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Top San Diego Sailing Trips

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13 Tours and Activities

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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
From
$110.00 USD
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  • Duration: 2 hours 30 minutes
  • Free Cancellation
From
$110.00 USD

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
From
$399.00 USD
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  • Duration: 3 hours
  • Free Cancellation
From
$399.00 USD

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
From
$79.00 USD
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  • Duration: 3 hours
  • Free Cancellation
From
$79.00 USD

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
From
$172.84 USD
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  • Duration: 4 hours
  • Free Cancellation
From
$172.84 USD

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
From
$88.99 USD
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  • Duration: 3 hours
  • Free Cancellation
From
$88.99 USD

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
From
$88.99 USD
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  • Duration: 3 hours
  • Free Cancellation
From
$88.99 USD

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
From
$350.00 USD
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  • Duration: 3 hours
  • Free Cancellation
From
$350.00 USD

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
From
$110.00 USD
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  • Duration: 2 hours 30 minutes
  • Free Cancellation
From
$110.00 USD

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
From
$125.00 USD
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  • Duration: 3 hours
  • Free Cancellation
From
$125.00 USD

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
From
$800.00 USD
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  • Duration: 4 hours
  • Free Cancellation
From
$800.00 USD

Private Sunset Sail for Two

Spend a romantic evening with your special someone onboard a private chartered sailboat. Your skipper will sail you past San Diego’s lovely shoreline, with views of Point Loma, Coronado Island, Shelter Island and Harbor Island while you relax on the deck. Watching the sun set over Point Loma with a glass of champagne is the perfect way to top off a day with the one you love.
  • Duration: 2 hours
  • Free Cancellation
From
$346.84 USD
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  • Duration: 2 hours
  • Free Cancellation
From
$346.84 USD

Private Half-Day San Diego Bay Sailing Tour

Treat your group of up to six people to a half-day private sailing tour of San Diego Bay. Relax on board the luxury sailboat as your captain takes you past landmarks such as Point Loma and Coronado Island. Snack on the provided appetizers and refreshments, including a glass of wine or beer. Your tour can be tailored to your interests, and you can choose from departures in the morning, afternoon, or in the evening for the sunset.
  • Duration: 3 hours
  • Free Cancellation
From
$578.84 USD
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  • Duration: 3 hours
  • Free Cancellation
From
$578.84 USD

San Diego Small-Group Sail

This 2-hour small-group sail seats up to 6 people. You can relax comfortably or invite a group of friends to sail along Point Loma in San Diego. Your guide will pass beautiful landscapes near San Diego's skyline. Enjoy the scenery and take home a souvenir photo (available for purchase). You can also learn the basics of sailing while gazing the sunset. Come and relax with a choice of beer or wine (the first drink is free).
  • Duration: 2 hours
  • Free Cancellation
From
$145.00 USD
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  • Duration: 2 hours
  • Free Cancellation
From
$145.00 USD


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