Sailing Trips in San Diego
Top 10 Best San Diego Sailing Trips
Found 38 Sailing Trips activities in San Diego. Sort by Popularity.Deluxe Sunset & Day Sail Small Group
Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect for up to six passengers. Glide through calm waters as the sky transforms into a masterpiece of color. Keep an eye out for playfu... More

Deluxe Sunset & Day Sail Small Group
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San Diego
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Superb201 reviews5
Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect....
Sunset Sail Along the San Diego Skyline
Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from the water. Â Our San Diego Bay Sunset Sailing Cruises provide an up-close and personal view o... More

Sunset Sail Along the San Diego Skyline
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San Diego
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Superb576 reviews4.9
Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on ....
Luxury Sailing Tour of San Diego's Bay and Coastal Waterways
This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways. You'll be on a beautiful Catalina 34' Sailboat enjoying the fresh air and best that San Diego has to offer. On your adventure yo... More

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways
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San Diego
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Superb200 reviews4.9
This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways....
Catamaran Sailing Adventure Premium 2.5hr Small group w/ drinks
With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepared to offer you a memorable day on the sea. 2.5 hour tour length is perfect for seeing all the beautiful sights. Catamarans reall... More

Catamaran Sailing Adventure Premium 2.5hr Small group w/ drinks
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San Diego
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Superb71 reviews5
With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepare....
2-Hour Private Sailing Experience in San Diego Bay
Our unique sail displays a peace sign because that is exactly what we share with our customers, peace. Peace is not always an easy thing to obtain in today's world. With all the stress life brings we are happy to provide a peacefu... More
Private Tour

2-Hour Private Sailing Experience in San Diego Bay
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San Diego
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Superb166 reviews5
Our unique sail displays a peace sign because that is exactly what we share with our customers, peac....
Private Tour
Private Sailing Charter on San Diego Bay
San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural wonder aboard a beautiful sailing yacht with a knowledgeable and friendly Captain? This private charterÂ... More
Private Tour

Private Sailing Charter on San Diego Bay
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San Diego
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Superb35 reviews4.9
San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. W....
Private Tour
Daytime Sailing Along San Diego's Skyline
Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor Sunroad Marina on Harbor Island on San Diego Bay, we often s... More
Private Tour

Daytime Sailing Along San Diego's Skyline
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San Diego
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Superb142 reviews4.9
Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on th....
Private Tour
Sunset or Afternoon Sail On A Vintage Yacht Beer & Wine Included
Book an unforgettable tour with Captain Phil and sail in style aboard, Liberty, a stunning replica of a 1904 gaff rigged friendship sloop. She is an elegant sight under sail, featuring; highly finished woodwork, bronze fixtures, a... More
Private Tour

Sunset or Afternoon Sail On A Vintage Yacht Beer & Wine Included
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San Diego
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Superb321 reviews4.9
Book an unforgettable tour with Captain Phil and sail in style aboard, Liberty, a stunning replica o....
Private Tour
Deluxe Day Sail in San Diego
Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego Bay offer a perfect blend of adventure and relaxation. With our passionate and kno... More
Private Tour

Deluxe Day Sail in San Diego
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San Diego
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Superb52 reviews5
Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our person....
Private Tour
Small-Group San Diego Afternoon Sailing Excursion
This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing you a comfortable, semi-private experience (or, grab five friends and fill up the whole boat!). Sit back, relax and enjoy the com... More
Private Tour

Small-Group San Diego Afternoon Sailing Excursion
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San Diego
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Superb523 reviews5
This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing....
Private Tour
Catamaran Sunset Sail Premium 2.5hr Small group w/ drinks
Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and lounging around watching sea life, and water rush by. The swift and stable ocean design ensures a comfortable, and exhilarating ride wit... More
Private Tour

Catamaran Sunset Sail Premium 2.5hr Small group w/ drinks
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San Diego
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Superb195 reviews4.9
Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and loungi....
Private Tour
Afternoon or Sunset Sail On A Vintage Yacht Beer & Wine Included
Book an unforgettable tour with Captain Phil and sail in style aboard Liberty, a stunning replica of a 1904 gaff-rigged Friendship sloop. Her best features include highly-finished woodwork, bronze fixtures, and gaff rigging that s... More
Private Tour

Afternoon or Sunset Sail On A Vintage Yacht Beer & Wine Included
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San Diego
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Superb76 reviews5
Book an unforgettable tour with Captain Phil and sail in style aboard Liberty, a stunning replica of....
Private Tour
Small-Group San Diego Sunset Sailing Excursion
Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This three-hour adventure on a Catalina sailboat is limited to six (6) guests allowing you a comfortable, semi-private experience (or, pu... More
Private Tour

Small-Group San Diego Sunset Sailing Excursion
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San Diego
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Superb578 reviews4.9
Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This th....
Private Tour
Spectacular Midday Sail
Join Captain Doyle for an unforgettable 2-hour sailing experience aboard our 35-foot sailboat, Luna. Enjoy wide-open views of the city's skyline and waterfront attractions as we sail among tall ships, mega-yachts, and military ves... More
Private Tour

Spectacular Midday Sail
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San Diego
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Superb3 reviews5
Join Captain Doyle for an unforgettable 2-hour sailing experience aboard our 35-foot sailboat, Luna.....
Private Tour
San Diego Bay Harbor Cruise: Private 2-Hour Experience
Explore the stunning San Diego Bay on a private 2-hour harbor cruise designed for up to 6 guests. Perfect for special occasions or a relaxing outing with friends and family, this charter offers breathtaking views of downtown San D... More
Private Tour

San Diego Bay Harbor Cruise: Private 2-Hour Experience
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San Diego
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Superb3 reviews5
Explore the stunning San Diego Bay on a private 2-hour harbor cruise designed for up to 6 guests. Pe....
Private Tour
2.5 Hour Private Sunset Sailing Tour in San Diego up to 12 guests
Sea Monkey Adventures is San Diego’s first family-friendly sailing tour company, dedicated to helping families create unforgettable memories. Our vessel is thoughtfully designed to be warm and inviting, featuring handcrafted yel... More
Private Tour

2.5 Hour Private Sunset Sailing Tour in San Diego up to 12 guests
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San Diego
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Superb72 reviews5
Sea Monkey Adventures is San Diego’s first family-friendly sailing tour company, dedicated to help....
Private Tour
San Diego Private Morning Sail up to 12 guests
This private morning sail is a great way to start the day. Mornings are best to go see San Diego's wildlife because there is little wind and few waves, allowing us to easily cross over to Point Loma. The bay will most likely have ... More
Private Tour

San Diego Private Morning Sail up to 12 guests
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San Diego
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Superb33 reviews5
This private morning sail is a great way to start the day. Mornings are best to go see San Diego's w....
Private Tour
2-Hour Sunset Sailing on San Diego Bay
Join Captain Doyle for an unforgettable 2-hour sunset sailing experience aboard our 35-foot sailboat, Luna. Enjoy wide-open views of the city's skyline and waterfront attractions as we sail among tall ships, mega-yachts, and milit... More
Private Tour

2-Hour Sunset Sailing on San Diego Bay
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San Diego
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Superb12 reviews5
Join Captain Doyle for an unforgettable 2-hour sunset sailing experience aboard our 35-foot sailboat....
Private Tour
San Diego Bay Sailing Tour
San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural wonder aboard a beautiful sailing yacht with a knowledgeable and friendly Captain? This group sail is li... More
Private Tour

San Diego Bay Sailing Tour
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San Diego
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Superb17 reviews5
San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. W....
Private Tour
2-Hour Morning Sail in San Diego
Set sail from America's Cup Harbor on your morning sailing tour, and enjoy the sights of Point Loma, San Diego Bay and the downtown waterfront. This two-hour adventure on a Catalina sailboat is limited to a maximum of six (6) gues... More
Private Tour

2-Hour Morning Sail in San Diego
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San Diego
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Superb25 reviews4.8
Set sail from America's Cup Harbor on your morning sailing tour, and enjoy the sights of Point Loma,....
Private Tour