February is a great time to escape Indiana’s winter weather! During our convention dates, Key West typically enjoys daytime highs around 77°F and overnight lows around 67°F. Expect plenty of opportunities for sunshine, although occasional cool fronts and ocean breezes can make evenings feel cooler. Pack a light jacket or sweater, just in case.

You have two main options:

Key West International Airport (EYW) is the closest and most convenient choice. You’ll arrive right on the island, just a short ride from Casa Marina.

Miami International Airport (MIA) offers more flight options and the opportunity to experience the famous Overseas Highway. The scenic drive from Miami to Key West takes approximately 3.5 to 4 hours without stops, depending on traffic. Allow extra time if you want to explore the Florida Keys along the way or stop at Harriette’s on Key Largo to pick up some Key Lime muffins to share with your favorite convention staff. 👀

Tip: The drive is beautiful, but it’s also mostly a two-lane highway. Plan accordingly, especially if you have a flight to catch on the way home.

We strongly recommend leaving the rental car behind if you’re flying directly into Key West. The island’s narrow streets, limited parking and busy tourist areas can make driving more trouble than it’s worth.

Uber, Lyft and local taxis are readily available for trips between the airport, resort, restaurants and attractions. You’ll also find plenty of places to explore on foot.

If you’re flying into Miami and driving down, consider returning your rental car once you reach Key West. You probably won’t need it during your stay.

Trust us. Spend your time enjoying the island, not hunting for parking.

Resort casual! Leave the suits and ties at home.

Think lightweight shirts, polos, sundresses, casual pants, shorts and comfortable shoes. We want everyone to feel relaxed and enjoy the island atmosphere while attending convention events.

For evening events, you may want to dress things up a little, but there’s no need to go overboard. Maybe bring a little something dark and moody for the Sponsors’ Party?

And don’t forget comfortable walking shoes for exploring Key West.

Still wondering what to pack? Check out Skyscanner’s guide to resort casual attire for ideas.

We understand. Things happen. But we also invest heavily in pre-planning and pre-booking for this event. Registrations canceled by Feb. 5, 2027, may be eligible for a partial refund. Please contact Andria Hine at Indiana Constructors, Inc. for details if a conflict arises.

Key West has a little something for everyone, from history and outdoor adventures to waterfront dining, live music and just the right amount of hijinks.

Explore the island’s colorful streets, visit a historic landmark, get out on the water or settle in for a spectacular sunset. Whether your idea of a good time involves snorkeling, sightseeing or a cold drink with a view, you won’t have to look far.

Here are a few places to start planning your adventures:

• Mallory Square Sunset Celebration
• Ernest Hemingway Home & Museum
• Truman Little White House
• Key West Butterfly & Nature Conservatory
• Dry Tortugas National Park