Patrick and Paige, both from Chicago and working in the real estate industry, chose to have a destination wedding for several reasons. They wanted an experience for their guests that would extend beyond just one night. They also wanted to get married in the winter months without having to plan for more than a year-long engagement. Ultimately, they chose Gasparilla Island, also known as Boca Grande, in Florida for its quaint charm and easy accessibility from the airport.

“We love Chicago and it will always be home, but getting married at the later end of the group of our friends made it so that people were excited to try somewhere new,” the couple says.

However, finding a venue that could accommodate two large groups of family and friends proved to be challenging. They had to be mindful of the cost and time commitment their guests would take away from work and family to join them. Fortunately, their wedding planner, Lauren at LK Events, was with them from the beginning and helped narrow down their list to find the best vendors in the area.

“We had a unique set of ‘wants’ and ‘musts’,” Paige says, “and she (Lauren) narrowed down our list by state, city and venue.”

As with any destination wedding, there were travel logistics to consider. While Florida typically has great weather in late January, guests flying from the Midwest and East Coasts had a harder time getting out due to cancellations and delays. However, once on the island, most guests were impressed with the quaintness of the town and the ease of getting around by foot or golf cart.

One thing that set Patrick and Paige’s wedding apart was the inclusion of do-it-yourself projects. They incorporated a family tradition of having crackers at the table each Christmas dinner and created custom-made crackers for each guest, which they popped simultaneously during the reception. Inside were small jokes, games, bubbles, and signature paper hats, which created great conversation and set a fun tone for the rest of the evening.

“Given the feeling that you are hosting a weekend rather than one night, we treated our guests to several events outside of the wedding night,” the couple says. “Because of the added events, we spent more than we would have on a typical wedding, but it was all worth it! We were so fortunate to have so many travel to Florida to be with us and it was such a unique experience.”

One piece of advice that Patrick and Paige received and followed was to not leave each other’s side the whole wedding night. It’s easy to be pulled in many directions and never experience the day/night together. 

“Your wedding is the only day of your life that you should both have the same memories together,” the couple says. “Having a destination wedding made it so that we were able to see all our guests throughout the entire weekend and not feel guilty staying within a hand grab of each other on the wedding night.”

Vendors: Photographer: Alisia Thompson; Wedding Planner: LK Events; Venue: The Gasparilla Inn & Club; Florist: Botanica International Design Studio; Rentals: Style House Rentals; Stationery: Magnificent Milestones; Hair & Makeup: Brides by Kelly Anne + Co; Gown Designer: Palazzo Bridal; Men’s Attire: Suit Shop; Bridesmaid Dresses: Jenny Yoo; Band: The Brett Foreman Band; Videography: Namesake Creative; Tent: Sperry Tents Naples; Photo Booth: White Tie Photobooths