Summer in the Keys: Island Vibes, Hemingway Days & Unforgettable Escapes

The heat’s rising, the breezes are salty, and the islands are humming— welcome to peak summer in the Florida Keys. Whether you’re dreaming of sunrise yoga in Key Largo, casting a line off Islamorada, or dancing to a Hemingway look-alike in a wool turtleneck (yes, really), this week is everything summer should be: sweaty, soulful, and absolutely unforgettable. The drinks are cold, the stories are tall, and the sunsets? They’re showing off. Let’s dive in.

🌅 Key Largo: Where Summer Awakens on the Reef

Wake up where the reef meets the road. John Pennekamp Coral Reef State Park is your launch point for snorkeling, kayaking, or diving the famous Christ of the Abyss.

For creature comforts, try Bungalows Key Largo or Baker’s Cay Resort.

Fishermen: Cast off from Pilot House Marina or book a reef trip with Blue Water Adventures.

Where to eat:

• Mrs. Mac’s Kitchen – A beloved pit stop with legendary key lime pie

• The Fish House – Fresh, dockside seafood and a killer sunset backdrop

🌿 Islamorada: Cast Away & Sip Local Flavor

Book deep-sea charters with Bud N’ Mary’s Marina – Legendary for offshore and backcountry trips, or wade into shallow flats with Florida Keys Fun Fishing.

Afterward, chill with tropical sips at Islamorada Brewery & Distillery.

Where to stay & eat:

• Long Key State Park – Waterfront camping for the adventurous

• Cheeca Lodge & Spa – Luxe comfort with a beach view

• Morada Bay Beach Café – Sunset dining on the sand

😂 Marathon: Middle Key Mischief & Island Charm

Explore sea life at The Turtle Hospital, then stroll Crane Point Hammock through shaded nature trails.

Grab a lobster Reuben from Keys Fisheries and unwind at Sombrero Beach.

Where to stay:

• Tranquility Bay Beach House Resort – Private villas, turquoise views

• Jolly Roger RV Resort – 11-acre family owned park.

📚 Key West: Hemingway Days & Island Soul

Hemingway Days (July 10–14) transforms the island into a literary street fair. The Ernest Hemingway Home & Museum is a must-see—six-toed cats included.

Bar-hop history at Chart Room Bar, catch tunes at Green Parrot Bar, or toast legends at Capt. Tony’s Saloon.

Must-dos:

• Ferry to Latitudes for breakfast on Sunset Key

• Dinner at Louie’s Backyard – Shrimp, sea views, and storied cocktails

• Authentic eats at El Siboney

• La Concha Key West – Freshly renovated boutique on Duval

• Pier House Resort & Spa – Gulf-front elegance with history

📅 Sample 3-Day Itinerary

Friday – Discover Old Key West

• 3 p.m.: Key West Art & History Museum

• 6 p.m.: Dinner + sunset at Schooner Wharf Bar

• 8:30 p.m.: Live music at Green Parrot, Capt. Tony’s, Irish Kevin’s

Saturday – Hemingway Days & Epic Eats

• 7:30 a.m.: Breakfast at Sandy’s Café

• 9 a.m.: Tour the Hemingway Home

• 3:30 p.m.: Explore the Mel Fisher Maritime Museum

• 4:30 p.m.: Browse Gallery on Greene

• 6 p.m.: Dinner at Louie’s or El Siboney

• 9 p.m.: Hit Hog’s Breath, General Horseplay, or Sloppy Joe’s

Sunday – Wrap It In Paradise

• 8:15 a.m.: Ferry to Latitudes

• 9:30 a.m.: Bike using Key West Walking Tours app

• 12 p.m.: Tour the Truman Little White House

✨ Why This Week Matters

• Hemingway Days connects past and present in unforgettable ways

• Food, drinks, and Cuban culture fuel island rhythms

• Mornings, sunsets, and starry nights remind you why this place is different

📸 Want In?

I’ll be at Harpoon Harry’s, chasing sunrise, eating conch fritters, and Hemingway‑spotting in between mojitos. Come join me.

Trivia Answer:
Though friends in Paris started calling him “Papa,” many say Hemingway gave himself the nickname around age 27—he hated being called Ernest, and “Papa” fit the swagger: part father figure, part fearless adventurer, fully in charge of the myth he built.

Here’s to salt-kissed nights, literary legends, and island mornings.
See you in paradise.

—Brian and The Florida Keys Road Trip Team