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All listings in Oakland

Great sailboat rentals near Oakland, California.

Page 1 of 120 listings

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

30ft Catalina Sailboat Charter in Alameda CA

5.0
$95/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
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
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
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
Instant Book
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 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
Instant Book
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
Instant Book
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
35' Cruising Catamaran on San Francisco Bay
Sailing in Oakland · 10 guests

35' Cruising Catamaran on San Francisco Bay

4.9
$225/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
$245/hour
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
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
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
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
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. 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.

  2. 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.

  3. 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!

  4. BH

    Brack

    30ft Catalina Sailboat Charter in Alameda CA

    The boat is well maintained and in great shape for her age. Captain Brad was fun and informative. As we had some sailing experience he allowed us at the helm.

  5. ML

    Meredith

    30ft Catalina Sailboat Charter in Alameda CA

    We had a great day on the bay with Captain Brad! Brad was very friendly and full of information about the bay, sailing, and the local areas. It was a very enjoyable day on the bay for our whole group! Planning was simple-- Brad is very communicative and made things easy!

  6. RF

    Russell

    30ft Catalina Sailboat Charter in Alameda CA

    This sailing experience with Bradford was exactly what we had hoped for and more! He is such a fun Captain letting us be active in the sailing and also time to sit back and enjoy the experience as well. We will certainly be back for another trip soon.