Over the past year and a half, we’ve traveled to Key West six or seven times either for work or short vacations. Our stays have ranged anywhere from four days to thirty. Below are a few tips on where to stay and what to do when you’re in Key West.  I tried to provide a good mix of touristy and off the beaten-path places that I’ve learned to love whenever we make our way down there.

Lodging

We’ve been fortunate enough to try a variety of housing options on our visits.  We’ve stayed everywhere from a friend’s house, a VRBO apartment, the Doubletree Hilton Resort by the airport, The Cypress House B&B and the The Conch House B&B.  Of all of these, the Cyprus House is my absolute favorite for a short stay.  They have a 4:30 p.m. happy hour each day where they serve rum punch and fairly good appetizers.  The rooms are huge compared to other B&Bs.  But, the true clincher is the staff.  They go above and beyond to ensure that you have a fun time by doing things like bringing you ice pops anytime you’re in the pool area! They also brought us a mini-cooler filled with ice so we could keep our beers handy and cold.

Brunch

Croissants de France. I’ve found that most tourists go to Blue Heaven instead (which is totally worth a visit), but Croissants has shorter wait times and their brunch is just as good in my opinion.

Lunch

Paseo Restaurant: I always order the chicken and rice with a side of elote (Mexican style street corn).  Recommend taking the food to go and eating somewhere else, since seating is limited.

Garbo’s Grill: Korean bbq and mahi mahi tacos.  The line is long, but worth the wait.

El Siboney: In my opinion, the best Cuban food on the island.  Bistec encebollado with plantains and rice.  Drooling just thinking about it.

Five Brothers: My one exception to El Siboney.  Five Brother’s has better Cuban sandwiches. Order one and peruse the small grocery store while you wait for your food.

Fried hogfish tacos at Hogfish Bar and Grill. Definitely an off the beaten path restaurant with plenty of outdoor seating and delicious seafood.

Faustos Supermarket: My go-to supermarket for good wine, chocolate, and cheese.

Bistro 245 at the Westin Hotel.  Spicy ahi tuna and avocado salad. Ranks in my top 5 lunches of all time.

Dinner

Nine One Five:  The restaurant we’ve eaten at the most.  We love their upstairs patio, incredible cheese plates, and cone fries.

El Meson de Pepe.  Our second favorite dinner spot.  Outdoor patio with an awesome live salsa band.  It’s also a great place to get dinner before attending a play at the Waterfront Playhouse.

Mangia Mangia.  Homemade pasta that is to die for in a super cute setting.  Great date night choice.

Last but not least, Better than Sex for dessert! Make reservations and eat a light dinner before going there.  All of the wine glasses are rimmed in chocolate and the desserts are almost true to the restaurant’s name.

Activities

Shopping:  If I had to pick one store it would be Wanderlust on Petronia Street. The selection is small, but amazing. The cost ranges from pricey to affordable with an incredible sale rack.  If you’re going to shop on Duval St., remember to bargain! Except for the brand-name chains, most store managers will negotiate over pricing.

Drag shows: A truly fun experience that everyone should have in Key West.  I’ve been to Aqua and Bourbon St. Pub.  Aqua is slightly more upscale feeling, while Bourbon St. has an edgier vibe.  Both are worth visits.

Sunset: All the tourists go to Mallory Square to get a glimpse of the buskers and enjoy a cocktail.  It’s definitely worth seeing once.  Particularly, the Catman’s act.

For a less touristy sunset and an incredible view of the city, visit the rooftop of the La Concha Hotel on Duval.  Arrive early enough so you can snag seating and order a cocktail before the magic begins.

Attractions close to Key West worth visiting

Bahia Honda State Park:  Beautiful state park where you can kayak, snorkel, and fish.  The park has camp sites and cabins if you decide to stay overnight.  I think this would be a great place for families with younger children.

Robbie’s of Islamorada:  Open air-market and a dock where you can hand-feed tarpon.  Again, this would be a perfect place to take younger children.