“Happiness is not a feeling. Feelings are evidence of happiness.” —Arthur Brooks
If you are in pursuit of happiness, you could either go for Peter Attia’s super informative podcast or rev your engine for a well-planned, adventure-fueled road trip with your loved ones and wind down the year on a high note! I intend to do both.
Florida panhandle area is one of the covert Winter destinations
Criteria for these winter road trips itineraries?
Idea is to drive South in a hunt for warmer places with a lot of sunshine and outdoor activities – both touristy and nature-fueled.
Here it goes, some of the best Winter Road Trips from Chicago.
1. Louisville and Kentucky Bourbon Trail Road Trip
Distance: 300 miles.
ETA: 5 hours
Trip Duration: 2-3 days.
The full blog for my 2021 trip is here.
Bourbon is a big draw of course, courtesy Bardstown Bourbon
Why visit?
Louisville & the surrounding areas are a hidden gem – being at the centerpiece of the famed Kentucky Bourbon Trail, it is obviously a must visit for every bourbon connoisseur but that’s not all, it has plenty of other family-friendly touristy activities as well:
Louisville Mega Cavern offers underground zip-lines, walking and tram tours and is a huge hit among kids.
Nulu neighboorhood is a catnip for foodies and recognized as one of the best grubbing localities in the country.
Mammoth Caves National Park – the longest cave system in the world, is pretty near-by and highly recommended.
Lantern Tour at Mammoth Cave, Courtesy nps.gov
Kentucky Derby Museum and Churchill Downs Race Track are iconic destinations for all very ages and almost always have events going on.
Courtesy: Kentucky Derby
Louisville Sluggers Museum is a big draw for the baseball fans.
Walk of fame at the Slugger Museum, Courtesy Slugger Museum
2. Smoky Mountains
Distance: 570 miles.
ETA: 9.5 hours with couple of short breaks.
Why visit?
Believe it or not, the most visited National Park in the nation is a catnip for tourists even in Winters!
Christmas lighting in Gatlinburg and Pigeon Forge is the main attraction, especially the SkyLift Park.
And there are trails, more than 350 of them! – The day temperatures hit 50s regularly, and the crowds are low, making it perfect to crank through some of the best hikes you would find. I would recommend using AllTrails to plan your hikes.
Check here for a detailed blog listing all activities.
Panoramic views from the SkyLift Park during the day (Courtesy: SkyLift Park)
Twinkling Holidays lights and a giant tree. Courtesy: SkyLift Park
One of many, many scenic overlooks at Smokey
Laurel Falls – one of the highly rated hikes in the region
Not everyday, you get a vacation rental right by the farmstead. Taken during my 2021 summer visit.
A fierce mama bear an the Cades Cove, Smoky trip is incomplete without a bear sighting
3. Memphis
Distance: 550 miles.
ETA: 9 hours with couple of short breaks.
Why visit?
Memphis, Home of the blues and Birthplace of Rock ‘n’ Roll, needs no advertising. Music, food, revelry, mild temps, family-friendly touristy activities, it’s got all!
Big River Trail – 70-miles of gorgeous biking trail across the Mississippi levee.
The picturesque Big River Trail, quite a feast for the biking enthusiasts
Big River Crossing – a mile-long sky bridge walk on Mississippi cutting through Tennessee and Arkansas with stunning views of the river.
Shelby Farms – Vast public urban park sprawling across 4500 acres, home to bison herd as well. Starry Nights event with dazzling 3.5 million lights is a major attraction during holiday season.
The iconic Beale Street – the home of the Blues and the true birthplace of Rock n Roll.
The weather is usually very cooperative as well, amplifying the outdoor experience.
Lastly, you would find ravishing views of The Mighty Mississippi, all around Memphis, that alone is worth the visit!
Big River Trailhead in Dec 2019
Mesmerizing views on the Big River Trail. Photo courtesy, Big River Crossing
Big River Trail: You cross over to Arkansas at the half-way mark
Shelby Farms: A must-visit fog-friendly public park for all ages. Courtesy: Shelby Farms
Starry Nights at Shelby Farms – Dazzling 3.5 million holiday lights. Courtesy: Shelby Farms
Shelby Farms: A doting mama buffalo. Courtesy: Shelby Farms
You cross over to Arkansas at the half-way mark
The Mighty Mississippi – As seen from the Riverfront Park in December
Beale Street – Live music, food and festive flavor all year
Tip: If you have more days, you can also hop over to Nashville or Chattanooga as part of the trip, they are hardly couple of hours away and have a ton of activities on offer.
4. New Orleans
Distance: 940 miles.
ETA: 15hours with couple of breaks.
Why visit?
Be it the revelries or the iconic food or the vast marshy wetlands or the live music OR the Mighty Mississippi, NOLA is an absolute bliss for all road trip and nature lovers!
Touristy Reasons – Café Du Monde and its highly acclaimed Café Au Lait and Beignet, Audobon: one of a kind insect museum, Louisiana State Museum – The Presbyére, French Quarters, Bourbon Street, Jackson Square, Riverwalk.
Hiking Trails, Louisiana Swamp and Plantation Tours – Cajun Encounters Swamp Tour, Cajun Encounters Plantation Tour, Bayou Sauvage National Wildlife Refuge: a protected marshland noteworthy of swarming wildlife, Barataria Preserve: hike through the celebrated Louisiana marshy wetlands.
Here is the full blog on NOLA.
As seen at Barataria Preserve, courtesy NPS
The iconic Café Du Monde
The rousing views of the Mighty Mississippi, as seen on the way.
A view to inspire Louisiana horror folklore legacy
Plantation Tour, Courtesy: Cajun Encounters
Cypress tress with their intricate knee system
5. Pensacola and Florida Panhandle
Distance: 940 miles.
ETA: 14 hours, with a 4-5 AM-ish start.
Why visit?
Pensacola offers something for everyone:
Hikes – Bayou Marcus Birding Trail, Tarkiln Bayou Trail – we saw a ton of live Pitcher plants in action here! and finally Northern Terminus of the iconic Florida National Scenic Trail.
American History/Forts – Fort Morgan, Fort Pickens.
Scenic Highways and Beaches – Pensacola and Gulf Shores beaches , Scenic Highway 30A, , Okaloosa Island Fishing Pier.
And of course, Pensacola Naval Air Station – home of the Blue Angels.
Water sports should definitely be on the menu as well, but it was too nippy for our December trip.
Check out the full blog here.
Bayou Marcus Trail is entirely on a boardwalk
Sunset #1 – as seen from the Okaloosa Island Pier
Sunset #2 at Fort Pickens Beach
Sunset #3 at Fort Morgan, Alabama
Live pitcher plants at Tarkiln Bayou State Park
Blue Angels at Naval Air Station
A brawny cannon at Fort Morgan
Find Pensacola’s best coffee at Coffee Guy Café
Don’t miss the Northern Terminus for Florida Trail, one of the 11 National Scenic Trails
6. Disney Orlando and Key West
Distance: 1550 miles.
ETA: Have to spread the drive over 2 days, Nashville or Chattanooga are great pit stops.
Why visit?
Disney and Universal theme parks at Orlando, Key West – southernmost city for Continental United States, miles of beaches, wetlands and gators at Everglades Alligator Farm, Kennedy Space Center at Cape Canaveral, Jet Ski/Snorkeling/Pontooning/Parasailing at Fury, congenial weather – what more could you want from the Sunshine State?
Check out the full blog here.
US Route 1, Courtesy Pom’ under Creative Commons
Airboat ride at the Everglades National Park, Courtesy Everglades Alligator Farm
Star Wars – Galaxy’s Edge Theme Park, Courtesy Disney
Magical Kingdom, Courtesy Disney
Dolphin Show, Courtesy: Theater of the sea
Evening cruise at Key West, courtesy Fury
Snorkeling at Key West, courtesy Fury
7. Branson
Distance: 520 miles.
ETA: 8.5 hours with couple of short breaks.
Why visit?
Holiday Attractions – Polar Express scenic train, Christmas festival at Silver Dollar City – a 1880’s styled theme park which goes all-in during holiday season with 7.5 million lights.
Polar Express Ride. Courtesy :Explore Branson
Polar Express getting kicked off. Courtesy :Explore Branson
An Old Time Christmas. Courtesy: Silver Dollar City
Only a few of 6.5 mil lights! Courtesy: Silver Dollar City
That’s it! Hope this helps you plan your next Winter Road Trip.
Windings to Unwind 
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