Sailing Trips in San Diego
Top 10 Best San Diego Sailing Trips
Found 39 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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Superb176 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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Superb566 reviews4.9
Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on ....
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

Sunset or Afternoon Sail On A Vintage Yacht Beer & Wine Included
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San Diego
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Superb307 reviews4.9
Book an unforgettable tour with Captain Phil and sail in style aboard, Liberty, a stunning replica o....
2.5 Hours of Fun: Catamaran Sunset Sail
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

2.5 Hours of Fun: Catamaran Sunset Sail
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San Diego
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Superb186 reviews4.9
Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and loungi....
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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Superb158 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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Superb34 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
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
Private Tour

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways
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San Diego
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Superb196 reviews4.9
This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways....
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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Superb570 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
2.5 Hour Catamaran Sail Adventure
With over 35 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
Private Tour

2.5 Hour Catamaran Sail Adventure
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San Diego
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Superb53 reviews5
With over 35 years of experience sharing our love of sailing with San Diego visitors, we are prepare....
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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Superb514 reviews5
This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing....
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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Superb140 reviews4.9
Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on th....
Private Tour
Private Sunset Sail for 3-6 People
Experience a private group charter with up to six passengers while sailing along the San Diego Bay. If you’re looking for a night of family fun, or to celebrate with your friends look no further. Leave your worries behind as yo... More
Private Tour

Private Sunset Sail for 3-6 People
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San Diego
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Superb12 reviews4.7
Experience a private group charter with up to six passengers while sailing along the San Diego Bay.....
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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Superb69 reviews5
Sea Monkey Adventures is San Diego’s first family-friendly sailing tour company, dedicated to help....
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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Superb49 reviews5
Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our person....
Private Tour
Sunset and Afternoon Sailing Tours Aboard A Vintage Yacht
This unforgettable 2.5 hour tour will circle you around the San Diego harbor during the most dramatic part of a California day. The multi-colored sky is the perfect backdrop for relaxing and enjoying our complimentary beer and win... More
Private Tour

Sunset and Afternoon Sailing Tours Aboard A Vintage Yacht
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San Diego
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Superb2 reviews5
This unforgettable 2.5 hour tour will circle you around the San Diego harbor during the most dramati....
Private Tour
San Diego Afternoon 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

San Diego Afternoon Sail
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San Diego
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Superb2 reviews5
Join Captain Doyle for an unforgettable 2-hour sailing experience aboard our 35-foot sailboat, Luna.....
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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Superb1 review5
Join Captain Doyle for an unforgettable 2-hour sunset sailing experience aboard our 35-foot sailboat....
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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Superb71 reviews5
Book an unforgettable tour with Captain Phil and sail in style aboard Liberty, a stunning replica of....
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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Superb32 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
Tall Ship Adventure aboard the Schooner Californian with General Admission
Californian was built from the ground up in 1984 at Spanish Landing in San Diego Bay. She was launched with great fanfare for the 1984 Summer Olympic Games in Los Angeles. In July 2003, the Governor signed a bill into law designat... More
Private Tour

Tall Ship Adventure aboard the Schooner Californian with General ....
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San Diego
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Exellent5 reviews4.2
Californian was built from the ground up in 1984 at Spanish Landing in San Diego Bay. She was launch....
Private Tour