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All listings in California

Incredible sailboat rentals in California, United States.

Page 2 of 5117 listings

Captained Sail on San Francisco Bay on 51' Morgan Out Island Ketch
Events in Sausalito · 30 guests

Captained Sail on San Francisco Bay on 51' Morgan Out Island Ketch

4.9
Superowner
Best of 2026
$650/hour
Create memories you’ll cherish for life! 47' Luxury Sailboat
Sailing in Newport Beach · 6 guests

Create memories you’ll cherish for life! 47' Luxury Sailboat

5.0
Superowner
$250+/hour
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
$750/hour
44' Luxury Cruiser Sailboat Charter  | San Francisco Bay
Sailing in Alameda · 6 guests

44' Luxury Cruiser Sailboat Charter | San Francisco Bay

5.0
$159/hour
Newport Harbor Sailing Adventure
Sailing in Newport Beach · 6 guests

Newport Harbor Sailing Adventure

5.0
$133/hour
42 Sailing Monohull Tours in Sausalito
Sailing in Sausalito · 6 guests

42 Sailing Monohull Tours in Sausalito

5.0
Superowner
$200/hour
Stunning 46' Bali Cruising Catamaran Charter in Marina del Rey, California
Sailing in Marina del Rey · 12 guests

Stunning 46' Bali Cruising Catamaran Charter in Marina del Rey, California

5.0
Superowner
$650/hour
San Diego Catamaran Charter | Private Sunset Sail & Harbor Cruises - 12 guests
Sailing in San Diego · 12 guests

San Diego Catamaran Charter | Private Sunset Sail & Harbor Cruises - 12 guests

5.0
$300+/hour
42ft Catalina MkII Sailing Yacht in The San Diego Bay, California
Sailing in San Diego · 6 guests

42ft Catalina MkII Sailing Yacht in The San Diego Bay, California

5.0
$285/hour
Private Harbor Cruise in Newport Beach, California
Tours in Newport Beach · 4 guests

Private Harbor Cruise in Newport Beach, California

5.0
$200/hour
60’ Premier Sailing Yacht in San Diego.
Sailing in San Diego · 35 guests

60’ Premier Sailing Yacht in San Diego.

5.0
$775/hour
Incredible 36' Cruiser For Rent
Powerboats in Long Beach · 10 guests

Incredible 36' Cruiser For Rent

5.0
$149/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
Pure Sport Catamaran Sailing on San Diego Bay
Sailing in San Diego · 6 guests

Pure Sport Catamaran Sailing on San Diego Bay

5.0
$220/hour
28' Party Catamaran with Trampoline for Bay Sails & Sunset Cruises!
Sailing in Marina del Rey · 8 guests

28' Party Catamaran with Trampoline for Bay Sails & Sunset Cruises!

4.8
$250+/hour
Pirate Ship in Avalon, Catalina
Sailing in Avalon · 6 guests

Pirate Ship in Avalon, Catalina

5.0
$150+/hour
Luxury Sail into a Deep, Relaxed State
Sailing in Marina del Rey · 6 guests

Luxury Sail into a Deep, Relaxed State

5.0
$200/hour
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
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
Bali 43 Complete comfort Catamaran
Sailing in Marina del Rey · 12 guests

Bali 43 Complete comfort Catamaran

5.0
$400/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
San Diego's Historic 1938 Sailing Yacht — Private Charters, Sunset Sails & Event
Sailing in San Diego · 30 guests

San Diego's Historic 1938 Sailing Yacht — Private Charters, Sunset Sails & Event

5.0
$600+/hour
1980 Catalina 38ft Sparkman & Stephens Sailboat in Long Beach
Sailing in Long Beach · 10 guests

1980 Catalina 38ft Sparkman & Stephens Sailboat in Long Beach

3.7
$120/hour
Classic 50ft Gulfstar Sailing Yacht
Sailing in San Diego · 22 guests

Classic 50ft Gulfstar Sailing Yacht

5.0
$750/hour

Sailing Reviews in California

  1. AS

    Andrew

    San Diego's Historic 1938 Sailing Yacht — Private Charters, Sunset Sails & Event

    Our birthday celebration aboard the Jada was nothing short of exceptional. The yacht is stunning, the atmosphere was perfect, and the crew delivered a flawless experience - attentive, welcoming, and effortlessly on point throughout the entire day. Every moment felt seamless and elevated. It was one of those days you wish you could relive again and again. We’ll absolutely be back.

  2. KI

    Keoni

    Incredible 36' Cruiser For Rent

    I want to start off thanking God for people like Captain Chris. I had the absolute pleasure of celebrating my 33rd birthday with Captain Chris, and I truly cannot recommend him enough. From start to finish, he exceeded every expectation. His boat was spotless, and his sailing was incredibly smooth—it honestly felt effortless and relaxing the entire time. What stood out the most was his professionalism and kindness. He was extremely accommodating, answered every call leading up to the trip, and made sure we had clear directions and everything we needed. He welcomed everything we brought onboard without any hesitation and never once made us feel uncomfortable or restricted—he simply allowed us to enjoy our time fully. Captain Chris has such a calm and respectful presence that at times we even forgot he was there, yet everything ran perfectly. That balance is rare, and he handled it beautifully. This experience meant more to us than just a birthday celebration. Our family had just experienced a loss, and this day gave us a moment to breathe, laugh, and reconnect. It truly felt like a healing escape, and Captain Chris played a huge role in creating that space for us. It felt like we were in a movie, and he was the one helping bring it all together behind the scenes. I’m beyond grateful for the experience and for his energy, professionalism, and generosity. If you’re thinking about booking—do it. You will not be disappointed. He is absolutely stellar. Thank you again, Captain Chris, for making my birthday unforgettable. 💛

  3. RP

    Rupal

    Captained Sail on San Francisco Bay on 51' Morgan Out Island Ketch

    We enjoyed a beautiful day on the water on Glory Days for a special graduation sail with our closest friends/family. We saw the Golden Gate Bride, Alcatraz and Angel Island. We loved being on the water and felt in great hands with Captain Dan and Kyle. They took great care of us and provided excellent service. Captain Pam coordinated all the details prior to the sail and provided clear and often communication, including a detailed PDF of what to expect prior to sailing. We had a wonderful time!

  4. CS

    Charlotte

    Captained Sail on San Francisco Bay on 51' Morgan Out Island Ketch

    We had the best day sailing with Captain Ed and Joan - part of Captain Pam’s crew! They kept us safe and worry free. We celebrated on Glory Days with a surprise engagement party, could not have been better experience! Captain Ed helped us maintain the surprise in the dock.

  5. BS

    Bob

    Captained Sail on San Francisco Bay on 51' Morgan Out Island Ketch

    Our sailing experience was everything we had hoped for. The communication was easy, the details of the trip were exactly as described, and Captain Ed & Joan were a pleasure to be with. Our 3 young grandchildren (10, 8 & 6) were all given a sailing lesson and the two oldest helped bring in the sails. I highly recommend this experience.

  6. NK

    Noah

    Captained Sail on San Francisco Bay on 51' Morgan Out Island Ketch

    I booked with captain Pam to take a group of employees out on the bay for Fleet Week. Our group had a wonderful time on the water, especially those visiting from out of town. Communication, planning, pick-up/drop off were all super smooth. Boat was a great size: big enough for group but small enough to experience some of the excitement of sailing. Would definitely recommend and book again for an excursion.