From our beautiful port of Bainbridge Island, just a 35 min. ferry ride from downtown Seattle, we offer private, customizable sailing experiences in Puget Sound & beyond
aboard our classic sailing vessel, TRUE.
Book with us today and give 1% back to the planet! Learn More
Sail Bainbridge acknowledges and recognizes with gratitude that we are operating on waters and lands historically and currently significant to the Suquamish and greater Salish tribes.
Experience unforgettable sailing adventures! Bask in the beauty of breathtaking vistas, from Seattle’s iconic skyline to the majestic volcanos and mountain ranges on the horizon. Immerse yourself in incredible wildlife encounters as you sail the pristine waters of Puget Sound. Join us for a variety of activities, including day sails, romantic sunset cruises, visits to remote Blake Island (Tatču), overnight adventures, week-long explorations of the San Juan Islands, and more. Whether you are a new customer or an old friend, we hope you’ll join us on the water and create cherished memories.
Sailing Puget Sound is an unforgettable experience. Come aboard, we’ll set sail and soak up the panorama of these beautiful and inspiring waters.
$425
Come aboard for an elegant and romantic sunset sail.
$545
Set sail for this idyllic State Park island that is only accessible by boat. This excursion includes adventuring ashore at Blake Island (Tatču), where you can walk the network of trails through the forest, or comb the beaches for treasure!
$995
Enjoy a two hour Sunset Sail and the most peaceful, romantic night at anchor, sleeping with the gentle sway of the harbor waters.
Light breakfast, tea & coffee provided.
$925
This four hour sail gives you more time with the wind in your hair! You’ll go a bit further, see a bit more, and spend lots of time sailing!
$795
This adventure has it all – plenty of sailing, island exploration and a peaceful night at anchor in an idyllic, tranquil harbor.
$1725
Our fast-boat – TOKI – is the little vessel that can! We are excited to add this quick and nimble little vessel to our offerings!
Ferries Delayed? Hop Aboard Toki for a Quick Seattle/Bainbridge Shuttle
Join us for a circumnavigation of Bainbridge Island, complete with history, wildlife and shoreline exploration!
$1225
Come enjoy two full days of sailing with an overnight at the dock, all to yourselves in an enticing location. The captain will stay ashore, giving you the freedom to come and go from the boat as you please, enjoying the charms of life on the waterfront.
Destinations include, Gig Harbour, Port Townsend, Poulsbo, Ballard
Starting at $2825
The San Juan Islands are the true gem of the Northwest sailing experience. Join us for an unforgettable multi-day adventure.
Starting at $8495
Have you ever experienced the magic of bioluminescence at night?
We can offer you a respectful and sacred space aboard, or transport you to a nearby destination for a ceremony or memorial. All are welcome.
Starting at $425
Our classic sailing vessel, TRUE, provides an incredible venue for a variety of photo shoots, with her sleek lines and teak finishes. With plenty of room for your photography team, product line, and models, we can build the perfect sailing excursion for you.
There’s skiable snow in British Columbia; and it turns out you can get there by boat.
Our eGift Cards are easy to purchase, easy to give, and don’t expire. Give someone special the gift of sailing, some time on the water with friends and/or family.
“Husband, father, captain of the sailboat True, indie-folk musician, life enthusiast. Ben is pure joy and endless energy, plucking crab from the ocean one minute and regaling us with stories about his grandfather the next. You meet a lot of people in this life. Some of them are ships in the night. Some stick with you. Some you borrow a piece from to make your own little boat just a little bit better.” – Johnie Gall
Ben first fell in love with sailing as a boy, visiting the Atlantic Coast of Florida, where his grandfather had 19ft daysailer. Years later, following a summer spent as crew on a competitive and successful racing yacht on Lake Michigan, the deal was sealed. He was hooked and has spent a good part of his adult life trying to find his way onto boats. As owner, caretaker and captain of the beautiful classic sailing yacht, TRUE, there is little he loves more than being on the water and sharing the experience with others.
Ben has over 5,000 miles of offshore sailing experience including passages up the West Coast of the US from San Diego to Seattle, the North Sea from Sweden to Orkney, Scotland, the North Atlantic from Key West to Bermuda and the Caribbean from Annapolis, Maryland to the British Virgin Islands. In addition, he has over a decade and many miles of experience sailing Puget Sound and the greater Salish Sea.
Ben is a USCG 100-ton Near Coastal Master, as well as CPR and Wilderness First Aid trained.
He is also a husband and father of two wonderful kids.
Ben and his wife, Deb, are also co-owners of the local marine and gifts shop on Bainbridge Island, just a couple of docks down. It’s the only waterfront store on the island and a treasure trove for boaters and non-boaters, offering essential marine supplies while also featuring a delightful selection of souvenirs, gifts, snacks/drinks. Be sure to check-it out!
“Husband, father, captain of the sailboat True, indie-folk musician, life enthusiast. Ben is pure joy and endless energy, plucking crab from the ocean one minute and regaling us with stories about his grandfather the next. You meet a lot of people in this life. Some of them are ships in the night. Some stick with you. Some you borrow a piece from to make your own little boat just a little bit better.”
“This is truly the best way to experience the natural glory of Washington. Everything from start to finish is easy, relaxing, and special. Ben is clearly an expert at sailing, which is seen through his knowledge and passion. By the end of the trip you feel like you saw an old friend and enjoyed the best of Seattle’s magnificent views.”
“There is so much I can say about Sail Bainbridge. Ben is a one of a kind human being and captain, and our trips on the beautiful SV True have been so important and memorable for us. Thanks Ben for all the memories and here’s many many more!”
“Wowee let’s just start with the boat. The most beautiful sailboat you ever did see. It was strong and steady, we felt safe and no where near seasick. The host/skipper was everything and more. He was super cool and friendly, and also very knowledgeable about the area and sailing. Our group had such an awesome, memorable experience we will definitely be back again!!”
“A magical evening sail our delightful host/captain Ben, followed by mother nature’s full evening “program” including a beautiful sun set, ferry lights on the water, sounds of fish jumping, the city skyline lights coming up as darkness fell, and much more. An unforgettable Airbnb experience!”
“My family and I had a special time on True. It was our sons birthday. Sailing to Blake Island was the perfect family adventure: a private, beautiful island park. Captain Ben handles everything beautifully, and is super friendly. True is a gorgeous, classic, spacious and comfortable boat in any weather. I loved the different trip options, we certainly will be booking again. Highly Recommend!”
“An AMAZING experience!!! If you’re looking for a special getaway, well- here it is. We spent the night aboard this classic vintage vessel in the middle of Eagle Harbor followed by a lovely 2 hour cruise the next morning. It was the PERFECT one night getaway! The beds, breakfast, and bean bags aboard deck were awesome. Ben and his deck hand Kenza were super hosts. There was bioluminescence in the water that evening that made the experience even more magical. My kids (17, 13, 11) will never forget this trip.”
“No better way to spend the afternoon! My family enjoyed the most relaxing, laughter filled afternoon on True. Ben is a terrific Captain who knows well his boat and the seas he sails. His stories are delightful, and he made us feel like old friends immediately. Thank you Ben!”
“Great time! True is a fantastic boat with plenty of style. Ben is a fantastic captain and a delight to be around. I cannot recommend sailing with him enough. Thanks for the great trip man!”
“I can’t say enough about how lovely this little getaway was. Coordinating with Ben to iron out the details of the reservation and get set up with a tour through Sail Bainbridge was a breeze. Ben was incredibly helpful, responsive and accommodating. The boat is beautiful, and exceeded my expectations. The bed alone was nearly more comfortable than my own! Waking up anchored at harbor was a new experience for me, and it couldn’t have been more idyllic. Our Sunday morning sail was the best way to cap the day and Sail Bainbridge made it especially enjoyable and easy. I would do it again in a heartbeat. Thanks for everything, Ben!”
“First, the entire experience was amazing from the process of making the reservation to the actual time on the water. The captain is an incredible person. I enjoyed getting to know him and sharing life stories. I originally thought I just wanted a couple hours of sailing but then the orcas appeared. It was amazing to watch two families of orcas begin hunting. So happy the captain was willing to change our plans. I would highly recommend Sail Bainbridge.”
“We had a fantastic sail with Ben aboard the beautiful TRUE! We loved sailing out past the island and saw Mt. Rainier, the Seattle Waterfront, etc. Honestly just being on the boat and out in the water itself is so magical. We loved the beanbags at the front to lounge out and taking in all the sights. Ben was very kind, accommodating, and we had great conversations. We loved our trip and we hope to be back again soon! :)”
“Perfect outing of sailing to Blake Island to explore and do a fun hike! We got to see the sea lions and porpoises while sailing! Our children said it was one of the best days of their lives! Doesn’t get any better than making memories like this!”
“Such a fun weekend! It is always nice to get a night out in the city, but to arrive by boat made for even more of a treat. Even in early spring, we were fortunate to get plenty of sun and winds at our back heading in –and we could not believe how close we came to the pod of orcas sailing home! That was definitely a highlight of the trip.”
“Excellent communication prior to arrival: Detailed instruction and advise, professional and welcoming. Ben made every effort to ensure a smooth stay. One night felt like a weeks holiday in terms of relaxation. The boat is in great shape and it felt like a floating home from home. We took a 2 hour sail before being dropped off for dinner in a local restraunt. Following the meal Ben ferried us out to the boat and then returned as arranged at 10am the next day to pick us up. Sunset and sunrise on the water in a calm and quiet harbour with a view of the Seattle skyline, just perfect! A great experience for the kids too; our 9 and 10 year olds even took turns stearing the boat while under sail and are still talking about it a week later. A great change from a hotel or house stay, I would recommend to anyone. ”
“What an amazing experience! Beautiful boat, great captain, a wonderful opportunity to take breathtaking photos, and enjoy time with friends. Thanks Sail Bainbridge!”
“Our sail to Blake Island was magical. Even with the city skyline in view, it felt like a whole different world. Because of Ben, we were able to relax, enjoy the trip and focus on the beauty around us. We were so thrilled when one of the kids shouted “whale!” Just off the boat spouted a humpback. We stopped to watch it a while, before heading off to anchor off Blake Island – a little green gem of a place, criscrossed with trails to wander and shores to explore. It was an amazing adventure. Thank you Ben and Sail Bainbridge! We’ll be back aboard soon.”
“Ben was the perfect host. Engaging, funny, knowledgeable, generous and extremely easy to get along with, but just as adept at knowing when to give us space to enjoy the experience. I can’t recommend the experience highly enough.”
“Perfect afternoon sail! My wife and I had the pleasure of spending the afternoon with Captain Ben on his lovely “True” sailboat. Ben was personable, professional and highly proficient at his craft. We couldn’t have asked for a better experience! If you are considering a sailing excursion out of Bainbridge, do yourself a favor and go with Sail Bainbridge. You will not be disappointed.
“It was perfect. We’ll never forget our amazing stay on Ben’s gorgeous sailboat. He was an amazing host, extremely accommodating and helpful. The sailboat had everything we needed for a super-comfortable overnight stay. I proposed to my now-fiancée on the anchored-out boat at dusk and it was the perfect romantic experience. It couldn’t have gone better. I feel so lucky to have been able to work with Ben on the perfect romantic excursion. We’ll definitely be back.”
“As we left the harbor in waning daylight, I was amazed by the views all around: majestic Mt. Rainier, the electric Seattle skyline, and the expansive Olympic Mountains. Taking in all of these views from the comfort and security of True while the charming Captain Ben was at the helm was a treat that won’t soon be forgotten.”
“We had a fantastic time with Captain Ben and went out with our family (including a one-year-old and five-year-old) and inlaws visiting from Vermont! Ben is a fantastic sailor, gracious host and quick to share helpful information about the island, sailing, etc. We highly recommend booking a tour with Sail Bainbridge.”
TRUE comes from the design desk of world-renowned naval architect, John Alden, who designed over 1000 boats, including the majestic schooners of the 1930s and 40s. His work, without question, represents great American boat design, and our 44-foot Pearson Countess Ketch, TRUE, is no exception.
