Alisanne Steele | June 15, 2026 | Wonder Awaits. Seize It
When Rabbit Hole Sailing launched earlier this year, we had a simple goal:
Get people out on the water.
Looking back over the past few months, it is hard not to smile.
Since beginning charter operations in March, SV Rabbit Hole has welcomed sailors with a wide variety of backgrounds and goals. Some came to refresh their skills, some came to prepare for future adventures, and others simply wanted to spend time sailing San Francisco Bay with family and friends.
One of the season’s first highlights was celebrating Opening Day on the Bay with a six-boat gathering and picnic at beautiful Ayala Cove on Angel Island. It was a wonderful reminder that sailing is about more than boats. It is about friendships, community, and creating memories together.
When Rabbit Hole Sailing launched earlier this year, we had a simple goal:
Get people out on the water.
Looking back over the past few months, it is hard not to smile.
Since beginning charter operations in March, SV Rabbit Hole has welcomed sailors with a wide variety of backgrounds and goals. Some came to refresh their skills, some came to prepare for future adventures, and others simply wanted to spend time sailing San Francisco Bay with family and friends.
One of the season’s first highlights was celebrating Opening Day on the Bay with a six-boat gathering and picnic at beautiful Ayala Cove on Angel Island. It was a wonderful reminder that sailing is about more than boats. It is about friendships, community, and creating memories together.
Since then, we have had the privilege of conducting multiple Check-Out Sails, helping experienced sailors become familiar with Rabbit Hole and preparing them for future bareboat charters.
We have also enjoyed numerous instructor-led Skills Development Sails, where sailors have focused on everything from docking and sail trim to boat handling, navigation, and building confidence aboard a larger cruising yacht.
Through our partnership with Pacific Wayfinder Sailing Academy, SV Rabbit Hole has also served as the classroom for multiple US Sailing certification courses, including Bareboat Cruising and Night Operations Endorsement programs. Watching students develop new skills, earn certifications, and take the next step in their sailing journey has been one of the most rewarding parts of our first season.
Perhaps the greatest milestone has been watching newly approved charter crews confidently cast off on adventures of their own.
To date, three different charter crews have successfully completed multi-day “Out the Gate” cruises, taking Rabbit Hole beyond the Golden Gate and into the coastal waters that inspire so many sailors to keep learning, exploring, and dreaming a little bigger.
Those voyages represent exactly what Rabbit Hole Sailing hopes to accomplish. We are not simply providing a boat. We are helping sailors gain the experience, confidence, and judgment to safely pursue adventures of their own.
By every measure that matters to us, this first season has been a success.
Not because of the number of charters.
Not because of the miles sailed.
But because of the people.
The friendships being formed. The confidence being built. The laughter shared at the dock after a great day on the water. The excitement of sailors taking the next step in their journey. The stories that come back with every returning crew.
And we are just getting started.
As we look ahead, we are excited to continue growing our community, expanding opportunities for sailors throughout the Bay Area, and hopefully adding J/24s to the Rabbit Hole Sailing fleet to support performance sailing, private coaching, and new skills-development opportunities.
Whether you are planning your first bareboat charter, earning your next US Sailing certification, joining a Community Sail, or simply looking for more time on the water, we would be honored to be part of your sailing journey.
No membership. No initiation fees. Just sailors, great boats, and the next adventure waiting beyond the harbor.
Here’s to growing confidence, lasting friendships, unexpected adventures, and many more stories still to be written.
Let’s go sailing.
Curiosity has a way of carrying us farther than planned.
Whether you are here to learn, explore, or simply enjoy time on the water, we are glad you have found your way to Rabbit Hole Sailing.
If you would like to sail with us on San Francisco Bay through a charter, instructor-led sail, or shared journey, visit our Contact page and get in touch. We look forward to welcoming you aboard.
Onward,
“The hurrier I go, the behinder I get.”
— Lewis Carroll