Key West might be known for its uniquely boisterous bar scene, but it also offers weekenders and road trippers an opportunity to find serenity within its lush outposts. For this trip agenda, we’re ditching Duval street for a more chill, exploratory experience, complete with spa vibes, bike rides, and of course, killer eats. 


Little Pearl serves an ever-evolving, four-course prix fixe dinner menu for $70 per person (exclusive of tax and gratuity) featuring eclectic fusion dishes. Selections like pickled ginger fritters, crispy corn “ribs,” couscous and seared fish, rice pudding pockets, and jalapeño yuzu sorbet keep the culinarily curious locals coming back for more. Reservations are highly recommended. 

On the way in or out of Key West, make a pit stop at the One Love food truck on Stock Island. One Love is parked at a Chevron gas station surrounded by island-inspired decor and music. The flavor-packed menu features classic Jamaican dishes like oxtail (only on Sundays) and jerk chicken alongside modernized meals like Mahi tacos and healthy but flavorful bowls. If the staff offers you soup while you wait for your order, no matter how hot it is outside, say yes: And don’t forget to order one of their delectable rum cakes for the road! 

Photo courtesy of Little Pearl


The Kimpton Key West is a collection of multiple properties throughout Old Town, featuring historic homes and bungalows converted into hotel rooms. Kimpton Key West’s complimentary perks include Continental breakfast (with easy-to-pack items like hardboiled eggs, avocado slices, and milk alternatives), book sharing, yoga classes, happy hour drinks (including local beers), and daytime bike rentals. The collection also boasts three pools and lush hideaways that beckon a reprieve on one of the many swing seats. And like all Kimpton properties, the hotel is pet-friendly. Roam between the properties to experience their distinctive personalities and offerings. 

Photo courtesy of Kimpton Key West


Carve out some time to take advantage of Kimpton Key West’s bike program to breeze through town. Check out the Little Free Pantry Project in Key West’s Bahama Village: The global initiative began in an Arkansas neighborhood in 2016. Here, the community keeps the pantry stocked with canned goods, nonperishable items, and home goods. Passersby can take what they need, no questions asked. The “pocked park” also features a library and art, so feel free to grab a book or give a book to mark your weekend excursion. 

Thankfully, Fort Zachary Taylor Historic State Park’s entrance isn’t far from Bohemian Village. History buffs can take a narrated fort tour at the park, nature lovers can ride through untouched landscapes, and beach babies can take a dip or snorkel in what is deemed “Key West’s Best Beach.”

Credit: Wander Wisdom


Prana Spa in Old Town is locally owned and operated and has brought internationally lauded treatments and wellness practices to Key West since 2013. Zen oozes out of every corner, from the quaint entrance garden to the soothing scents to its welcoming, grounded staff. Prana’s services include Thai massage, Ayurvedic full-body sensory treatments, and facials. The second-floor, tree-house-like space is perfect for couples looking to share an intimate moment of rejuvenation. You’ll feel brand new after a visit. 

Photo courtesy of Prana Spa in Old Town

Looking for more on Key West? You can check out our guide to exploring Key West like a local here.

Cover photo courtesy of Kimpton Key West