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Top California Sailing Trips

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San Diego Whale Watching Cruise and Maritime Museum Entry

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 4-hour 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. Your cruise includes refreshments and a complimentary same-day admission ticket to the San Diego Maritime Museum.
  • Duration: 4 hours 30 minutes
  • Free Cancellation
  • Duration: 4 hours 30 minutes
  • Free Cancellation
From  
$79.00 USD
From  
$79.00 USD
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San Francisco Bay Sailing Cruise

Admire San Francisco and its surrounding sights from the water on a San Francisco Bay sailing cruise. On board a catamaran, you’ll 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 90-minute tour.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
$45.00 USD
From  
$45.00 USD
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America's Cup Sailing Adventure on San Francisco Bay: Day Sail

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.
  • Duration: 2 hours 30 minutes
  • Free Cancellation
  • Duration: 2 hours 30 minutes
  • Free Cancellation
From  
$150.00 USD
From  
$150.00 USD
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Classic Sailboat Afternoon Harbor Tour

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.
  • Duration: 2 hours 30 minutes
  • Free Cancellation
  • Duration: 2 hours 30 minutes
  • Free Cancellation
From  
$110.00 USD
From  
$110.00 USD
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America's Cup Sailing Adventure on San Francisco Bay: Race Day

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.
  • Duration: 150 to 300 minutes
  • Free Cancellation
  • Duration: 150 to 300 minutes
  • Free Cancellation
From  
$180.00 USD
From  
$180.00 USD
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Sail Stars and Stripes America's Cup Racing Yacht

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.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$125.00 USD
From  
$125.00 USD
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Classic Sailboat Sunset Sail

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.
  • Duration: 2 hours 30 minutes
  • Free Cancellation
  • Duration: 2 hours 30 minutes
  • Free Cancellation
From  
$110.00 USD
From  
$110.00 USD
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Tall-Ship Sunset Sail on the San Francisco Bay

Watch the evening lights come on around the San Francisco Bay on Sundays during a 2-hour sunset sail from downtown Sausalito. Cruise aboard a handsome schooner that passes landmarks such as the Alcatraz Island, Crissy Field, Fort Mason, Fisherman's Wharf, Coit Tower, Angel Island, the Golden Gate Bridge, and the Bay Bridge.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$69.00 USD
From  
$69.00 USD
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Small-Group San Diego Afternoon Sailing Excursion

This three-hour adventure on a Catalina-style sailboat is limited to 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.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$88.99 USD
From  
$88.99 USD
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Small-Group San Diego Sunset Sailing Excursion

Sail into the setting sun aboard a Catalina style sailboat during this intimate 3-hour cruise with a small group. Feel like you have the ship all to yourself on this trip that’s limited to just 15 total guests, watching as the last rays of the sun drop into the glistening waves. Enjoy complimentary 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.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$88.99 USD
From  
$88.99 USD
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San Diego Half-Day Marine Wildlife Tour with Lunch

Spend the day communing with California’s marine life during this 4-hour, small-group, wildlife and whale watching tour aboard a vintage sailing yacht. Travel in style on a boat that seats 6 guests maximum, sailing from San Diego Harbor into the Pacific to search for the tell-tale blow spouts of whales along with other sea creatures like pelicans, sea lions, cormorants and more. An included gourmet box lunch keeps you fueled up for more adventures. A guide, glass of white wine or craft beer, and other drinks are also included.
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
$172.84 USD
From  
$172.84 USD
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San Diego Bay Sailing Tour

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.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$79.00 USD
From  
$79.00 USD
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3 Hour Private Sail For Up To 6 People

San Diego’s many harbors and islands make it the perfect city for an afternoon cruise, but the ferries and cruise ships on offer can often be crowded or noisy. Avoid the crowds and the line for the bar on this private sailing tour around the bay or island of your choice. Sail around the calm harbor waters and see iconic San Diego landmarks like the Coronado Bridge and the USS Midway.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$350.00 USD
From  
$350.00 USD
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Sunday Morning Eco Sail on the San Francisco Bay

Cruise the bay and find yourself beneath the Golden Gate Bridge on a 2.5-hour Sunday morning eco sailing tour from Sausalito. Take in fantastic views of San Francisco and Alcatraz while gliding through the bay, and look for native marine life like porpoises and seals with the help of an onboard naturalist.
  • Duration: 2 hours 30 minutes
  • Free Cancellation
  • Duration: 2 hours 30 minutes
  • Free Cancellation
From  
$69.00 USD
From  
$69.00 USD
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Private Sailing Charter on San Diego Bay

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.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$399.00 USD
From  
$399.00 USD
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NEW TO VIATOR

Alcatraz and San Francisco Bay Sailing Cruise

Alcatraz admission tickets often sell out, which can make it hard to explore the prison at the time you’d like to go. Book this Alcatraz and San Francisco Bay sailing package to secure your visit to Alcatraz, and take a leisurely sail across the bay, too. You’ll also get access to the prison's award-winning audio tour that’s available in eight languages.
  • Duration: 3 to 5 hours
  • Duration: 3 to 5 hours
From  
$95.00 USD
From  
$95.00 USD
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2.5 Hour San Diego Sunset Sail

Set sail at one of the best times of day—sunset—during this San Diego Bay cruise. Board a comfortable sailing yacht and cruise along San Diego's coastline, taking in views of the scenic waterfront, military vessels, and historical landmarks. Catch sight of marine life and enjoy spectacular photo ops. Gorgeous sunset views and Champagne makes this tour a great choice for couples or travelers celebrating a special occasion.
  • Duration: 2 hours 30 minutes
  • Duration: 2 hours 30 minutes
From  
$109.00 USD
From  
$109.00 USD
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3 Hour San Diego Sailing Adventure

Take in the sights, sounds and stories of the bay on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from the water.Our San Diego Bay Sailing Adventures provide up-close access to scenic waterfront architecture, military crafts, historical landmarks, natural sea life and spectacular photo opportunities. On this sailing trip, you'll also have the opportunity to see dolphins, sea lions and naval ships on board a 37-foot sail yacht.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$109.00 USD
From  
$109.00 USD
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America's Cup Sailing Adventure on San Francisco Bay: Express Sail

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.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$100.00 USD
From  
$100.00 USD
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Luxury Scenic Sailing Tour

Set sail on San Diego Bay with this San Diego sightseeing cruise. Catch sight of San Diego attractions like Coronado Island, Point Loma, and the downtown skyline as you cruise across the bay. You can relax on board, too, enjoying included snacks or bringing your own beverages to keep you refreshed while you sail.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$79.00 USD
From  
$79.00 USD
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America's Cup Sailing Adventure on San Francisco Bay: Sunset Sail

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.
  • Duration: 2 hours 30 minutes
  • Free Cancellation
  • Duration: 2 hours 30 minutes
  • Free Cancellation
From  
$180.00 USD
From  
$180.00 USD
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NEW TO VIATOR

Sea Life Excursion 4 hour cruise seeking out sea animals. Includes sack lunch.

We are set apart from other operators with our clean and quite boats, included sack lunches or hors d'oeuvres and small intimate cruises. There are no large noisy crowds and the animals are not afraid of our boats because there are no noisy diesels or diesel stink. Our intimate groups allow more flexibility to explore during your 4 hour adventure!Sailing and boating lessons by appointment, please call!
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
$85.00 USD
From  
$85.00 USD
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Nature Cruise and Whale Watching Tour

Private small group whale watching/nature sailing tour on San Diego Bay on a unique 1914 replica Friendship Sloop. All boat tours use traditional sailing methods for wildlife sighting and sightseeing San Diego landmarks. Cruise out to the open ocean and for gray whale viewing, a 4-hour tour. Beer, wine, soft drinks and snacks included. You are welcome to bring your own food and drink as well. Wildlife of all kinds will be seen, such as sea lions sea birds; whale/dolphin sightings cannot be guaranteed, but fun is a sure bet.This most classic of San Diego boat tours is conveniently located 2 miles from downtown San Diego, just across from the airport. Experience the bustling activity of the bay, wildlife, and a stunning view of the city skyline on a San Diego nature cruise with us aboard the Liberty.
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
$800.00 USD
From  
$800.00 USD
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NEW TO VIATOR

3 Hour Private Sailing Tour

A fully restored 69 foot private sailing ship for your own private group. We can comfortably accommodate 12 passengers, we have a bluetooth stereo, and a immaculate interior belowdecks. There is a clean restroom belowdecks and we have a tremendous crew. You will have a Captain and two crew on board to assist with all the sailing, answer any questions, and to assist you in anything needed. If you would like you can assist in hoisting and trimming sail, or, you can sit back and enjoy a cold beverage and some salami, cheese, and crackers.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$1,210.00 USD
From  
$1,210.00 USD
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