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Sailing with Grandpa Jake

May 05, 2009

Grandpa Jake is 86 years old and has sailed on San Francisco Bay since he was a kid. It was his first sail in 15 years! Grandpa Jake was thrilled to be back on the water - he took the helm as soon as we left Sausalito. He sailed us out past the Golden Gate Bridge where we found dolphins chasing our wake when we passed by the south tower.


The winds picked up to 20 knots and we reefed the main. When we reached Pac Bell Park, I offered to take the helm, but Grandpa Jake said, “I’m driving. You can drive tomorrow.”


We sailed a complete loop around Alcatraz island. Grandpa Jake remembers when it was still an active prison, and he regaled us with stories of sailing past Angel Island in the 1940’s and 50’s. It was wonderful trip back in time and I learned so much about the history of San Francisco boating. 


Only when we finally returned to the dock would Grandpa Jake give up the tiller and let me dock the boat.


-Captain Kirk

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By Kirk Millar • 18 Jul, 2023
It was a beautiful, Thursday evening in mid-July on the San Francisco Bay. Our guests who were visiting from Kansas City, along with their 2 grandchildren from Colorado, prepared for their summer evening sail, hoping to witness the breathtaking beauty of the Bay Area at sunset. Little did they know, they were about to be treated to a surprise that would make their experience all the more incredible—a rare, fog-free evening on the bay!

Supporting Future Service Dogs with Canine Companions

By Kirk Millar • 10 Jul, 2023
Come sailing with us and part of your charter will be donated to Canine Companions!

Angel Island Picnic

27 Jun, 2023
Welcome to Angel Island. We had another wonderful trip from San Francisco for an Angel Island picnic and history walk. Two boats with 30 passengers.  We started from San Francisco at 10 am and motor-sailed out to the Golden Gate Bridge. Under the bridge we got to see the Marin headlands and the Point Bonita Lighthouse. We got to howl under the bride - and hear our echo. Everyone got a hand at steering the boat as we went over to the calmer area near Angel Island. We saw LOTS of harbor seal sleeping on the docks at the island - they did not seem to care that we were visiting. Great picnic lunch with more sandwiches, snacks, desserts and drinks than could be eaten. Some of the group decided to hike around the island on the fire road (2 1/2 hour hike). Others decided to go on the more leisurely Angel Island history walk with Captain Kirk. Great views of Tiburon, Belvedere, the entire San Francisco bay entrance and the Golden Gate Bridge. Discussion about the history of San Francisco Bay, the Gold Rush, Civil war, building of the bridges, the end of the ferry services up to modern maritime traffic. Sailing back to San Francisco at the end of the day it was windy along the "slot". A few brave souls got some salt water spray on the front of the boat. The sun was out with a few puffy clouds and just a hint of fog. A perfect day.

Sailin' Savvy

By Heather • 23 Sep, 2021
Step it up a notch. Kick the sad 2020 work-from-home vibes to the curb. Put on your finest sailing garb and take a cruise in the bay! Our guests today looked pretty dapper, picnicking and watching the world go by under their jazzy straw hats. These hep-cats started the morning in Alameda, our newest home for Osprey. It was a calm, quiet morning, and as with fall sailing, the day turned out to be warm and pleasant. No more wild gusty winds like in the summer - September is the start of the best season to enjoy the SF Bay.

Dock & Dine

By Heather • 09 Aug, 2021
Why not escape the cloudy, foggy summer in San Francisco? Osprey met our intrepid travelers at Pier40 in San Francisco and set out, using the chilly winds and favorable tides to carry us across the central bay. Breaking into the warm sunny skies over Sausalito, Tiburon, and Belvedere, we could just begin to see our final destination: lunch at the historic dock and restaurant, Sam’s Anchor Cafe. Our custom lunch trips bring lots of smiles and laughter - such fun to end the sailing adventure, glide into the dock, and enjoy delicious seafood & cocktails waiting for you. We store all your belongings so you can fully enjoy an escape from the average day and spoil you and your friends to a real icon of the bay sailing scene. This is a subtitle for youpost
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