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48 Hours in Key West: Summer Weekender Edition

In our family, making the most of summer means frequent weekend trips. It also means cramming as much leisure time into 48 hours as possible. For my husband and I, Key West is always an obvious choice, as it's a short plane ride from Boston and it never lacks for things to do.
07/22/2016 01:59pm ET | Updated December 6, 2017
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In our family, making the most of summer means frequent weekend trips. It also means cramming as much leisure time into 48 hours as possible. For my husband and I, Key West is always an obvious choice, as it's a short plane ride from Boston and it never lacks for things to do. For this trip we opted to fly into Fort Lauderdale and rent a car so we could enjoy the scenic drive down the coast and the old Seven Mile Bridge (True Lies, anyone?). Here's how we made the most of our time there.

Stay
We opted for a romantic getaway off of the main strip, also known as Duval Street. For this retreat we chose the newly opened Gates Hotel, which is right off route 1. The property features a quiet pool (although sometimes there is live music in the afternoon) a funky outdoor bar, and a food truck serving breakfast, lunch, and dinner. (Important to note, there is no brick-and-mortar restaurant here.) We found that it was hassle-free living while still feeling a bit luxe. Our room featured a king bed, modern furnishings like new wood-look tile and a sliding barn door to the bathroom. The Gates offers on-site bicycle rentals, although I imagine it would be difficult to stay here without a car, as the surrounding neighborhood is pretty unexciting (and route 1 can be very busy). There's also no direct beach access from the property so be prepared to relax by the pool.

Eat
For a quick bite that won't break up your day, try DJ's Clam Shack on Duval Street. Being from Boston I live for a good lobster roll, and DJ's did not disappoint (we ate there twice in one weekend). For fancier fare book a reservation at Latitudes on Sunset Key -- it's just an 8-minute boatride from Key West, which only adds to this outing's appeal. Try the yellowtail snapper with savory chive risotto and jicama-lime salsa.

Play
The Gates recommended we check out one of its partners, Rodriguez Cigar Factory, on Fitzpatrick street, and it ended up being one of the highlights of the trip. Owner Danny DiFabio welcomed us warmly with complimentary Cuban coffee and a cigar to enjoy while we learned the history of his family's business (his grandfather started it in 1947 and his grandmother still helps hand-roll the cigars). His passion for cigar making -- from farming to selecting and aging the tobacco leaves and beyond -- made the tour both educational and exciting. The best part? He and his grandma helped us each roll our own cigars -- a souvenir we ended up saving to celebrate closing on our first house.

Drink
Take a tour of First Legal Rum distillery where chef-turned-distiller Paul Menta recounts the history of rum running on the island and why his rum actually dispels hangovers. Then sip cocktails dockside while watching the sun go down at the aptly named Sunset Pier.

Dance
Once the sun sets do not snooze on the local music scene: Local family band the Doerfels are consistently a crowd pleaser -- playing classic rock and bluegrass covers with a few originals mixed in -- and Patrick and the Swayzees perform modernized doo-wop classics with enough energy to make even the tiredest of feet go wild.