The white shingled inn with a wraparound porch and Adirondack chairs on a green lawn
Executive retreats · Boston

Leadership retreats for Boston teams.

We work with leadership teams across the country, from our home in Dallas–Fort Worth. If your team can get away, take it somewhere great. The right place helps a team slow down and think together. If you’d rather stay close to Boston, we’ll run it there. Either way, we interview every leader, design the days and run the room in person.

51places across the U.S. in our guide
3within a few hours of downtown Boston, for teams that want to stay close
In personboth founders on site, wherever you go
Fly inBoston Logan (BOS)
Get away

Take your team somewhere great.

If your team has the time and the budget, we always encourage getting away. A few days with nowhere else to be gives leaders room to think and talk. A few of the places we’d start with:

See all 51 places in the guide

Close to home

Or stay near Boston.

The North Shore, Cape Cod and the coast of Maine put Boston teams on the water within a few hours. They are at their best from late spring into early fall. Every place has room for the whole team to work, eat and stay together.

Coast · Under one roof

The Inn at Castle Hill

Ipswich, MABest May to June and September to October$$ to $$$

A team of 8 to 10 can take the whole inn, meet all day in a private tavern room, and walk straight out to a 2,100 acre coastal estate between sessions. It is under an hour from Logan, there are no TVs in the rooms, and the quiet setting keeps people focused on each other.

Group: 8 to 10, up to 22 if some share

The Everest Climb

How a retreat works for a Boston team.

We interview every leader before we write a word of the agenda. For a team in Boston that happens by video in the weeks before. Then we meet you at the place you chose, across the country or close to home, and run the retreat in person.

  1. 1Discover

    Working sessions with you and a one-on-one interview with every leader.

    Weeks 1–3
  2. 2Design

    A custom agenda built from what we heard. You sign off before anything is set.

    Week 3
  3. 3Connect

    Your team gets to know each other beneath the roles.

    Retreat day 1
  4. 4Clarify

    An honest look at what's working and what isn't.

    Retreat day 1–2
  5. 5Align

    Two or three priorities and a plan the team wrote together.

    Retreat day 2
  6. 6Sustain

    A written readout of what we heard, what the team decided and who owns each priority.

    After the retreat
Questions

Retreats near Boston.

Do you facilitate leadership retreats for Boston companies?

Yes. Everest Collective is based in Dallas–Fort Worth and works with leadership teams across the United States. We interview every leader before the retreat, usually by video, then the two founders facilitate on site, wherever the team goes.

Should our team travel or stay close to Boston?

If the team has the time and the budget, we encourage getting away. The place is never the most important part of a retreat, and the right one still helps leaders slow down, step out of the day to day and talk. When travel doesn’t fit, a place within a couple of hours of downtown Boston works well too.

Where can a Boston leadership team hold a retreat nearby?

For a team that wants a house to itself, everyone with their own bedroom: The Inn at Castle Hill, Grey Havens Inn. For a team that would rather each leader have a room at the same hotel or resort: Chatham Bars Inn. All are within a few hours’ drive of downtown Boston.

When is the best time for a retreat near Boston?

Most of the places on this page are at their best in May, June, September, October. Each venue page lists its own best months and what to plan around.

How far ahead should we plan?

About eight weeks from the first conversation to the retreat covers the leader interviews and agenda sign-off. Popular venues book group dates months ahead, so pick the place early.

Can you find and book the venue for us?

Yes. Choose full service and we find the venue, book the rooms, plan the meals and run the schedule. Or book it yourself and we bring the interviews, the agenda and the facilitation.

You pick the place

We’ll handle the rest.

Tell us about your team and what it needs. We’ll send a short list of places, anywhere in the country or close to Boston, and how we’d run the days.