Chicago to Florida Road Trip – Disney and Key West

South Florida attracts bazillion tourists each year during the Holiday season. So, here goes a little FOMO-laden motivation for your next trip to the Sunshine State.

Florida – the irresistible trio of sunshine, beach and clear blue water. Courtesy TripGazor under Creative Commons

How to Plan your road trip?

•  It could be overwhelming to choose from extremely wide gamut of activities on offer. So,  here are my recommendations to plan your trip:
Florida Keys and Key West
 –  Theater of the Sea, Glass Bottom Boat Tour, Sunset Cruise, Snorkeling, Jet Ski and other adventure sports of your preference.

The dolphin show at Theater of the Sea is captivating. Courtesy: Theater Of The Sea

Fort Zachary Taylor Historical State Park and Beach – Try visiting the southernmost state park in the continental US. You get access to an awesome beach offering a ton of activities for family along with a dash of history.

Fort Zachary Taylor is known for an expansive collection of pre-Civil war armament. Courtesy MittenStatePhototog under Creative Commons

Other noteworthy mentions – Kennedy Space Center, Everglades Alligator Farm

Time your visit and view the rocket launch at the space center. Courtesy: Kennedy Space Center

•  You need 2 days for the road trip so plan your pit stop, we stayed around Chattanooga. Goes without saying, choose a hotel which offers breakfast and in close proximity to the highway. I usually pick a highway Holiday Inn.

• Run through this indispensable emergency checklist.

• Run though these tech essentials to turbo-charge your road trips.

Our Trip Details from Naperville

December 21 – 31, 2018

Road Trip
Naperville to Orlando, FL.

Day 1: Naperville to Chattanooga
11 hours ETA with liberal breaks
Started at 10 AM and did a pit stop here at Chattanooga, TN around 10 PM with multiple breaks (lost an hour due to time zone change).

Day 2: Chattanooga to Kissimmee, FL
9 hours ETA with liberal breaks
Started at 10 AM and reached late night.

As you drive towards Florida Keys, the last 100-mile stretch is via the superlative Overseas Highway with its stellar views.

US Route 1, Courtesy Pom’ under Creative Commons


We stayed at this swanky brand new cottage from Vrbo inside Solara Resort.

Courtesy: Vrbo

You get access to Solara Resort amenities too, Courtesy: Vrbo

Courtesy: Vrbo

Disney World at Orlando

Anyone who’s been to a Disney resort, would concur that the entire experience and showbiz is majestic.

Magical Kingdom

Magical Kingdom looked enchanting at the core. Holiday season is a special time to visit the parks.

Magical Kingdom, Courtesy Disney

The geodesic sphere at Epcot. Courtesy Disney

Star Wars – Galaxy’s Edge

Disney’s newest park is a major crowd puller for the Stars Wars franchise fans.

Courtesy Disney

Tip: One skill paramount for the great Disney experience is to optimize your FastPass+ or Lighting Lanes strategy. I have created a detailed guide here to help you devise and flaunt your Lightning Lanes strategy and perform overall park planning like a pro.

Theater of the Sea at Islamorada

We thoroughly relished all the shows and the extravaganza, great entertainment for the entire family.

Courtesy: Theater of the sea

Everglades Alligator Farm

The Airboats make such a deafening noise, that they provide headphones to stay sane during the ride. We did our airboat tour and the alligator encounter from Everglades Alligator Farm and yes, the experience was pleasurable (an unpaid testimony to their highly rated reviews).

The airboat ride was quite zippy, Courtesy Everglades Alligator Farm

You could pet little gators as well, Courtesy Everglades Alligator Farm

Not for the faint hearted, Courtesy Everglades Alligator Farm

Glass Bottom Boat Tour

This should be an enjoyable experience on most days. But the day we went in, the seas were very turbulent and after looking at the marine life from the glass bottom for a couple of minutes, most of the adults felt queasy and had to head back on the upper deck to nix the mal de mer. I would rather skip describing the scene on the upper deck.

Tip: Do your travel companions a favor and skip this, if the seas are turbulent.

Glass Bottom Boat Tour. Courtesy: Fury

Kennedy Space Center

Kids of adults, all would be awe-struck and inspired by the exhibits and the spectacle. A must visit indeed! And try to time it with a rocket launch if you can.



Key West – Water Adventures

Key West offers a ton of water activities for the entire family – Jet Ski, Snorkeling, Pontooning, Parasailing, Evening Cruise. We did sunset cruise, parasailing and jet ski from the highly rated adventure company Fury. The overall experience was highly positive and would unequivocally recommend them.

A stilling sunset at Key West, courtesy Anupam under Creative Commons

Snorkeling at Key West, courtesy Fury

Fort Zachary Taylor State Park and Beach

Yes, Florida has bazillion beaches but I would instead rave about this unorthodox choice as it offers a rare triumvirate of beach, state park and historical fort.

Bonus – you would visit the southernmost State Park in the entire Continental US.

Beach at Fort Zachary offers a ton of activities and a cafe. Courtesy TripGazor under Creative Commons

That’s it. Hope you have your next unforgettable Florida experience soon.

Please leave some feedback in the comments section on your thoughts on this post.

One thought on “Chicago to Florida Road Trip – Disney and Key West

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s