Recent Searches
Clear

Top California Sailing Trips

Category
Filter
Select Dates
Today
Tomorrow




42 California Sailing Trips

Sort by:Featured

Did you know?You can reserve your spot today and pay when you're ready.
Learn more
Did you know?
You can reserve your spot today and pay when you're ready.Learn more

San Diego Whale Watching Cruise

San Diego Whale Watching Cruise

star-5
Go whale watching from San Diego aboard a replica of a historic sailing schooner that won the world’s first America’s Cup sailing competition in 1851. Throughout your cruise, your expert guide shares informative commentary about gray whales, dolphins, and other marine animals, along with details about the US Navy sites you pass as you head out on the Pacific Ocean.
...  More
  • 4 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$85
From  
US$85
Learn More
  • 4 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Classic Sailboat Sunset Sail

Classic Sailboat Sunset Sail

star-5
Watch the sun set over San Diego during an all-inclusive small-group cruise aboard a classic sailboat. Pass landmarks such as the Maritime Museum, Coronado Bridge, and USS Midway, and look for sea lions, dolphins, and other wildlife around San Diego Harbor on the 2.5-hour cruise.
...  More
  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$110
From  
US$110
Learn More
  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

San Francisco Bay Sailing Cruise

San Francisco Bay Sailing Cruise

star-5
Admire San Francisco and its surrounding sights from the water on a San Francisco Bay sailing cruise. Onboard a catamaran, sail past the iconic Golden Gate Bridge, legendary Alcatraz Island, and the hamlet of Sausalito. Take advantage of great photo ops while you soak up the sea breeze during this scenic tour.
...  More
  • 1 hour 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$45
From  
US$45
Learn More
  • 1 hour 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Reserve Now & Pay Later
Secure your must-do activities without being locked in
Luxury Catamaran Sailing Charter

Luxury Catamaran Sailing Charter

star-5
The Malarky is a 47' Luxury Catamaran, the largest in Mission Bay. Our on-board Captain and Crew will assist you with any needs while you enjoy adventuring Mission Bay, and the Southern California Coastline. Port LoungeIndoors or outdoors the Malarky has plenty of space to entertain and dine. The indoor dining area is located on the port side, surrounded by comfortable lounge cushions, beautiful wood work, large windows, allowing you to dine in style.Starboard LoungeRelax in the spacious lounge area located inside the cabin on the starboard side. Enjoy the beautiful craftsmanship, comfortable lounge cushions, coffee table, inviting window light, calling you to slow down and relax in style.Aft DeckEntertain outside with a view and the cool sea air. The aft dining area offers plenty of comfortable shaded seating with a large table.State RoomsEquipped with 4 modern decorated State Rooms with flat screen televisions in each - with restrooms on both sides of the boat.
...  More
  • 2 to 8 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$1100
From  
US$1100
Learn More
  • 2 to 8 hours
  • Reserve Now & Pay Later
  • Free Cancellation

San Diego SUNSET Cruise Experience

San Diego SUNSET Cruise Experience

star-5
San Diego's best kept secret awaits aboard your private SUNSET cruise on San Diego Bay. See the beauty of downtown cityscape, Embarcadero, Maritime Museum from the ocean which offers a different vantage. Sip cocktails, share a romantic moment, drop a proposal for engagement, or just enjoy a one of a kind San Diego sunset. Flexibility to customize your itinerary to your own preferences, perfect for couples. Enjoy intimate moments with friends and family aboard a "classic" Slocum styled sailing vessel. She is from an era where sea-going was for exploration of new worlds and becoming a rare experience today.These classic designs were used in the popular "Captain Ron" or "50 FIRST DATES" movies due to their classic lines. Beautiful hand carved old growth Burmese teak, and bronze accents throughout. Great vessel for spectacular photo opportunities, or to venture to times long past. A Once-in-a-Lifetime Experience!
...  More
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$275
From  
US$275
Learn More
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Afordable Luxury Sailing Tours of San Diego's Bay and Coastal Waterways!

Afordable Luxury Sailing Tours of San Diego's Bay and Coastal Waterways!

star-5
This is a personal tour from one to six passengers that is engaging and diverse tailored to the specific selected tour option(s) Both private and mixed tours are available.
...  More
  • 2 to 3 hours
  • Free Cancellation
From  
US$99
From  
US$99
Learn More
  • 2 to 3 hours
  • Free Cancellation

Sail Stars & Stripes America's Cup Racing Yacht in San Diego

Sail Stars & Stripes America's Cup Racing Yacht in San Diego

star-5
Cruise around San Diego bay aboard an authentic 1992 America’s Cup racing yacht and travel at twice the speed of the average sailboat. The Stars and Stripes USA-11 is one of the fastest and best known America’s Cup racing yachts. It was designed and built to be raced in San Diego, and has been restored to pristine condition. Take a turn at the helm and join in grinding the winches to raise and trim the sails.
...  More
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$125
From  
US$125
Learn More
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Small-Group San Diego Afternoon Sailing Excursion

Small-Group San Diego Afternoon Sailing Excursion

star-5
Enjoy a sailing adventure on a Catalina-style sailboat with just six people for a comfortable, semi-private experience (or, find five friends and fill up the whole boat). Sail in San Diego Harbor during the day. Sit back and relax to enjoy the water views while enjoying complimentary beer, wine, soft drinks and snacks.
...  More
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$95
From  
US$95
Learn More
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Small-Group San Diego Sunset Sailing Excursion

Small-Group San Diego Sunset Sailing Excursion

star-5
Sail into the setting sun aboard a Catalina style sailboat during this intimate cruise with a small group. Feel like you have the ship all to yourself on this trip that’s limited to just 12 total guests, watching as the last rays of the sun drop into the glistening waves. Enjoy the included beer, wine, soft drinks and snacks during the ride, as well as jackets and wind gear in case you get cold. You can even plug in your own music to add to the fun. Departure times vary throughout the year. Guest must contact Sail San Diego after purchase for the exact departure time.
...  More
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$95
From  
US$95
Learn More
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Sunset Sailing Tour of San Diego Bay up to 6 Guests

Sunset Sailing Tour of San Diego Bay up to 6 Guests

star-5
A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several different types of sunset sailing charters and boat tours. Our sunset sailing charters and boat tours take you on an exciting tour of San Diego Bay. Book a sunset sailing boat charter and stretch out in the San Diego sunshine with a trusty skipper at the helm, A sunset sailing boat tour on San Diego Bay with Pacifica Sailing Charters is the perfect sailing experience for you and your guests. With over 20 years of boating on San Diego Bay and the waters surrounding the San Diego harbor, our sunset boat charters and sunset sailing boat tours are rated #1 on Google, Yelp, and TripAdvisor.
...  More
  • 2 hours
From  
US$120
From  
US$120
Learn More
  • 2 hours

sailing tours of Bodega Bay

sailing tours of Bodega Bay

star-5
This is a unique experience because you get to sail a 33' boat with a licensed captain. You can be involved as much or as little as you want
...  More
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$119
From  
US$119
Learn More
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation

America's Cup Sailing Adventure on San Francisco Bay: Day Sail

America's Cup Sailing Adventure on San Francisco Bay: Day Sail

star-5
Tread in the footsteps of world-champion sailors on this 2.5-hour America’s Cup Day Sail on San Francisco Bay. You’ll board a high-speed International America’s Cup class yacht and take a turn on the official race course from the 2013 competition. With a skilled sailor in charge, you’ll take your turn as crew working the sail trim controls and even have a chance to skipper the boat. After departing from San Francisco’s famous Pier 39 you’ll take to the Bay and cruise beneath the magnificent Golden Gay Bridge. There’s no better way to see the Bay than this sailing trip with USA 76.
...  More
  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$150
From  
US$150
Learn More
  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Harbor Sailing Tour in San Diego --> Private Yacht for Small Groups!

Harbor Sailing Tour in San Diego --> Private Yacht for Small Groups!

star-5
Go sailing on San Diego Bay with up to six friends on this private 2.5-hour sailboat charter. Pass by sights such as the Maritime Museum, USS Midway, Star of India, Coronado bridge, and more. Your captain shares commentary and provides refreshments such as white wine and fruit. You might see Navy ships near the Navy base, and glimpse marine life such as seals and seabirds.
...  More
  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$350
From  
US$350
Learn More
  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Classic Sailboat Afternoon Harbor Tour

Classic Sailboat Afternoon Harbor Tour

star-5
See San Diego on a small-group 2.5-hour cruise aboard a classic 32-foot (10-meter) sailboat. Munch on light snacks, accompanied by craft beer or wine, while taking in landmarks like the Maritime Museum and USS Midway, in addition to wildlife and the bustling San Diego Harbor.
...  More
  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$89
From  
US$89
Learn More
  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

2-Hour Sunset Sail on the San Francisco Bay

2-Hour Sunset Sail on the San Francisco Bay

star-5
Come aboard the Privateer for a beautiful sailing journey along the San Francisco Bay where you can enjoy sightseeing at the most beautiful time of day—sunset. Coast along as you spot out Alcatraz, the Sausalito shoreline, and the Golden Gate bridge, all with a drink of choice in your hand.  
...  More
  • 2 hours
From  
US$65
From  
US$65
Learn More
  • 2 hours

1.5-hour San Francisco Bay Sailing Tour

1.5-hour San Francisco Bay Sailing Tour

star-5
Take a relaxing afternoon sailing cruise aboard a traditional sailboat on the San Francisco Bay. Cruise past landmarks such as Alcatraz Island, Angel Island, the Sausalito waterfront, and Golden Gate Bridge, and see the San Francisco skyline on your way back to Pier 39. Includes two drinks, and personalized attention from the crew and captain.
...  More
  • 1 hour 30 minutes
From  
US$49
From  
US$49
Learn More
  • 1 hour 30 minutes

San Diego Bay Sailing Tour

San Diego Bay Sailing Tour

star-5
Set sail aboard a comfortable sailing yacht on a small-group excursion from San Diego. Cruise around San Diego Bay, taking in views of the scenic waterfront, military vessels, and historical landmarks. Travel past Point Loma and Coronado, and catch sight of wading birds, sea lions, and maybe dolphins. Try your hand at sailing the yacht, or simply relax on the deck and enjoy the views.
...  More
  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$84
From  
US$84
Learn More
  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Golden Gate Bridge Sailing Tour

Golden Gate Bridge Sailing Tour

star-5
Go sailing on the San Francisco Bay on a spectacular 2-hour sailboat cruise from Pier 39 at Fisherman's Wharf. Head to the Golden Gate Bridge for sweeping views of the Marin Headlands, Tiburon and Sausalito, then glide across the bay, passing Angel Island, Alcatraz Island, The Presidio, Crissy Field, Ghirardelli Square and the Bay Bridge. You can enjoy two complimentary glasses of sparkling wine, beer or soda, and ask your captain and crew any questions you may have along the way.
...  More
  • 2 hours
  • Free Cancellation
From  
US$65
From  
US$65
Learn More
  • 2 hours
  • Free Cancellation

Private Sailing Charter on San Diego Bay

Private Sailing Charter on San Diego Bay

star-5
Sail the lovely waters off San Diego on a private yacht charter. The itinerary is up to you, or your captain can suggest some places to go. You can opt for a whale watching tour (seasonal), or lay anchor and go for a swim. If you prefer, choose a bay tour; seeing the sights like the Hotel del Coronado, Point Loma Lighthouse, Tijuana, and the San Diego skyline.
...  More
  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$410
From  
US$410
Learn More
  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

America's Cup Sailing Adventure on San Francisco Bay: Race Day

America's Cup Sailing Adventure on San Francisco Bay: Race Day

star-5
Climb aboard USA 76, an International America’s Cup Class racing yacht and join the crew to race against 40 other yachts in a regatta on the San Francisco Bay. Participate with active crew roles: try pinning the sail trim, take a turn at the helm, or just sit back and enjoy the ride. Learn the history of the ship and have a safety interdiction from your US Coast Guard Licensed crew.
...  More
  • 150 to 300 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$180
From  
US$180
Learn More
  • 150 to 300 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

America's Cup Sailing Adventure on San Francisco Bay: Express Sail

America's Cup Sailing Adventure on San Francisco Bay: Express Sail

star-5
Experience the San Francisco Bay on a 2-hour sailing tour aboard a boat that competed in the America’s Cup, one of the world’s most prestigious sailing competitions. Depart from a convenient location on Pier 39 for this family-friendly sailboat tour, which offers sweeping views of Alcatraz, the Golden Gate Bridge, Sausalito, the city skyline, and more.
...  More
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$100
From  
US$100
Learn More
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Bachelorette Sailing Party on San Diego Bay up to 12 Guests

Bachelorette Sailing Party on San Diego Bay up to 12 Guests

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 12 guests. Enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarines, not to mention an incredible abundance of sea life including Sea Lions, Dolphins and Whales. Whether you need a classic sailboat or catamaran for your Bachelorette Party, we can provide a private catamaran that is roomy, comfortable and stable. Much heavier than traditional boats today, Sea Esta will provide a steady, smooth sail no matter what the conditions. This large and stable catamaran is perfect for sightseeing around San Diego Bay and the perfect bachelorette party yacht for you and your guests.
...  More
  • 2 hours
  • Free Cancellation
From  
US$1200
From  
US$1200
Learn More
  • 2 hours
  • Free Cancellation

3-Hour Sailing Experience

3-Hour Sailing Experience

star-5
We offer the only REAL SAILING EXPERIENCE in Dana Point, California, allowing guests who wish to do more than sight-see to take control of the sailboat (of course, our experienced Captains will be by your side to teach you and help you every step of the way).
...  More
  • 3 hours
  • Free Cancellation
From  
US$595
From  
US$595
Learn More
  • 3 hours
  • Free Cancellation

America's Cup Sailing Adventure on San Francisco Bay: Sunset Sail

America's Cup Sailing Adventure on San Francisco Bay: Sunset Sail

star-5
Take the helm of an International America’s Cup Class yacht on a 2.5-hour sail that traces the official course of San Francisco’s 2013 America’s Cup race. Cast off from the city’s bustling waterfront, and work alongside the crew to trim sails and operate the hoist while you head towards the Golden Gate Bridge. Enjoy fresh Pacific breezes as you get underway, and capture unforgettable images of Alcatraz, the San Francisco skyline, the bridge and the soaring Marin Headlands from the deck of the USA 76.
...  More
  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$180
From  
US$180
Learn More
  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation


icon_solid_phone
Book online or call
(888) 651-9785
(888) 651-9785