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All listings in Oakland

Great sailboat rentals near Oakland, California.

Page 1 of 123 listings

30ft Catalina Sailboat Charter in Alameda CA
Sailing in Alameda · 6 guests

30ft Catalina Sailboat Charter in Alameda CA

5.0
$95/hour
Safe & solid sailing catamaran - Green power! Stunning beauty & great location!
Sailing in Richmond · 6 guests

Safe & solid sailing catamaran - Green power! Stunning beauty & great location!

5.0
$162+/hour
Schock 35 Cruiser Racer in San Francisco Bay
Sailing in Alameda · 6 guests

Schock 35 Cruiser Racer in San Francisco Bay

5.0
$134/hour
44' RACER CRUISER ROLEX BIG BOAT SERIES WINNER  | San Francisco Bay
Sailing in Alameda · 6 guests

44' RACER CRUISER ROLEX BIG BOAT SERIES WINNER | San Francisco Bay

5.0
$239+/hour
Nicest Certified Sailing Yacht on the West Coast for 10 Pax Package
Sailing in San Francisco · 10 guests

Nicest Certified Sailing Yacht on the West Coast for 10 Pax Package

5.0
$600+/hour
Instant Book
Frostbite-Free Sailing Adventures - Catamaran w/ Sunroom - Captained
Sailing in Alameda · 6 guests

Frostbite-Free Sailing Adventures - Catamaran w/ Sunroom - Captained

5.0
$300/hour
FAST J/105 Sailing Yacht Charter Downtown San Francisco, California!
Sailing in San Francisco · 6 guests

FAST J/105 Sailing Yacht Charter Downtown San Francisco, California!

5.0
$300+/hour
Sailing Charter On 72' Tall Ship on SF Bay, California- up to 49 passengers
Events in San Francisco · 49 guests

Sailing Charter On 72' Tall Ship on SF Bay, California- up to 49 passengers

5.0
Superowner
$1,467/hour
Beneteau Modern Premium Sailboat from San Francisco
Sailing in San Francisco · 6 guests

Beneteau Modern Premium Sailboat from San Francisco

5.0
$220+/hour
42' Luxury Catamaran – Private San Francisco Bay Charters for 12 - Oakland
Sailing in Oakland · 12 guests

42' Luxury Catamaran – Private San Francisco Bay Charters for 12 - Oakland

New
$575/hour
Nicest Certified Sailing Yacht on the West Coast for 15 People Package
Sailing in San Francisco · 15 guests

Nicest Certified Sailing Yacht on the West Coast for 15 People Package

New
$650+/hour
35' Cruising Catamaran on San Francisco Bay
Sailing in Oakland · 10 guests

35' Cruising Catamaran on San Francisco Bay

4.9
$225/hour
Charter this Ultra-Luxury Beneteau 37 Sailboat downtown San Francisco
Sailing in San Francisco · 6 guests

Charter this Ultra-Luxury Beneteau 37 Sailboat downtown San Francisco

5.0
$400+/hour
Instant Book
Limited Availability
The nicest Charter Sailing Yacht in the West - Downtown San Francisco
Sailing in San Francisco · 20 guests

The nicest Charter Sailing Yacht in the West - Downtown San Francisco

4.9
$750+/hour
Instant Book
Sailing Lessons on the San Francisco Bay
Tours in Berkeley · 4 guests

Sailing Lessons on the San Francisco Bay

5.0
$123+/day
35.5' Hunter-Legend Cruising Monohull
Sailing in Oakland · 6 guests

35.5' Hunter-Legend Cruising Monohull

5.0
$115/hour
40' Luxury Cruising Sailboat – Private Charters for 8 Guests
Sailing in Richmond · 8 guests

40' Luxury Cruising Sailboat – Private Charters for 8 Guests

New
$232/hour
Luxury Bay Sailing Experience – Private 42' Yacht, Comfortably Seats 10 Guests
Sailing in Oakland · 10 guests

Luxury Bay Sailing Experience – Private 42' Yacht, Comfortably Seats 10 Guests

New
$265/hour
Nicest Certified 53' Santa Cruz Sailing Yacht on the West Coast - 20 Pax Package
Sailing in San Francisco · 20 guests

Nicest Certified 53' Santa Cruz Sailing Yacht on the West Coast - 20 Pax Package

New
$750+/hour
Instant Book
Sail the San Francisco Bay on a Beneteau 45 Cruising Monohull
Sailing in Oakland · 6 guests

Sail the San Francisco Bay on a Beneteau 45 Cruising Monohull

New
$200/hour
Instant Book
50' Beneteau - Classic nautical soul meets modern comfort and high-tech
Sailing in Alameda · 6 guests

50' Beneteau - Classic nautical soul meets modern comfort and high-tech

New
$250/hour
Charter 30ft Sabre Cruising Monohull In Berkeley, California
Sailing in Berkeley · 6 guests

Charter 30ft Sabre Cruising Monohull In Berkeley, California

New
$150/hour
Sleek Modern Luxury Sailing Yacht from Beneteau
Sailing in Oakland · 5 guests

Sleek Modern Luxury Sailing Yacht from Beneteau

New
$150+/hour

Sailing Reviews in Oakland

  1. OM

    Olaf

    Schock 35 Cruiser Racer in San Francisco Bay

    From the beginning until the end of this turn everything top. My wish to sail under the Golden Gate Bridge we did and on top we could watch seals, Dolphins and Wales!!! Dan is a fantastic Skipper and human Person! See you soon, Olaf

  2. AR

    Arielle

    Sailing Charter On 72' Tall Ship on SF Bay, California- up to 49 passengers

    Our team had such an incredible experience! The boat was absolutely beautiful, exactly as pictured and even better in person. The crew was amazing! So friendly, attentive, and welcoming from start to finish. Couldn’t have asked for a better trip.Highly recommend!

  3. Dan

    Dan

    35' Cruising Catamaran on San Francisco Bay

    Very nice boat. Very well equipped. Brand new main sail. We sailed as a bare boat. Mary was very accomodating. Anni gave us good instructions on all the operations of the boat. I have sailed many times in SF and knew the area well. The boat performed as expected in the bay.

  4. JW

    John

    30ft Catalina Sailboat Charter in Alameda CA

    Super skilled, entertaining captain… beautiful sail, highly recommended.

  5. BJ

    Bruce

    30ft Catalina Sailboat Charter in Alameda CA

    Wonderful sailing experience with a very knowledgeable, engaging, fun loving, and story telling Capt Brad. The pre-sail communications were spot on and timely. Once Capt Brad assessed the interest level (high) and capability (hard working but novice sailors) of our grandsons (ages 12 & 8) he had them working ropes an steering when safe and under his watchful eye. Already looking forward to our next sail with Capt Brad.

  6. JN

    Josephine

    30ft Catalina Sailboat Charter in Alameda CA

    We went sailing with my husband, and Brad was our amazing captain! His communication was clear and timely from start to finish. We were running about 10 minutes late and messaged him — he responded immediately, remaining calm, professional, and welcoming. The entire 3-hour experience was perfect. We truly enjoyed every moment and can’t wait to sail with him again in the future. Thank you, Brad!