Orlando and Beyond: Florida Road Trip

A 7- 10 day Florida road trip itinerary of rides, flea-markets, shopping, road trips, beaches, history, live music, hiking and more rides

We were ready for some sun. Jill and I have a credit card that has an annual companion fair as a perk. Our companion fair was about to expire, so a trip we were a-taking. Because we have done A LOT of “winter” recently, I looked up the warmest place in North America in January—which was Florida. Florida road trip here we come!

I thought: theme parks and rides (I LOVE rides!). I thought a road trip with great play lists and cool mid-century modern buildings and beaches.

Jill thought: we should see if my nephew can come to Disney World! And so we invited her brother and his wife as well as her parents to come to Disney World to share the joy with Sevy the 3-year-old. Jill’s parents were up for an adventure and immediately responded with a responding “Yes! We are in!”. Her brother never responded at all. Hence, the planning for our all-adult kid-less trip to Disney World and Florida commenced.

We managed to pack a diverse amount of awesome into 6 nights and 7 days. Our Florida trip included 2 theme parks, a day at a massive flea market in Florida, a Steampunk Festival, shopping, a road trip up the east coast, a stay in St. Augustine the oldest city in the USA, bike rides, beaches, a drive through the Ocala National Forest, a hike on the Florida Trail, and ending with live music and more rides.

Practicalities about travelling in Florida

Below is our itinerary with information. But first some practicalities and facts about travelling to Florida.

General Information

• January is not beach and bathing suit weather in Florida. I was sadly disappointed that I didn’t get a tan and that I needed my warm clothes such as long pants, socks and long sleeves and jackets at night. We didn’t pack for this weather well and had to buy warmer clothes. You can wear flip flops in the day, and can break out shorts or a dress on the warmer days, but make sure you bring some warmer items.
• A car rental is a MUST. Even if we had have just stayed in the Orlando area, you need a car. Things are spaced out. The roads are good, and if you have Google maps or a GPS it’s easy to get around. While there is Uber and Lyft and cabs and public transit, Orlando is a place to drive in. It’s quite far between places you will want to go, and who wants to waste half a day transiting about the vast landscape???  Fill up your rental car far in advance of the airport, as there are no gas stations nearby and you will get dinged with excessive refuelling costs.
• Once you leave Orlando you are in the “Deep South”. Let me tell you, it’s not like Canada, where we harken from. There are a lot of accents, and there is a racial and political divide that felt noticeable. There are a lot of Trump signs, Confederate flags and bumper stickers and supporters which boggles my mind. I actually feel I had a bot of culture shock.
• There is a serious “gun culture”. As a Canadian, where guns are just not part of real life, and only police and hunters generally have guns, the visibility of guns and pro-gun propaganda is alarming. It blew my mind that I could walk through a flea market and buy a gun from a dude who made his own paper sign “Guns for Sale” with spray paint. This is F*ed up. At one booth and old man was playing with his guns on display, and actually turned around and pointed the gun into the crowd, directly at Marilyne, and pulled the trigger. WTF. He didn’t even seem to think this behaviour was problematic, even though he could have killed someone if he had forgotten a bullet in the gun. Many gun advocates argue that it is safer if people have guns because if a crazy person comes along shooting things up, other people can take them out with their own guns: I have to say I did not feel safer knowing many of the people around me had guns on them. Nope. Not on teeny bit safer. America has a serious gun problem that is visible and disturbing.
• There’s a whole lot more to Florida than Orlando and theme parks, although those are pretty fun.

Where to stay in Orlando

The Thorton Park/ Lake Eola, Winter Park or College Park areas of Orlando are all central, hip areas that are reasonably safe, with restaurants and amenities. Any of those areas would be good to stay in for a few days.

There isn’t really a clear gaybourhood in Orlando, although the above areas would all be good for a stay. Alternatively, right down town has the most gay events and venues.

We found an Airbnb in Orlando with a great back yard and pool in the College Park area. This area was fairly central, but also easy to get in and out of downtown and around Orlando from, although a little further from downtown than other areas. Thorton Park had been my first choice, due to the park area and its close proximity to downtown for food and entertainment, but our first booking was cancelled and I couldn’t find another suitable place for 4 adults in the price range we wanted.

Renting an Airbnb and having our own space for three nights in Orlando let us cook half of our meals at home, which was handy for building in some “down” time, but also good for the budget.

A 7-10-day Itinerary for Orlando and a Florida Road Trip

We did the following Florida road trip itinerary in 6 nights / 7 days. The itinerary can be adjusted easily to make it work for you. It could easily be adapted for 10 days, which would be perfect, but 7 worked well. There are things I would do differently, now that I know what I know, and I have noted that in the itinerary. Some of the below event are only on certain days, which are noted, in case you need to plan around those. I also have provided information as to where you might want to take extra time if you have more than 6 nights.

Day 1 (Saturday): Get there

Get to Florida and settle into our Airbnb for three nights in Orlando. Hit up the Publix grocery store for goods.

Day 2 (Sunday): Renninger Flea Market, Steam Punk Festival, and a Bonfire

Day: Flea markets and Rad Finds

The Renninger’s Flea Market takes place on each Saturday and Sunday in Mount Dora- about a 30-45 minute drive from Orlando Florida. In addition, it hosts theme days and special events. Quite wonderfully, on the day we went there was a Steampunk Festival and flea market, which was entirely unique, with extraordinary outfits and very interesting booths as well as live music and entertainment.

The flea market is massive- so large it is difficult to see everything in one day. It’s a great way to spend a day near Orlando.

For more information read my blog post “Rad Finds In Florida: Renninger’s Flea Market and Steampunk Festival”.

Evening: Dinner and hang

Dinner we hit up the Graffiti Junction burger place in College Park. Paul had seen their burgers and wanted one! They are known for their great burgers and toppings. The burgers were delicious, although I expected them to have a wider range of toppings considering the hype. The fried cheese curds are to die for and we ordered two plates because we couldn’t get enough. Graffiti Junction is clearly a locally loved place and the industrial graffiti lined place was filled with young families, children running amuck, groups of tattooed friends and beer drinking folk. Our multi-generational Canadian party was a bit out of place but no one cared.

Once back at our Airbnb we headed to the back yard with glasses of wine and started a bonfire in the fire pit and watched the sparks until bed. Pretty satisfying.

Day 3 (Monday):  Shopping by day, Disney World’s Magical Kingdom by night

Day: Shopping at Winter Park and Outlet Mall

On day three we struck out to shop until we drop. We started by going to the lovely Winter Park area, where there is a street of unique local shops and eats, lined on one side by a park. There is a train station here as well, if you are training about.

Jill also found a great dress shirt at a men’s fashion store (not pictured here). The clothing here was stylish. So stylish that the owner rather condescendingly and passive-aggressively told Marilyne (Jill’s mom) that her shoes looked “comfortable”. Reportedly, her shoes are in fact very comfortable, even if they didn’t meet the uppity owner’s style sense. His attitude was a bit of a turn off, but the shirt is very nice.

There are a number of outlet malls in the same area of Orlando, near the Disney theme parks. You can shop for days if you choose.

We hit the outlet mall closest to downtown, Outlets Orlando, where we power shopped for 2 hours. Jill got her wedding pant (maroon to wear with her baby blue and navy vintage suit) and we bought matching leather Converse for our wedding shoes (Jill’s are white to match my dress, and mine are navy blue to match Jill’s suit. How cute are we going to be???)

Day 4: Florida Road Trip up the east coast to St. Augustine

On Day 4 we packed our newfound items and luggage into the car and struck out on a Florida road trip. We headed to the east coast for some beaches on our way to our destination, St. Augustine.

From Orlando we heading for the little coastal town of New Smyrna Beach, known for it’s surfing and  shark bites! Here we would start our northern journey along the scenic A1A coastal road north. Orlando to New Smyrna Beach is approximately 90 km / 1+ hour drive on the highways.  The journey from Smyrna Beach to St. Augustine takes a further 2 hours without stops, due to the lower speed limits on this scenic route.

Along this leg of the Coastal Road Trip on Hwy A1A, from south to north included this and more (for more on the spots along the route see my other blog post):

• In Smyrna Beach we searched for sharks teeth on the beach and checked out the shops before lunching and hitting the road going north.

• Dayton Beach wins for coolest buildings and adorable colorful mid-century modern hotels and motels, many with original old-school signs.  A drive through this old area of Daytona Beach is colorful and charming.
• Remote beaches galore, with little town, park, nature reserves: we stopped at the Washington Oak Garden Park, which is a protected area of trees, as well as sand  dunes and a large beautiful beach.

We landed in St. Augustine around 4:00 pm  in the afternoon.

For more information on the towns, beaches, and things to explore along the east coast of Florida, see my post “Road Trip! East Coast Florida Beach Towns and Beaches”.

ADD A DAY IDEA: if you have extra days, consider a night or two in New Smryna Beach or an old/ redone kitchy motel along the Daytona Beach waterfront. See this post for more information and ideas.

Day 5: St. Augustine and the little pink Florida Motel

St. Augustine was a great place to spend time. We could have spent longer here; if you have extra days, consider spending more than 2 nights in St. Augustine. 

St. Augustine is touted as the “oldest city” in USA. The town centre is walking only area. It is chock full of little stores, ice crème shops, restaurants, and live music venues. In the day and the evening live music could be heard pouring out of places. St. Augustine was lively, remarkably hip for a tourist destination, and full of history and personality.  

We stayed at the wonderful little pink Florida Motel: a revamped sweet mid-century modern motel with free bikes. It was a joy.

For more on St. Augustine, including where to stay, eat and things to do, click here for my blog post: “A Guide to St. Augustine Florida, the Oldest City in North America: Our Favourites and Photos”.

Day 6: Florida road trip- the northern beaches, hiking the Florida Trail in the Ocala National Forest and back to Orlando

Coastal A1A Road North

From St. Augustine we continued to travel north along the A1A to Jacksonville Beach.. The total distance is approximately 50 km, and takes about 45min – 1 hour without stops. Much of this road is a spit surrounded by conservation areas—the Guana Tolomato Mantranzas National Research Reserve.

We stopped at the Second Parking lot , where we took a trail through the trees that brought us to a pretty cool tiny airplane crash on the non-coastal side of the highway. We took another trail across the highway that took us a vast gorgeous and completely deserted beach.

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For more information on the towns, beaches, and things to explore along the east coast of Florida, see my post “Road Trip! East Coast Florida Beach Towns and Beaches”.

Add A Day Option: The whole section of the A1A road along the spit has a bike lane both ways on a long flat well paved road, and would be a lovely way to integrate an overnight bike trip…. Or if you are like Paul go back and forth in one day. If you are a cyclist, I would suggest considering adding a day and integrating little overnight bike jaunt: you could bike from St. Augustine to Jacksonville where you could stay overnight and then ride back the next day.

Ocala National Park and Hiking on the Florida Trail

From Jacksonville, if you take the route we took, through the Ocala National Forest, then onto to Orlando it takes approximately 3.5 hours of driving. 

The Ocala National Forest spans over 600 square miles in central Florida. We stopped at Silver Glen Springs Recreation Area off road 19 for a picnic, which turned out to be a stunning little spot, with an aquamarine little lake, that apparently is Manatee habitat.

We wanted to do a hike and settled on doing would do a small section part of the Florida Trail for a small 1.5-2 hour hike. The Florida Trail runs 1000 miles through Florida and is designated as a National Scenic Trail in the USA. The part of the trail we picked was not glorious, unfortunately, but there are clearly gorgeous areas and wonderful hiking. My post talks about alternate hikes that would have been better, based on our experience, and if we could choose our hike again.

For more information on hiking in Florida, see my post “Hiking in Florida: the Ocala National Forest and the Florida Trail”.

Add a Day Option/ What I would do with this day instead: We tried to do too much this day; this trip would be better over 2 days—one for the coastal area, and one for hiking in or near Ocala National Forest, where a longer and nicer hike could be done. If I were redoing this day again, I would skip the drive north up the beach area, and would just strike out toward Orlando, through Ocala National Park with enough time to do the St. Francis Trail, which is a 12.9km loop, located in the south end of the Ocala National Forest (directions are in my other blog post).

Back in Orlando:

We stayed that night at a generic hotel near the airport Sleep Inn & Suites Orlando because it was near the airport and had a shuttle for Marilyn and Paul. It actually was a pretty good place to stay, with big rooms and a swimming pool and hot tub outside, at affordable prices. After enjoying a hot tub and wine, we struck out for our best dinner experience yet, in a restaurant suggested by the hotel only 2 km away.  

Fish on Fire was our favourite dining outing in Florida! Who would have thought right near the airport???? We drove up to the retro styled restaurant that looked hopping busy with fun-goers. We walked inside and there was a full blues band playing awesome music! The food was full-on deep south American style. I ordered the catfish basket with 2 full fried catfish, Jill ordered a massive plate of pulled pork and collard greens and corn followed by banana cream pie, Marilyne had the grouper fish of the day, and Paul ordered the blackened chicken (although he considered the alligator basket). The food was delicious all round, the music was fantastic and we had an unexpectedly great time on our last night of the trip.

If we go back to Florida, we will go to Fish on Fire again for authentic feeling deep south American food and music.  

Day 7: Marilyne and Paul leave on an early flight and Michelle and Jill go to Universal Studios Islands of Adventure!

Waahoo!!!! More rides! Goodness, the rides are fun at Islands of Adventure.

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Click here for my post “How to Kill it at Universal Studio Islands of Adventure: 2 Adults; 4 Hours“.

We then drove to the airport, dropped our car off painlessly at Hertz and caught out 3:55pm flight home to British Columbia, Canada. What a day!