29 Amazing Executive Retreat Ideas for 2021

It’s that time again…time for a getaway with your team. Sure, location an essential part of offsite planning, but what will you do when you get there. As much as we love a good “two truths and a lie” icebreaker, your retreat has so much more potential… I mean we’re talking epic. And with every epic retreat, there’s a theme. So saddle up cowboys and grab your backpacks wanderers cause we have this retreat is about to get a serious makeover, we’re talking early 2000s rom-com makeover serious.

Already have a theme in mind? Here’s a fast pass to skip the line:


The Scouts: Glamping Edition

The Wild West

Amazing Race

New Heights

Through the Screen


1.Wellness Inner Zen

Next stop: relaxation station! Okay, so maybe that came off a bit like an excited soccer mom trying to rally her kids to play in midday come in the Floridian summer sun, but I promise this retreat is so much more. No orange slices needed to motivate this team; although cucumber slices are highly encouraged! Face masks, yoga, and wine …yes, we know the way to your heart. This theme stresses the importance of work-life balance. With an emphasis on team appreciation, it’s no wonder everyone will be leaving refreshed.


Team Building:

2. Paint and Sip

Calling all Van Goghs…and his distant, we’re talking the third cousin, twice removed distant, relatives. It’s your time to shine with this creative bonding event. Whether you decide to follow a Bob Ross youtube tutorial or hire a third-year art student named Cherry to lead, this event is sure to be a favorite. The best part? Abstract art is all the rage, so maybe your bird looks a bit like a decapitated banana, it’s all part of the artistic vision. Finger-painting is not frowned upon.


3. Spa Day

Now, this is where the cucumbers come in handy. There’s no better way to reward your team for their hard work than a trip to the spa. Chances are your wellness venue has a spa onsite, but if not there are plenty of other options; you can get crafty with it and make at-home facemasks while relaxing by the pool or you can treat your team to an offsite spa, extra props if it has a jacuzzi.

4. Wine Tasting

Honestly, is it really considered self-care without a glass of wine? But I mean really why stop there? Not only is wine tasting a great way to explore the culture of your city, but it’s also an activity that everyone can get behind. With an instagrammable vineyard for the mini influencers, cheese and wine for the foodies, and grape-stomping for the adventurers, what more could you really ask for?


5. The Scouts: Glamping Edition (lots of team bonding)

Whether you were part of a troop or not there’s a reason girl/boy scouts is so iconic. Sure, a relaxing get-away to the spa is great, but some times what we really need to recenter us is to get in touch with our more primitive side…okay, so maybe it’s more glamping than roughing it in the wild, but you can still tell your friends that you were “one with nature.” In all reality, this natural retreat is complete with cozy cabins and quirky yurts… and of course bonfires.

Icebreaker: Suddenly

Gather around the campfire, it’s time for stories! I bet you didn’t think polar bears and spaceships belonged in the same universe, but with this icebreaker anything’s possible. The parameters for this icebreaker are simple. Someone starts telling a story and after three sentences end it with “when suddenly.” It’s now the next person’s job to fill in what happened; keeping going until you’ve created a masterpiece.

Team Building:

6. Karaoke

Maybe “America’s Got Talent,” but does your company? It’s time to find out with some karaoke. Break out the bubbly and belt until your heart’s content. Sure, regularly karaoke’s great, even if Lane’s a bit of a mic hog, but why not spice it up? Add a little cayenne to your bonding event by splitting up into teams. Give each time enough time, 15 minutes is plenty, to decide a band name, pick a song, and choreograph some sick dance moves. Who knows maybe they’ll even break out the costumes! Not sure your ready for the humiliation your cat scratched voice brings, take a fun twist on a classic with Lipsync Karaoke.

7. Through the Dark

Nothing screams team-bonding like an obstacle course…well except an obstacle course where the participants are blindfolded. Okay, before you start bringing up logistical nightmares and employee life insurance, I promise it’s not as cruel as it sounds. Make a course by wrapping a rope around different obstacles. Blindfolded participants will use the rope and non-blindfolded teammates to make it to the end, safely. Not only will this undoubtedly be hysterical, but it’s also a great exercise for developing trust and communication.


8. Order Up

I’m sure you’ve heard that “the way to somebody’s heart is food.” While this is the same with your team. But why not add a little friendly competition into the mix? But competition with a dash of teamwork and a pinch of bonding, after all every good cookoff requires teamwork. I mean, even Chef Gordon Ramsay has sous-chefs. After splitting up into groups, pick a category and give everyone a time limit to create a masterpiece. Full disclosure: this event may be accompanied by a symphony of exploding fire alarms and banging pots.

9. Kayak Tour

We’re in the great outdoors and that means…kayaking. You could opt for paddleboards, but with sdfjldsjflksdjlfjdslkfj.


10. Wild West

Saddle up boys, it’s rodeo time! After all, they don’t call it the wild west for nothing. Okay, so maybe “Billy the Kid” not exactly what you’d consider a role model, especially in a work environment, but what better way to blow off some stem than by….


– The Story Behind Your Name

I found this to be a very powerful post-dinner, “sit around with the beverage of your choice” activity. No set up is needed. You might want to use a timer so folks don’t go on and on.

Talk about the origin of your full name. That is the only prompt. You learn about the person’s origin story, something about parent(s), cultural heritage. This can be powerful and really funny (our own Lindsay Hoffman was named after a 70s actor named Lindsay Wagner who played the Bionic Woman – I laugh every time I think about it.) STICK TO IT OR MAKE IT UP

Team Building:

11. Hog Call

Everyone pairs up. Each couple comes up with their own distinct hog call, then spreads out and blindfolds themselves. The pairs make their hog calls to try to locate their partner. First to do so wins.

12. Visit a ranch

A ranch is a classic retreat location, and it’s easy to see why. Ranches offer the opportunity for fresh air, plenty of meeting space, and room for outdoor activities. And they often include any and all of the amenities you could possibly need.

Many ranches offer excellent group rates and have plenty of team-building activities and even spas on site, so your leadership members can work, play constructively, and unwind — all in one place. Ranches are nestled around most major cities, so you can keep travel costs and carbon emissions down. If you want to create a ranch-like retreat experience at a Peerspace venue, just ask the host about the amenities they offer.



13. Hit the Saloon



15. The Amazing Race (adventure)

When your executives need a break from sitting at their desk jobs, a day of outdoor fun is the perfect retreat idea. You can choose from activities like boating, hiking, obstacle courses, paddle boarding, biking, ziplining, or even charity races or triathlons. This retreat option also doubles as a team-building event, so you can be assured that you are using everyone’s time and resources wisely. Effective executive retreat ideas are nearly endless when you’re out and about enjoying Mother Nature.

The Soundtrack of Our Lives

This one comes courtesy of Lab member Robin Adelson from The Jefferson Awards Foundation. Her organization honors community service and volunteerism. Everyone submits the name of a song. The only prompt: This song represents the soundtrack of my life. Someone creates a Spotify (or your favorite music streaming service) playlist that either provides background music for dinner or a break or you can make a game of it and have folks guess whose song is whose. Thanks to music streaming services, this is so easy to do and both fun and insightful.

Team Building:

16. Campfire

17. Mini Olympics


 18. Go-Kart Racing

Nothing like a little competition to bond a group together. An adrenaline-pumping event like kart racing is a great way to get employees to interact with one another in a totally new and fun way. Just make sure everyone pays attention during the safety lecture.



20. Tourists (New Heights) Location Based (ICEBREAKER. LONG EVENT. SHORT EVENT.)

Icebreaker: Office Trivia

Out with the old, in with the new. Well, not quite. Before you take on a new place familiarize yourself with the OG: your company.

Office Trivia

Who says trivia night only takes place at the bar? Office trivia is the perfect way to bring a large group of colleagues together and challenge the brain in areas that don't necessarily apply to their daily jobs. Break the company into teams of four or more and offer small prizes for the teams who score the most points.

Want to write your own trivia questions? For reference, trivia questions are generally sorted into categories -- four or five trivia questions per category -- with optional bonus questions at the end of the game. While you can give each question a point value, you can also assign each team a certain amount of points per category that they can bet, instead. Each team can then bet as many or as few points as they want per question until they've used all their points for that category.

Not prepared to create your own trivia questions? Hire a trivia organization to host a trivia night at your office. There are tons of national trivia companies who'd be happy to host an event right on site -- District TriviaThe Trivia Factory, and the Big Quiz Thing are just a few of them.

Team Building:



23. Mystery Dinner

Mystery dinners are one of the most beloved traditions here at HubSpot. On a single night, you send a group of folks from different teams within your company to dinner somewhere in your city (or at someone's house). The dinner is hosted by one of your company's leaders and paid for by the company. These dinners allow random groups of people from the same company to spend an evening chock full of good food and conversation together.

What makes them a mystery dinner? The only thing participants should know about the dinner ahead of time is the date and time. Then, on the afternoon the dinner is supposed to take place, send each group an email with the name of the restaurant they're going to and who they'll be going with, so they can arrange transportation together.

Optional: Give every dinner host the name of a restaurant or bar to invite everyone to congregate at once the dinners are over.

24.  Improv Workshop

Comedy and improv events are fun, interactive experiences that'll have your employees roaring with laughter while teaching them useful communication and soft skills, like focus and trust. Depending on your budget, you could do anything from simply playing improv games with your employees to bringing in professionals to run competitive, fast-paced activities.



25. Through the Screen

1. Tour a new city Take a day trip to a nearby town (or even to an unexplored corner of your own town) and find all of the hidden gems. It could be a self-guided tour if you want more flexibility, or you could work with a walking tour company. Design your tour around a theme like food, history, or art — or a mix of all three — and choose an ending destination like a hotel, resort, Peerspace venue, museum, or civic center where your executive team can get down to business.

As far as executive retreat ideas go, this one is affordable — especially since it doesn’t require too much travel — and a great way to get everyone out in the fresh air while still having all of the comforts of urban surroundings. Eco-friendly event tip: Consider carpooling or finding a walkable city to minimize your team’s carbon footprint.


Team Building:


27. Dive deep.

Before the retreat, we nominate a few folks to give 30-minute presentations on topics about which they’re deeply knowledgeable. These deep dives have covered everything from the art of negotiation, to how to have difficult conversations, to our rebrand. The talks teach us something new, and they shine a spotlight on team members in a special way that’s hard to reproduce once we’re back to our normal grind. POWERPOINT PARTY!!! this are all the rage, rankin office snacks or an explanation as to why….


28. Cocktail Party

29. Escape Room

Bonus Alert: offsite event./.

Taylor Moreno