Even if you meet someone 30 times for coffee, it’ll never equate to the connection that forms when you’re trying to change a flat tire together on a remote island without cell service. (Yes, that happened to me.) That’s why I’ve made it a personal mission to create memorable group trips that provide space to share experiences and grow relationships (ideally with no flat tires).
I started hosting curated trips in college for my business society. As I entered the workforce, I began theming trips around learning new skills, bonding over specific topics, or going on unforgettable experiences. My goal is to handpick professional contacts for trips that accelerate bonding and promote collaboration.
If you’re thinking you’d love to go on a trip but don’t have the time, I challenge you to reframe your thought process. These trips aren’t just vacations — they’re opportunities to learn something new, build deeper relationships, reflect, recharge, and invest in your future success. Group trips are a way to access people for longer periods than you otherwise would and bond over topics outside of work. Plus, you can outsource a lot of the planning, which is a huge benefit as a busy professional.
How Group Trips Prompt Self-Reflection, New Opportunities, and Growth
For years, I attended Jeff Bezos’ annual, invite-only MARS retreat. At this event, top leaders in machine learning, automation, robotics, and space gather to listen to thought-provoking lectures about the future of technology, bond over meals, and engage in activities such as hiking and martial arts. In just a few days, people with similar professional interests meet and form long-lasting connections.
These retreats are some of the most productive “workcations” I’ve attended. They gave me time to self-reflect on my own work, learn from thought leaders, and turn professional contacts into friends. After every MARS retreat, new businesses form and people change roles. These retreats are fun and successful, driving new ideas, strong partnerships, and individual growth.
The MARS retreat resembles many of the trips I’ve been doing for 15 years, and it’s the perfect playbook for planning a professional getaway.
Here are the five key ingredients for success:
- Curation. Curate a group based on a common thread: an interest in meditation, experiences as women finance executives, etc. It’s important to handpick the right mix of people to ensure they get something valuable out of the trip.
- Purpose. There must be an explicit purpose for the trip. For example, if you want to host a meditation retreat, you should plan to spend three hours each day meditating and bringing in teachers. You can use the rest of the time for general bonding and group activities.
- Length. The trip should be at least three and a half days to give people time to build meaningful connections. (This does not include travel time.)
- Quality. My recommendation for a three-to-five-day trip is about 20 people. But if you want to maximize your efforts, you could invite up to 100.
- Downtime. Each day should have a few hours of downtime for the group to recharge and connect.
“The time to build a network is always before you need one.” – Douglas Conant
Group Trips Aren’t as Difficult to Plan as You Might Think
Remember, group trips are an investment in your future success. To make them more feasible from a planning perspective, try out these three types of trips:
1. Center your trip on learning a new skill for self-development.
Everyone has hobbies and skills they want to learn, so use those as conduits to bring people together and bond with professional contacts. For instance, pre-pandemic, a group of entrepreneurs in Silicon Valley went on annual kitesurfing trips around the world (including Richard Branson’s Necker Island). Hire a company that does custom tours to learn something new, such as mountaineering, sailing, or cooking. These companies will set a price and then usually take care of everything once you touch down — all you have to do is book a flight.
I did a four-person girls’ trip to French Polynesia, where we spent a week getting our catamaran skipper certifications. It was one of the most fun trips I’ve ever taken. We all studied together to take tests, practiced our skills on the catamaran, and bonded over a common goal. We also had a blast swimming with sharks, cooking meals together off the boat, and sailing around Bora Bora. We still regularly chat on our WhatsApp group about sailing and have been looking for more ways to put our certification to use.
2. Use pre-planned trips to meet new people.
Many companies offer incredible journeys with set dates, prices, and itineraries. You can travel at a better rate by inviting specific people you’d like to get to know on these trips. A couple of examples of ones I personally like are El Camino Travel (small group travel for women); For the Love of Travel (small group travel for Millennials); Modern Adventure (luxury culinary and wine tours); Abercrombie & Kent (global luxury tours); &Beyond (small group safaris); Nat- Geo Expeditions (history- and culture-themed trips); and Healing Holidays (wellness retreats).
Your communication skills are your greatest strength as an entrepreneur. You have to know what to say when networking, team building, and talking with investors. Going on a group trip expands your professional circle and allows you to encounter new social situations that can help you grow as a communicator.
3. Book a villa at a destination with many bonding activities.
I recommend the Caribbean for this approach! Look for homes that have a concierge or staff. These individuals can help you with responsibilities such as cooking, cleaning, or booking activities to remove those day-to-day stresses so you can focus on bonding with the people you’re traveling with. I curated a five-night trip to the Cayman Islands with 20 handpicked people where we all stayed in the same house. It was basically a summer camp for adults. We did night kayaking in a bioluminescent bay, sailing, and group yoga.
Many people on the trip didn’t know one another, but they were all Millennial tech professionals. This common thread created an opportunity for folks to have hours-long conversations. Have your guests facilitate events or conversations that play to their strengths. While on our trip, one individual hosted a yoga class, another taught everyone about body posture, and a third gave a lecture on trends in the tech industry. By planning daily events and topic-based meals, you force people to open up, reflect, and be vulnerable in front of each other.
Making time for group travel — not to mention handling the logistics — can seem daunting with your busy schedule. But you will be glad you took the leap. The growth you’ll experience will be more than worth it.