Travel Blog with Tessa in Key West

Had a wedding at the Hemmingway House in Key West and luckily for me, Tessa was available to second-shoot with me, so we turned it into a mini-vacay.

Partying on Duval, taking full advantage of the *loose* public intoxication laws, and abandoning your responsibilities to embrace the island lifestyle are definitely the most common ways to enjoy this Southernmost piece of paradise. But (among all of that), finding the quiet moments and romantic corners in this little drinking town is what we do best. Here’s our guide based on our recent trip: below you’ll find links to where we spent our date nights, our drunk nights, where to stay, what to do, and some tips for throwing a destination wedding in Key West.

STAY

Speakeasy Inn

Location: On Duval St. in the Boutique and Gallery District

We opted to stay right in the midst of everything at a Bed & Breakfast right on Duval St. The Speakeasy Inn was the home of Raul Vasquez, a cigar selector, and rum-runner. Now it boasts 19th-century vibes while providing quaint and fairly private accommodations in the most convenient location of Old Town Key West (plus a rum bar around front where the locals hang out to listen to live music on the wrap around porch!)

We spent an average of $129/night to stay at the Speakeasy Inn during the summer season and would definitely stay again!

DO

Rent bikes from Fury Rentals

You’ll find bike rentals all over town (and scooter rentals and golf cart rentals and basically every other method of getting around), but we chose to rent bikes through Fury rentals. It made it sooo easy to get around town. The bikes cost $15/day.

You can also book other excursions through this company. We really wanted to do a sunset sail with them but never got to do it. Sunset sails are $37/person and it includes champagne!

EAT

One of the first spots we biked to on day 1 was Date & Thyme – an organic cafe, juice bar + health food market in the heart of Key West. After stocking up on some healthy munchies for the b&b, we grabbed a quick breakfast from the cafe. We split a “Rise and shine bagel” – cashew cream cheese, tomato, and avocado, on a plain whole wheat bagel and an Acai bowl – frozen acai, blueberries, banana, and goji berries, blended with house-made coconut milk, and topped with crunchy granola, coconut akes, goji berries, and cacao nibs.

Finding vegan-friendly foodie spots is always a win for me even though I’m not vegan, I prefer to eat as plant-based as possible! I paired my meal with my typical matcha latte (so many dairy-free milk options #blessed) and Hector had the Azteca latte – espresso, steamed milk, pure chocolate, chili, and coconut sugar! Wtf. Freaking yum.

After exploring Duval street all day in the Florida heat, we deserved something frozen and fruity so we stopped at one of the many “Tropical Drinks” stands on the side of the road and ordered an overpriced + oversized Pina colada in a pineapple. Worth it.

There are *technically* no laws that allow public alcohol consumption in Key West, but from what we were told there is a general consensus that no one enforces the law. Therefore all the bars and restaurants serve to-go drinks and everyone is free to enjoy the town, beer in tote. I’m with it.

Dinner

For dinner, we headed down to the marina so we could eat by the water. We decided on The Commodore Restaurant to eat allll of the seafood. If you can, try to hit happy hour from 4-6:30 for half price off appetizers and drinks!

Second Day

Spend a day soaking up some sun at Fort Zachary Taylor State Park. Seriously the most beautiful beach in Key West. There is a bar/casual food on the property, as well as umbrellas and chairs for rent. We biked here and it was $5/person to enter the park.

The storms started to roll in around 4pm but we played on the rocks until the very last minute anyway <3

DATE NIGHT

Wine + appetizers at Blackfin Bistro where the food was freaking insane (100% order the mussels) and the service was amazing. We sat at the bar and talked to the owner for a while. I loved everything about this place. Then we headed directly across the street for dinner at Nine One Five. We sat on the wrap-around patio upstairs and people watched while we ate. I highly recommend this place, but definitely make a reservation especially on weekends.

Sunset

Mallory Square for the sunset festival. We watched acrobats, and sword swallowers, and torch jugglers, while sipping margaritas from Agave 308 and nibbling on street corn from one of the vendors.

We ended the night at El Meson de Pepe with some drinks and dancing! There’s an outside area with a live salsa band and its so much fun to people watch. Plus there are tons of chickens walking around lol. So much fun.

On the way home, we stopped for some INCREDIBLE slightly tipsy late-night pizza from Onlywood Pizzeria Trattoria. We may have gone back 2 more times before the 4-day trip ended. Whoops!!

Last Day / Wedding Day

Our two days of play ended with a full day of “work” – aka shooting a dope-ass destination wedding which started in an amazing 2-level cottage. The property also has a pool (!!) and costs an average of $121/night. They got married and celebrated with 30 of their closest friends and family at the Ernest Hemingway House. If you don’t know, this place is famous for having a shit ton of CATS that roam/live on the property. What. A. Dream.