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!