A Special Soiree Weekend in Sarasota

One thing I’ve been hearing from you guys is that you want to hear more about my current travels right after they happen. Well, ask and ye shall receive! I’m jumping in to start sharing some posts from Florida and Tennessee, a trip so fresh I haven’t unpacked from it yet.

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I won’t lie — before my childhood friend Steve announced his wedding was taking place in Sarasota, Florida, I don’t think I could have pointed to the place on a map. But I was thrilled to make my way there regardless, one stop on a long road trip through Florida that worked out to be more perfectly timed than any of us could have imagined.

Sarasota Travel Blog Weekend

Sarasota Travel Blog Weekend

Why? Because while my other childhood friend Kristin and I — who was also making the trek south with her boyfriend Mark — were weighing up the various wedding hotels, we realized that her recently retired parents Marc and Laura would be renting a house in nearby Siesta Key at the same time while they explored future relocation spots. It just so happened to be a three bedroom house. And they just so happen to be the people I consider my second parents. And so we decided to all have a massive weekend-long sleepover party. What could be more perfect?

After a night in Tampa with my aunts, I drove down to Sarasota just in time to spend a few hours oooh and aaaahing over Marc and Laura’s cute rental before getting ready for the rehearsal dinner at Michael’s Wine Cellar.

Sarasota Travel Blog Weekend

It was a beautiful night! We got to connect with several other wedding guests, meet the beautiful bride Ali’s family, and beam through sweet speeches from family and friends.

Kristin and I even made an appearance in a giggle-worthy photo from a high school homecoming dance in the slideshow — what’s a childhood BFF’s wedding without a reminder of how badly you used to do your eyebrows?

Sarasota Rehearsal Dinner

Sarasota Rehearsal Dinner

The next day, Marc and Laura treated us to a beach day at their favorite stretch of sand on Siesta Key. I could see why they loved the place. The beach was almost Caribbean feeling! I couldn’t be happier to be kicking it in a beach chair with some of my favorite people — and a guidebook.

Siesta Key Beach

Siesta Key Beach

Siesta Key Beach

We didn’t linger too long of course — we had a wedding to get ready for! The nuptials were taking place at the Ritz Carlton Sarasota, so I knew we were in for a treat.

Sadly, after months and months of drought, Florida was hit hard with storms that week, and the ceremony had to be moved inside. My heart broke for the bride who’d planned such a beautiful outdoor ceremony, but I don’t think anything could kill the vibes once the live music cued up for the bridal party’s stroll down the aisle. Our friend Chris was one of the groomsmen and it was hard not to cheer when he started off the procession!

Ritz Carlton Sarasota Wedding

Ritz Carlton Sarasota Wedding

Ritz Carlton Sarasota Wedding

I love the Jewish wedding tradition of having both parents walk the bride down the aisle.

Ritz Carlton Sarasota Wedding

Ritz Carlton Sarasota Wedding

It was very surreal watching someone I’ve known since we were both in braces make such a beautiful commitment. I’ve grown to love Ali over the years of crashing with the two of them on some of my trips through New York City, and I truly can’t imagine a better fit for Steve — he really did crush this whole “choosing a life partner” thing.

Ritz Carlton Sarasota Wedding

Ritz Carlton Sarasota Wedding

And then the party got started! Since I know how much work brides and grooms put into their weddings, I texted them the next morning with a detailed list of everything I loved: the food was phenomenal; the band was so much fun; the room was grand and stunning.

I absolutely loved dancing the night away with some of my hometown besties!

Ritz Carlton Sarasota Wedding

Ritz Carlton Sarasota Wedding

Ritz Carlton Sarasota Wedding

Ritz Carlton Sarasota Wedding

Ritz Carlton Sarasota Wedding

Ritz Carlton Sarasota Wedding

Ritz Carlton Sarasota Wedding

The next morning, we went with Kristin’s parents for a hangover brunch and wedding recap at Sun Garden Cafe, which was my personal favorite meal of the trip. The outdoor seating area was adorable, and my fresh veggie omelette was just what I needed. After, we cruised around to Lido Key — which I didn’t find anywhere near as impressive as Siesta Key — and finally up to St. Armands Circle.

Sarasota Travel Blog

Sarasota Travel Blog

Sarasota Travel Blog

There, we found ourselves at the roof deck of the Tommy Bahama restaurant, where the tropical drinks cemented the magical feeling I had that I was truly on vacation. (It might have been the company, too, who I have years of traveling to Myrtle Beach with under my belt.) How I resisted the dessert tray, I’ll never know.

Tommy Bahama Restaurant Sarasota

Tommy Bahama Restaurant Sarasota

Tommy Bahama Restaurant Sarasota

Tommy Bahama Restaurant Sarasota

Tommy Bahama Restaurant Sarasota

That night, Marc and Laura treated us to a very special goodbye treat — a sunset cruise to the sandbar off Siesta Key.

Sunset Cruise Siesta Key

Sunset Cruise Siesta Key

It was a very cool trip that included beer, or you could bring your own booze — however, the second I realized there was no bathroom onboard I abstained from all liquids. Better safe than sorry, y’all.

The tour kicked off with our guide pointing out all the notable real estate in the area, either homes built by celebrities or with wild stories of wealthy owners. We ate it up like the good little tourists we were.

Sunset Cruise Siesta Key

Sunset Cruise Siesta Key

Sunset Cruise Siesta Key

Sunset Cruise Siesta Key

We also passed a bird sanctuary, some interesting mangroves, and most excitingly — dolphins! I smiled at the memory of seeing them underwater on a dive in Honduras years ago, and found myself feeling lucky to get to be in their presence out in the wild again.

Sunset Cruise Siesta Key

Sunset Cruise Siesta Key

Sunset Cruise Siesta Key

Yet the highlight was still to come — pulling up to an expansive sandbar in the sea. We were set loose to hunt sea shells, stick our toes in the sand, and wade around into the sunset.

That weekend, Marc and Laura had told us that Marc’s other daughter would be visiting the next weekend — and her boyfriend was planning to propose! We were so enamored with the sandbar that we all hatched the plan that her boyfriend should pop the question in this exact spot… complete with Kristin and I doing a full pre-enactment so Marc and Laura could work out their photography angles, ha ha.

Sunset Cruise Siesta Key

Sunset Cruise Siesta Key

Sunset Cruise Siesta Key

Sunset Cruise Siesta Key

Sunset Cruise Siesta Key

Sunset Cruise Siesta Key

Sunset Cruise Siesta Key

Sunset Cruise Siesta Key

Post-cruise, we grabbed a pizza from hip and happening Siesta Pi Pizza before turning in for the night. I couldn’t think of a more perfect note to end the weekend on.

It was such a lovely weekend full of amazing friends, and friends who feel like family. I was so grateful to Steve and Ali for bringing us all together to celebrate, to Marc and Laura for opening their home-away-from home, to Chris for being my dance-floor buddy and to Kristin and Mark for letting me be their third wheel.

I couldn’t ask for a more relaxing way to kick off Florida!

Ritz Carlton Sarasota Wedding

Ritz Carlton Sarasota Wedding

Next up, Orlando, Tampa, and St. Pete!

Florida Fanatic: My Summer Plans for the Sunshine State

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, Florida Man Twitter account) 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 (and actively is!) 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 Volcano Bay 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 amazing dives (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 Kristin’s coverage 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!

Which trip would you like to see me go on?

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 Avis Now 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 contact 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 Official Car Rental Partner 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.