Six Secrets for Planning a Retreat for a Group of Friends

Six Secrets for Planning a Retreat for a Group of Friends


Stop talking about it! Here’s how to make a group getaway actually happen.

You’ve envisioned it for ages—escaping for a retreat with a group of dear friends. You’re laughing together in terry-cloth robes and mud masks. Or maybe your gang is at a wilderness retreat, journaling around a fire pit. Perhaps your group is together deepening a faith practice, experiencing a festival, or traveling in an exotic locale. But getting your squad off on a retreat can easily become a logistical challenge. (Ever heard the term herding cats?) Here are six secrets for turning a “maybe someday” dream into a concrete and pleasurable reality.

  1. Think big picture. Clarity is important. One person’s idea of a retreat might be learning Artic survival skills while another envisions painting mandalas, so it’s key to determine what level of adventure and what types of activities the group is most comfortable with. Is there a certain presenter your group of friends would love to hear? Would everyone enjoy a creativity retreat? Mindfulness and meditation? Yoga and vegan food? Be honest with each other about budget and expectations, and be fair when it comes to choosing a geographic location. If everyone is spread all over the U.S., for example, you might consider rotating: One year your group could do a retreat in the Southwest and the following year head to the mountains of North Carolina.
  2. Block off time like a boss. The earlier everyone can block off a week or a weekend and keep it as sacred space for the trip, the more likely it is this retreat is going to actually happen. Planning far ahead lets everyone set aside money for their retreat budget; arrange for child, house, or pet sitters; and figure out any other logistics, such as getting a passport. Even for a relatively simple weekend away, plan at least three to eight months in advance. Otherwise, you’ll face an endless chorus of “well, how about the 22nd?”
  3. Play to the strengths of your group members. Some people are savvy deal shoppers, who nimbly leap from to Priceline to Travelocity and other travel-planning sites, comparing flight prices, departure times, and rental car offers. Other people are allergic to that type of thing, but will happily research which guided hikes or ayurvedic treatments the group should sign up for. Designate based on people’s interests and skillsets, and tasks will fly off the to-do list.
  4. Select one form of communication. Decide as a group how you’ll plan your retreat (an email thread? A monthly Zoom?) and stick to it. Nothing is more annoying than getting endless texts from one person, having to return calls from another, and being asked, “didn’t you read Susie’s email?” from still another.
  5. Ask about a group discount or exclusive rental. If your group is large enough, you may be able to secure a cabin, building wing, or entire retreat center for your group, depending on the venue. You may also be able to get group discounts. Either way, be sure to ask about the available options when booking for a group.
  6. Embrace “you do you.” Yes, you’ll be together with dear friends and the main goal is bonding. However, remember that everyone is a little different. If one person wants to slip off for a solo botanical garden exploration, and the rest of the group wants to try Watsu and a cooking class, no hard feelings. You can meet back up at lunch and you’ll have even more to talk about.

*When this article was originally published in November 2020, the COVID-19 crisis had affected travel and many retreat centers. It was written with the hopeful assumption that planning far ahead—especially necessary when traveling with a large group—would take us into a window of time when greater mobility was again possible. For many of us, that time has come or is in close view.

Join Us on the Journey

Sign Up

Enjoying this content?

Get this article and many more delivered straight to your inbox weekly.