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The Perfect Two Day Florida Itinerary

When you think of Florida, you probably think of white sand beaches, palm trees, and theme parks, and you wouldn’t be wrong! But Florida is such an expansive state that offers so much cultural and geological diversity and we want to show you a small part of the slightly lesser known side of the Sunshine State.

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Day 1:

We’ll be starting our adventure on the west coast in Crystal River with one of the most unique experiences we’ve ever had the opportunity to partake in...

8:00 am: Rent Kayaks and swim with Manatees at Crystal River Kayak Company (1422 SE US Hwy 19)

In fact, this experience is so unique that Crystal River is the only place in North America that you can legally swim with Manatees! If you aren’t up for the cold water or swimming with creatures the size of a small car (they’re harmless we promise), then you can always take in the beauty from above the waterline and stay in the kayak!

After a few hours of paddling and snorkeling, you’ve probably worked up an appetite, and you can’t come to the coast without having some good seafood! Don’t worry though… if you’re not a seafood fan, these restaurants offer some grass and grain fed dishes as well.

11:00 am: Early Lunch

  • Seafood Seller & Cafe

  • Dan’s Clam Stand

  • Charlie’s Fish House

Now that you’ve replenished your energy, you’re ready for our next adventure! Swimming with manatees was just the start of the fun! Next, you’re going to make the short one hour drive to Ocala where you’ll be zip lining over an abandoned quarry!

11:45 am: Head to Ocala for zip lining at The Canyons Zip Line & Adventure Park (8045 NW Gainesville Rd, 1 hr drive)

12:45 pm: Check-in for zip line tour

With the “Big Cliff Canyon” tour you’ll be soaring through the trees on 9 different zip lines, traversing 2 different rope bridges, and rappelling from a 25 foot platform in the treetops! And did we mention that you’ll be zipping at speeds up to 65 mph, 130 feet above the canyon?! Don’t worry though, you’ll be accompanied by 2 very knowledgeable tour guides that routinely perform safety checks on all of your gear to make sure that you make it to the other end of that zip line safely! By the way, if you want to have the best time, ask for Michael and James as your guides! They’re the best!

1:00 pm: Zip line tour at The Canyons Zip Line & Adventure Park

After an action packed day of adventure and thrill seeking, we’ll wind it down for the evening and head over to Flagler beach for happy hour while listening to the waves crash on the sand.

4:00 pm Head to Flagler Beach (1 hr 30 min drive)

Our favorite spot for an evening wind down is the Funky Pelican. Grab a seat on the back patio and watch the day turn to night over the Atlantic!

6:00 pm: Happy Hour Drinks in Flagler Beach

  • Funky Pelican

  • Tortuga's Florida Kitchen & Bar

  • Johnny D’s Beach Bar & Grill

  • Break Awayz

For dinner, Martin’s Restaurant & Lounge is a favorite for us. It’s a no frills, laid back steak and seafood restaurant with the biggest prime rib you’ve ever laid eyes on, but you really can’t go wrong with any of these options.

7:30 pm: Dinner

  • Martin’s Restaurant & Lounge

  • Beach Front Grille

  • Oceanside Beach Bar & Grill

  • Funky Pelican

  • Johnny D’s Beach Bar & Grill

It's been a long and eventful day, so you deserve some rest, plus, you're going to need it for all of the exploring we've got planned for day 2!

Day 2:

It’s an early start to day 2, but we promise it will be worth it!

6:00 am: Wake up in Flagler Beach, FL

Today, we’ll be exploring the oldest city in America, St. Augustine!

7:00 am: Head to St. Augustine (45 min drive)

Once you arrive in St. Augustine, you’ll need to fuel up for the day!

8:00 am: Breakfast

  • The Kookaburra

  • Maple Street Biscuit Company

  • Schmagel’s Bagels

  • The Blue Hen Cafe

We tend to opt for lighter breakfast options, so we grabbed something small at The Kookaburra, but any one of the options here won’t disappoint!

After breakfast, you’ll head to the trolley depot to start our adventures for the day!

9:15 am: Old Town Trolley Tour (167 San Marco Ave)

  • Stop #1: The Old Jail: 9:15 am (1 hr)

  • Stop #2: Visitors Information Center: 9:26 am

  • Stop #3: Potter’s Wax Museum: 9:28 am (1 hr)

  • Stop #4: City Gates: 9:30 am

  • Stop #5: Colonial Quarter: 9:31 am

  • Stop #6: Best Western/Bay Views: 9:33 am

  • Stop #7: St. George Street: 9:37 am

  • Stop #8: Churches: 9:43 am

  • Stop #9: Villa Zorayda Museum: 9:47 am

  • Stop #10: Lightner Museum: 9:50 am

  • Stop #11: St. Augustine Distillery: 9:54 am (45 min)

  • Stop #12: San Sebastian Winery: 9:56 am

  • Stop #13: Whetstones Chocolate Factory: 9:57 am (45 min)

  • Stop #14: Plaza de la Constitucion: 10:01 am

  • Stop #15: Spanish Military Hospital Museum: 10:02 am

  • Stop #16: Oldest House: 10:16 am

  • Stop #17: Castillo de San Marcos: 10:23 am

  • Stop #18: Ripleys Believe It Or Not: 10:26 am

  • Stop #19: Old Town Trolley Welcome Center: 10:28 am

  • Stop #20: Mission of Nombre de Dios: 10:31 am

  • Stop #21: Old Senator Tree: 10:33 am

  • Stop #22: Fountain of Youth: 10:34 am

*The bolded stops are stops that we enjoyed and recommend, but don’t let our suggestions keep you from getting off and seeing (or tasting) other stops as well! Flagler College (across the street from the Lightner Museum stop) is an architectural masterpiece and definitely worth a visit!

The Old Town Trolley Tour is an excellent way to see and learn SO much about St. Augustine, so we highly recommend it! If you aren’t familiar with the Old Town Trolley Tour, it is a hop-on, hop-off narrated trolley that makes 22 stops around the city before ending back where it started. They run every 15 mins, so you won’t have to wait long for a trolley at any of the 22 trolley stops. The drivers are super knowledgeable on the history of the city making it a fun and informative experience. If you’ve never taken the Old Town Trolley Tour before, we recommend taking the full 1.5 hour loop before getting off. This way you can make note of the stops that you want to get off on for your next loop.

At this point, you may or may not have seen and done everything along the trolley tour that you wanted, but either way, it’s time for lunch!

1:30 pm: Lunch

  • Spanish Bakery & Cafe

  • Burrito Works Taco Shop

  • Ben’s Soft Pretzels

  • Osprey Tacos

  • Mojo BBQ

On this particular trip, we decided to pop into Spanish Bakery & Cafe for a quick bite before exploring St. George Street, and it didn’t disappoint. The Empanadas and Black Beans & Rice were delicious! We also made a pit stop into Ben’s Soft Pretzels for a little snack as well. Who doesn’t love pretzel bites and beer cheese?! Mmmmm… If you want to continue on the trolley at this point, you absolutely can, but we opted to explore St. George Street.

3:00 pm: Explore downtown St. Augustine/St. George Street

There are tons of options for pre-dinner drinks/appetizers, but here are a few options to get you started...

5:30 pm: Happy Hour/Small Plates

  • No Name Bar

  • The Tini Martini Bar

  • A1A Ale Works Restaurant & Taproom

With so many great dinner options in the area, it’s hard to decide, but one of our favorites is Cap’s on the water. It’s a little over 5 miles out of the downtown area, but the food is excellent and the views are amazing! But, if you opt to stay closer to downtown, any of these options will be excellent.

7:00 pm: Dinner

  • Cap’s on the Water

  • Catch 27

  • St. Augustine Seafood Company

  • Harry’s Seafood

  • A1a Ale Works Restaurant & Taproom

After getting your daily dose of fresh seafood we know that you’re probably ready for a nap, but we’ve got one more exciting excursion planned where you’ll get to know the darker, spookier side of St. Augustine...

8:30 pm: Ghosts & Gravestones Ghost Tour

On this 1 hour bus tour you’ll be taken through some of St. Augustine’s most haunted sites and told the stories of how they became so paranormal. We found some of the stories fascinating and the tour guide/actor that narrated the entire tour was very enthusiastic and did an excellent job of drawing the crowd into each story.

And that wraps up our 2 day Florida itinerary! We hope that this has helped you plan you next trip to this beautiful state! Let us know your favorite things to do, see, or eat in Florida, and tag us on Instagram on your next visit to the Sunshine State!

Click HERE for access to our FREE digital library for all of our printable itineraries! Hope it helps on your next adventure to Florida!

1 Comment

Marcy Patterson
Marcy Patterson
Nov 05, 2023
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