The Art of Badassery Retreat in Montauk!

15 years ago I dreamed of hosting an empowering retreat filled with outdoor moving meditations, workouts that make you feel strong in your mind and body and community that fills your spirit in Montauk.

In fact, I priced it out and even made my first flyer.

But I wound up moving across country and I put it on the back burner.

I finally realized that I couldn’t wait any longer.

With burnout on the rise among women, it’s Imperative that we take proactive steps to fill our cup before it runs dry. This retreat signifies an act of putting OURSELVES first and making our wellbeing the highest priority.


My vision is that we go WAY beyond the typical yoga retreat.

My intention is that you will leave this retreat with:

  • deepening your connection to yourself through different styles of meditation and mindset practices
  • awakening your badass spirit through different styles of movement
  • a desire and plan to prioritize yourself and your wellbeing moving forward
  • new connections and community that support your goals


We will walk through The Art of Badassery framework that helps women reclaim and level up their power within. Come to learn and leave as a “Black Belt In Badassery”!

Practice different styles of meditation for nervous system regulation. Destress and dive deep into practices that will help you raise your vibration.

Learn to feel powerful In your body through the ancient Eastern arts. Jenn will be leading classes for all fitness levels and you will leave with systems to keep your practice going at home.

Healthy, communal meals will be shared. Vegetarian and locally sourced, pescatarian options will be available. The menu will be designed to nourish your body for energy.

Need to get some work done or simply want some alone time? You will have the option to have free time or go on weather dependent activities like beach walks or sightseeing.

Connect with nature In one of the most beautiful places In the country.

Have you been yearning to fill your cup with connection and community, unplug from the hustle, bustle and To Do List, prioritize your needs, wants and wellbeing…. 

and maybe fill your belly with lobster rolls….🦞

Don’t wait 15 years to do something that will make you feel strong, safe and powerful TODAY!


Location: The Sole East Resort, Montauk, NY

Thursday, October 10th, 2024
Arrival and Check In
Welcome Group Dinner and Programming

Friday, October 11th
Movement, Meditation, Programming and Meals

Saturday, October 12th
Movement, Meditation, Programming and Meals

Sunday, October 13th
Movement, Meditation and Final Group Brunch
Departure by 1pm

This retreat has LIMITED AVAILABILITY and will definitely sell out.


Shared standard room: $2045
Shared standard garden view: $2145

King Bed standard solo room: $2595
King Bed garden view room: $2745

Prices are per person.

Early bird discount: $300 off until August 1st.

$500 deposit due upon booking to hold your spot. Fill out the form below and then Jenn will connect with you for deposit details.

What’s not Included?

One offsite dinner
One offsite lunch
Travel Insurance
Optional excursions/activities

Transportation Tips:

If flying into NY the closest airport is ISP, Long Island MacArthur Airport. About 1.5 hour drive from airport to Montauk.

If flying into JFK your options are to rent a car and drive 2.5 (ish) hours to Montauk (depending on traffic). Or you can take the JFK airtrain to Jamaica station. From there you can catch the Long Island Railroad to Montauk which is about a 3 hour train ride. Be aware that the trains to Montauk run about every 4 hours so you would have to time this with your flight, which might be tricky.


Jenn Cassetta Is a nationally sought after speaker, author and high performance coach. With over two decades of experience, Jenn has been helping thousands of women feel strong, safe and powerful from the streets to the boardroom. Her background is both diverse and deep and includes a 3rd degree black belt in Hapkido, Masters degree in Clinical Nutrition, certifications in Health Coaching, High Performance Coaching and Neuro-Linguistic Programming.


If you are ready to take the next step…