Simply the Best of Key West: Staff Picks And Favorites Around Town

As 2018 comes to a close, we wanted to share some of the Management and Staff’s favorites across the island and what they refer to as “simply the best of Key West.” Truth be told, we may be giving away some of the local hot spots and hidden gems that our friends in town would probably prefer we keep quiet, but we just want to give a shout out to some of the places we think you should visit when you arrive.

Drink + Eat

Key West Lobster Shack

A small shack filled with lots of flavors and ideally located for our guests because it’s directly across the street from our beach resort.  The menu lists lobster done a variety of ways including a few of our favorites: lobster bisque, traditional New England Roll, a tasty Key Lime Lobster roll – a must try!  The Key West Lobster Shack is open 11am – 7pm, 507 South Street. Eat in or take out, and grab a cold beer, wine or soda.

Harpoon Harrys

They serve Breakfast all day long!  That’s just one of the reasons we love Harpoon Harry’s located at 832 Caroline Street, by the Historic Seaport.  This cash-only diner is offering hearty American comfort food in a cheerful atmosphere with quirky accents.  It’s the pink building on the corner with the bike on the roof.  Open 6:30am – 9pm, service Breakfast All Day + Lunch + Dinner.

“This classic greasy spoon is a short morning bike ride away from Duval Street and close to the historic seaport. A 50s-style diner, the eatery sports a funky, colorful decor complete with ample counter seating ~ Claudia Miller, USA Today 10Best

Hot Tin Roof

Great place for a romantic dinner and Sunday Brunch.  The restaurant is located at the Ocean Key Resort & Spa and features indoor seating for 60 and an outdoor deck overlooking Key West Harbor, for up to 40 people.  As you can see from the photo above, the view is spectacular!  Great food mixed with views like this makes it one of our favorites to eat and drink with friends and lovers.  Open for Breakfast, Dinner and Sunday Brunch.   Breakfast: Monday – Saturday 7:30am – 11:30am, Sunday 7:30am – 11:00am.  Dinner: Daily 5:00pm – 10:00pm, Sunday Brunch: 11:30 – 2:30pm.  Reservations: 305-296-7701.

The Café at Louie’s/Wine Bar

(Upper Deck)

The Cafe at Louie’s located upstairs and referred to as the “Upper Deck” offers a perfect setting for sipping and tasting elegant small plates. Enjoy fine wines by the glass complemented by the island’s best panoramic view of the ocean.  Louie’s is a favorite of locals and tourists, but the Upper Deck is our staff pick for the best TAPAS and favorite easy dinner place to go.  The Cafe at Louie’s is located at 700 Waddell Ave., open 5pm – 9pm Tuesday through Saturday.  (305) 294-1061.

Santiago’s Bodega

Tapas to the People!  Located off the beaten path in Bahama Village is where you’ll find Santiago’s Bodega, another unique and charming tapas-style eatery.   Make sure to try the house-specialty sangria and tasty Spanish tapas.  Open for lunch and dinner seven days a week from Lunch 11am – 5pm, Dinner 5pm – 10pm.

Bars & Nightlife

Mary Ellen’s Bar

A fun neighborhood bar located at 420 Appelrouth Lane (just off Duval)
Open 11am – 4am – breakfast, lunch, dinner, and drinks
The best ooey-gooey grilled cheese sandwiches on the island and fun game nights like Trivia Tuesdays!  This place is happening, cool, hip, funky and they come up with the most unique theme nights. Check out all the events on Mary Ellen’s Bar Facebook Page.


Located at 420 Duva Street, in the back of La Trattoria Restaurant, is where you’ll find Virgilio’s ~ Key West’s premier martini bar with live entertainment every night.  They are also serving late night food 10:30-close.  Our favorites include Latin Nights with local band Caribe.  This is the place to grab a martini, enjoy the fabulous local entertainment, dance the night away and have fun! Open 6pm – 4am.  Check out Virgilio’s Facebook Page for daily updates.

The Green Parrot

Unique to The Green Parrot and on our Management Must See and Do list is “Sound Check.”  This happens on Friday, Saturday, and Sunday from 5:30 to 7 PM  where visitors get to experience a full 90 minute set of great music.   The Green Parrot is known for bringing the best musical acts from across North America to Key West …and it’s a cool bar you really need to visit.

On the Water

Danger’s Wind & Wine Sunset Sail

Coastal Living Magazine ranked Danger Charter’s Wind and Wine Sail one of the top two Sunset Sails in all of North America. If you want an upscale, yet relaxed and intimate, sunset sail, this is the one you want to book.

Fury’s Ultimate Adventure

This is a full day action-packed adventure on the water!  If you want to experience snorkeling the reef to gliding down our water park slide, this popular adventure is the perfect excursion for those wishing to sample lots of water sport activities all in one day.


Snorkeling, Sunset Cruises and the finest sailing yacht in the Keys! Enjoy the luxury of personalized attention on a beautiful sailing yacht maintained to the highest standards.  Floridays is conveniently located at the Hyatt Centric Resort and Spa in downtown Key West.

Museum & Attractions

Truman Little White House

This is Florida’s only presidential museum and was the winter White House for our 33rd president where he spent 175 days here in Key West during 13 vacations.  In this tour you’ll discover the exciting history of President Harry S Truman and tour his unique historic home and museum, the Little White House.  The museum is open from 9am – 5pm and is located at 111 Front Street.

Conch Train Tour

This is a 90-minute sightseeing adventure, and history tour of the island has been entertaining visitors since 1958.  There’s so much to see and learn about the island, and this is and a great way to capture the history and charm of Key West in a short period.   It’s one of the most popular Key West attractions that delivers a truly great experience for all.

Now that we’ve shared some of our favorite things to do in Key West, we want to hear all about your favorites.  Share them with us on our social networks! #somolife