St. Michael’s, Maryland | August 24th - 26th

The Weekend Regatta.

Hobby Focused | Wellness Retreats

A bedroom with white wooden walls, a bed with white bedding, a nightstand with a vase of pink and white flowers, a drink, sunglasses, and a magazine.

The Weekend

View of a sailboat with white sails on blue water, seen through a window with a wooden frame, under a beige awning on a clear day.
“...because time is the new luxury””
— Forbes Magazine

August 24th - 26th

The Wildset Hotel
St. Michaels, MD

All-Inclusive | Limited Spots (12)

3-day 2-nights

The Bestie (2 People Per Room):

$1,950 Shared Room - Per Person

The Solo (1 Person Per Room):

$2,300 Private Room

What’s Included:

3-day, 2-night luxury accommodations

Immersive sailing lessons

Private Regatta race

Movie night under the stars (drinks & snacks included)

Daily breakfast, lunch, and dinner

Wine, cocktails, and non-alcoholic beverages served with meals

Yoga sessions

Farewell sound bath experience

All taxes and gratuities included

** Payment Plans Available**

A $550 deposit is due at registration and goes toward your balance. 3% processing fee applies.

Not included: travel insurance, beverages and snacks beyond the itinerary and personal incidentals.

The Itinerary.

We gather Sunday to Tuesday—when the world is quieter, and leisure feels more intentional.

    • Check-In

    • Pre-Dinner Meet & Greet

    • Welcome Dinner

    • Bonfire

    • Breakfast

    • Daily Meditation

    • Sailing Lesson & Regatta!

    • Bayside Lunch

    • Afternoon Yoga

    • Chef Dinner

    • Movie Night - Under The Stars

    • Breakfast

    • Farewell Sound Bath

    • Checkout

Multiple racing sailboats with black, gray, and white sails on open water during daytime, competing in a regatta.

The Retreat.

Weekend Reset is our signature escape for those who treat time like the new status symbol.

Think slow mornings, insanely good meals, and vibe-y days filled with movement, creativity, and play. One minute you're sailing, the next you're in a sound bath wondering why you ever settled for stress.

It’s where real convos replace small talk, your nervous system finally chills out, and joy isn’t a reward—it’s the baseline.

Two people practicing yoga on a wooden deck in a forest, facing a scenic view of lush green trees and houses on the hillside.

The Society.

In a world obsessed with doing more, we’re here to celebrate simply being.

Society of Leisure is a space for those who know the real flex is a rich life—one shaped by hobbies, curiosity, and meaningful connection, not just productivity and performance.

We exist for those who crave depth in a swipe-right world, who find luxury in slowness, and who understand that presence is more powerful than a packed schedule.

We create immersive retreats designed to help you unplug—through movement, nature, creativity, and spectacularly good food.

Because this isn’t about escaping your life. It’s about building one you don’t need to escape from.

Welcome to the society.