A Weekend Getaway in Key West

A Weekend Getaway in Key West

Words by Ashley Locke
Photos by Greg Ceo Studio

The last few months have been unlike anything we’ve ever seen before. Businesses and schools closed, office work moved into homes, travel plans were cancelled, and playdates turned into zoom calls. Many of us were cooped up in our homes, apartments, and condos for months. Having a backyard became a luxury. There was a time when we thought summer may not get to feel like summer after all, but there’s good news now—summer vacation is back on.

In the south, it’s not summer without a trip to the beach. When you need a real break from it all, there’s no better place to get away than Key West. You don’t have to believe us—Jimmy Buffett, Ernest Hemingway, and Harry S. Truman called it home. With the beautiful beaches, authentic Cuban food, rich history, and a bustling nightlife, Key West captures everything you need in a vacation—and just steps away from it all? Newly renovated The Reach Key West.

The Reach, part of the Hilton’s Curio Collection, is home to the only natural sand beach on the island. Each of the 150 teal and teak rooms has a balcony, alongside amenities like blackout curtains, workstations, and coffeemakers. Nautical details like a curved vanity reminiscent of a boat’s hull and porthole mirrors bring the beachfront inside. 

What lies outside the rooms is just as exciting as what’s inside. The resort boasts relaxing outdoor spaces, a state-of-the-art fitness center with Peloton technology, and an onsite Escape Room experience. The hotel also offers experiences like jet ski tours, snorkeling, beach yoga, and sand sculpting classes. There truly is something for everyone to enjoy!

In between adventures, you can stop by The Reach’s all-day, beach-front restaurant, Four Marlins. Enjoy a sunrise breakfast, sunset appetizers and cocktails, or anything in between. There’s indoor and outdoor seating, but you won’t want to miss the view. 

Another bonus? Everyone who stays at The Reach also gets access to their sister property, the Casa Marina. That means access to more private beachfront, Spa al Mare, two outdoor pools, and more. You get the best both hotels have to offer. 

If you’re ready to relax, The Reach is the place to do it. It’s not just a hotel––it’s the best way to experience the true culture of Key West. Check out our weekend guide to Key West below!

A Weekend in Key West:


  • 4:00 PM: Check in to The Reach. (Forget your swimsuit? Don’t worry––their on-site store has everything you need!)
  • 5:00 PM: Book an appointment for a facial or massage at Spa al Mare.

  • 6:30 PM: Hit the pool or the beach for a relaxing evening.
  • 7:30 PM: Grab a seat on the patio at Four Marlins for sunset dinner and cocktails. (The Blistered Shishito Peppers and Fresh Agave Margarita are a must-try.)
  • 9:30 PM: Return to your room and rest up! Slide the balcony door open for calming ocean sounds.


  • 9:00 AM: Grab breakfast at Four Marlins. (We recommend the Avocado Toast!)
  • 10:00 AM: Gather the family for a sand sculpting class. Your sandcastles will never look the same!
  • 11:30 AM: Rent a jet ski and spend some time on the water.
  • 1:00 PM: Stroll to Mallory Square for an authentic Cuban lunch at El Meson de Pepe.

  • 2:30 PM: Walk off lunch and shop around. (Make sure to stop by KINO Sandals!)

  • 4:00 PM: Head to Papa’s Pilar Rum Distillery for a tour and tasting of their award-winning spirit.

  • 6:00 PM: Slurp down some oysters with dinner at Conch Republic Seafood Company.

  • 8:00 PM: Catch an Uber back to The Reach for sundown cocktails at Four Marlins.


  • 9:30 AM: Head to Blue Heaven for breakfast—and don’t be afraid to order a slice of Key Lime Pie. 
  • 10:30 AM: No visit to Key West is complete without stopping by the Hemingway House! Take the tour and hang out with the six-toed cats that roam the property.
  • 12:00 PM: Stop by Garbo’s Grill for lunch. The Korean BBQ Tacos or the Mango Dog are mouthwatering!
  • 2:00 PM: Rent a bike and ride around town. It’s a perfect time to stop for a photo-op at the Southern-Most Point of the Continental U.S.

  • 4:30 PM: All aboard the Appledore II and sip on cocktails while watching the sunset from the water.

  • 6:30 PM: Stop for dinner at Sloppy Joe’s, then stick around for live music and drinks.

  • 8:00 PM: Spend the night dancing on Duval Street!


  • 11:00 AM: Pack up and check out. (Sad, we know!)