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What makes a good destination for a company retreat — and why TPG chose Monterey
Editor’s note: See Monterey provided the TPG team with accommodations for three nights at the Hyatt Regency Monterey Hotel and Spa on Del Monte Golf Course, along with some activities and meals. However, the opinions expressed in this article are entirely those of the writer and were not subject to review by the destination or …
Editor’s note: See Monterey provided the TPG team with accommodations for three nights at the Hyatt Regency Monterey Hotel and Spa on Del Monte Golf Course, along with some activities and meals. However, the opinions expressed in this article are entirely those of the writer and were not subject to review by the destination or any other entity.
When you hear about a company retreat, you might imagine traveling to an urban destination with massive hotel complexes just to sit for hours in windowless conference rooms and spend evenings schmoozing over room-temperature drinks. You probably don’t imagine jetting off to a charming, nature-filled town along the Pacific Ocean.
However, in 2024, TPG skipped the likes of Las Vegas and New York City to host its team-building retreat in Monterey, on California’s central coast. Since it’s a place more about outdoor activities and epicurean pursuits than corporate strategy sessions, Monterey may not seem like the typical destination for a business trip. However, it turned out to be a great place for our content team to strengthen bonds and foster in-person connections.
Here are some reasons why it worked for us and some things to consider when choosing a destination for a team-building, off-site retreat of your own.
Feels remote without being remote
The beauty of Monterey — well, aside from the seaside cliffs, clear blue water, rolling hills and colorful piers — is that it’s actually easier to reach than you might think. Conferencegoers can fly directly into Monterey Regional Airport (MRY), about 3 miles from downtown.
MRY is a small airport, though, so prices can be high and route options limited. Since TPG staffers were flying to California from different cities around the world, San Francisco International Airport (SFO) offered cheaper and more direct flight options. SFO is about a 1 1/2- to two-hour drive from Monterey, so TPG arranged transportation via a shuttle bus service. The other Northern California airport option is San Jose Mineta International Airport (SJC), and some TPG staffers found flights there. Of course, neither option is as convenient as flying directly to the destination, but it does prove that hosting a retreat in a scenic destination isn’t as difficult as it may seem.
Another perk of Monterey’s small-town vibe is that it encourages groups to stay together after work hours. During a trip to a sprawling city like Las Vegas or New York City, staff members might peel off to see local friends, catch a show, go to a sports game or do something else once the work day ends. However, thanks to Monterey’s more secluded atmosphere, TPG staffers stuck together to explore the small city once meetings wrapped, and we even planned evenings out in the nearby hamlets of Carmel-by-the-Sea and Pacific Grove. Copy Editor Will Gordon said one of the best bonding experiences was spending free time exploring the area’s bars and restaurants with other staffers.
Key takeaway: Heading to a not-so-corporate destination encourages staff members to spend more quality time together — an outcome that is definitely worth a bit of extra planning and transportation time.
Access to points hotels with meeting spaces
The TPG team stayed at the Hyatt Regency Monterey Hotel and Spa and held meetings in its on-site conference rooms. The large ballroom was well suited for our companywide presentations, while the smaller rooms nearby worked well for breakout groups and activities.
Casual spaces around the hotel — such as various gardens, the gym, spa, golf course, tennis courts and two pools — also provided easygoing backdrops for team members to gather casually when we were not in work meetings. Plus, the plethora of indoor and outdoor spaces allowed people to enjoy the beautiful mid-October weather while mingling before and after planned events.
“I loved the hotel we were at, with all its amenities like the hammock garden, giant board games, racquetball and hot tub,” Associate Writer Rachel Craft said.
And, of course, our staff has many points enthusiasts who welcomed the opportunity to earn World of Hyatt points on a work trip. Although the destination covered most of TPG’s rooms, we prioritized finding points hotels for the whole group. This way, people paying for nights could earn points and elite credits, and they could enjoy any elite-status perks they were entitled to. If we had been paying for the whole group, we would have set up a Meeting Planner account with World of Hyatt to maximize our points earning even more that way.
Monterey is also home to some other points hotels with meeting and event spaces. For example, travelers who favor Marriott properties can stay at the Monterey Marriott or Monterey Beach Hotel, a Tribute Portfolio Hotel. Companies that have many IHG One Rewards members can opt to stay at the InterContinental The Clement Monterey.
Hosting a company retreat at a points hotel can help staff members earn loyalty status or stockpile points to use during their vacations with friends and family. Depending on the program, your company can also earn some meeting planner points. The prospect of earning points and elite status might convince more team members to attend by adding an extra incentive.
Key takeaway: During a work retreat, the hotel is more than just a place to sleep — it’s a place for everyone to continue hanging out after work hours. Choose a property that has plenty of dynamic third spaces and one that allows staff members to earn points while staying there.
Plenty of team bonding activities
Planning a company trip is different from planning a family vacation or a getaway with friends because there are many more interests and opinions to consider. For example, some people will want to relax when meetings end, while others will be eager to do something active.
“When on company work trips, you have a lot of different personalities, but Monterey had plenty of team activities to suit everyone’s liking,” Senior Editor Lauren Wassum said.
Before TPG’s trip, each staffer was asked to select an activity from a list of potential options throughout Monterey County that included a guided hike in Big Sur, a kayaking paddle around Monterey Bay, a biking expedition in town, a leisurely walk through nearby Carmel-by-the-Sea, and a wellness session at Carmel Valley Ranch.
I went on the kayaking excursion, where guides from Monterey Bay Kayaks led our group through the Monterey Bay National Marine Sanctuary. We paddled around seals, sea lions and otters for a few hours while the guides taught us all about the area’s ecosystem.
“Seeing birds, sea lions and sea otters from a kayak was definitely a highlight of the trip,” Rachel said.
Credit Cards Editor Daisy Hernandez selected the biking option. “E-biking was a great way to see Monterey up close and personal,” she said. “We rode through cute neighborhoods and got to see whales and sea otters. The guide we had did a fabulous job of showing us stunning views and sharing some of the local history.”
Witnessing wildlife and enjoying the picturesque landscape together was a quick way to help everyone bond. In the evening, when the whole team merged for dinner, it was exciting to hear stories about everyone’s experiences that day.
Plus, it’s hard to deny the effect a bit of sunshine and a sea breeze can have on your mood. Monterey’s sunny weather and mild temperatures during TPG’s mid-October visit made all the outdoor activities possible and put everyone in good spirits.
Key takeaway: Beautiful views, recreational activities and shared experiences are the perfect combination when it comes to building relationships with others. Exciting, outside-of-the-conference-room events help folks learn more about each other and find common interests, which unobtrusively helps future cross-team collaboration.
Evening events are important
On our final night in Monterey, the TPG staff took a bus to Rustique Winery in nearby Salinas for a group dinner, where we gathered in a rustic barn surrounded by rolling hills and mountains — a scenic way to end the trip and celebrate the work we accomplished during the week. We dined on tri-tip steak, roasted farm-fresh vegetables, macaroni and cheese, and arugula salad, and we sipped on rose of pinot noir from the Balestra Vineyard, chardonnay from the Gularte Vineyard and pinot noir from the Silacci Vineyard.
Of course, as one of TPG’s favorite underrated U.S. wine regions, Monterey County has no shortage of wineries, vineyards and tasting rooms for company events. You can book spaces at Holman Ranch Vineyards, Folktale Winery and Vineyards and A Taste of Monterey, to name a few.
You might also consider hosting an event at one of the area’s other beautiful locales, such as a nearby golf course (like the iconic Pebble Beach Golf Links) or a more unconventional venue like the Monterey Bay Aquarium.
Downtown Monterey and Carmel-by-the-Sea also have restaurants suitable for large group gatherings as well as for smaller group dinners. One night, the TPG team split into five small dinner groups and ate at different restaurants around town: Montrio, Alvarado Street Brewery, Flaherty’s, Schooners and Wild Fish.
“I loved that the seafood and produce I had at Wild Fish was sourced directly from local fishermen and farmers located within miles of the restaurant,” Senior Travel Editor Lyndsey Matthews said. “My favorites were the tempura-fried sablefish collars and the marine tonic cocktail made with kelp-infused gin.”
My group went to Alvarado Street Brewery, and we enjoyed bar food like burgers, salads, sandwiches and pizza alongside craft cocktails. There were about 10 people from all different teams at the dinner; I loved chatting with staff members whom I don’t normally work with and learning more about their interests and their roles at the company.
Key takeaway: Settings matter when bringing people together. For example, a bunch of small-group dinners might be a better way to foster connection than one big, formal event would be. And if you do want to host a bigger companywide event during a retreat, it’s best to choose a place with a scenic atmosphere and plenty of space for mingling.
Easy ways to extend
Avid travelers know how terrible it is to leave a destination and feel like you didn’t get to truly experience it. From iconic golf courses to Big Sur’s scenic hiking areas and plentiful beaches, there were many places to visit in the Monterey area. Since the retreat ended on a Thursday, some TPG employees used their work trip as an excuse to extend their stay and explore a bit more. Not only did this bit of leisure time allow everyone to unwind and reflect on the week of meetings, but it also boosted morale by making the retreat feel more like a getaway than a required trip.
“Beyond our activities at the retreat, there was so much to explore in Monterey and Carmel-by-the-Sea, so I knew I had to extend my trip a few extra days to see the area,” Lauren said. “As a foodie, there were plenty of dining stops I had to make, like the Fisherman’s Wharf in Monterey for a bowl of fresh clam chowder and La Bicyclette, a European bistro loved by celebrities like Taylor Swift located in downtown Carmel-by-the-Sea.”
Managing Editor Jordan Waller had made the trip to Monterey from his home in the United Kingdom, so he tacked on an extra few days to see the sights in San Francisco and make the long flight worth it.
“I’d recommend cycling over the Golden Gate Bridge, hopping on a ferry to Alcatraz and burning some small change at the Musee Mecanique — a fascinating collection of antique arcade machines that are all playable,” he said.
Key takeaway: Companies should plan retreats that end just before the weekend and select destinations that have many activity options. This way, employees — especially those coming in from faraway destinations — can extend their stay to have a more well-rounded experience. It’s also a major plus when companies ask hotel and travel partners in advance about the rates for adding on extra nights.
Lots of transportation options
While Monterey isn’t a major urban area, there are still plenty of ways to get around town. For some small-group activities, TPG staffers used Uber and Lyft to efficiently get to an assigned destination. For larger group activities that were a little farther away — like the dinner event at Rustique Winery — the whole TPG team hopped on a large shuttle bus.
When I woke up early one morning, I was able to Uber to Carmel-by-the-Sea and enjoy a coffee near the ocean before heading back to the hotel for meetings. And when a group of us stayed out in town later than others, it was easy to find transportation back to the hotel. It would’ve been difficult to break off into smaller groups and be spontaneous with plans if there were no accessible modes of transportation.
Additionally, staffers had many ways to get from the various area airports to Monterey. Some chose to rent cars at the airport and make the drive independently, while others took the TPG-provided buses.
Key takeaway: Don’t choose a destination so remote that ride-hailing services or other transportation options are difficult to access.
Tips for planning your own company retreat
The coronavirus pandemic made many companies let go of office spaces and put group gatherings on hold. Years later, millions of Americans still work remotely.
Remote work allows for a comfortable work-life balance and makes personal travel more flexible, but it can sometimes make people feel isolated from their co-workers. So, retreats are great ways for digital-first companies like TPG to bring their teams together, make fun memories and remind everyone of the company’s shared goals.
It’s smart to pick a dynamic retreat destination that doesn’t feel too buttoned-up. It can be tempting to opt for convenience and head to a tried-and-true urban conference destination next to a major airport, but there’s a risk that people might leave more jaded than invigorated.
So if you want to plan a more exciting team getaway, there are a few key things to consider. First, research what kind of off-site activities are available in the area and choose nature-focused excursions that encourage everyone to connect and enjoy the destination. Also, look for points hotels with common spaces that promote group gatherings and allow everyone to mingle in a casual setting. If you’re planning evening events or dinners, try to find memorable spots with nice views or unique offerings.
Whether you head to Monterey or choose a similar destination, you’ll notice how the power of travel and shared experiences can foster connection and strengthen team bonds.
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