Everything you need to know about planning a destination wedding — in a single weekend

I recently returned from a 5-day whirlwind trip of flying and then driving down to Key West, attempting to plan my entire wedding. I returned in the early hours of Monday, only to turn around and head straight to work. 

** I will most likely NOT visit again until it's your wedding day. **

And guess what: Wedding planning is not like what it is in the movies. 

Well, it kind of is.

But mostly it isn’t. 

There’s the face we all make when you realize the actual cost of catering – or the cost of a single fork. 

And then there’s the bickering and “gentle” opinion sharing of what everyone likes and doesn’t like. 

But the biggest thing about planning a destination wedding is that you can’t just pop over to your vendor. And when you’re a wee bit of a bridezilla like me, you can’t control every little detail. 

So if you're planning your wedding from afar, take it from me: You need to spend a few days at your destination wedding. But then the rest will be c'est la vie. But honestly, though. 

xx phoebe 



Research is key

Whether you're using WeddingWire, Google or the sound advice of your best friend, DO YOUR RESEARCH. Research your vendors and your venues. Shop around when something seems funny. Read books about wedding planning — like Weddiculous (a gift from my sister-in-law to-be). 

BUT, when it comes down to visiting your destination for a few days, you're not going to have time to look up restaurants, etc while you're there. You'll be booked solid with vendor meetings, checking out hotels, etc. I planned out meals (and back-up meals) plus things to do for every day.


You need to keep your budget in mind. 

I am not a budgeter. I'm terrible at it — and yes, I'll spend my paycheck on new shoes, sheet masks and lattes then wonder where my $$ went. Which is why I constantly thank the Wedding Wire gods that they created the Budgeter. I could go on a long tirade about it, but I won't because once you're planning a wedding, you'll just get it. 

Honestly, though, it was really useful when we'd all be going into vendor meetings or tastings or whatever and thought to ourselves, "okay, how much money should we be spending here? how do we know if they're totally out of our budget?" 

You really need to go to your destination for a few days to plan and sort out logistics

One thing my dad said to me that I'll never forget is this: Nothing on the internet is the same in person. And he was right.

I read about a girl that planned her wedding at the Hemingway House from across the country, without EVER visiting Key West. She had never been to Key West, and she wasn't going to go until two days before her wedding. If just thinking about it sends you into a panic attack, you're not alone. I read the story and wanted to scream. 

And honestly, though, I love all of the vendors that we're working with, but I am not trusting enough to have never met them or seen the venue. 

...and you'll want to check out accommodations while you're down there. 

 We'd all looked at TONS of hotels and inns and B&Bs online, and we each had our own favorites. But when we got there to tour, it was a completely different experience. Perhaps the photos were outdated. Or the website had conveniently left out how thin the walls were. Or that one inn's website was awful but in-person, it was an actual dream. Regardless, if you're doing a destination wedding, EVERYONE will be from out of town, and you'll want to make sure that you can recommend places to stay that you're confident will be a nice stay AND hit everyone's budget. 


Cake tasting is not what you'd expect

True story: I was REALLY excited for this whole trip down to Key West because of the cake tasting. I was stoked to be able to taste the vegan cake and pick out a perfect wedding cake with Maxim. In my mind (try not to laugh), we sat in a fancy room with petite fours of every cake-filling-icing flavor we could imagine. We'd take little nibbles of each, washing it down with coffee and milk. That is not the way it goes (though it's still delicious and REALLY fun). Basically, you receive trays of cake, with labels for each cake flavor and plastic shot cups filled with icing. And you have at it. Tasting, licking, discussing, etc. 

But something to also remember is that not all bakers are accommodating to special diets and lifestyles. Maxim and I are lucky to have found a baker than made us a custom, 100% vegan tasting tray so that we'd be able to really choose our flavor combinations. 

Come hungry for the catering tastings

You'll regret it if you don't. They feed you. A LOT. 


So use your venue's day-of coordinator, if they have one.

I don't have a wedding planner. On a prospecting call with one, the woman kindly explained that while she'd be happy to take my money, it'd be a waste — I had already done everything. I like order and control when it comes to events with my name on it, so you can imagine how laid back I am with Maxim and I's wedding. 

I can not stress this enough: THEY KNOW YOUR VENUE LIKE THE BACK OF THEIR HAND. This is so important for a crazy number of reasons. But especially if you're getting married at a historical venue, or one that’s normally open to the public, you want someone there that knows the property and knows how to keep all of the vendors — and general public — in line. 

Regardless, if you want to spend the money on a wedding planner, it will take a LOT of the stress off for you and your family. But if you don't (like me!) lean heavily on websites like Wedding Wire and try to book a venue that has its own day-of coordinator. 

The venue we chose has its own day-of coordinator, Vicky. Praise The Lord that Vicky exists, because she is like just the best parts of a wedding planner. She knows the venue like the back of her hands, she's no bullsh*t, she loves weddings and she'll be honest with you about your ideas. And whenever I'd freak or have a question or ANYTHING, Vicky would be just a single text away. She kept everyone in the family calm and relaxed — and THAT, my future wedding planners, is priceless. 

We went to the venue EVERY. SINGLE. DAY. (it's open daily to the public for tours), and we'd loiter around, checking out the space, watching which vendors were setting up for that day's wedding, etc.


Decision fatigue will definitely hit you. 

I think it hit Maxim and I after three full days of meetings with a plethora of DJs, caterers, florists, designers, etc. We'd been looking a

Take advice from the pros

Sometimes when we meet with vendors or experts, we'll think to ourselves, "no, that's not my vision." or "that's awful, why would they suggest that." I know I can definitely be guilty of it. But more often than not, your vendors are really trying to help — they don't want bad reviews or a bad business. They know that this is a hugely important day for you. 

Story from the trip: We met with a florist and designer that was talking to us about tenting, the need for tenting, etc. It was slipped in that a lot of people like clear tents. My dad and I looked at each other and shared a look like, "Oh my goodness, is this person a designer? That is so tacky." The designer clearly caught on, because soon photos were being passed around. "Wait until you see it in person." 

So we did. 

The next day, at the Hemingway House, a wedding was being set up with (you guessed it) a clear tent. And it was BEAUTIFUL. Yup, we decided. We're definitely doing the clear tent. and case in point — at night, the tents combine the beauty of a clear night wedding with the protection of a tent. 



Be clear about what you want/don't want with your vendors. 

They're trying to do a good job. And it helps no one if you sit there with your mouth shut — let them know that you have purple, prefer carrots over cucumber and that you want a clear tent instead of polka dot one. 

Oh, and definitely have a themed pinterest board at the read. All. The. Time. 

Leave buffer time in-between each vendor meeting.

This was probably the biggest mistake I've made (so far!) with wedding planning. When we went down to Key West, I tried to book us SOLID. As in, back-to-back-to-back meetings with no time in-between. I imagined that I was giving ourselves MORE time than needed for each meeting and that the extra would serve as our travel time. 

But I was wrong. OH, was I wrong. 

More often than not, your meetings will go WAY over. Either I'd get really interested or deeply attached to one detail that would become a 20-minute conversation. Or the parents would continually ask questions for a while to keep themselves at ease. Or maybe the business-side of the meeting started late because you got busy chit-chatting all about the coincidence that both your mothers are British. 


Compromise is golden

Such a truism for life, but it feels even more important in this instance. Weddings are a BIG deal that often involves big money for more than just a few people. 

When Maxim and I started wedding planning, as you may remember, he wanted a beachy-tropical wedding and I wanted to be in DC. But I also wanted a vegan-heavy menu. So we compromised. 

And there's more compromise to come, I'm sure. We're still deep in planning and coordinating and decision-making, but hopefully, this has given you just a little insight into the realities of wedding planning at a destination. Honestly, though, blogging about planning a wedding has been the most introspective, cathartic experience I've ever experienced. I love being able to share what Maxim and I are going through, what we thought was normal (but wasn't), and what we thought was really odd (but was totally normal).

WeddingWire is your best friend. 

So I started using WeddingWire a LONG time ago (like when I first got engaged and couldn't even think about wedding planning). And it's like changing. I researched all of my vendors, put them on a spreadsheet and compared. As we add to our guest list, we import their names and information into the online seating chart planner. And (thank god) they have a check list sorted according to months to make sure you're on track. 


p.s. Did you plan a destination wedding? Are you in the midst? Send me your stories → phoebe@honestlythough.org


WeddingWire was kind enough to sponsor this post.