Our Key West Wedding
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Pre-Planning:
Everyone’s first question is always, why did we choose Key West? When we first started dating we both spoke often about the fact that we didn’t place a high value on getting married. As a child, I never dreamed of my wedding, aside from one single fact - if I ever did actually find someone I was willing to marry, I’d get married on a beach. Somewhere along the 6 years of our relationship, we began to talk about having a wedding, mainly just as an excuse to get to bring all of our favorite people together in one room. Combined, Drew and I have attended over 40 weddings, and we had a very long list of things we didn’t want and still, only that one wanted idea that we’d get married on a beach.
We originally started looking in St. Simons Island, GA, as that is where Drew’s mom has lived for the past 12+ years, and we’ve been vacationing there since 2017. We love the island so much, but quickly realized it would be a hard location for our friends and family to get to as it involves having to rent a car. We went to Key West together in 2017 and had an absolute blast, so it quickly came up when we started brainstorming again.
We got engaged in Asheville in November 2020 and by March 2021 I had found a few locations in Key West that I wanted to see in person, so my mom and I (always looking for an excuse to go to Florida) decided to head down to check it out. Stick with me, I promise this is relevant - we stayed at a “budget” hotel in Key West that had decent reviews when we booked and the price was awesome, but the room was not. This hotel was once a motel and it was given a very lazy bandaid to try and fix it up - this was only the start of my gripes throughout the trip. Each location we saw just didn’t fit the bill - the reception was in between the hotel buildings (anyone could walk through), the ceremony faced a mining rig across the water, and there was no place for people to stay on site. So, by the time we’d seen three spots, I was dejected and overwhelmed by the cost. Drew happened to be at the Cleveland Yacht Club and mentioned in passing to someone that I was in Key West looking at venues. They suggested a spot to him, saying they’d just attended a great wedding there recently. Brevity is not my specialty so instead of just saying the rest was history I feel it is important to mention that my mom, aunt, and I went to check out this spot and the combination of my broken spirit & a snide comment about the space from my mom, I never even toured the space. We saw the main restaurant but never saw the event space.
I headed home to Drew really unsure of what we were going to do…. but we kept coming back to the suggestion, and eventually after speaking to the event coordinator realized it was exactly what we wanted. So began the process of planning a wedding from 1,000 miles away.
I was once an event planner, so I knew I could handle the planning and I loved how responsive the team at First Flight Brewery was, they made everything really easy. I searched the internet for a Florist, and that was all we needed. We originally looked at renting furniture for our beach ceremony but realized it wasn’t worth the cost for our < 20-minute ceremony. I sourced champaign flute table cards from a local calligrapher, drew up a design for mini wallets to give as gifts (and wristlets for my bridesmaids) with my friend Anne at Anne Cate, and I ordered some items on Etsy (namely these napkins with our doggies on them and a card box). Plus, my friend Grace helped me place numbers & words on acrylics signs for our table and bar signage using her circuit.
A few additional things we did:
Ordered our save the dates from Staples (FTW) and stated RSVP was online on our free TheKnot website.
Didn’t send invites (major money savings)
Sourced a (mainly) local photographer to save on travel costs
Purchased a ceremony arch from amazon, would it have lasted more than an hour? No. Was it $300 cheaper than the florists to rent? Yes.
Elected to have the bar on consumption instead of paying per guest for alcohol. We saved around $1,200 this way.
Limited our guest list to 50 guests
Vendors:
Venue + Food: First Flight Island Restaurant & Brewery
Photographer: Kassidy Sopko Creative
Florals: Jacque Barnes Flower Co.
Wedding Week
Sunday/Monday:
Ok, so we’ve got this thing all planned, our tickets have been purchased for months and we’re getting all of our last minute details done at home, like me getting a manicure, hair cut, etc…. and then we hear about this winter storm that’s going to paralyze the east coast and hinder travel for days. I was a WRECK. I couldn’t decide what the right thing to do was! In the weeks leading up to the wedding, I was working for myself, and a few wedding guests were leaving earlier than us so I thought about changing my flight but didn’t want to leave Drew behind. After a solid day of going back and forth on us both leaving early because of this storm, we decided it was worth it. I was able to change my nail appointment (but not fit in a pedicure) and I (eventually learned) had the wrong date on the calendar for my haircut so I was able to get a few highlights but not exactly what I wanted as they (very graciously) fit me in the day before we left.
Original Flight: Friday morning directly into Key West via Miami, New Flight: Wednesday at 6 am direct into Miami from Cleveland
Wednesday:
Once my cousin Kate learned of our plan to stay in Key Largo for a few days after changing our flights to land in Miami, she decided to join us and used points to get us rooms at Baker's Cay (a spot we’d both seen on TikTok). The stress of getting to Florida and leaving before the storm was erased as soon as we got to Key Largo and had a cold beverage outside at a local bar & grill. Plus, my mom had been gone for the entire month, so it was great to meet up with her in the sunshine too. Once we checked in to our hotel and hung around the property for a while we decided to meet up for dinner with my mom and our family friends Kurt and Anette. We picked Snappers Oceanfront Restaurant & Bar and after we’d been seated for a while I walked inside to go to the bathroom. When I came back out Drew’s uncle and aunt were at our table!!! We knew they were in the keys but didn’t know they were so close, they had seen me walk inside and found our group. We had an amazing night drinking and laughing outside. Kismet for real!
Thursday:
With an extra day to hang out, we had the best day paddle boarding on the ocean (included in our Baker’s Cay stay), eating fresh food like our acai bowls for breakfast, and headed to Key Largo Fisheries Backyard Cafe to spend $60 on delicious stone crab for lunch (seriously go here asap). We enjoyed a champagne toast at sunset and dined outside on the roof of Baker’s restaurant, Calusa. The seafood we delicious there, too.
Friday morning we got ourselves packed up and ready for our drive down the keys. We stopped at Harriette's Restaurant for breakfast, based on Uncle Mike’s recommendation that they had awesome muffins (they did).
Key West Weekend:
Friday:
When we arrived in Key West, other members of our group had already arrived early, having also escaped the storm, and we met up with them for lunch. We walked to First Flight after lunch so we could all see it in person for the first time and LOVED it. Drew felt like it was truly perfect for us, and it was for sure.
At this point I felt like the stress of the trip and changing plans was starting to weigh on us, so we took some time to decompress and ended up playing a card game at the hotel before getting ready for dinner. It felt nice to relax for a minute. For dinner, we met up with our friends Pete & Sandra and Kelly & Michael who had arrived that afternoon for a drink at The Tipsy Rooster, and as we were all hanging out our officiant just walked right up to us. This was definitely a nod to one of my favorite highlights of the weekend, being able to just run into everyone we knew while on the island. From The Tipsy Rooster, we headed to Milagro and had an excellent dinner and then we headed out to start our “bar crawl” which ended up just being attended by our dinner guests and my whole mom’s side of the family. As my uncle will tell you, we were terrible at actually crawling, but we did make it to Fat Tuesday for our first frozen drinks of the trip.
Saturday:
Drew’s mom and stepdad had arrived in to town late the evening before, so we met them for breakfast. Drew and my mom was able to schedule me a pedicure, something I’d just assumed at this point wasn’t going to happen because nowhere in Key Largo had been open for my original plans. Overnight, we’d learned that my friend Mary Kate had made it out of Cleveland to Charlotte, but couldn’t catch a single flight to Florida after their original flights were canceled, so they drove the 13 hours to Key West and arrived right before I finished my pedicure. I walked to their hotel the Kimpton to grab a drink and hear their whole saga - we are so thankful they were willing to do that to be with us to celebrate! MK’s luggage was lost, so she actually ended up wearing one of my dresses to our cocktail hour haha. We also learned that my dad’s Saturday morning flight was canceled once he arrived at the airport, and they’d made it to NYC to try and get down to Florida. Spoiler alert: they ended up having close to a 24-hour travel day, but made it to Key West around 10 pm…. and they did get to fly directly into Key West. My dad’s bag was also lost lol. We were very thankful our wedding was on a Sunday!
With the help of Drew’s Dad, we hosted a cocktail hour at Alonzo’s Oyster Bar for everyone that had managed to arrive! It was so fun having everyone together, however, the restaurant was not at all prepared for our group. They had a hard time keeping up with our drink orders and had set up tables that made it almost impossible to navigate around. After the cocktail hour, we headed to dinner at Sunset Pier with our officiant, JB, and his girlfriend, Ashley, and enjoyed a super relaxing stress-free moment on the water. Drew and I are not the type that likes a lot of attention so we were definitely feeling the social fatigue!!
From dinner, we started a group text with everyone from the wedding to kick off a bar crawl starting at Sloppy Joe’s. This time we managed to crawl! We grabbed a bunch of additional people at Flying Monkeys and then headed to Capt Tony’s Saloon where the live band was playing total jams. We worked up an absolute sweat dancing along to the music. We walked home to our hotel that night and definitely participated in a few drunk shenanigans along the way.
Sunday: Wedding Day!
Sunday morning Drew and I managed to grab breakfast together just the two of us and it was a magical way to kick off the day. After breakfast, I got everything together and headed over to my mom’s suite to start getting ready. We’d booked two suites at Santa Maria Suites (we being my mom’s room and our suite) and they ended up being perfect for getting ready. Each suite has two bedrooms upstairs (with attached baths) and a kitchen and living room downstairs. It was nice to have an actual space to get ready and serve lunch for everyone… plus the hotel’s courtyard ended up being the best place for our photos. See below - you can’t even tell it’s the hotel’s pool courtyard (thanks Kassidy!!!). We had our friends coordinate pictures so Drew and I wouldn’t see each other before the ceremony.
We hired a trolly to shuttle people the 5 minutes to the public beach where we’d had friends help us get the amazon floral arch set up for our florist. (Side note: we could not have pulled off doing all of our decor ourselves if it wasn’t for the help of Kate, Justin, Kurt, and MK). After the shuttle took everyone, it came back from me and my dad and the photographer. We arrived at the beach and Kassidy our photographer got set up and then my dad and I walked over and the ceremony kicked off! Seeing everyone there for us along with the florals for the first time was so fun. Also seeing Drew :) he hadn’t seen my dress up until that point! Our officiant JB cruised through our ceremony and we were able to grab photos with everyone before the shuttle returned to take us all to Mallory Square. We were actually about 30 minutes ahead of schedule.
While I don’t typically love the cocktail hour picture idea, we wanted people to be able to experience the sunset at Mallory Square which is a must for first-time visitors, so it timed up well with us also taking pictures. So, it worked out that we didn’t take group photos beforehand. We were able to grab drinks and walk around Mallory Square snapping photos along the way. We honestly had too much time, so we walked to the venue early, but I didn’t want it to be incomplete, so we stopped at a bar across the street. JB and Ashley were already there so we joined their table and tab, and when Drew stuttered when ordering us “a dark and stormy”, we got 8 dark and stormy cocktails delivered to us instead. A nice laugh for everyone once we figured out what happened - even if the bartender made us pay for them all lol.
Walking into the venue to see everything set up was amazing - it was everything we’d pictured and so much more.
We did not pick MOH/Best man so we had each member of the bridal party speak for 1 minute (some took my requirement more seriously than others). Our speeches kicked off with my uncle Willy sharing our family’s favorite german toast, which he had everyone recite in german. Then my mom speaks and makes me cry + then Roxy (Drew’s mom) and Tom (My dad) have to try and follow her up, haha.
We had asked on our itinerary and wedding website that no one share photos of us (the couple) on social media. We encouraged them to share photos of themselves in attendance at our wedding but we wanted to discourage phone use as much as possible AND we’d hired an amazing photographer! In the last few minutes of our photographer’s time we had her grab a full crowd shot - one of my favorites of the whole night, and then let anyone who wanted a photo with us join us at their great backdrop to take a photo. This was such a fun touch!
After that, the food came out, and the staff was excellent at making sure we were eating and drinking while mingling with people. We wrapped up dinner and headed to the dance floor. We concluded the night at First Flight with Drew and me dancing to Buonasera by Michael Buble, which we had not at all rehearsed but everyone thought we had. We then went back to Capt Tony’s Saloon on the way home for more dancing and to sign a dollar bill for the wall!!
Monday:
We woke up and met a group that was headed out that day for a brunch (Drew and I rented bikes because at this point we were dead from walking and dancing everywhere, haha). Then we got to spend some time by the pool and taking naps before our sunset cruise that evening. We also had to head to the airport to rent a car for our drive to Miami the next day. We had a great time on the cruise, the weather was great and it was nice to chat with some of the wedding guests we hadn’t had as much time with!
Tuesday:
We woke up very early to kick off our drive to the Miami airport with Courtny and Gentry (the four of us in a mini cooper, seriously lol). We made great time and Drew and I headed off for San Jose, Costa Rica.
