Trip OverviewDay Sail to the San Juan Islands
Departing from Skyline Marina, we begin our journey by crossing Rosario Strait with a course set for Bird Rocks. Along the way, always be on the lookout for local wildlife like harbor seals, porpoises, bald eagles, gray and humpback whales, and, if we’re lucky, orcas.
We’ll anchor for lunch and explore James Island before heading out for our next paradise, Watmough Bay, where you can explore the shoreline, hike to the lookout, swim, or try paddleboarding near the kelp beds.
On the return sail, join Captain Paul at the helm and learn to sail Windy, or sit back and enjoy the peace of the wind in the sails as we make our way back to Anacortes.
San Juan Islands Expedition (Approx. 9 Hours)
10 am - 7 pm
Private all inclusive charter 1–4 passengers: $1,400
Washington sales tax applies.
This Sail Is for You If…
You want to experience the San Juan Islands without planning an overnight trip.
You’re excited by a full day of sailing, wildlife, and exploring ashore.
You want a private, all-inclusive adventure thoughtfully curated for your group.
“Sailing with Paul Porter is the absolute best!”
My friend and I spent a picturesque September Saturday aboard Windy and loved every minute of it. Paul was safe and efficient, effortlessly guiding us around the San Juan Islands. Windy, our majestic vessel, was stocked with everything our hearts could desire from charcuterie spreads to stylish lifesaving floatation devices. Local historical facts and information about the wildlife were provided as we went from one adventure to the next.
The fun started with stand-up paddleboarding, followed by a picnic on our own private island. The afternoon included a small hike and a tequila sunset. Highly recommend for dates, ladies’ days, and family memories.
Shanon Cousineau 07/2025
An absolutely delightful day sailing in the San Juan Islands!
My spouse and I spent a full day sailing with Captain Paul Porter aboard his trimaran. WINDY. It was one of those rare days when everything seemed perfect.
We left Skyline Marina in Anacortes in the morning and sailed across to Rosario Strait to James Island. We docked and went ashore for an invigorating hike through the wooded hillside. When we returned to the picnic area, Captain Paul was preparing a gourmet lunch on a camp stove. We had couscous with vegetables, roasted eggplant, lemon pepper chicken with pesto and tangy goat cheese finished with a balsamic reduction and herbed Italian olive oil. It looked beautiful, smelled enticing, and tasted even better as we accompanied it with refreshing Arnold Palmers.
Back aboard WINDY, we sailed on through sunshine and calm waters. At one point while we were lounging in the sun, we found ourselves thinking that perhaps a little something sweet would be nice. As if he had read our minds, Paul popped up from the galley and asked, “Would you like a dark-chocolate-covered-salted-caramel?” Yes, indeed! It was completely unexpected and delightful - and somehow summed up the entire day.
At Bird Rocks we lingered just offshore observing six sea lions playing and basking in the sun. Then we sailed on to strikingly beautiful Watmough Bay on Lopez Island. We beached WINDY, hopped ashore, and enjoyed another glorious hike through the woods.
When we returned to the boat with the sun getting lower in the sky, another surprise awaited us: a colorful appetizer spread of little veggie and cheese kebabs, Brie, crackers and cucumbers, red bell peppers, Marconi almonds, and tiny, tasty gherkins. It was a feast for the eyes and for the palate.
Finally, we sailed back toward Anacortes to Skyline Marina. As the sun disappeared behind Fidalgo Island a pod of porpoises swam by - as though the San Juan Islands had arranged a final farewell for us. It was a perfect end to a perfect day.
Captain Paul is a wonderful host and a first rate sailor. Throughout the day he combined safety, smooth sailing, opportunities to explore ashore, delectable food, wildlife, and thoughtful little surprises into an experience that felt both adventurous and wonderfully relaxed.It was absolutely delightful from beginning to end, an experience we will cherish.
Joy 08/2026
Sailing Itinerary
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Skyline Marina
We’ll meet at Skyline Marina in Anacortes, where parking and restrooms are available. From here, we’ll step aboard, participate in our safety briefing, and set sail to the Islands.
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Bird Rocks
These small rocky islands are home to seabirds, seals, and sea lions. Sailing past, we often spot cormorants drying their wings while witnessing the strength of the currents flowing by.
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James Island
Our first stop is James Island, a quiet marine park accessible only by private boat, with beaches and walking trails to explore as Captain Paul prepares lunch.
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Boulder Island
Don’t miss the opportunity to paddle the kelp forests off Boulder Island, with views of the Cascade Mountains and the Olympic Peninsula in the distance.
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Watmough Bay
Watmough Bay is one of the San Juan Islands’ hidden gems. Take a short steep hike to a breathtaking viewpoint, or simply relax on the beach and enjoy a swim in the calm, sheltered waters.
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Happy hour is a must
Taste local favorite meats, cheeses, and snacks prepared for you by Captain Paul, sourced from Whidbey Island, so we set sail satisfied and ready for the final adventure.
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Our sail home
We’ll end the day with a sunset sail back to Skyline Marina, watching the sky change colors as our trimaran dances in the evening breeze.
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.
General Information
How do we reserve our trip?
Please contact us through our contact page with your preferred date and time. Reservations are confirmed with a 50% non-refundable deposit by credit card. The remaining balance is collected at the dock before departure.
What is included in the all-inclusive trip price?
Two rounds of alcoholic or non-alcoholic beverages, snacks, lunch, 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, if you’d like to create a custom journey in advance, 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?
We love having families on board. Please include your children’s ages in your email so we can discuss whether this trip is a good fit for you.
