Trip OverviewA 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
Rates
All-inclusive for up to 4 guests in three private staterooms: $13,600 + tax
Retreat Itinerary
-
![]()
Private float to Whidbey
Arrive at SeaTac Airport and step into a waiting shuttle bound for a private seaplane. Take off and fly by the Seattle skyline, head up the coastline, and touch down outside the Captain Whidbey Inn.
-
![]()
Land at Captain Whidbey
These small rocky islands sit at the entrance of Penn Cove and are home to seabirds and seals and sea lion. Sailing past, we often spot cormorants drying their wings and seals lounging in the sun
-
![]()
Explore Penn Cove
We’ll stop at James Island, a quiet marine park with beaches and trails, the perfect spot to enjoy lunch and stretch your legs before we sail on.
-
![]()
Boulder Island
Leaving the Amalfi Coast behind, we sail to the island of Capri, navigating among iconic grottos, super-yachts, and dramatic limestone arches. After lunch and a swim, we cross the Gulf of Naples to Ischia, where we anchor beneath the striking Castello Aragonese, an island castle once home to exiled royalty and medieval nobility.
-
![]()
San Juan Island experience
Watmough Bay is one of the San Juan Islands’ hidden gems. Guests can take a short hike to a breathtaking viewpoint over the cove, or simply relax on the beach and enjoy a swim in the calm, sheltered waters.
-
![]()
Lunch at James Island
We’ll end the day with a peaceful sail back toward Skyline Marina, watching the sky change colors as the sun sets over the islands.
-
![]()
Sail to Watmough Bay
Description goes here -
![Views overlooking the islands]()
New List Item
Description goes here -
![]()
An Evening sail home
Description goes here
Lodging at The Captain Whidbey Inn
✓ Waterfront access
✓ Fireplace and outdoor fire pits
✓ Gardens and Sauna
✓ Outdoor lounge seating overlooking the water
✓ Restaurant and coffee shop on site
✓ Views of Windy on the private dock out front
✓ Private float plane flight to Captain Whidbey
✓ Two rooms for 4 nights at Captain Whidbey
✓ All curated meals, snacks, and beverages made by our local chef
✓ Private sauna experience at Snakelum Point
✓ Dinner at Goldies on Sunday night.
✓ Island transportation and airport transfer (rental car)
✓ Documentary photography and coaching
✓ Trip coordination & concierge planning
✓ All guiding, instruction, and facilitation
✓ Paddle-boards and water-sports equipment
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.
Our Trimaran
Corsair 24 MK1
Guests – 4
Interior heat - Main Cabin
Demensions – 24' by 18'
Sail plan – Mainsail, Jib, Screecher, and asymmetrical Spinnaker Windy offers a comfortable and unique day-sailing experience. With her midship, forward lounging nets, and a beam of 18 feet, she has a surprising amount of enjoyable space.
Windy combines lightweight performance and comfortability, making her ideal for afternoon sailing in the protected waters of Penn Cove and the San Juans. Windy has a cozy cabin heater, deck blankets, and automatic life jackets for all guests.
General Information
How do we reserve our trip?
Contact us by email with your preferred listed date, and reserve your trip with a 50% nonrefundable deposit by credit card.
What is included in the all-inclusive trip price?
One round of alcoholic and non-alcoholic beverages, an appetizer, snacks, and photographic coverage of your trip by Captain Paul.
What’s not included in the trip price?
All onshore expenses, gratuity, and transportation to and from the boat.
Can we request a custom itinerary?
Yes, within the time and area of our charter. If you’d like to create a journey elsewhere, please let us know.
What are the guest requirements?
Guests must be comfortable boarding and moving around a sailboat, able to swim, willing to wear a provided life jacket, and meet a per-person weight limit of 250 lbs, with a maximum total of 850 lbs for up to four guests.
Can you accommodate dietary restrictions & preferences?
With advance notice, we’re happy to accommodate when possible. Just include any details in your email.
What is your age limitation?
Our age limitation is based on the size of our child life jackets, which typically fit children around 4–5 years old depending on weight. Please specify in your email, as we love having families aboard.