Sailing Trips in San Diego
Top 10 Best San Diego Sailing Trips
Found 34 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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Superb145 reviews5
Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect....
Small-Group Sunset Sailing Experience on San Diego Bay
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

Small-Group Sunset Sailing Experience on San Diego Bay
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San Diego
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Superb553 reviews4.9
Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on ....
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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Superb162 reviews4.9
Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and loungi....
Sunset Sail On A Charming 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 Sail On A Charming Vintage Yacht - Beer &. Wine Included
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San Diego
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Superb296 reviews4.9
Book an unforgettable tour with Captain Phil and sail in style aboard, Liberty, a stunning replica o....
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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Superb189 reviews4.9
This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways....
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

Small-Group San Diego Afternoon Sailing Excursion
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San Diego
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Superb504 reviews5
This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing....
Small-Group Yacht Sailing Experience on San Diego Bay
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

Small-Group Yacht Sailing Experience on San Diego Bay
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San Diego
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Superb134 reviews4.9
Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on th....
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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Superb64 reviews5
Sea Monkey Adventures is San Diego’s first family-friendly sailing tour company, dedicated to help....
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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Superb562 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
Private Day Sailing Experience in San Diego up to 12 guests
This private day sail, is a excellent if you are looking for a more exciting sail! Day sailing is best to go see our San Diego landmarks along downtown where we will see the US Midway, Sea port Village, the Rady shell and we might... More
Private Tour

Private Day Sailing Experience in San Diego up to 12 guests
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San Diego
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Superb61 reviews5
This private day sail, is a excellent if you are looking for a more exciting sail! Day sailing is be....
Private Tour
Small Group Sunset Sail in San Diego- Public Sail up to 6 guests
Join Sea Monkey Adventures for a 2-hour sailing tour on San Diego Bay. This small-group sail is perfect for solo travelers, couples, or friends looking to experience the bay from the water without booking a private charter. Relax ... More
Private Tour

Small Group Sunset Sail in San Diego- Public Sail up to 6 guests
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San Diego
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Superb45 reviews5
Join Sea Monkey Adventures for a 2-hour sailing tour on San Diego Bay. This small-group sail is perf....
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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Superb20 reviews5
Set sail from America's Cup Harbor on your morning sailing tour, and enjoy the sights of Point Loma,....
Private Tour
Afternoon Sail On A Charming 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 Sail On A Charming Vintage Yacht Beer &. Wine Included
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San Diego
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Superb67 reviews5
Book an unforgettable tour with Captain Phil and sail in style aboard Liberty, a stunning replica of....
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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Superb48 reviews5
Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our person....
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
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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Superb49 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 Sailing Trip
Leave the streets 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. Whether you’re looking for an intimate adventure, ... More
Private Tour

Small-Group San Diego Sailing Trip
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San Diego
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Superb49 reviews4.8
Leave the streets behind as you cruise the San Diego Bay and marvel at the cityscape. The vibrant wa....
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

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
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

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

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