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All listings in Oakland

Great sailboat rentals near Oakland, California.

Page 1 of 124 listings

Cruise with Catalina 25 Sailboat in Alameda California
Sailing in Alameda · 4 guests

Cruise with Catalina 25 Sailboat in Alameda California

5.0
$80hour
30ft Catlina Sailboat Charter in Alameda CA
Sailing in Alameda · 6 guests

30ft Catlina Sailboat Charter in Alameda CA

5.0
$115hour
Excellent yacht for the SF Bay!   Wind power/green clean fun! In Richmond, CA
Sailing in Richmond · 6 guests

Excellent yacht for the SF Bay! Wind power/green clean fun! In Richmond, CA

5.0
$140-$215hour
Schock 35 Cruiser Racer and 44ft Racer cruiser for 6 people in San Francisco Bay
Sailing in Alameda · 6 guests

Schock 35 Cruiser Racer and 44ft Racer cruiser for 6 people in San Francisco Bay

5.0
$120hour
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
$225-$300hour
38' Catamaran Sailing in San Francisco
Sailing in Alameda · 12 guests

38' Catamaran Sailing in San Francisco

4.8
$250-$450hour
2011 Catalina MK 250 II
Sailing in Alameda · 6 guests

2011 Catalina MK 250 II

New
Snoozed - Active 02 May 2024
Add a SPARK to Your Special Event with a 65 ft Sailboat Cruise on the Bay
Sailing in San Francisco · 28 guests

Add a SPARK to Your Special Event with a 65 ft Sailboat Cruise on the Bay

4.9
$675hour
Sail Modern Premium Sailboat from San Francisco
Sailing in San Francisco · 6 guests

Sail Modern Premium Sailboat from San Francisco

5.0
$180-$200hour
Luxury Sailing Yacht on Santa Cruz 50 Sailboat Downtown San Francisco, CA
Sailing in San Francisco · 20 guests

Luxury Sailing Yacht on Santa Cruz 50 Sailboat Downtown San Francisco, CA

4.9
$450-$900hour
Celebrate your special event in style with a fun Cruise on SF Bay
Sailing in San Francisco · 28 guests

Celebrate your special event in style with a fun Cruise on SF Bay

5.0
Superowner
$650hour
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
$1,267hour
Charter in style on a Beneteau First 38S5 designed by Philippe Stark
Sailing in San Francisco · 7 guests

Charter in style on a Beneteau First 38S5 designed by Philippe Stark

5.0
$75-$119hour
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
$350-$400hour
Cruising Monohull Half-Day Skippered Charter for 6 people in Emeryville, California
Sailing in Emeryville · 6 guests

Cruising Monohull Half-Day Skippered Charter for 6 people in Emeryville, California

5.0
$595day
Tripp 43 Cruiser Racer Sailing Yacht in Alameda, California
Sailing in Alameda · 6 guests

Tripp 43 Cruiser Racer Sailing Yacht in Alameda, California

New
$199hour
35' Cruising Catamaran on San Francisco Bay
Sailing in Oakland · 10 guests

35' Cruising Catamaran on San Francisco Bay

4.7
$225hour
Sailing Lessons on the San Francisco Bay
Tours in Berkeley · 4 guests

Sailing Lessons on the San Francisco Bay

5.0
$123-$245day
35.5' Hunter-Legend Cruising Monohull
Sailing in Oakland · 6 guests

35.5' Hunter-Legend Cruising Monohull

5.0
$115hour
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
$200hour
Catamaran Spring Sailing, no fog, mist, perfect views
Sailing in San Francisco · 12 guests

Catamaran Spring Sailing, no fog, mist, perfect views

New
$250-$450hour
Full-Day Skippered Charter Cruise in San Francisco Bay onboard 35' Vintage Racing Sloop
Sailing in Emeryville · 2 guests

Full-Day Skippered Charter Cruise in San Francisco Bay onboard 35' Vintage Racing Sloop

New
$795day
Charter 30ft Sabre Cruising Monohull In Berkeley, California
Sailing in Berkeley · 6 guests

Charter 30ft Sabre Cruising Monohull In Berkeley, California

New
$195person
Frostbite-Free Sailing Adventures - Catamaran w/ Sunroom - Captained
Sailing in Alameda · 6 guests

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

New
$383hour

Sailing Reviews in Oakland

  1. Raoul

    Raoul

    Cruise with Catalina 25 Sailboat in Alameda California

    What a fantastic rental! The boat is in great shape, communication with Colton was excellent and overall a wonderful experience. I’d recommend to anyone!

  2. Mykola

    Mykola

    Charter this Ultra-Luxury Beneteau 37 Sailboat downtown San Francisco

    Everything was great, Drew is a very nice person and he explained everything.

  3. Ld

    Lara

    Cruise with Catalina 25 Sailboat in Alameda California

    If you are a sailing enthusiast, the boat is perfect for an authentic experience among friends and sail a few hours taking advantage of the bay wind. Colton is very attentive to provide all the necessary details and was super helpful with any questions or issues we had

  4. BW

    Bryson

    30ft Catlina Sailboat Charter in Alameda CA

    I booked this listing because I wanted to sail on a Catilina 30 on SF bay, but I found a new friend in Captain Brad. His boat is fantastic for cruising the bay. I have some experience on this exact boat, and I appreciate that he let me man the helm for a majority of our voyage. We booked 4 hours and I wish I had booked more. we will definitely be back; we could have spent the whole day cruising around the bay. Thank you, Captain Bradford, for a great experience; you are Alameda's best kept secret! No better way to experience SF bay than on your boat.

  5. KV

    Kim

    30ft Catlina Sailboat Charter in Alameda CA

    We had a wonderful afternoon sailing with Captain Brad. My husband is a sailer so we wondered what it would be like to have someone else at the helm, but Brad was very willing to let my husband take a turn. We had a fun afternoon and I look forward to going out with Captain Brad again soon!

  6. ma

    mushahid

    30ft Catlina Sailboat Charter in Alameda CA

    Bradford was right on time. We went out till bay bridge and turned back . We sailed on our back and it was a great experience. He humbly agreed to our request to watch sunset on bay and stayed back late for our . The weather was just not in our favor or else we might have gone till alacatrez. Had a amazing trip sitting at the front of the boat 🚤. His boat is very clean and we enjoyed our conversations with Bradford . Wouldn’t think twice to book with Bradford if we decided to go sailing again.