Christmas Road Trip from Chicago to Disney (Orlando) and Key West

Why Disney?
Needs no explanation, its Disney!

How to Plan your visit?

•  Choose if you have the appetite for the road trip or want to fly instead. We did the former, being road trip addicts.

• Run through this indispensable emergency checklist.

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

•  Choose the time, preferably skip peak periods like kids summer or winter break. We went bang in the middle of winter peak time, December 23-26, 2018 and still survived with some scruffs and scratches (a.k.a. had lot of lessons learnt for the next trip!).

•  Decide if you want to visit other areas, we visited Key West and loved it thoroughly.

Our Trip Details from Naperville

December 21 – 31, 2018

Road Trip
Naperville to Orlando, FL.

Day 1: Naperville to Chattanooga (9 hours per Google Maps)
Started at 10 AM and did a pit stop here at Chattanooga, TN around 10 PM with multiple breaks (lost an hour due to timezone change).

Day 2: Chattanooga to Kissimmee, FL (8 hours per Google Maps)
Started at 10 AM and reached late night.

Phase 1: Disney

We stayed at this cottage booked from Vrbo, which was then brand new and missing basic necessities. We wasted a lot of time to get the home up and running for next few days but it was worth the lift, for our first Disney experience.

The very First Ride – Soarin’ Around the world!


The Disney Lessons Learnt
After spending numerous hours of my life in the waiting lines for the Disney theme parks , here goes my hard earned cheatsheet:

  • Try to stay in the Disney Resort, because if you do, you will get 60 days of advance booking window for FastPass+ tickets vs 30 day window for non-resort guests. This comes very handy for booking rides like Avatar Flight of Passage which, if you don’t have FastPass+, could result in 3 hours+ of waiting time.
  • The day your booking window opens, you should book FastPass+ reservations bang at 7 AM EST, even if you are in West Coast otherwise you will miss out on some reservations.
  • You can only make 3 FastPass+ reservations at a time. In order to make additional FastPass+ reservations, you will need to consume (or the ride time needs to expire) all 3 passes. So, make your first 3 FastPass+ reservations early in the day, so that you can make additional reservations.
  • Goes without saying, you need to wisely use your advance FastPass+ reservations for the rides which have the most wait times.
  • For Magical Kingdom, we faced huge jam near the entrance. There were some online suggestions to park at Epcot instead and take the mono rail to Magical Kingdom but we didn’t try it.
  • Since the parks are huge, it helps to carve out a path for your visit otherwise there could be a lot of walking. Some websites have very detailed 1 or 2 day Disney Plans which can help you immensely to pick up an optimized path. Here’s one of my favorite links on UnderCoverTourist.

My FastPass+ Recommendations


Frozen Ever After
The Seas with Nemo
Soarin’ Around the world
Mission: SPACE

Other recommendations:
Test Track
The Seas with Nemo & Friends
The Living With The Land

Magical Kingdom:
Seven Dwarfs Mine Train 38″
Space mountain – I didn’t like it personally, just a roller coaster in the dark.
Splash mountain 40″
Enchanted Tales with Belle
Rapunzel and Tiana at Princess Fairytale Hall

Other recommendations:
Big thunder mountain railroad 40″: Nice and easy roller coaster with small drops and jerks.
The Barnstormer
Jungle Cruise
Dumbo the flying Elephant
Peter Pan Ride: Very average. Almost on slow motion, this might pique interests for hardcore Peter Pan fans, not much excitement for others.

Animal Kingdom:


Avatar Flight of passage (this is so busy that you might not get the FastPass+ unless you are staying in Disney resort and have 60 day advance booking window)
Na’vi River Journey
Kilimanjaro Safari: If you can, try to get an evening time as night safari at least for us was an exquisite experience where most of the animals were sassy.
Kali River Rapids: we were disappointed as there was hardly any splash 😦

Other recommendations:
Maharaja Safari: Very unstrained walking trail in the middle of nature.
It’s tough to be a Bug: Awesome entertainment, specially for young kids (don’t miss it!)
The tree of life (close to the Its Tough to Be a Bug show): they have a light show in the evening.
Discovery Island Trails
Conservation Station

Avatar – Flight of Passage


Phase 2: Key West

We stayed at Gilbert resort in Key Largo. Nicely priced but would prefer to plan better (rather than our 2 week prior booking) and stay right at Key West itself. This was slightly dated place but has private beach, pool and full of lovely beach side shacks with live music.

Their specialty food was hog fish which tasted like dog food with cream cheese spoiling the overall taste.

The fish tacos were good though, included stuffing like Pico De Gallo which were making it very flavorful.

We visited Theater of the Sea on our first day in Key Largo which had several animal and bird shows.

Theater of the Sea at Islamorada




Key West 

There was huge rush on the highway 1 (surprise!) so we missed our Parasailing reservation. They “key” in the key west is to start very early if you are going in the rush season and have a time bound reservation.

We did Jet Ski from Fury, it was thrilling experience; I had my daughter ride pillion and kid in the front. At times, we went 40 Miles+, which made the hair and ear scream due to the gushing winds. The entry to the docks was nestled inside Hyatt Centric hotel. There is some discount if you book the early 8:30 AM jet ski. We had lunch at White Tarpon Deli on Front St which had nice Tuna Tacos.

The Key West sunset is simply one of the mesmerizing sights on the planet, the ladies took the evening cruise and the whole experience was awe-inspiring.

We had dinner at Seagrass Thai restaurant before leaving, the Sushi was scrumptious (we consumed Sushi roll – I believe was called ‘Jamming’ roll). Most of the other rolls had cream cheese in them which seemed like a slap in the face of Japanese cuisine.

Glass bottom boat ride

We drove for around 45 mins from the Gilbert hotel to reach the harbor. The ship had completely different name (Arabian Queen) from the one we reserved – ‘Princess’ which confused the hell out of us and led to us almost missing it. The entry was adjacent to some hotel and we hurriedly parked there so that we don’t miss the ride. The ride starts with a 45 min journey to take you on top of a very shallow coral reef and then a speaker provides commentary for the coral life which you can observe via the glass bottom in the lower chamber of the ship. Very rare experience for kids, but please don’t do it when you have high tides. We had a horrible experience where the boisterous party at the beginning quickly became a barfing fest due to half of the people getting sick, mostly adults, unfortunately. 

Driving back from Keys to Naperville

12/29 – left from Gilbert resort and went backwards to the keys to first do glass bottom ride, then went to Everglades National Park, then went to the hotel at Kissimmee. The Days Inn hotel was one of the worst ever, almost everything was excruciatingly bad and the nightly rate was not super cheap – 140$.

12/30 – We fled from Days Inn as soon as we could and had lunch on the way at subway. Extremely time consuming experience with 75 Mins wasted. Had dinner at Woodlands Restaurant in Nashville, ordered in advance and were in and out in 45 mins, we learnt the art ordering in advance after 30 hours of road trip. Everything was little over sized and we ended up over ordering. Stayed at Best Western at Bowling Green, nightly rate was 46$ with breakfast and it was an order of magnitude better than our Days Inn stay 😊

12/31 – Left for home from Bowling Green and reached Naperville in 7 hours with just one lunch break and still had the energy to go for New Year Party!

That’s it.

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

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