Join us for an unforgettable Fall weekend in the US Capital.

Experience D.C. in all its glory through the eyes and ears of one of our local Fellows, Kelsey Kelleher (Breakouts II)

Expect Michelin star meals, kickass workouts, delicious wine, an abundance of superb history, and plenty of inspiring late-night conversations.

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Arrival at St Gregory Hotel

Check-in from 4 PM. St Gregory is a 15-minute Uber or Lyft from Ronald Reagan Airport (DCA). We have a block of rooms reserved.


Welcome Drinks & Introductions

We’ll enjoy a few delicious pre-dinner drinks in the stunning St Greg as you get introduced to the group. 


Chef’s Table Dinner at Roses Luxury

Join Chef Aaron Silverman on his infamous roof garden for a world-class evening at his adored Michelin-starred restaurant.

2014 Best New Restaurant in America, Bon Appétit.
2015 Most Outstanding Restaurants, No.1, GQ
2015 Top Ten Restaurants, No.1, Washington Post.
2016 Best Restaurants in America, Hall of Fame, Eater.
2017 Michelin Star, the Michelin Guide



Monuments Night Walk

We’ll close out the evening walking the monuments and soaking in D.C’s incredible history under the stars.




Morning Workout

We’ll begin Day #2 by getting the endorphins flowing. Nothing builds community more than getting your arses kicked together.




Time to refuel before our first work session of the weekend.


Keynote & Workshop #1

We’ll have a world-class local artist, entrepreneur or academic run a workshop for us around the central theme of the weekend.

1:30 PM

Lunch at Old Ebbitt Grill

You ain’t been to D.C until you’ve dined at Old Ebbitt. Perched by the White House, this restaurant just oozes history. 



We’ll spend the afternoon wandering through the city and soaking up the sights with our local tour guide, Kelsey.


Chef’s Table Dinner at Maydan

Is there anything better than watching food cook over an open fire? Maydan is a Mediterranean nirvana with a Michelin star to boot.

2018 Best New Restaurants in America, Bon Appétit.
2018 Best New Restaurants in America, No.1, GQ

2018 Best Middle Eastern Chefs, Esquire.
2018 Restaurants of The Year, Food & Wine.
2020 Michelin Star, the Michelin Guide


Private Cocktail Hour at St Gregory Hotel

Join us for cocktails, charcuterie, and conversation by the fire at the St Gregory Hotel’s Tier 2 event space.

Let your hair down and meet the best of our community in a fun and relaxing environment over a stiff pour (or two).



10-12 PM

Keynote & Workshop #2

We’ll have a world-class local artist, entrepreneur or academic run a workshop for us around the central theme of the weekend.


Depart for Winery

We’ll enjoy an afternoon at a local Virginia vineyard.


Winery Tour

We’ll escape the hustle and bustle of the city for some delicious wine and reflective conversations on the weekend thus far. 


Cuban Night

Breakouts V Fellow, Olivia Hernandez, is inviting us into her home for a taste of her lineage. Expect divine Cuban food and plenty of cigars.




Live Podcast Recap

We’ll record a live podcast at the hotel to reflect on our incredible weekend in D.C.



Check out by 11 AM from St Gregory Hotel. It’s a short 15-minute Uber or Lyft to Ronald Reagan Airport (DCA).


What's the deadline to reserve my spot?

All retreat deposits must be submitted by Thursday, September 30th to secure our room block at the hotel. If you do not submit your deposit by this deadline, you do not have a guaranteed spot at the retreat.

Deposits are 50% of the total retreat cost. The remaining balance will be billed automatically on October 14th.

What's included in my ticket?

All lodging, workouts, event tickets, experiences, and dinners are included in your ticket. Breakfast, Brunch and Lunch are not. 

Dinners include wine pairings. If you’d like to order something else at dinner, you’re more than welcome. Just know it’ll be on your own tab. 


Is my deposit refundable?

No, it is not. All retreat deposits are non-refundable due to the cost of reservations, experiences, meals and lodgings associated with the weekend.

If you decide to drop out after you’ve paid your deposit, it will be not returned.

Do I have to stay for all three days?

No, you don’t. We understand that people have busy lives and varying budgets. However, we’d be lying if we said the three days wasn’t worth its weight in gold. It’s the best way to fully unplug and feel the magic of what the community and host city has to offer.

If you’re only coming for two days, enter code “DC2DAYSONLY” at checkout.

Can I share a room?

Yes, you can. If you have a roommate selected, enter code “DCROOMSPLIT2” or “DCROOMSPLIT3” at checkout depending on the number of days you are attending.

If you want to share a room, but don’t yet have a roommate confirmed, please reach out to Cornelius (cornelius@everydayentrepreneur.co) directly before signing up.

When will I receive pictures from the retreat?

Pictures from the professional photographers are typically shared within 1-2 weeks after the retreat ends. You’ll be the first to know when they are available. We share them via email.