Sailing Trips in San Diego
Top 10 Best San Diego Sailing Trips
Found 33 Sailing Trips activities in San Diego. Sort by Popularity.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
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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
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
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
San Diego's Best Sunset Sail Aboard a Classic Sailing Yacht
Sail liberty sunset cruises offer an exclusive small group sailing adventure for up to six individuals. Immerse your family and friends in the many sights of San Diego Bay, while enjoying the personalized touch of a family-owned a... More
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
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
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Private Tour
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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
Private Tour
Private Sailing Tour -2 Hour (Up to 12 Passengers)
Christened in 1934, Cloudia is a beautifully restored, rare example of a classic Norwegian double ended ketch. Inspired by the original designs of famed naval architect Colin Archer (1832-1921), from Larvik, Norway, the Cloudia is... More
Private Tour
Deluxe Sunset Sail in San Diego
Experience the stunning beauty of San Diego Bay at sunset! Our boat charter mono hull is the perfect vessel for a sunset sail, with space for up to 6 passengers. As we sail through the calm waters of the bay, keep your eyes peeled... More
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
Day Sail Aboard a Classic Yacht: San Diego's Best-Kept Secret
Sail Liberty offers topnotch sailing for up to six passengers. Enjoy an unforgettable harbor tour on our 1904-replica sloop. Her wooden mast and teak accents make it one of the most photographed sailboats in the harbor. Our highly... More
Private Tour
San Salvador Spanish Galleon Adventure Day Sail with General Admission
Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step on board this 16th century Spanish galleon. The San Salvador is a replica of Juan Rodriguez Cabrillo’s ship that arrived at the ... More
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
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
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
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
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 as we set sail from Sunroad Resort Marina on Harbor Island. We'll sail along Sailing in San Diego Bay we often see Sea Lions and occas... More
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