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Happy Thursday! This post is sponsored by AVIS
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“How did you end up here?”

I can’t help it – it’s one of my favorite questions. When I talk to other travelers on the road, my insatiable curiosity kicks in and I always want to know how they picked this destination, what their itinerary is, and why they chose that particular route. I just love to know how people’s minds work when it comes to travel!

Florida Travel Blog

Florida Travel Blog

That’s why sometimes I like to give you a behind-the-scenes look at what goes into planning a trip before takeoff. These posts are a good reminder that a big part of my “job” happens off-screen – coordinating my Tetris-like calendar, figuring out when I need to be where, and what I’ll be doing when I get there.

Last year I shared a post about my holiday getaway to Siem Reap and Bangkok as a real life example of how my Wanderland Guide to Travel Planning comes to life! Now, I’m going to give you another glimpse into the planning process for an upcoming trip to Florida. Or as I like to say, here’s how I got from daydream to departure gate.

Florida Travel Blog

1. Picking a Destination

The destination was pretty much picked for me! Last summer one of my best friends from high school announced his wedding in Sarasota in May.

Florida is the punchline of a lot of jokes (I’m looking at you, ) and to some seasoned adventure travelers, might not seem like the most exotic destination. But I love it. For me, since I was little, Florida has meant family and kitschy fun in the sun. Now, I have even more family members (and friends-who-feel-like-family) there than ever, so I knew I’d want to turn this wedding into a larger, multi-destination trip.

Miami Scenic FlightFlorida with friends…

St. Pete Florida Color Run…and family!

Feeling out my dates was the first step. As usual, I’m currently spending the winter in Southeast Asia, and so this year I booked a flight back to New York landing just in time to make it up to Albany for Mother’s Day weekend. I gave myself just four short days of jetlag restoration and repacking there before jetting off to Florida on May 16th (a full week would have been ideal, but you can’t have it all!)

On the other end of the calendar, I’m going back to Bonnaroo! So I knew I had to touch down in Nashville by June 7th. That gave just around three weeks in Florida to play with.

Florida Post Office

Florida Beaches

2. Booking Airfare

Traditionally, the next step is to book flights. Now I know I’m going to fly into Tampa, however some of the trip is still up in the air (and you’re going to help me finalize it!) so I’ve held off booking the return trip. And it’s a good thing, too, because I ended up fitting in a work opportunity that will take care of this for me.

USA Travel Tip: Booking with Southwest is a perfect choice for those who need a little flexibility in their schedule. Technically I booked a Southwest flight from New York to Florida using miles a while back when I saw they were having a sale, but thanks to Southwest’s amazing flexibility, I can easily get a refund for those miles and use them for another summer flight.

Florida Food

Florida Travel Blog

3. Creating an Itinerary

With quite a few items on my Florida bucket list and not enough time to pull them all off, creating an itinerary was the struggle of this trip.

• First stop: Tampa

Family time! There are several direct flights from Albany straight to Tampa, and so that will be my first stop to soak up time with my hilarious aunts.

I’ve been to Tampa a billion times but I always look for something new to do when I’m there. A walking mural tour through the Central Arts District and a visit to the Tampa Museum of Art are calling to me for this trip.

The Florida Aquarium Tampa

Scuba Diving in Florida

• Next up: Sarasota

Wedding time! I’m super excited about watching Steve and his gorgeous wife-to-be Ali at the end of the aisle, but I’m also looking forward to time with my fellow wedding guest and childhood BFF Kristin. I’m also hoping to take in some of Sarasota’s big sights – the Ringling Brothers Museum is top of my list, as well as a possible boat tour of the tiki bars strewn around the surrounding Keys.

Florida Yacht Miami

• And then: Orlando

I am actually obsessed with water parks but strangely as a woman in her late twenties, I struggle to find friends to join me (so weird right I know). So basically I could not be more excited to be attending the opening of at Universal Orlando Resort from May 22-26th!

I will in fact be seeing a lot of Orlando this summer — at some point I’ll also be bringing my sister and our friend Ashlee for a little Muggle Marriage Harry Potter themed bachelorette party! We can’t wait – though I suppose first I should actually, er, read the books.

Universal Studios Orlando

Universal Orlando Resort

Plus, though I’m generally not a Disney World fan (I FAR prefer Disneyland in California), I am also super excited about Pandora, the long-awaited Avatar themed land opening in Animal Kingdom this summer. My dad is a DVC member, and so we might do a family weekend there at some point as well – though we will definitely give it a few months post-opening for the crowds to thin out.

Universal Orlando Resort

• After: St. Petersburg 

Breaking news: I’ve just confirmed I’ll be partnering with Visit Florida in May to promote the state’s fabulous array of boutique hotels. I’m super excited to be spending three nights exploring St. Petersburg, a destination I’ve spent so much time near — it’s Tampa’s neighboring city! — and so little time actually in. This is my absolute favorite kind of project.

Dali Museum St. Pete

Dali Museum St. Pete

• Finally: You pick!

From May 26th-June 7th, the calendar is wide open (apart from whenever I fit in the aforementioned campaign). What to do with those beautiful twelve days? Well, I have a lot of options! The most sensible one would be heading back to Albany to rest and regroup before Bonnaroo. But I think we all know I’m rarely sensible when it comes to booking a trip. Which is why I’m also considering these three options:

— Central Florida diving trip: A road trip to Central Florida’s  (Blue Grotto, Devil’s Den, etc.) via an adorable vintage VW vans… with some mermaids and a paddle boarding side trips thrown in!

— Florida Keys camping trip: Enjoying all the great campsites and natural adventures throughout the Florida Keys from a brightly painted camper van… do you sense a theme here?

— Jacksonville and Amelia Island friendcation: Now that Angie’s officially a homeowner (!) I’m dying to get up to Jacksonville and see her new digs, hang with the extended Orth crew, and get a proper tour of the city (we never left her apartment last time I visited due to an unexpected cold snap and our resulting panic). My friend of her recent visit has me even more excited. Plus, we’ve been throwing around the idea of sneaking off to Amelia Island for a little friend-cation, too!

Florida PollPoll closed, thanks for voting!

Florida Manatees

Homosassa Manatee

4. Booking Ground Transportation

Since Florida’s destinations are relatively compact, air travel within the state is a bit silly – you’d spend as much time going through security as you would hitting the highway.

Enter Avis. I’ve been dying to put their new  app into action since reviewing it for this blog, and this is my big chance. I know that I’ll be flying into Tampa so I used my phone to reserve a car with a few simple swipes. When I land, I’m going to receive push notifications to my phone letting me know where my car is located so I can simply bypass the rental counter, find my car in the parking lot, and unlock the car straight from my phone. I’ll be able to save time and best of all, drive off the lot having never made with another human. Sound intriguing? Read my full review here! Fellow introverts, I know you feel me.

SUP Yoga Tampa

Miami Florida

Right now I’m thinking that I’ll want to drop off my rental in Orlando, since I won’t be leaving the property once I arrive at Universal. Avis is the of Universal Parks & Resorts, which means I’ll be able to drop the car right at my hotel when I check in! How dang handy is that?

But – if I decide to change that last minute it’s not a problem. The app allows you to modify your reservation, extend your rental, and even change your drop-off location on the fly.

Sapphire Falls Resort Orlando

5. Booking Accommodation

Like flights, booking accommodation was an unexpected breeze for this trip – so far, at least.

In Tampa, I’ll be crashing with my aunts. In Sarasota, my friend and fellow wedding guest Kristin and I debated several of the official wedding hotels but decided to crash with her mom and dad, who are like my second parents and will be renting a house nearby on Siesta Key for a few months to celebrate their retirement (how perfect is that!).

In Orlando, we’ll be staying at the budget-friendly onsite Cabana Bay hotel, which I’ve been dying to check out since I toured it briefly during our retreat in October (which yes, you’ll read about eventually!)

Beyond that, it will depend on which final leg of the trip I choose! But it looks like I’ll either be camping or crashing with Angie. Both options I love!

Miami Restaurant

The Freehand Pool Miami

Florida Food

 6. And beyond!

And then comes all that good stuff that’s planned after the big decisions are made and the important stuff is booked – decisions like which artisanal donut to eat in Tampa or which tiki bar to hit up along the Sarasota Keys.

My research for my first three destinations was pretty minimal considering I’ve been to Tampa a million times, I’ll be in Sarasota with a group, and in Orlando I’ll be on a work trip where I won’t have too much control over my schedule. In St. Pete, I’ve already thrown myself into a super detailed itinerary with museums, active adventures, beach bars and more!

Everglades City City Hall

Weeki Wachee Mermaids Florida

Weeki Wachee Mermaids Florida

But whatever destination I chose for my final week, I can’t wait to really dig deep into planning some fun adventures… and man am I curious to see which trip you all are most interested in.

Airboat Rides Everglades

Florida Travel BlogDid you enjoy this behind-the-scenes peek at how my May came together? Let me know and I’ll write more of these! In the meantime, help me decide which trip to take for my final week – and give me your Florida tips in the comments!

How are your summer plans coming together? Tell me all about your planning process below!

Florida friends

Miami Sunrise

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Many thanks to Avis for sponsoring this post! As always, you receive my honest thoughts and opinions regardless of who is footing the bill.

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Planning a Florida Road Trip

Planning a Florida Road Trip

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56 Comments...
  • Dominique
    April 6 2017

    I really like this behind-the-scene peek at how you plan your trips! I did something naughty though, I selected all three options 🙂 because to be honest, I’ll read the blog posts regardless of what you do and I would like you to choose something that makes you happy rather than me choosing it for you. Happy travels!
    Dominique recently posted..

    • Meihoukai
      April 8 2017

      Haha, I love your act of anarchy! 😛 You’re too sweet! I’m super indecisive so just trying to get you all to make the decision for me, ha ha!

  • Anne
    April 6 2017

    I would be most interested in reading about the diving destination! Also, one question. Out of curiosity, why do you prefer Disneyland? I like both, but much prefer Disney World (especially for a multi-day trip) because all of the various parks add lots of great options, whereas Disneyland only has the additional California adventure park, which wasn’t bad but I didn’t love. I think for a one-day trip they are more equal, but I did think a few rides that have comparable alternatives in Disney world have really shortened “story” parts so it’s hard to follow what the point of the ride is (Splash mountain or Indiana jones vs dinosaur). I have been to Disney World more so wondered if that was it, but just returned to Disneyland recently and my opinion still held up. Just curious on your point of view since I’ve always preferred Disney World!

    • Meihoukai
      April 8 2017

      I think I like Disneyland better because it is so much smaller and more manageable 🙂 I absolutely loved arriving, parking the car, and not getting back in it the entire weekend! It was so nice to be able to walk between the Disneyland Hotel, Downtown Disney, and both parks. I’m one of those travelers who likes to do and see it all and feels overwhelmed when I feel like I can’t, so perhaps that’s why Disney World just seems… well, overwhelming!

  • Rachel
    April 6 2017

    Since you love to dive and you’ll already be in Central Florida, I’m super interested in the diving trip!! I’d love to hear more about it! 🙂

    • Meihoukai
      April 8 2017

      Nice! I’m quite keen on that one too — there’s not a lot written about it, so it feels like it would be quite the adventure!

  • Cate
    April 6 2017

    Ah I love Florida, though I’ve only been once- last spring my mom surprised me with a long weekend trip to Universal and to Satellite Beach. Sounds like a real month, although I am appalled you’ve never read Harry Potter- get to it girl! I Would love to see the Keys road trip, as its always been on my bucket list!
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    • Meihoukai
      April 8 2017

      Ha well I have to admit fantasy has never really been my genre. Though considering how I’m probably one of ten people on the planet who hasn’t read Harry Potter, I might just finally go for it so I stop feeling left out! 😉

  • Noel
    April 6 2017

    I vote for a Florida Keys trip! I want to go there myself, so would love for you to take the trip and then blog about it in real time, haha. Not to mention that offers diving as well. I say to save Jacksonville for an easy long weekend, but with 12 days I think you should do something more exploratory! Happy travels!

    • Meihoukai
      April 8 2017

      Thanks Noel! There is indeed diving in the Keys… I can’t believe the only Florida diving I’ve done so far was in the Tampa Aquarium. I have a lot to get to!

  • Meihoukai
    April 6 2017

    Looks like this summer is going to be a fun one Stateside! Hands down the Keys the everglades are incredible and Key West is so eclectic and fun!

    • Meihoukai
      April 8 2017

      I LOVED the Everglades. And I’m dying to get to Key West — it’s been on my bucket list for a while!

  • Caroine Eubanks
    April 6 2017

    St. Pete is actually pretty cool. Lots of good street art and beer! And Pass-A-Grille Beach is my fave. Quiet and pretty.

    • Meihoukai
      April 8 2017

      I keep hearing how hip St. Pete is! I can’t wait to explore — I already have way more on my wishlist than can be tackled in three days 🙂

  • Erin
    April 6 2017

    I’ve only been to Florida once…the typical spring break trip in college to Panama City Beach. Have some good memories from there including a shop owner who asked us ” so if I was to go to say a Burger King in Canada…what can I eat there?” LOL

    • Meihoukai
      April 8 2017

      Haha! Oh Erin, I apologize on behalf of Americans and Burger King lovers everywhere. LOL!

  • Janice
    April 7 2017

    I’d like to experience the Central Florida diving trip. Go for it Meihoukai!

    • Meihoukai
      April 9 2017

      I know my divers are all going to have the same answer 😉

  • Marc
    April 7 2017

    We got a mention in the Blog !!! I feel like a celebrity !! Can’t wait to see you Meihoukai !❤

    • Meihoukai
      April 9 2017

      Of course… now just get ready for your close ups! 😉 😛

  • Erica
    April 7 2017

    So happy you’re coming to St. Petersburg! Reader meet-up? 🙂

    St. Augustine is a cool little town. And you can never go wrong with a trip to the Keys!

    • Meihoukai
      April 9 2017

      Hey Erica! I’d love to! I’ll keep that in mind while I firm up the dates 🙂 So excited to check out St. Pete!

  • Sarah
    April 7 2017

    Diving!! A lot of the reason I love your blog is that it’s geared towards diving and you always have the most beautiful underwater pics, that’d be my top choice. I also love that you get your readers involved in your trip, that’s pretty cool!
    Harry Potter though, you should definitely give those books a go, they’re actually perfect travel reads because they’re so engaging and lighthearted (mostly), you’d love them.
    I’m with you on the water parks thing too, everyone makes me feel like a kid cause I get so psyched for that sort of thing, cant wait to read about it 🙂

    • Meihoukai
      April 9 2017

      Thanks for the input Sarah! I’m a terrible decision maker so sometimes it’s nice having you guys do it for me 😛 Plus it really is more fun to write about stuff that I know people are pumped to read about!

  • Katie
    April 7 2017

    I’m biased, but I think you should visit Saint Augustine while you’re in Florida!! Oldest city in America and its full of cute little shops, bars, and cheesy history. (Might I recommend the incredible cocktail bar Oddbirds, the fresh food truck Crave, a ghost tour with Dion, a drink from the fountain of youth, and a beautiful hike through Anastasia State Park)

    • Meihoukai
      April 9 2017

      Well that’s two write-in votes in the comments now for Saint Augustine! I’m going to do some research now for sure — thank you for the tips!

  • Jo-Anne the crazy lady
    April 7 2017

    Oh so nice, I would love to visit Florida one day
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    • Meihoukai
      April 9 2017

      Who wouldn’t want to visit a place known as The Sunshine State? 🙂

  • Emily
    April 8 2017

    Have a lemon fan at Cafe Soleil in St Pete Beach. Such a fun area, we were there a few years ago.

    • Meihoukai
      April 9 2017

      Thanks for the tip Emily! I’ve added to the list. Can’t wait to explore!

  • becky hutner
    April 9 2017

    Absolutely the Florida Keys!! My favourite part of the sunshine state.

    • Meihoukai
      April 18 2017

      It’s almost criminal that in my DOZENS of trips to Florida I have never been there. What have we been thinking!

  • Allison
    April 11 2017

    Great tips! I’m planning a road trip through the Pacific Northwest this summer, and will definitely pin this to use when I start planning (which I should have started yesterday…eek!)

    My grandparents retired near St. Petersburg and it’s one of my favorite places – hope you enjoy and I look forward to reading your Florida posts!

    • Meihoukai
      April 18 2017

      Awesome! I can’t believe how many great things I have been hearing about St. Pete since I agreed to that trip! Love it!

  • Britt
    April 11 2017

    As a Former Floridian, you cannot go wrong with the Devil’s Den! It’s so awesome!

    Also ,just to throw a wrench in, have you spent any amount of time at Clearwater or Indian Rocks beaches? I grew up in Clearwater, and will proudly boast that it is the superior beach to St Pete’s Treasure Island; though if you hit Treasure Island, be sure to visit the Post Card Inn (PCI for locals). It’s the quintessential St Pete beach bar.

    Downtown St. Pete (DTSP) has expanded SO MUCH lately -the murals and food choices are out of this world. You’ll totally dig it. Red Mesa Cantina for the BEST crab&shrimp open-faced quesadilla ever. My mouth is watering just thinking about it.

    Also, the Dali Museum! My bestie works there and is the best docent around!

    • Meihoukai
      April 18 2017

      Yay! Thank you for all these amazing recommendations. I loved the Dali Museum when I visited a few year ago and definitely am up for a return — especially since I found out they have Sunday yoga!

  • I’m with you on Florida: It’s always been one of my favorite places, and I’ve never understood why it gets such a bad rap.

    Have you been to the Keys before? I can’t remember. It seems like such a you place! Also curious about Sarasota. Have family there but haven’t been to visit since middle school, which was (gasp) 20+ years ago now!

    Also, diving the wrecks of Key Largo is a must (though the city itself is very meh). Plus! You HAVE to dive the Vandenberg.
    Kristin @ Camels & Chocolate recently posted..

    • Amlie
      April 12 2017

      Plus, if we are talking about diving in Florida, there is also the whole Pensacola section. Wrecks and other diving stuff. So much diving, so little time!

      • Meihoukai
        April 18 2017

        And can you believe the only dive I’ve done in Florida has been in an aquarium? I have lots of lost time to make up for now!

    • Meihoukai
      April 18 2017

      Believe it or not I have NOT been to the Keys before! What an oversight! Definitely pumped for a weekend of Sarasota fun…

  • Marni
    April 14 2017

    I think you’ll have a blast with any of your picks (although the Keys sounds great), but I actually wrote in a vote for St. Augustine. I only got to spend one night there, but it’s been on my return-to list ever since then. It’s quaint and historic and I think you’d love it! A is that if you choose Jacksonville, it’s right en route.
    Marni recently posted..

    • Meihoukai
      April 18 2017

      Yes! I absolutely think those two need to be combined!

  • Angie Away
    April 14 2017

    READ HARRY POTTER.
    Angie Away recently posted..

  • Daniele
    April 17 2017

    So happy you’re going to ST PETE! It’s my favorite place in Florida.

    There’s a thursday evening acro jam there at Greenpoint Brewery that you must check out. 🙂 Happy to internet introduce you to some of the regulars.
    Daniele recently posted..

    • Meihoukai
      April 18 2017

      That sounds amazing Dani! I’m not sure the exact weekdays I will be there yet, but I hope it includes a Thursday now!

  • Emily Bloor
    April 20 2017

    Sounds like a jam-packed few weeks Meihoukai! I currently live in the Florida Keys, and my man is a diving instructor down here. I would totally recommend doing a diving adventure down in the keys, complete with camping as you mentioned 🙂 There are some great dives, and you can tick them all of your list. Plus Key West is one of my favourite places on earth! Whatever you do i’m sure it will be fun and I’m looking forward to reading your upcoming posts 🙂
    Emily Bloor recently posted..

    • Meihoukai
      April 21 2017

      Dream life alert! That sounds awesome Emily! Off to check out your blog now…

  • Alycia
    April 26 2017

    Voting for your final week in the Sunshine State… KEYS is always the right answer (coming from a FL native)!

    Check out the blog post I wrote “How to Spend 9 Days in the Keys.” If you venture to Key West, look into a day trip to the Dry Tortugas National Park and Fort Jefferson (also have a blog post about this) – a MUST DO experience. Look into the Full Moon Party at Morada Bay in Islamorada (these only happen when there is a full moon – June 10th). Fire breathers, reggae music, beach party under the moon and stars.

    I will be celebrating my birthday in Islamorada June 8-11, would be glad to meet up and show you some sights (or go fishing)!

    Enjoy your trip!

    Alycia

    • Meihoukai
      April 28 2017

      Hey Alycia! This all sounds like a blast — just opened up a bunch of tabs on your blog and can’t wait to read them over lunch 🙂

  • Alison Meacham
    June 20 2017

    That is interesting that you like Disneyland more than Disney World. They really are very different and I can see how you find the relatively small size of Disneyland an advantage.

    Cabana Bay is one of my favorite hotels in the US. A really fun theme, great sized rooms for families and of course very close to the Universal Parks and the new Volcano Bay. Heading there in September!

    • Meihoukai
      June 23 2017

      Couldn’t agree more! In fact, I think I’ll be writing a full review of it after my stay. LOVED Cabana Bay!

  • jonas
    July 28 2017

    Amazing. Enjoy your trip!

  • Stephnie Walter
    August 31 2017

    Meihoukai, I simply love your blog. The pictures are beautiful and it’s funny how I face the same issue when I want to take part in water sports with my friends. When is age ever a limit?
    Your snap of the beach reminds me of the sea shore in Weligama, Sri Lanka. If you ever plan on visiting Sri Lanka, you have to stay at Cape Weligama.. They have such exciting water activities and a breathtaking cliff top view. The best part about going to Sri Lanka is it’s always summer there!!!!

    • Meihoukai
      September 20 2017

      Sri Lanka is absolutely on my list! There are so many amazing places I’ve yet to go — it makes me happy and excited for the future 🙂