Island Books specializes in used books, local and South Florida Authors, Ernest Hemingway special editions and biographies, as well as national best sellers. The shop smells of old book glue and caries that unmistakable Southern Florida charm known only throughout the Keys. Island Books does a fantastic job of showcasing and promoting local talent, whether it’s through book signings or readings. Their mission focuses on the support of local businesses, and they vow “If you don’t like to read, you haven’t found the right book.”

Books & Books

If Island Books is where you go for salvaging cheap used copies or discovering a local author, Books & Books is where you take your pick of national best sellers. The shop offers over 5,000 titles, so you’ll have a wide selection of genres, topics, and popularities. Their curation is fantastic; I found the most unique book about seashells next to the Zabar family biography. Now that’s a selection! Books & Books also offers signings, readings, and special events to engage with and grow their community of readers. They aren’t just focused on the literary arts either. The store has a whole section devoted to fine arts, where customers can purchase canvases, oil and acrylic paints, calligraphy pens, artisanal journals, you name it. We love seeing small businesses go to extraordinary lengths to preserve the arts within their communities.

Eaton Street Seafood Market

Whether you’re craving lobster, crab cakes, smoked tuna, or other seafood delights, Eaton Street Seafood Market promises a memorable dining experience in Key West. For offering such a wide variety of high quality seafood, Eaton Street specializes in casual dining. It’s as unpretentious as it is delicious. Their prices are reasonable for the quality they offer, but the menu does offer some splurge items. So if you are on a budget, just be vigilant. You’ll have options on how you want to eat: either buy and take home to prepare or have your fresh catch cooked on site. I ordered a couple of stone crab claws just to satisfy my craving (to make a meal out of these would have bankrupt me). I also ordered the shrimp salad on a croissant: cool, refreshing, and outstanding!

Duval Street Bars

The sun is beginning to set, and you’re ready to take on the night. Duval Street is obviously the move. Whether you want to drink and dance the night away or just browse through different shops, there is plenty to do on Duval Street. We stopped at a couple shops and boutiques to browse, but the main event was the drinking and live music for our trip. Below is a list of all the bars that come highly recommended on or around Duval. What, you thought you were just getting a rough Key West itinerary? WRONG! I go above and beyond here, especially when it comes to adult night-time activities, ok? Each has its own vibe and energy, so make sure you pick whichever matches your energy. Or pull an appetizer sampler and try them all – just make sure you properly hydrate.

1. Sloppy Joe’s – the oldest bar in Key West. Great live music and cocktails. They also have a great rooftop.
2. The Green Parrot – the last bar on Highway 1. It’s also a great venue for live music. In their own words: “The Green Parrot is a jury of non-judging peers, a rugged and ragged council of friends.”
3. Smallest Bar in Key West – this is not an exaggeration. Smallest Bar fits no more than 6 people at a time, and that’s extremely generous. Stop by just to say you had a drink here, but nothing more.
4. Tiki House – the name says it all. Come for the tiki-inspired cocktails, stay for the setlist.
5. The Bull & Whistle – it’s actually a combination of three separate bars, each with a unique vibe. Which one fits your energy?
   • The Bull – a long bar with tables for dining and live entertainment.
   • Whistle Bar – second story bar featuring billiards tables and a balcony overlooking Duval.
   • The Garden of Eden – the rooftop bar where “clothing is optional”.
6. Irish Kevin’s – don’t get me wrong. I love a good Irish pub. But I’d go to Irish Kevin’s for the Guiness Ruben sandwich before anything else! Chase it with a shot of Jame-O. Sláinte!

Kermit’s Key Lime Pie Shoppe

It’s been a long day. You’ve been on the go since sunrise, and you’ve more than earned yourself a sweet treat. And what kind of sound Key West itinerary excludes indulging in a slice (or three) or Key Lime pie? Not this one! We’re headed to Kermit’s. It’s the perfect balance of sweetness in the custard filling, salty from the crust, and acidic from the bite of lime. There are many places on the island that offer pie on the go, but our favorite was Kermit’s because of the variety and the on-the-go pie on a stick. Choose from classic Key Lime or strawberry, then enhance the experience with chocolate or white chocolate dipped. Each bite is both savory and refreshing. Can’t ask for a better nightcap, so grab a stick and head to the shore to watch the most gorgeous sunset on an action-packed day.