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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Superb234 reviews5
Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect....
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
Catamaran Sunset Sail Premium 2.5hr Small group w/ drinks
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San Diego
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Superb210 reviews4.9
Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and loungi....
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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Superb39 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
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
Private Tour
Sunset Sail Along the San Diego Skyline
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San Diego
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Superb592 reviews4.9
Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on ....
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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Superb73 reviews5
Sea Monkey Adventures is San Diego’s first family-friendly sailing tour company, dedicated to help....
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
Likely to Sell Out Small-Group San Diego Afternoon Sailing Excursion
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San Diego
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Superb528 reviews5
This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing....
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
Likely to Sell Out Luxury Sailing Tour of San Diego's Bay and Coastal Waterways
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San Diego
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Superb204 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
Likely to Sell Out Small-Group San Diego Sunset Sailing Excursion
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San Diego
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Superb585 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
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
Likely to Sell Out Deluxe Day Sail in San Diego
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San Diego
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Superb56 reviews5
Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our person....
Private Tour
San Diego Bay Sail Aboard a Vintage Yacht Beer and 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
Likely to Sell Out San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included
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San Diego
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Superb329 reviews4.9
Book an unforgettable tour with Captain Phil and sail in style aboard, Liberty, a stunning replica o....
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
Likely to Sell Out Daytime Sailing Along San Diego's Skyline
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San Diego
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Superb145 reviews4.9
Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on th....
Private Tour
Cerulean Sea Charters 3-Hour Private Cruise
Enjoy the breathtaking San Diego coastline with our Classic Sail Charter, perfect for up to 6 guests. This 3-hour private sailing adventure offers the ideal blend of relaxation and exploration, with opportunities to see whales and... More
Private Tour
Likely to Sell Out Cerulean Sea Charters 3-Hour Private Cruise
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San Diego
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Superb1 review5
Enjoy the breathtaking San Diego coastline with our Classic Sail Charter, perfect for up to 6 guests....
Private Tour
San Diego Half-Day Marine Wildlife Tour with Lunch
Experience an exciting adventure while sailing along the San Diego coastline. Venture off into the Pacific Ocean and catch a chance to see local marine wildlife in its natural habitat, including sea lions, pelicans, and migrator... More
Private Tour
Likely to Sell Out San Diego Half-Day Marine Wildlife Tour with Lunch
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San Diego
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Superb27 reviews4.8
Experience an exciting adventure while sailing along the San Diego coastline. Venture off into the P....
Private Tour
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
Private Tour
Likely to Sell Out Catamaran Sailing Adventure Premium 2.5hr Small group w/ drinks
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San Diego
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Superb77 reviews5
With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepare....
Private Tour
Deluxe private Sunset & Day Sail
Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling voyage takes you through breathtaking waters, past iconic landmarks, and into the heart of coastal paradise. Feel the wind in your... More
Private Tour
Likely to Sell Out Deluxe private Sunset & Day Sail
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San Diego
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Superb2 reviews5
Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling ....
Private Tour
Private Sunset Sail for Two
Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise along the vibrant waterfront and marvel at the cityscape. Create a memory of a lifetime while sailing past Downtown, Point Loma, an... More
Private Tour
Likely to Sell Out Private Sunset Sail for Two
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San Diego
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Superb5 reviews5
Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise a....
Private Tour
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
Likely to Sell Out 2-Hour Private Sailing Experience in San Diego Bay
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San Diego
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Superb168 reviews5
Our unique sail displays a peace sign because that is exactly what we share with our customers, peac....
Private Tour
San Diego Sunset or Afternoon Sail on Classic Yacht
Book an unforgettable tour with Captain Phil and sail in style aboard Liberty, a stunning replica of a 1904 gaff-rigged Friendship sloop. Our boat features highly-finished woodwork, bronze fixtures, and gaff rigging that showcase ... More
Private Tour
Likely to Sell Out San Diego Sunset or Afternoon Sail on Classic Yacht
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San Diego
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Superb79 reviews5
Book an unforgettable tour with Captain Phil and sail in style aboard Liberty, a stunning replica of....
Private Tour
2-Hour Sunset Sail from San Diego
Leave your worries behind as you cruise the San Diego Bay and marvel at the cityscape. The vibrant waterfront offers expansive views of Downtown, Point Loma, and Coronado Island. Experience the setting sun cast its brilliant color... More
Private Tour
Likely to Sell Out 2-Hour Sunset Sail from San Diego
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San Diego
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Superb72 reviews4.8
Leave your worries behind as you cruise the San Diego Bay and marvel at the cityscape. The vibrant w....
Private Tour
Likely to Sell Out Private Sunset Sail for Two
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San Diego
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Superb6 reviews5
A Romantic Private Sail for Two on the San Diego Bay offers a Beautiful Sunset and Downtown City Sky....
Private Tour