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Celebrating America's 250th Anniversary
ON THE ROAD FLORIDA / 250
Discovering Florida's Historic Gems
February 28 - March 6, 2026
ITINERARY
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* * * IMPORTANT NOTE * * *
WE WOULD LOVE FOR YOU TO BRING YOUR ANTIQUE CAR ON THE TRIP
BUT EVERY CAR, ANY MAKE, ANY YEAR, IS WELCOMED
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VIDEO REFLECTS THE ORIGINAL ITINERARY
JUST EXCHANGE STUART FOR TALLAHASSEE AND YOU'L BE UP TO DATE
AND THE START WILL BE FROM LA TRATTORIA PAMPERED CHEF RESTAURANT
Day
1
1
Vintage Automobiles, Victorian Charm and Fabergé Eggs!
Sunday April 19 <> Miami to Stuart
Picturesque coastal town with a standout automobile collection and classic Americana
*
Morning Experience
BREAKFAST INCLUDED
At La Trattoria Pampered Chef
This is the START of our journey
8:00 AM - 9:00 AM
Day Experience
Arrive in Stuart at 11:00 AM
Things to do on your own
Possible early hotel checkin
Visit the Elliot Museum
Go for a swim at the beach
Explore Historic Downtown Stuart
Relax at one of the resort pools
Enjoy a refresher at the beachfront bar
Lunch or dine at one of the many restaurants
Day
2
2
Colonial Heritage & America's Oldest City
Monday April 20 <> Stuart to St. Augustine
America’s oldest city—colonial history, forts, and iconic architecture
*
Lunch Experience
Joe's Crab Shack Waterfront
APPETIZERS INCLUDED
Entrée on your own
12:00 PM - 1:30 PM
Historic Monument
Fort Matanzas National Monument
ADMISSION INCLUDED
2:30 PM - 4:30 PM
Arrive St. Augustine
Arrive 5:00 PM
Villa 1565 Hotel in St. Augustine
Wine & Cheese Welcome Reception
Things to do on your own
Free Time to Explore / Dine
Explore St. Augustine Night Life
Visit one of the many quaint restaurants
Day
3
3
St. Augustine Full-Day of Exploring and Entertainment
Tuesday April 21 <> St. Augustine All Day!
Free Time - All Day and Evening to do whatever your heart desires
*
Tour - St. Augustine
St. Augustine Old Town Trolley
ALL DAY TROLLEY TICKET INCLUDED
Trolley will pick you up at the Hotel
The day is yours to explore this amazing city
The tour takes you around to all the points of interest
Visit a Wiskey Distillery, a Winery, a Chocolate Factory & more!
Many places offer FREE tastings and samples
See the Changing of the Guard in the Fort
Dine at one of the many fine restaurants
Get Off and On the Trolley as many times as you'd like
Just show the driver your GROUP wrist band!
Day
4
4
Small town Victorian Charm
Wednesday April 22 <> St. Augustine to Mount Dora
Charming historic district, lakeside scenery,cozy inns, and small-town Florida character
*
A DAY TO EXPLORE AT YOUR LEISURE
Arrive 11:00 AM
Things you can do on your own
Possible early hotel check-in
Visit one of the antique shop
Explore the many lakes and inns
Stroll along the downtown shops
Enjoy the shops, cafes, and waterfront views
Lunch of Dine at one of the many restaurants
Day
5
5
Natural Springs - Legendary Show - Historic City
Thursday April 23 <> Mount Dora to Ybor City
Underwater Mermaid Show - Entertaining travelers since 1947
*
Experience a Natural Wonder
Weeki Wachee Springs State Park
ADMISSION THE SPRINGS AND SHOW INCLUDED
Arrive 11:00 AM - Leave 3:30 PM
Evening Arrival
Historic Ybor City - Tampa
Arrive 5:30 PM
Ybor City Historical ambience
Culture, history, and legendary neighborhoods
Free Time to Explore / Dine
Many Dining & Nightlife Options
The evening is yours to enjoy!
Day
6
6
Gulf Coast Scenic Drive - Amazing Views
Friday April 24 <> Ybor City to Fort Myers
Coastal Lunch Stop
Casey Key Fish House - Siesta Key
LUNCH INCLUDED
11:00 PM - 1:30 PM
Grand Finale Celebration
*OPTION* TO OPT OUT OF THE TOUR EARLY
AFTER THE FINALE CELEBRATION....
You can OPTIONALY choose to stay longer
on the beach and finish the tour on your
own later, or just head back home from
this stop! Choice is Yours!
Afternoon Arrival
Fort Myers Hotel
Arrive 4:00 PM
Free Time to Explore / Dine
EXCEPT if you are goin on the Train
Murder Mystery Dinner Train
Seminole-Gulf Rail Line
If you will be attending, RESERVE your tickets
Ask to sit with OnTheRoad250 Group
Must be at the train at 6:30 PM
Murder Mystery Dinner Show
Someone (not from the GROUP!) will die during the train ride
It's up to you to figure out WhoDunit
Excellent Prime Rib Dinner
Other Dinner Options Available
Day
7
7
Historical Origin of Inventions we "couldn't" live without today
Saturday April 25<> Edison / Ford Legacy Winter Estates Museum
*OPTION* TO OPT OUT OF THE TOUR EARLY
IF YOU STAYED FOR THE TRAIN LAST NIGHT
You can OPTIONALY choose head home right
from here after checkout. It is not
required to visit the Ford & Edison Museum
Visit to Museums
Edison & Ford Winter States Museum
9:30 AM - _____
Stay as long as you like
Lunch
On Your Own
Your Choice - The Day is Yours!
Return Home
Fort Myers to Home
You choose the time
Extra Day in Ft. Myers Area
Many Places to see, dine, and enjoy
If youd like to stay another day for additional sightseeing
The hotel will let you reserve the room at the group rate
Day
X
X
"Rules of the Road" and Important TOUR Information
Little things that will make your trip even more enjoyable
General Information
The driving force behind this TOUR is for us to create a unique travel experience for you; to ensure that you have a Great Time, that you Learn about our History, that you Share this unique experience with others, that you make new friends, and that you go home with many lasting pleasant memories! While at the same time, we raise awareness to the charitable work being done by the Be Kind Foundation and we celebrate the 250th Anniversary of our Wonderful Country!
About the Route and Directions
Detailed Route Maps and Itinerary will be provided
The ON THE ROAD – FLORIDA/250 ROUTE is not the fastest route, it is the Scenic Route. I will be a more entertaining and informative ride if you follow the directions by clicking “CLICK – FOR ROUTE” in each segment. You will see places (hidden treasures) in our beautiful state that you would never see otherwise using the super highways. However, if you would like to proceed directly to the next stop or Hotel, from any point in the route, then GPS yourself to it. All addresses are published on the ON THE ROAD – FLORIDA/250 Route Book. You can even leave the tour at any time you please, but for your safety, please keep us informed. Keep in mind that if you skip a stop or go the direct route, you will miss any planned activity along the way.
Thank You For Your Support!