Key Links to a Florida Keys Winter Getaway

by Mark Strand, MidWest Outdoors Editorial Director

The Florida Keys are sights and sounds and smells and aqua-blue reflected light and the pace fits the place and if you’re looking for a great combo trip for the family or you and your buddies you’ll find what you seek.

You don’t go to the Florida Keys just to fish and because it’s water on your left and water on your right it’s hard to keep the smile off your face no matter what you’re there to do. You run the string that extends the southern end of Florida and sometimes it seems as if you could dip your toes in the water on the right and cast a lure over the road and into the water on the left. It reeks of fish and fishing, but in a good way, and when you’re fleeing a Midwest winter and driving with the windows rolled down it just plain feels good to be there.

My wife Jill and I flew south in mid February from the frozen tarmac of Minneapolis-St. Paul and a few hours later rented a car in Miami and worked our way out of the city and down to Key Largo. Over seven days we drove from Key to shining Key all the way to Key West and snaked our way back, stopping to hang out, do some fishing, and eat at restaurants we miss every day.

As a fitting kickoff for our new series called MidWest Outdoors Winter Getaways––which focuses on warm-weather destinations with good fishing––we drove the entire length of the Florida Keys down and back. The feature “Key to Shining Key” appeared in the November, 2019 issue of MidWest Outdoors. Here are links to many of our favorite stops and spots.

Restaurants we Liked

Sundowners restaurant in Key Largo:

Mrs. Mac’s Kitchen, Key Largo: 

The Fish House, Key Largo:

Hogfish Bar & Grill in Stock Island: 

Blue Heaven restaurant, Key West:

Stoned Crab restaurant, Key West: 

Three Hands Fish, Key West: 

Morada Bay Beach Cafe, Islamorada: 

Marker88 restaurant, Islamorada:

Chef Michael’s restaurant, Islamorada: 

Places we Stayed

Amsterdam’s Curry Mansion Inn, Key West:

Islander Resort Bayside, Islamorada: 

(we stayed at Bayside Townhomes)


John Pennekamp Coral Reef State Park, Key Largo:

Ernest Hemingway Home tour, Key West:

Mandy Miles, author of Key West Dos and Don’ts: 100 ways to Look Like a Local 

book on Amazon: 

Fishing Contacts

Bud N’ Mary’s Marina, Islamorada: 

Robbie’s Marina of Islamorada/Hungry Tarpon Restaurant:

(we fished with Capt. Phil Leonard of Mike Patterson’s Fin-Tastic Charters)

Captain Stan Miles