Need an escape from endless shoveling, worries about heating costs, and that cold white stuff that makes going about your daily business so difficult–if not downright dangerous? I do. Let’s go. Imagination is free.

This tropical locale is the kind of place where the biggest decisions are which restaurants to choose, which activities to enjoy, and which drinks to sip as we laze away the days.

Landing at your island destination, you enjoy the freedom that comes along with shedding heavy layers of clothes and leaving your daily routine behind. You check into your accommodations. It’s everything you hoped for. When you pull back the curtains of your luxury suite that leads to your private balcony, you wonder why you waited so long to make that leap and visit the southernmost city. Your view overlooks Mallory Square, one of the world’s most famous places to people-watch and enjoy the sun set. Oh, but the clock tower at nearby Key West Museum chimes one, so you figure you have plenty of time to explore before considering the night’s entertainment.

One of those balconies has your name on it. :)

What will you do first? If you stroll down Key West’s main drag, Duval Street, you choose to stop for at Hog’s Breath Saloon, where you strum your fingers to the live music and chat with fellow escapees on the adjacent bar stools as you sip a Hogarita or two. Waving goodbye to your new friends, you finish your drink and head into the brilliant sunshine for another adventure. You make your way toward Upper Duval, stopping to read the crazy t-shirt sayings at the tacky souvenir shops or visiting bars such as Sloppy Joe’s, Irish Kevin’s, Rick’s, The Bull & Whistle, Fat Tuesday’s, and Buffet’s original Margaritaville.

Fogarty’s on Duval

If you opt to visit a number of those establishments or even one for an extended period of time, be prepared to learn the true meaning of the phrase “Duval Crawl.” Otherwise, you can choose to continue your walk to the Butterfly Conservatory and South Beach.

South Beach, Key West

Butterflies and beaches aren’t on the agenda for your first day? Retrace your steps, making a right at the Conch Train station and heading past the Hyatt Resort to the Key West Historic Seaport. You could relax on the deck of Turtle Kraals and watch the comings and goings at the marina or trek the boardwalk until you spy another eatery that fits your style.

The Boardwalk

After your late lunch, you could shop (perhaps buy a bottle of wine for later in the evening), talk with local tour charter vendors to book a ghost tour, sunset sail, fishing boat, jet skiing or kayaking eco-tour for later in your stay, or return to the hotel for an afternoon siesta. Before you rest, however, don’t forget to talk with your concierge about selecting just the right restaurant for that romantic dinner before you join the crowd headed to Mallory.

Mallory Square Performer

After your scrumptious meal and a picturesque sunset you wind your way through entertainers and tourists to Old Town’s quaint side streets, breathing in the ambiance and architecture of the city before returning to Front Street and your hotel. If you’ve had enough excitement for your first day, you can choose to stroll hand-in-hand to your suite, open that bottle of wine and enjoy your loved one’s company.

The following morning…you’re off to a new adventure. What will yours be?

Sailing in Key West Harbor