Every now and then we get a real wedding couple who so eloquently describe their destination wedding day and everything that went on leading up to it. In these special cases, we like to step aside and let the couple tell their story. It also gives our readers the chance to see what questions we like to ask of the couples in order to curate inspiring real destination wedding stories. Today’s couple, Kristen and Matt, who said their “I do’s” in Key West, Florida, shared their story in length and detail we don’t want you to miss:

Q: Why did you choose to do a destination wedding?

We have always loved travel and adventure and are we are not very traditional. Because of this, and since being married was always more important to us than a big, fancy wedding, we considered eloping, but ultimately decided it was important to us to have our closest family and friends with us to celebrate our marriage. Having a destination wedding was a perfect compromise for us to feel like we were doing things “our way” and staying true to ourselves rather, while still being surrounded by an intimate group of loved ones, and getting to celebrate our relationship and create memories to last a lifetime. 

We also lived in NYC at the time, and most of our friends and family would be coming in from out-of-town if we had gotten married there. While beautiful and exciting, the city can be difficult to get into and to navigate once there for out-of-towners. We knew if we got married close to home, it would be stressful for many of our guests and we wouldn’t get much time with them. 

Q: How did your family and friends respond to the decision? If any of them had a negative reaction, how did you resolve it?

The response to our decision to have a destination wedding was overwhelmingly positive. I can’t say that many people were surprised since our friends and family know that we love to travel and usually do things “our own way.” Mostly, I think people were just excited we were having a wedding at all, rather than eloping, and almost everyone was even excited to be able to take a trip to a new, “bucket-list” destination to celebrate our wedding with us. 

Our only concern in choosing to do a destination wedding was whether it would put any strain on our guests – financially or logistically – to have to take time off work and to travel for our wedding. We went out of our way to make it abundantly clear to everyone invited that while we would be overjoyed to have them with us to celebrate our wedding, we completely understood it was a huge financial and time commitment and that there was absolutely no pressure to attend if it didn’t work for them.

Now, after our wedding looking back, we couldn’t have imagined it going any better for our guests. Everyone who came really embraced our wedding as not only a celebration of us but as a special getaway/family vacation for them. 

Q: How/why did you choose the location/destination? Did you run into any issues specific to this destination and how did you resolve them?

While we initially dreamed of a faraway, “exotic” location (in fact, Matt joked his ideal elopement was just the two of us, climbing up the side of a mountain), we wanted to strike a balance between having a destination wedding somewhere beautiful, and choosing a location that was accessible enough that most of our guests would still be able to come. As most of our loved ones live on the East Coast, we felt Florida was easily accessible for most by a short plane ride, but Key West would still feel tropical and a world away from the suburbs and cities up north where we all live. Matt’s dad was actually the one who, on a whim, asked if we had considered Key West. We had never been before, but once we started looking into it, and found the Hemingway Home, we knew right away it was perfect for us and exactly what we were looking for! 

The only issue we were concerned with was timing our wedding around the weather. Our venue didn’t have a “back up” indoor location in the event of rain, only the option of a tent. We both really wanted to have our entire wedding – ceremony, cocktail hour, and reception – outside and didn’t want to pay for a tent we didn’t want and would probably not end up using anyway, so honestly, we took our chances and we got really lucky that it was a perfect, cloudless day with no rain in sight!

Q: How would you describe your overall experience of planning a destination wedding?

I’m very organized and interested in event planning, and I was never concerned with having a big “perfect” wedding, so I was honestly surprised that the first month (or so) and last month of planning were actually pretty stressful for me. A lot of this stress was due to trying hard to stay within our budget without compromising elements that were important to us and our wedding vision, but some of the stress was definitely compounded by the fact that we were planning our wedding – without a planner – while working full-time thousands of miles away. Luckily, we had amazing vendors who were very gracious about working with us over countless phone calls, e-mails, and text messages as we ironed out all of the details. 

Q: Did you use any resources when planning your destination wedding that you feel would be helpful to other couples? i.e. books, a wedding planner, referrals?

Getting married in a small, close-knit wedding town like Key West, it was also helpful that all of our vendors knew each other and worked closely together on weddings and events every single day. This meant we were able to get recommendations from our vendors we were already happily working with – like our incredible photographer, Iris Moore. It really put us at ease not being able to be in-person to “control” every detail because our vendors knew and liked each other and were used to working together. This made us a lot less fearful of how smooth our wedding day would go even though we had a ton of vendors all working together and even though we planned from afar. Our venue also had a list of preferred vendors that they knew and trusted to work with, so we also referenced that in our selection of vendors. I can’t say enough about using “word of mouth” recommendations and seeking out other people’s experiences to add to your own judgment and gut instinct on vendors, especially when you are planning a destination wedding and can’t check everything out in person. It definitely served us well and we were happy with every single vendor we chose!

Q: Did you include any do-it-yourself projects in your wedding/reception? If so, please describe them.

We knew we wanted to make our day as unique and personalized as we could, so we had a lot of fun focusing on the “little details” of our wedding and reception. One thing we decided to do last-minute was to add a wedding program. We ordered the template off Etsy, and before we flew down to our wedding, I ran to FedEx and printed our customized programs off and cut them all by hand myself. That was a little last-minute addition we were definitely glad we had at our ceremony.

We also ordered little wooden cut-outs of each guest’s name off Etsy to put at each place setting. While not DIY by us, it was our own vision, and we tried to incorporate little touches from our own imagination anywhere we could, to make our wedding feel more intimate and special to us, and to make our guests feel special and welcomed, as well. 

Other special touches we ordered ourselves included everything on the welcome table. We worked closely with Sweet Carolina Collective to design custom signs and a custom card box for our big day. Since we love to travel, in lieu of a guest book, we had a guest globe (from Etsy) for our guests to sign, that said, “And so the adventure begins,” accompanied by a custom sign from Sweet Carolina Collective that said, “You mean the world to us, please sign our guest globe.”

One of the most meaningful parts of our wedding for us was incorporating my Aunt Donna, who passed away shortly before our wedding after a heroic battle with ALS. We decided to forego favors and instead opted to make a donation in my aunt’s honor to the ALS Association. For us, no matter how cute a favor maybe, there was no more meaningful or important way to spend our money than putting it towards a cause so close to our hearts. 

Also, my mom surprised us by putting together the most beautiful, special, personalized, thoughtful, and on-theme tropical welcome bags for us guests – complete with tropical flower gift bags, water bottles, a map of Key West and all the fun activities and sites to see, a vintage-inspired Key West postcard and lots of Key West-themed goodies – including key lime cookies! It was such a special, personalized surprise and I am so happy we had this done for our guests – it made it a lot more meaningful and was a nice surprise for everyone coming in from out of town.

Q: What were the travel logistics like for your guests? Did you run into any issues and how did you resolve them?

Overall, we were pleased to hear that 99% of guests described their travel as super quick, easy, and stress-free! After harboring some guilt/worry about having a destination wedding since everyone had to travel, it was great to see that in reality, everyone who came to the wedding did so because they genuinely wanted to be there and were in fact excited to travel and have a mini-vacation in a beautiful tropical place in addition to celebrating our wedding. And all those who drove through the Keys to get there, really enjoyed that part of the trip and the stunning water views, as well. We did our best to communicate to our guests about our travel and wedding plans – letting everyone know when we would be arriving and departing, and what events and activities (and for whom) we were putting on during the wedding week so that everyone knew when they wanted to fly in and out. We also booked a big block of rooms at a beautiful hotel right across the street from our venue, and invited our family and closest friends to book their rooms there at a discounted rate, if they all wanted to. Luckily, no matter how far anyone traveled to get there, once our guests arrived, they were able to spend the whole week/long weekend car- and worry-free! Everyone was able to congregate around the pool for breakfast, afternoon-mojito and pool breaks, and late-night chats, while able to walk from there all around town and to see all the sites. 

Q: How were you able to coordinate with vendors from afar? Did you run into any issues and how did you resolve them?

Technology is a game-changer for destination wedding planning! Particularly in the first and final months of planning, but really through the whole year of our engagement, I was constantly emailing, texting, and calling back and forth with our vendors to coordinate and plan everything for our wedding. Most of our vendors were extremely responsive and happy to help us plan remotely. This was due to one, the fact that being a destination wedding town, vendors in Key West are used to having brides plan from afar, but also owing to the fact that responsiveness to e-mails and inquiries was absolutely a factor we weighed into our vendor-choosing decisions. We were so lucky to have vendors that absolutely loved their work, were super engaged in the planning process with us and were excited to communicate with us remotely to iron out all the details for our big day.

Q: Do you feel you spent more or less money by choosing to do a destination wedding?

While we would have tried to stick to a similar budget no matter where we got married, since we lived in NYC at the time, I imagine we ultimately would have spent more money had we gotten married close to home rather than in Key West just because the NYC area is so expensive. From what I’ve heard, the venue and vendors would likely have cost a lot more in NYC than in Key West. That being said, it’s amazing when you plan even a small, intimate, destination wedding, how much costs can add up, and keep in mind that you will be adding travel costs – flights, hotels – on top of that. 

Q: How do you think your wedding would have been different had you not held it away from home?

The main word our guests still use to describe our wedding day is “magical” and that is exactly what we wanted. Every wedding is beautiful and special and meaningful in its own way, but what we really wanted to achieve for our wedding was a feeling of being transported. We wanted to be in a relaxed, tropical paradise, in a lush garden surrounded by our closest loved ones, celebrating our marriage and not having to worry about rushing anywhere, or traffic, or day-to-day stresses of “real life” or logistics, and we wanted for our guests to be included in that feeling, too, and that is exactly what having a destination wedding achieved. By the time our wedding day came, everyone was so comfortable with one another and was so happy and well-rested and relaxed, so they were able to step into our wedding with total presence and peace of mind, and just focus on celebrating and having fun. 

Q: Overall, do you have any special advice you would like to share with our readers to help prepare them for their day?

A few practical tips I would suggest that helped us or that I wished we had known: don’t be afraid to ask for help – people want to help and like being involved, and it will alleviate stress from you leading up to and on your big day. Even if you don’t go with a planner (we didn’t use one either), try to get a day-of-coordinator – it will take a ton of stress and strain off you so that no matter how hard you worked leading up to the big day, on the day that counts, your wedding day, you can just relax and be present and enjoy. 

Lastly, a small, but important suggestion we wish we had thought of before our wedding. We wish we had asked for takeaway plates from our (absolutely amazing) caterer! Our wedding food was the best food we have ever tasted, and our caterer was incredible about serving us with absolutely everything first and giving us so much food during the wedding. 

Finally, don’t be sad thinking that it’s only one day that will go by so fast and be over so soon. Not only is your wedding day just the start of your lifelong marriage (the most exciting adventure and reason for it all, anyway), but it will become a cherished lifelong memory to be shared not only between you and your spouse, but also with all of your guests, that everyone will look back on, and talk about, and remember so fondly forever – even more so when you choose to have an exciting destination wedding! 

Vendors: Photographer: Iris Moore Photography; Equipment Rentals: Eventfully Yours Rentals; Dress Store: RK Bridal NYC; Beauty: Bella Luxe Hair & Makeup; Officiant: Rev. Steve Torrence; Musicians: Bongo D Steel Drums; Reception & Ceremony Venue: Hemingway Home; Video: 5801 Weddings; Floral Designer: Milan Event Florals; DJ: Visualize Entertainment; Accommodations: Lighthouse Court; Caterer: Great Events Catering