Happy Thursday! This post is sponsored by AVIS .
“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!
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.
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.
Florida with friends…
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.
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.
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.
• 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.
• 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.
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.
• 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.
• 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!
Poll closed, thanks for voting!
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.
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.
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!
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!
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.
Did 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!
Many thanks to Avis for sponsoring this post! As always, you receive my honest thoughts and opinions regardless of who is footing the bill.