They handled this by making their plans clear to everyone in their lives. “We made a couple of hard rules … just immediate family, eliminating all cousins, aunts, and uncles,” Jen says. With friends, they tried to simply cut down to the closest of the close, keeping in mind who would likely get along and have a great time together. They wound up with a group of 22, and nearly all of the guests stuck around for several days of festivities.
Tell your guests to save the date as early as possible
Booking travel to Santorini was a large and expensive ask for their loved ones, so as soon as they’d booked their date and venue the couple let people know so they could begin making plans. In the case of Joe’s family members, that meant getting passports, too, as they’d never left the country before. “Invitations and save the dates and everything came later, but for the people we knew we really wanted to be there and we wanted to invite, we let them know as early as possible,” Jen says.
The advice their guests sought over and over after this announcement wasn’t where to stay or which route to book: “The biggest question by far was, What do I wear? How should I dress?” Jen says. In response, the ever-organized bride created a whole section on their wedding website dedicated to attire, with a lookbook for both men and women. “The vibe, keywords, dos and don’ts—I tried to make it pretty comprehensive,” she laughs.
Choose a venue with a built-in planning team
Santorini offered a host of space options, and the couple found a unique method of narrowing them down. “We are both recovering product managers, so we put a spreadsheet together. We listed five or six criteria we cared about, and ranked them against the criteria,” Joe says. They filtered down and filtered down until they hit three venues, then called them each to learn about their availability, event packages, and prices.
They eventually chose Canaves Oia Suites because of its location, views, menu options, and for the major perk that a wedding planner was included in the package. “One of the challenges with a destination wedding is that a lot of people go in advance and try out everything on the menu and get a tour of the place. We did all of that remotely,” Joe says, so working with a single point person made it significantly easier. “It wasn’t turnkey, but it wasn’t as difficult as it would’ve been had we chosen to [create] something from the ground up.” From there, Jen managed everything related to the wedding day itself, while Joe plotted the group activities for the rest of the week.
Rely on a classic itinerary
To create that group vacation vibe they were going for, the pair made a plan for their guests the week of the wedding, and they were welcome to join in as much of it as they were interested in. While that could have been another logistical headache, they made it easy by choosing their favorite activities from their engagement trip, like wine-tasting at Venetsanos Winery, a sunset catamaran ride with Sunset Oia, and a trip to Paros with a guided tour there. When slotting that calendar, they tried “to think about the energy of the group and the distances people are traveling to get there, and how you can still show them a great time,” Joe says. “How do you want people to feel going into your wedding? Are they rested? Have they been up drinking the night before?”
