Trip Overview

A family reatreat

Join us for a cinematic experience in the Pacific Northwest, exploring by air, land, and sea through the lens of Captain Paul and his team. Every moment is curated for you to enjoy the beauty of the landscape, wildlife, the local flavors, and the simple joy of being together. We’re here to make space for the moments your family will carry forever. That’s the heart of our work and what we love to create in this magical place we call home.

  • Every day on this retreat offers moments that invite presence: a sail, a walk, a cold plunge, a floatplane ride, a shared meal. These experiences stay with us long after the week is over.

    Our approach is gentle and intentional. We create environments where your family can slow down, sometimes speed up, and notice more, so you can experience each other in a way everyday life rarely allows. Nothing is forced; connection happens naturally through adventure, learning, and being immersed in a beautiful place with a crew who loves facilitating truly epic days.

    This retreat isn’t built around structured sharing or staged conversations. We simply step aboard our performance trimaran and head into the islands, where moving together as a crew brings out a kind of insight and connection no discussion could create.

    In the end, it’s about creating the moments your family will carry forward forever.

2026 Dates:

July 24th - 27th

All-inclusive for up to 4 guests in three private staterooms: $13,600 + tax + tip

Retreat Itinerary

Lodging at The Captain Whidbey Inn

✔ Trip coordination and concierge planning

✔ Private floatplane arrival from Seattle to Captain Whidbey Inn

✔ Four nights lodging at Captain Whidbey Inn on Penn Cove

✔ Restaurant, tavern, and espresso bar on site

✔ Outdoor lounges overlooking the water

✔ Gardens, wellness studio, and sauna

✔ Historic lodge fireplace and outdoor fire pits

✔ Access to complimentary bicycles

✔ All guiding, instruction, and daily adventure facilitation, including guided hikes, paddles, sails, snorkels, and immersive experiences

✔ Curated meals, snacks, and beverages prepared by our local chef

✔ Private sauna and cold plunge experience at Snakelum Point

✔ Dinner at Goldie’s restaurant on Sunday evening

✔ Island transportation and airport transfers

✔ Documentary storytelling and a photography album

  • A white trimeran docked at a marina, with a dock and water in the foreground, and trees and a shoreline in the background.
  • Person sailing a boat on open water with land visible in the background.
  • Sailboat with people on calm water near forested shoreline at sunset.

Our Trimaran

Guests – 4

Interior heat - Main Cabin Dimensions – 24' by 18'

Sail plan – Mainsail, Jib, Screecher, and asymmetrical Spinnaker

Windy offers a comfortable, unique day-sailing experience, with an 18-foot beam and expansive nets between her hulls that create a surprising amount of open, enjoyable space on the water. Her modern sail plan and performance-driven design ensure every outing is engaging and exhilarating for both first-time boaters and seasoned sailors.

Windy combines lightweight performance with comfort, making her ideal for sailing the waters of Penn Cove and the San Juan Islands. A private onboard toilet and cozy cabin heater provide comfort throughout the day, while on-deck blankets keep you warm. Automatic life jackets from Mustang Survival provide state-of-the-art safety for every guest.

Explore our trip map

Please familiarize yourself with the region through our custom trip map. Each pin marks a stop on our tour and offers a glimpse into the experiences we look forward to guiding you through during your time aboard.

Join us for a reatreat this summer!