leadership

4-Night Executive Retreat

Lakeside Property, Enter Wellness4 days / 4 nights2–6 guests · private stay
Open-air lakeside meeting space at sunset
Candlelit lakeside dinner with wine pairing
Wine tasting flight on the deck
Misty lake kayaking at dawn

Overview

For founders, co-founders, and leadership pairs who need to make the decision they've been avoiding. Strategy without a conference room.

Four days of structured mornings, open afternoons, and long dinners. Bring your leadership team, or come as a founding pair — the property is fully yours.

What's included

  • Private whiteboard studio + boathouse workspace
  • Optional facilitator for strategic sessions
  • Chef dinners with wine pairing every night
  • Sauna, cold plunge, kayaks, guided hikes
  • Off-site programming coordinated for you

Rhythm of the retreat

Day 1

Arrive & align

Afternoon check-in. Welcome dinner on the deck. Frame the week: what decisions get made here.

Day 2

Strategy morning

Facilitated session in the boathouse. Open afternoon (kayak, sauna, or work). Chef dinner, wine pairing.

Day 3

Deep work

Long working morning. Guided hike after lunch. Fireside conversation & long-table dinner.

Day 4

Commit

Closing session: what changes, who owns it, when. Farewell dinner.

Day 5

Depart

Slow breakfast, checkout by 11am. Written summary and action list sent within 48 hours.

Included

  • 4 nights, full property (private)
  • Chef breakfast, lunch, dinner daily
  • Wine pairing at every dinner
  • Boathouse & whiteboard studio access
  • Written session summary on departure

Not included

  • ·Ground transport (car add-on available at booking)
  • ·Facilitator ($3,500 flat add-on)
  • ·Additional guests beyond 6

What guests say

★★★★★

"We came in stuck on our roadmap. We left aligned, and my co-founder and I are still friends. Worth every dollar."

Priya M. · CEO, Series B SaaS
★★★★★

"Best off-site we've ever run. The property does half the work for you."

James W. · Founding partner, VC firm
★★★★★

"Chef, sauna, dock, whiteboard, sleep, repeat. We booked next year before we left."

Lena T. · COO, health-tech

Your hosts

The Enter Wellness team

Property hosts

Facilitation is optional — bring your own coach, or we'll pair you with one we've worked with for years.