Doug and I have been together for over nine years. Unfortunately we really never had the opportunity to put our relationship front & center due to life’s road bumps. That said, when we had the moment to celebrate our unicorn love, we decided to throw a party. We were sick of seeing relatives and friends at somber events such as hospitals or funerals. We wanted something fun and uplifting to share with our family & friends – we decided to have a destination wedding. 

It was so worth it!

This was the second time around for both of us, neither experiencing what an elaborate wedding was all about. Doug’s first was at a courthouse and mine was in VEGAS (not a typo). We both decided we wanted the experience and went all in!

I thought I would share my takeaways from planning our destination wedding in Key West, Florida.

Get Organized! 

Travel time: Pick a location that is a short airplane ride away, and if possible, a short drive from the airport – there is nothing worse than getting off a plane to only have to deal with additional travel details to get to your destination.

Why this location? Decide on a place that YOU both enjoy and has significance – Doug always wanted to get married on a beach and we really enjoy the location of Key West as it ticks a lot of boxes for all types of travelers (and personalities).

Venue: Choose a venue that will benefit you with points. We are Hilton loyal and we are very savvy with making the most out of our points when charging using specific credit cards. The points earned on your wedding costs could go a long way in covering your honeymoon or any other travel expenses.

Get a really good wedding planner: This is especially true for a destination wedding, and sometimes mandated by the venue (as it was with us). Initially, I did not think it was necessary being we were having a small wedding – you will be surprised on the number of vendors, coordination, etc that is required, regardless of the size.  I learned this very quickly and was so grateful we hired a Saint named Nikka at Soire Events.It is super important to pick someone who is LOCAL.  We decided to go with the full planning package. My DIY days are over and I really wanted to be present & in the moment. Nikka took all the stress out of the wedding planning and let us just simply have fun – not to be bogged down with details. While I was dancing the night away she was in the background handling all the logistics such as handing out our tip envelopes. She literally packed us up after the wedding, collected all items left behind by guests and walked us to our room. We would not have truly enjoyed our day if it was not for her! 

Pictures: Find a quality photographer who has worked at your venue a ton. We hired Iris Moore Photograpy She was so efficient, knew every angle of the venue, a working relationship with all the venue staff (and other vendors) and let us be ourselves which ultimately has led to some wonderful pics. The day after we signed the contract,  I received a lovely email with a timeline to what iIcan expect all the way to when we would receive the photos.  In addition, and a true sign of someone who values your business, we received not long after signing with Iris a thank you box full of Key West goodies. More importantly, she has worked closely with Nikka in the past – who also highly recommended her. We just got our sneak peek and we are eagerly awaiting our photos and will post once we get.

Makeup and Hair: Find a makeup artist that knows how to deal with the climate. Instagram is the most authentic place to locate such information and that is where I found Frankie. I used Frankie Makeup Artistry and Hair Design prior to my wedding day. I put her work to a test by scheduling a trial.  We did a trial and afterwards I toured around Key West, went on a ferry to Sunset Key for dinner and her work looked amazing after all of that. She does not filter her work so you know exactly what you’re getting. 

Vendors and Social Media Filters: Be aware that many of the vendors including florists filter their work. The pictures you see on their websites may not be what you are actually getting. Be sure to ask if they used filters or you will be disappointed on your wedding day.

Florist: Once again I used Instagram as my go to for authentic reviews, We opted with Duarte Florist Design. The owner is extremly talented and I let her do her thing with her creativity. I showed her several inspirational photos and she took it from there. The flowers far exceeded my expectations. My biggest fear was thin and not full and lush arrangement and that she did not do. My flowers where over the top lush and full. I highley recommend that you do not opt for an elaborate arch that you cannot reuse in the reception. We opted with substantial wood colums with beautiful sprays on each side.After the ceremony was completed the florist took them inside the reception and reused them. 

DJ: Once again Nikka helped us with choosing our DJ, Eddie B and Company . Nikka had worked with a specific DJ named Roberto and a very talented percussionist. Thankfully Nikka had video of their work and we loved everything about their vibe. Roberto was such a professional and really set the tone for a fun night. The percussionist far exceeded my expectations and was amazingly talented! We highly recommended booking them. Please note they did travel from Miami and you do have to provide them with a hotel room. 

Dessert vendor: We opted for  Cupcake Sushi Pick something unique and fun! Nikka highly recommended cupcake sushi and we were pleasantly surprised. We opted for the cart and had a talented attendant prepare the dessert sushis. Our guests loved watching as sushi chefs prepared the rolls in front of them. I loved that Nikka made sure we had our own stash in our hotel room after the event. The owner’s story is very inspirational and worth reading on her website. You may want to pick up and move to Key West and start a business:)

Selfie Mirror Vendor: Mirror Me 24K  This was a very last minute decision and was a home run with all of our guests. I initially got this for the young crowd however to my surprise everyone loved it! Our wedding planner actually owns this business and she had an assistant stationed with it to help our guest sort out how it works. The best part of this is you get everyone’s pictures emailed to you in a link. The guest actualy get there printed prictue right on sight,  My favorites are the outtakes.

Officiant: I highly recommend that you meet with your officiant prior to your wedding and get to know him or her. We chose Reverend Steve Torrence.  Reverend Steve is an ordained and licensed wedding ceremony officiant,and has been officiating weddings in Key West for over 25 years. He takes pride in working closely with each couple with the philosophy that each ceremony be intimate and personal, and the goal that your Key West wedding be an absolutely wonderful experience. We loved the fact that he was open to performing a ceremony that incorporated two faiths. Not only was he creative with his readings and message, he had a great sense of humor that added to the charm of the ceremony. We absolutly adored Steve and plan on meeting up with him on our next trip to Key West.

Marriage License: This was such a pleasant process especially coming from NYC. We walked into a quaint courthouse with not a soul in sight. The entire process took us 20 minutes at most. More importantly there is no waiting period for marriage license in Florida if you are from out of State. I was surprised to learn that Key West is the second popular place in the country to get married. The clerk told me they provide 20 -30 licenses a day. However, you would not know that. It was such a calm and peaceful transaction from start to finish. A lovely employee took a picture of us on the steps of the court house afterwards.

Keep it SMALL:   The fairy tale is to have a huge wedding, making sure you invite the fifth cousin from an uncle.  This is your day – you want to have an enjoyable day, no family bickering, and more importantly, a great vibe.  We only invited our close friends and family. We made a concise decision to keep all Judge Judys’ and Debbie Downers of the world off of the list.  Do not put up with the guilt trips over invites. Only invite those who bring you joy and who have mutually supported you through the good and the bad. Do not care who is insulted or who is gossiping about not being invited.. The only care you should have is what and who makes you happy. This is your day and you want to ensure you are celebrating with those people you want to be there, not the “traditional policy of inviting this cousin or neighbor or distant friend”.  And look at the big picture – managing your guest list correctly will free some of your wedding budget up for truly magical experiences that everyone will enjoy.

Create Experiences and Moments

We really wanted to make sure our guest had a memorable moment/experience at the wedding, without having every minute of their day planned – remember, a destination wedding is also a mini vacation for a lot of your guests so don’t tie them to a 24/7 schedule of events. Despite keeping our guest list small we had many people make significant sacrifices to attend, and wanted to show our appreciation. Some of the things we did to show our appreciation are.

Welcome Bags: Etsy is your best friend when you are planning a wedding.Canvas bags with a palm tree, our initials and the wedding date printed on it – a great item for the pool.  We included a welcome card, front & back, that first thanked everyone for coming, reminded them of the website to consult and gave the timeline of events, And it was filled with snacks and a bottle of Prosecco. If staying at our hotel we had them delivered; if at other resorts, we took a drive and left the bag for when they checked in (HINT – good idea to get the arrival/departure date & hotel of all of your guests) We hired Ana from Effortless Creations to assist with the logistics. I had everything delivered to her and she added her creative touch. Thankfully she also dealt with delayed shipment issues.

Welcome Sunset Sail : The night before the wedding we chartered a catamaran through Fury for a welcome sail.  Drinks and horderves were served. The staff were excellent and more importantly fun!

Conch Train:  We hired the local iconic Key West Conch Train as the shuttle to take our guests to and from the welcome sail. This was a semi surprise for most of our guests. The driver went above and beyond and made stops for the people who wanted to explore Duval street after the sail. We arrived home to a handwritten note from our driver thanking us for the business! 

Transportation:  In our case we had a few neighbors on our flight to Key West.  We hired a sprinter van to take us to the airport.  And for the return home, there were 14 of us on the same flight!  We did the same thing.  You will be surprised on how well received this is if you have friends & family traveling on the same flight with you.

Destination Airport:  We arranged for a sprinter van to pick us up on arrival and when all 14 of us left on the last day, we sorted out two cars to take us to the airport together

Dinners: Besides us, my sister and two of her kids, our neighbor and Doug’s friends from the UK were in town in advance of everyone else arriving.  We had made a reservation at our favorite restaurant, Cafe Sole, for all 13 of us.  Our treat as a thank you in advance for folks coming out. And the last night in Key West, we invited anyone who wanted to come for dinner out with us.  We had a lovely group of 19 join us to cap off a wonderful few days of love & fun at Blue Heaven.

Golf Cart– We ordered a six person golfcart from Hydo Thunder for our guest to use and explore the area. We highly recommend the electic golf cart and most hotels have charging stations. Offer the cart to your guest so they can go on a adventure of their own.

Free time:  As noted, do not schedule activities every day – your guests want to enjoy the destination too. Our Website and welcome letter was used as a guide for fun activities and restaurant recommendations. Limit the scheduled activities beyond the wedding so they can get a taste of why you chose this location in the first place. We opted not to do a day after brunch. Instead, we offered a Sip and Dip at your leisure. We rented a cabana and lounged by the pool/beach. If our guests wanted to join us for a cocktail and some poolside food they were more than welcome. That said, no feelings were hurt if they wanted to do their own thing. Surprisingly we had a bit of a crowd and it started to rain but that did not stop anyone.

TIP:  Key West is not an easy place to get to (connections may be needed) and it is expensive.  We felt that our guests were making an investment in our story by traveling there (and the hotels) so we did not want them to give gifts or pay for dinners that we were a part of. We stated this on our website under the gift registration page. We appreciated them making the journey to be with us and couldn’t thank them enough!

Amazon: I had a ton of stuff shipped to my wedding planner from Etsy and Amazon. Feel free to view my Amazon Wedding Finds.

Biggest Reccomendation– Donts sweat the small stuff, Things will go wrong however it’s just a small minor detail in a much larger picture. Just have fun, dance the night away and be in the moment.