For driven guys who want to GROW and CONNECT while on an adventure!

...not attend another boring conference or stuffy mastermind.

Our Ethos

What if you could uplevel your peer group, have meaningful conversations about life and business AND go on an epic adventure ALL AT THE SAME TIME?!  

Welcome to Guys Trip!

There are 3 things you can expect when you attend one of our trips:

Unique and once in a lifetime activities in inspiring locations that will be sure to help add more fun and aliveness into your life

Fun

No matter what you are building – carefully craft every moment of your story online. Brands built with love are the ones that stand out.

Build authentic and profitable relationships with like-minded guys and have conversations that are meaningful and matter

Connect

No matter what you are building – carefully craft every moment of your story online. Brands built with love are the ones that stand out.

See what sits on the other side of your comfort zone when you're brought to the edge (sometimes literally)

Grow

No matter what you are building – carefully craft every moment of your story online. Brands built with love are the ones that stand out.

Same intention, similar design, different offerings for different guys

We have different types of trips

Tournament:  who doesn't like a little friendly competition?  Stay tuned!  More details to come soon for our 1st Annual Golf Tournament coming late Fall of 2023.


Escape the City:  for the guys earning multiple six figures and seven figures who want to recharge out of a big city!  Expect high-end accommodations, once in a lifetime activities, and world-class food and drinks.  Locations are unique and likely rugged and remote!

Journey Together:  there's something special about climbing a mountain together.  Expect a physical element to these trips that will require you to prepare in advance.  These trips will likely help you cross something off your list!


Northwoods:  join Guys Trip founder Kyle Depiesse at his cabin in the woods!  For guys newer in their entrepreneurial or personal growth journey or guys who want to spend time in the woods and leave a busy and hurried pace of life behind for a weekend.  We'll spend a lot of time outside doing Northwoods things (chainsaws, axes, bonfires, cross country skiing, sauna and polar plunging!).

Featured Experiences

Check out what's next in 2023!

Inca Trail PERU Guys Trip - Journey Together Edition 2023

Cusco

September 8 - 14 2023· 6 nights

Inca Trail PERU Guys Trip - Journey Together Edition 2023

A True Bucket-List Trip!

FROM$5500/pp

Maine Guys Trip - Escape the City Edition 2023

Bar Harbor

October 1 - 4 2023· 3 nights

Maine Guys Trip - Escape the City Edition 2023

Adventure on the Coast!

FROM$7500/pp

What people are saying

Check out our testimonials

What really made this such a great experience is the like-minded guys that come along with you!

Chris Harder

I knew I needed something to recharge my batteries but I couldn't put my finger on what I needed.  I committed to one of these events and this trip immersed me around other high-level men.  Kyle delivered on giving us a wide range of experiences.  I left feeling reenergized and full of new ideas and connections that propel my business and personal life forward!

Dr. Matthew Zanis

The best experience I've had in a long time!  Kyle put together an amazing group of guys and from start to finish he took care of us and created events that were above anything I could've ever imagined!

Mike Ayala

The Blog

A space dedicated to bringing you inspiring conversations on the podcast (Reaching Beyond) or insightful thoughts meant to challenge and call you into a more meaningful and full life experience!

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Guys Trip: An Intro

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