There’s still a chill in the air so why not go south to St. Augustine, the “Nation’s Oldest City” where we’ll step into a warmer climate perfect for strolling quaint brick lined streets and exploring the many historical charms. Founded in 1545 by the Spanish and named after a feast day, St. Augustine’s old city is steeped rich with history and home to some of the oldest buildings in the U.S. So much of the history is preserved today right down to the narrow lanes and alleys lined with century old buildings with beautiful Spanish colonial architecture, many dating to when the Spanish first settled. With 450 years of history, there’s a lot to explore! Wander through the oldest of the old from a fort to a store and lots of fun things in between, take a deep breath in as you squeeze down the narrowest street in America, and step foot on the oldest street in the U.S. Wander into the magnificence of the former Ponce de Leon Hotel and an historic Gilded Age masterpiece, then take a walk through a district founded by freed slaves.
History doesn’t stop here! Our travels take us to Amelia Island where we’ll step into history in downtown Fernandina and embrace the wonders of nature while exploring the island’s enchanted rivers, marshes and greenways. It’s the perfect getaway to put some spring back in your step!
Day One: St. Francis Inn
After arrival in St. Augustine, we’ll check into the charmingly cozy St. Francis Inn, where every guest room is unique.
Unpack, relax and unwind or start exploring but join us tonight for an included dinner at a nearby local restaurant.
Day Two: Villa Zorayada
This morning we step into the Gilded Age at Villa Zorayada, a Moorish revival architectural masterpiece inspired by the Alhambra Palace in Grenada, Spain. Our tour will take us through the 139 years of Zorayada’s history including memories from its time as a gambling casino, restaurant and speakeasy to the impressive original art and antique collection of previous owners.
A treasure sure to impress is the priceless “Sacred Cat Rug” which is over 2400 years old and made from the hairs of ancient cats who roamed the Nile River.
Lunch St. George Street:
Take a stroll on nearby St. George Street, for pedestrians only, where boutiques, bistros, galleries, and gift shops are tucked into cubbyhole sized storefronts throughout the narrow avenue.
Grab some lunch on your own and get lost amongst the side streets to find yourself immersed in history.
Whetstone Chocolate Tasting:
Don’t have dessert, because next will be a four-tiered tasting experience at Whetstone Chocolates, perfect for that chocoholic.
Optional: Lincolnville District Walking Tour
After our sugar fix, you’ll have the option to have the afternoon to yourself for more exploration or join us for our optional Lincolnville Historic District walking tour. Founded in 1866 by former slaves, this district is St. Augustine’s most prominent historic black neighborhood.
We’ll wander through black history past notable architecture from the Victorian era seeing interesting sights along the way.
The rest of the evening is yours to spend how you please with dinner on your own.
Day Three: Castillo San Marcos
We start our day with a walk the oldest masonry fort in the continental U.S., Castillo San Marcos, a large Spanish stone fortress built to protect and defend Spain’s claim in the New World. Wander through history in rooms that once housed soldiers and prisoners and within the large interior courtyard and gun deck offering great views of the city.
Don’t miss the cannon firings and weaponry demos offered throughout the day.
The afternoon takes us to a second place where history comes alive, the magnificent former Ponce de Leon Hotel.
Marvel at the amazing Spanish Renaissance architecture decorated with Tiffany Stained Glass windows, hand painted murals, and more secrets to be discovered.
Optional: St. Photios
After we’ll relax with an included lunch nearby then if you are up for more wanderings, join us as we explore St. Photios Greek Orthodox National Shrine filled with Byzantine art, beautiful frescos, and bone fragments of 18 saints.
Now it’s time to take a rest before we meet for our included dinner.
Optional: Ghost Walk
If you’d like to walk among the ghosts tonight on our Beyond the Grave walking tour, we’ll retrace some of our steps today, hearing the haunted side of history with evidence of paranormal happenings.
Day Four: Trolley Ride
Today is trolley day, where you can ride, then hop on and off as you please. It’s the only place in town where you can go straight to jail! This isn’t just any old jail, this Old Jail was designed by wealthy Henry Flagler to look like a hotel in the Romanesque Revival style and painted in an unassuming color in order to disguise it’s function.
There’s also the Oldest Store Museum, where you never know what you might find, an amazing Live Oak canopy draped in Spanish moss on Magnolia Street and the 600-year-old Live Oak, Old Senator, among many other interesting sights to see.
St. Augustine Lighthouse:
Let’s meet later this afternoon, for a short ride out to the black and white striped St. Augustine Lighthouse. Climb the tower for the best views in town and view the exhibits depicting 500 plus years of maritime history.
The remainder of the night is yours to find a great place for dinner on your own.
Day Five: Tolomato Boardwalk
We say goodbye to St. Augustine, but there’s much more of the area to explore! Just off the coast of northeast Florida lies Amelia Island, first inhabited by Timucuan natives about 1000 when they named the island Napoyca. This barrier island maintains much of its unspoiled setting with abundant native wildlife, pristine waters and preserved park lands to explore.
But first, let’s take a nice, serene stroll along the Tolomato Boardwalk for some spectacular views and fresh salty air.
Work up an appetite, because an included lunch is next at the chill, riverfront Sandollar Restaurant.
It’s a must stop at Big Talbot State Park to visit Blackrock Beach for a surreal setting of massive driftwood trees and black rocks filled with tidepools of sea life.
If time remains, we can take a quick peek at the equally amazing Boneyard Beach.
Day Five: Amelia Island
Our home for the next two nights will be at the Addison on Amelia, located in the center of the Fernandina Beach Historic District where colorful buildings and Southern Victorian architecture line the streets and Spanish moss dangling from branches of giant oak trees dances in the ocean breeze.
This enchanting Victorian seaport village was once a stomping ground for pirates, Gilded Age millionaires, bootleggers, shrimpers, and many other colorful characters. Sit back and immerse in the charmingly historic surroundings and wander to find a delicious dinner on your own.
Day Six: Fort Clinch State Park
We step into nature and history today on a visit to Fort Clinch State Park with miles of beaches and trails to explore as well as a majestic Civil War fort. Learn about the life of a Union soldier while walking through the fort’s many rooms, galleries, and grounds.
Then take a stroll along the Willow Pond Nature trail leading to real Florida with a magnificent forest of historic live oaks, lush palm trees and magnolias.
Day Six: Shark Tooth Adventure
Best of all, have a shark tooth adventure! Sharks have been patrolling the waters off Amelia Island since the last Ice Age, leaving behind an endless supply of teeth to be found on the beaches.
Since a single shark can make between 30,000 to 50,000 individual teeth in a lifetime, there’s a good chance of finding maybe one!
Day Six: Cat Boat Ride!
After an included lunch downtown, it’s time for an exhilarating excursion! We’ll have the fun opportunity to ride your own 2 person Cat boat on a guided tour through some of the most beautiful backwater and marshlands surrounding both Amelia and Cumberland Island with a stop on a captivating island for a scenic break.
If you don’t feel up for the adventure, sit back and relax on the Beach Creek Tour cruise that navigates the waterways of Cumberland offering scenic views of salt marshes, native bird life, and the Dungeness mansion ruins.
The evening is yours to roam the historic streets and enjoy a lovely dinner on your own.
Day Seven: Breakfast & Flight Home
Now we make our way back to the airport where we’ll find ourselves soon enough in the warmth of home.
Pricing & Departures:
Air transportation is provided by United Airlines. A surcharge will apply if United Airlines increases the price of its airfare. One piece of luggage per person (baggage fee by United is not included) and one small carry-on are permitted. A valid, government-issued picture ID is required to board the plane.
Tuesday, March 19 : Flight # departs Newark at AM and arrives in Jacksonville at PM
Monday, March 25: Flight # departs Jacksonville at PM and arrives in Newark at PM
Price per person is $3,395 Twin & $4,475 Single. No reservations accepted without a deposit of $350 per person. Make checks payable to “Group Tours & Travel”, and mail to our address above. Final payment is due January 18, 2024. There are no refunds if cancellation occurs after January 18, 2024. Group Tours is not responsible for any delays, cancellations, injuries or circumstances beyond its control and reserves the right to change the itinerary. All trip components are subject to change in accordance with Government, State and Local guidelines and/or mandates. Travel protection/cancellation coverage is available and highly recommended. This tour will run rain or shine.
The Educated Wanderer
Group Tours & Travel
PO Box 632 Berwyn, PA 19312