When Chicagoans Tiffany and Greg decided to escape the colder temperatures for the tropical warmth of Maui, Hawaii on their first vacation together, the couple was unaware they would be falling in love with the destination they’d later say “I do” in.

“It [Maui] is also where we got engaged, so it holds a special place in our hearts. We instantly knew it was where we wanted to get married after deciding to have a destination wedding.”

The couple then did extensive research into wedding venues on all of the Hawaiian Islands, keeping a couple of key parameters in mind – it needed to be private, by the ocean and not on sand. Maui’s Olowalu Plantation House had all this and more.

“Since it is such a big ask to travel,” Tiffany says, “we wanted to give everyone time to plan, so opted for a longer engagement and sent Save-The-Dates a year and a half in advance.”

Knowing it would be no easy feat to plan a wedding across the country (and the Pacific Ocean), the couple recruited the help of wedding planner, Erica Goldsmith of Couture Events.

“We trusted her fully in recommendations and had a strong collaboration throughout the process,” the bride says.

Tiffany and Greg also looked to Pinterest for inspiration and to communicate their ultimate design vision to Erica. The couple also reached out to their family who owns an acrylic and printing business, which you can imagine came in clutch for all the wedding signs!

“We ended up utilizing them to create a custom seating chart designed by our planner,” Tiffany says.

Due to COVID travel restrictions, travel logistics were in constant limbo leading up to the wedding day. To keep guests informed, the couple created a separate page on their wedding website, in addition to the standard travel information, where they laid out all the steps guests would need to take to ensure they met the travel requirements.

As crazy as the travel logistics were, Erica, facilitating most of the communication with vendors, relieved the couple of the normal pressures of planning from afar. Additionally, Tiffany and Greg took a trip out to the island a few months before the wedding to meet the florist, caterer, and tour the venue.

After a year and a half of planning through a pandemic, the couple was finally able to enjoy their dream wedding in a location that held so much significance in their love story. The entire wedding celebration had a fun and funky tropical vibe that tied in aspects of the Hawaiian locale and tributes to their families. 

“There is something about traveling that reminds you how important being present is and we felt that with our guests,” Greg says. “Everyone was emersed in the celebrations and joyful to be in Hawaii, which brought the perfect energy for kicking off the next chapter of our lives.”

Vendors: Photographer: Angie Diaz Photography; Wedding Planner: Erica Goldsmith of Couture Events; Ceremony/Reception Site: Olowalu Plantation House; Florist: Bella Bloom; Stationery: Shin Dig Bespoke; Cake: Cake Fanatics; Rentals: Inspiration Event Rentals, Rio Event Design, Set Maui and Hostess Haven; Cinematographer: Caleb Dunham of No Ka Oi Media; Musician: Marvin Tevaga; DJ: Jay Langworthy, DJ Boomshot; Caterers: Cutting Edge Catering and Garnish Craft Cocktails; Calligraphy: Miss B CalligraphyHair & Makeup: MeiLi Autumn Beauty; Gown Designer: Emmy Mae Bridal; Gown Store: Bella Lily Bridal; Veil: remade from MOB, alterations by Only The Best Bridal Couture; Bride’s Shoes: Malone Souliers; Rings: Shane Co. and James & Sons; Groom’s Clothing Designer: Indochino; Groom’s Shoes: Christian Louboutin; Bridesmaids Dresses: Show Me Your Mumu