Trip OverviewA Family Retreat
Set out on a cinematic Pacific Northwest adventure, exploring by air, land, and sea with Captain Paul and his team.
Each day brings a new way to discover the region, from wildlife and dramatic coastal landscapes to local flavours and experiences few visitors ever have. We handle the logistics so your family can step fully into the adventure, follow their curiosity, and return home with stories they will share for years.
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Each day of the retreat includes simple shared experiences — sailing, walking, cold plunges, time in town, and meals enjoyed together. These moments create space to slow down, be present, and reconnect in a setting that feels both natural and memorable.
Our approach is thoughtful but unforced. Families and groups spend meaningful time together through guided outdoor experiences that encourage participation, curiosity, and learning. Connection develops naturally through movement, fresh air, and the shared rhythm of time on the water.
Rather than structured workshops or staged conversations, we step aboard our performance trimaran and set a course into the surrounding islands, allowing the environment itself to shape the experience.
Private All-Inclusive Retreat
For up to four guests
Two private guest rooms included
Retreat rate: $13,600
Applicable taxes are additional.
This Retreat Is for You If…
You want a guided family adventure where everyone can learn, participate, and try new things at a pace they can enjoy.
You’re interested in an immersive Pacific Northwest adventure by land, air, and sea.
You value natural beauty, local food, and meaningful time together.
Retreat Itinerary
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Private float to Whidbey
Arrive at SeaTac Airport and step into a waiting shuttle bound for your private seaplane. After takeoff, fly past the Seattle skyline before following the coastline north and touching down outside Captain Whidbey Inn.
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Settle at Captain Whidbey
Put your bags down in your rooms and join us for lunch on the dock, where fresh ingredients and thoughtfully prepared flavors are served with views over Penn Cove.
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Explore Penn Cove
With time to relax after lunch, we gather at the dock for our explore Penn Cove sail, passing the mussel farms where seals sun on the rafts, blue herons fly overhead, and madrona trees hang over the shoreline bluffs.
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Dinner, Smores and sunset
Bring the day to a close with dinner on the deck at Captain Whidbey’s restaurant overlooking the water. Unwind, take in the freshness of the Pacific Northwest evening air, and rest well before the adventures ahead.
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San Juan Island experience
Begin the day with coffee and breakfast at the Captain Whidbey coffee shop before setting out on a scenic 40-minute drive across Deception Pass Bridge and out to Skyline Marina to meet Captain Paul and Windy.
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Lunch at James Island
Step aboard Windy, stocked with lunch, snacks, and all the gear needed for a day in the islands. Sail toward James Island for lunch and a walk along a shoreline only accessible by boat, passing Bird Rocks where seals, sea lions, blue herons, bald eagles, and occasionally orca whales can be seen.
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Sail to Watmough Bay
Continuing south, we sail to Watmough Bay for a paddleboard tour through the kelp forest. After anchoring just off the beach, we head ashore for a walk to the rope swing, beachside appetizers, a refreshing swim, and time to relax.
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![Views overlooking the islands]()
Views of the Olympics
Lace up your shoes for a short steep hike to a great view over Watmough Bay and the Olympic Paninsula.
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An Evening sail home
As the sun sets, we sail back to the marina before returning to Captain Whidbey for a relaxed evening reflecting on the day’s adventures by the fireplace.
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Morning sauna and swim
Sleep in before joining us for brunch by the beach, followed by time to enjoy our private mobile sauna by the water, paddleboard along the shoreline, or take a peaceful beach walk.
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Evening walk at Ebeys Landing
After time to relax at Captain Whidbey, join us for an early-evening walk along the bluffs at Ebey’s Landing, overlooking the Olympic Peninsula and the Strait of Juan de Fuca where we sailed the day before.
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Closing Dinner at Goldies
Bring the retreat to a close with a shared meal at Goldie’s, where wood-fired cooking, seasonal ingredients, and a lively local atmosphere create the perfect setting to reflect on the experience together.
Your Stay at Captain Whidbey Inn
Personalized retreat planning and concierge support
Private floatplane arrival from Seattle directly to Captain Whidbey
Four nights of waterfront lodging on Penn Cove
On-site restaurant, tavern, and espresso bar
Outdoor lounges with sweeping views of the water
Gardens, wellness studio, and sauna
Historic lodge fireplace and evening fire pits
Complimentary bicycles for exploring the island
Daily guided exploration and hands-on adventure, including sailing, hiking, paddling, snorkeling, and enjoying the islands
Seasonal meals and refreshments thoughtfully prepared by our local chef
Private sauna and cold-plunge experience at a private beach at Snakelum Point
Sunday evening dinner at Goldie’s restaurant
Island transportation and airport transfers
Documentary storytelling and a professionally curated photographic album
Life Aboard Our Performance trimaran
Windy is thoughtfully equipped to make time on the water both comfortable and exhilarating.
A heated cabin offers warmth when needed, while deck cushions and pillows create inviting spaces to relax as we sail swiftly across the water. Mustang inflatable life jackets provide modern safety, and a premium Bluetooth sound system adds a welcoming atmosphere to the experience.
Paddle boards are on board for both day trips and multiday adventures, and her ability to sail quickly in light wind and glide right up to the beach with her shallow draft makes her an exceptional adventure craft.
Relaxation on deck
Deck cushions and expansive trampoline seating
Comfort throughout the day
Heated cabin and private marine toilet
Safety and onboard amenities
Modern equipment including Mustang inflatable life jackets, racing sails, Bluetooth sound system, and onboard refrigeration
Hands on sailing
Lightweight performance design for small crews of up to four guests
Explore our trip map
Each pin marks a place along the journey and offers a glimpse into the experiences that shape your time on the water together.
