Dock & Dine

August 9, 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.


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There’s no better lunch after a morning sail: Sam’s Anchor café looks like a yacht club from another era with its wooden deck looking out over the dock, beautiful bay windows and crisp white wooden siding. Just sail in, tie up at the dock, and climb the gangway to await one of the best dock-side lunches in the bay.

June 2024 – Golden Gate Ashes

By Kirk Millar • June 26, 2024
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The Surprising Gift of Clear Skies

By Kirk Millar • July 18, 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 • July 10, 2023
Come sailing with us and part of your charter will be donated to Canine Companions!

Angel Island Picnic

June 27, 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 • September 23, 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.
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