The Classy Guide to Key West

The Hemingway Home & Museum — Even if you haven’t read all of Hemingway’s works, this is an absolute Key West must. The grounds are home to over 60 cats descended from Hemingway’s own pet, about half of whom have six toes (one even has seven). Your ticket comes with a free guided tour, which is definitely recommended but not required. Pro tip: Arrive early to beat the heat!

West Martello Tower and Key West Garden Club — This adorable garden is tucked right into the Smathers Beach area, so definitely stop by after the beach! Home to a butterfly garden, tons of orchids and beautiful walking paths. They request donations to keep up the grounds.

Watch the Sunset On Sunset Pier (or better yet, a sunset cruise!) — Grab a drink before the sunset on the long Sunset Pier jutting out on the western side of the island. Or if you’re inclined for a romantic option, book a sunset sailing cruise! Reach out to me for a fantastic sailing company recommendation.

Shopping

Key West Pottery — A jaw-dropping display of colorful and creative talent. This artist duo creates the funkiest shapes in addictive colors. They ship worldwide and there are lots of small gifts and mugs to securely fit back in your suitcase as well.

Low Key Fashion House — The most high-end boutique on the island. They offer a small but mighty collection of previously owned designer handbags (think Gucci, Hermes, YSL), and clothing from tasteful clothing lines (think Simkhai, Amanda Uprichard, and Mother jeans).

Uva Wine Shoppe — Mark gives amazing recommendations and is clearly passionate about wine. I definitely learned a thing or two about champagne while I was there!

Clé — The headquarters of a family-owned interior design company, Clé offers gorgeous original watercolor paintings by local artists, bedding, and interesting furniture pieces.

Besame Mucho — A quirky and eclectic collection of home decor, jewelry, skin and hair care, stationary and more. Pro Tip: If you’re buying a gift for someone, they have lovely gift wrap!

Beaches

Smather’s Beach — Although a short drive away from the main area of town, it is absolutely worth spending a day at Smather’s Beach. The sand bar is incredibly shallow and the water is stunning. As of March 2024, there is construction on the road running alongside the beach, but it doesn’t deter from the beauty of the beach itself. Rent chairs and umbrellas, and either pack a cooler and lunch, or walk over to the Margaritaville Resort across the street for lunch.

Higg’s Beach — A convenient location to walk to if you’re staying in Old Town. While not the absolute prettiest beach around, you can rent umbrellas and have access to Salute! On The Beach, a open-air seafood/Italian spot with a great happy hour.

Breakfast/Brunch

Bagatelle — A classic brunch spot that lives up to the hype. Order the Southern Benedict — it was specially designed just for the restaurant by a James Beard Awarded chef. Pro Tip: Reserve a seat along the balcony upstairs for great people-watching while you eat.

La Grignote — The menu is huge, and seems to hit all the things I’d want for breakfast, brunch or lunch. Fantastic coffee and an enticing array of pastries. Request a seat on the front patio to watch the world go by as you dine.

Fine Dining

Little Pearl — This little seafood restaurant and wine bar is quite simply delectable, and one of my top recommendations on the island. They offer a set menu, but there are a few options for each course. The oysters were incredible, the fish prepared beautifully, and the mini assorted cannolis were a fun treat! Be sure to get a reservation early.

Lola’s Bistro — This hole in the wall spot is a local’s favorite choice for a nice date night. Lola’s only takes dinner reservations at 6:15 and 8:00pm sharp, they only take Venmo or cash, and are completely BYOB — so come prepared! Pro tip: Visit Uva Wine Shoppe about two blocks away right before your reservation — Mark will give you great suggestions!

Cafe Marquesa — Located on the corner of the lovely Marquesa Hotel, this upscale cafe has a creative menu, wonderful service, and great drinks.

Snacks/Bar Food ////

Kaya Island Eats — This casual outdoor restaurant and bar should not be overlooked. Their Caribbean-inspired menu just gets it right. Their Jamaican Jerk Chicken Wings were truly the best I’ve ever had in my life — dry-rubbed, drizzled with an insane jerk sauce, and topped with goat cheese… enough said!

Date & Thyme Organic Cafe and Market — Smoothie, juice, salad bowl, baked good and organic grocery heaven! A wonderful spot to stop by on a morning stroll for coffee and breakfast.

Funky Rooster Coffee House & Wine Bar — A coffee shop that feels like it could be your grandma’s, in the best way. Quality coffee and homemade pastries and desserts. Graciously long happy hour for afternoon wine!

Blue Heaven — A favorite for laid-back eats and famous key lime pie. Great live music as well.

Eaton Good — Located on adorable Eaton Street, this casual outdoor spot serves up incredible breakfast pastries, and also serves barbeque for lunch and dinner.