The Art and Science of Planning the Perfect Group Trip

Shared experiences are the surest way to build new bonds and shore up old relationships. But pulling off a truly great group trip takes a whole lot more than making sure there’s enough bed space for everyone. It takes considering dietary restrictions and thinking about ways to fill up downtime and finding the kind of communal spaces that can foster connection. In other words, it takes a ton of planning and a little bit of finesse. Whether you’re looking to host a cool corporate retreat or a fun family reunion, these tips will help you maximize your attendees’ enjoyment and minimize your stress.

1) Keep Downtime Top-of-Mind

When deciding whether or not to go on a group trip, the biggest determining factor for attendees is often the area’s recreational activities. Do your colleagues love wine? Then they’ll probably love trying the Rhone varietals in Alma Rosa’s open-air tasting room. Do your nieces and nephews love animals? Then they just might love hand-feeding ostriches at Ostrichland U.S.A. too. As you’re considering when and where to plan your group trip, make a list of all the attractions and activities that each destination has to offer—and don’t forget to list on-site amenities either. A quick dip in the pool between breakout sessions can help keep attendees more engage—and make their afternoons more enjoyable. [in-text link 1: https://almarosawinery.com/visit/tasting-room-experiences/] [in-text link 2: https://www.ostrichlandusa.com/]

2) Make Room for Togetherness

On any group trip, the most memorable and meaningful interactions are often unplanned. They’re the conversations around the campfire that stretch late into the night. They’re the early-morning omelet fests that leave dishes dirty and bellies full. They’re the big ideas and far-fetched dreams that are shared over games of bocce ball. When you’re searching for the perfect place to host your group trip, make sure it offers the kind of communal spaces where your attendees will naturally want to congregate.

3) Prioritize Personal Space

Like many of the best things in life, togetherness is best enjoyed in moderation. It’s important to ensure that the accommodations you book offer plenty of space for solitude. And it’s equally important to make sure that your itinerary leaves enough time for people to enjoy it. Because, as any family reunion organizer can tell you, a little bit of decompression and a good night’s sleep can be the difference between a respectful debate and an afternoon-wrecking fight.

4) Make Sure Meals Aren’t Left to Chance

Hanger can hamper all kinds of great experiences. And when you’ve got a party of 18, finding food on the fly can be more than a little challenging. That’s why it’s always a good idea to plan group meals well in advance. If you’re planning for a group of 10 or fewer, you can start by creating a list of everyone’s dietary restrictions and preferences and cross-checking the menus of local restaurants against that list. If you’re planning for a larger group, it may be easiest to ensure that everywhere you eat offers dairy-free, gluten-free and vegan options. Reservations are always recommended for group meals. But, as the organizer, it’s also important to remember that you don’t have to be responsible for planning every last lunch. It’s okay to occasionally ask attendees to fend for themselves—so long as they have enough time and advance notice to do so.

5) Use Commonalities to Create Shared Experiences

Whether it’s family bonds or commercial ties that are bringing your travel companions together, there’s something you all have in common. And by tapping into your shared connections, you can plan activities and excursion that feel meaningful for everyone. For instance, if your grandmother used to make spritz cookies for the holidays, you can plan a trip to Olsen’s Danish Village Bakery in Solvang to sample their butter cookies. (They sell them by the bucket!) Or if the theme of your corporate retreat is Driving Change, you can plan an outing to Mendenhall’s Museum of Gasoline Pumps and Petroliana to see just how much driving and car culture have changed over the last 50 years. Using commonalities to inspire group activities not only increases participation but also gives everyone in attendance one more thing to share. [in-text link 1: https://olsensdanishvillagebakery.com/] [in-text link 2: https://www.mendenhallmuseum.com/index.php]

Between the logistics involved in ensuring that everyone has a place to sleep and the creativity required to come up with fun things for everyone to do, planning a group trip isn’t easy. But with a good organizational system and a few guiding principles, you can foster the kind of shared experiences that make relationships richer. And in our opinion, that makes every minute of the planning process worth it.

If you’d like to learn more about hosting your group getaway at Flying Flag, our group travel team will be more than happy to help answer questions, book accommodations, secure conference rooms and recommend anything from a good caterer to a great winery. Just drop us at line at 805.691.8086.