Sailing Packages

The Captain

Ben first fell in love with sailing as a boy, aboard his grandfather’s daysailer on the East Coast of Florida.  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 sailing yacht, TRUE, there is little he loves more than being on the water and sharing the experience with others.

Ben is a United States Coast Guard Licensed Operator, and has First Aid/CPR certification.

He is also a husband, father, and professional musician with the indie-folk band, St. Paul de Vence.

Sailing Packages

All sails are private booking for 1-6 guests
Prices do not include tax

View our cancellation policy here

Two Hour Sail

Sailing Puget Sound is an unforgettable experience.  Come aboard, we’ll set sail and soak up the panorama of these beautiful and inspiring waters.


Half Day Sail

Join us for four hours of sailing and exploring.  Leave your worries behind, but bring your sense of wonder.  This sailing package provides the opportunity for more time under sail, and a great way to view wildlife.


All Day Sail

Take the whole day and settle into life under sail.  This package gives you the opportunity to learn the ropes and lend a hand with the sailing, or just relax; this is your day on the water.


Blake Island

Set sail for this idyllic State Park island that is only accessible by boat.  This excursion includes adventuring ashore at Blake Island, where you can walk the network of trails through the forest, or comb the beaches for treasure!


Adventure Sail Overnight

Come enjoy two full days of sailing with an overnight at the dock, all to yourselves.  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 and Port Townsend.

Starting at $1895

Six-Night San Juan Adventure

Exploring the San Juan Islands under sail is an unforgettable experience.  Join us for a six night adventure through these gems of the Pacific Northwest.

Starting at $7000

Ceremonies & Memorials

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 $300

Chili Sail
(Winter Only)

Enjoy the hidden splendor of winter sailing; with a warm bowl of homemade chili and a comforting hot drink as you take in the surroundings and wildlife.

Available November – March.


Island Sail & Stay (Winter Only)

This package offers an opportunity to enjoy the hidden splendor of winter sailing, followed by a stay ashore in our cozy 200 sq ft architecturally designed backyard guesthouse.



“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
Johnie GallSix Night San Juan Adventure

“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!”

Kimberly & Family
Kimberly & FamilyBlake Island Daytrip

“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!”

AnnaSail & Stay

“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.”

Andrya Cooper
Andrya CooperBallard Sail & Overnight

“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. ”

James & Family
James & FamilyA Three Hour Tour & Night at Anchor

“The day was crisp, the snow peaked mountains surrounded us in a glimmering sea. Charismatic Captain Ben sailed us around Bainbridge to explore the sights. We were greeted by many doe-eyed seals on our voyage and will never forget this adventure. True was a gorgeous and classy boat, comfortable and spacious. My friends and I will be making this trip again!!”

Eden Whitmire
Eden WhitmireA Five Hour Tour

“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.”

Euan Fraser
Euan FraserSunset Sail & Night at Anchor

“My happy place – sailing with Captain Ben at the helm. Even on a wild and wintry day I love being wrapped up in one of the on-board fluffy blankets with my hat and gloves and scarf, curled up in a comfy corner of the cockpit watching the world go by. All those people on the huge Seattle Bainbridge ferry slipping past us must wish they could swap places even for a few moments.  The boat is so stable and Ben such a terrific captain that it’s easy to get lost in my own world quite oblivious to all the activity going on around me as we tack back and forth across the Sound, Mt Baker in one direction, Mt Rainier the other. And if the chill gets a bit much then below decks in a comfy chair beside the big upper level windows is a great place to hang out. Now I just can’t wait for the summer to lay about on the forward deck sipping a cool drink and dreaming my life away.”

True Henderson
True HendersonAll Day Sail

“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.”

Brent Tongco
Brent TongcoSail & Night at Anchor

“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.”

Emily Crandal & Family
Emily Crandal & FamilyBlake Island Overnight

“From the moment you walk onto True you feel like you are stepping back in time to a place where everyday life just drifts away. This boating experience does not compare to many others. True is full of character that is beautifully enhanced by the enthusiasm and experience of the captain, Ben, who is happy to share his knowledge.

It would be an understatement to say that this boat is very comfortable. From a dining area with spectacular views to a relaxing lounge, True has everything you need to get away from it all. The galley along with a large bedroom and bathroom with fresh smelling hand lotion, are just some of the creature comforts onboard. Then you step outside onto the spacious deck and see nothing but the beauty that surrounds you. To be sailing on the Puget sound in a boat such as True can only be described as a wonderful experience.”

Sylvia Isaacson
Sylvia IsaacsonA Three Hour Tour

“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.”

Jeff Engebretson
Jeff EngebretsonSunset Sail

Ready to book your adventure? Got some questions? Send us an email or give us a call! 206.788.6512

Harbour Marina:  233 Parfitt Way SW, Bainbridge Island, WA 98110  |  Slip #23

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