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Top 10 Best San Diego Sailing Trips

Found 30 Sailing Trips activities in San Diego. Sort by Popularity.
 
-15% Deluxe Sunset & Day Sail Small Group

Deluxe Sunset & Day Sail Small Group

(5 of 255 reviews)

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

Special Offer
Free Cancellation
Start From $101.15
(Saving 15% ) $119.00
 
-15% Deluxe Sunset & Day Sail Small Group

Deluxe Sunset & Day Sail Small Group

  • San Diego
  • Superb255 reviews5

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect....

    Special Offer
    Free Cancellation
    Start From $101.15
    (Saving 15% ) $119.00
 
 
-inf% Sunset Sail Along the San Diego Skyline

Sunset Sail Along the San Diego Skyline

(4.9 of 611 reviews)

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.  Our San Diego Bay Sunset Sailing Cruises provide an up-close and personal view o... More

Special Offer
Free Cancellation
Start From $99.00
(Saving inf% ) $0.00
 
-inf% Sunset Sail Along the San Diego Skyline

Sunset Sail Along the San Diego Skyline

  • San Diego
  • Superb611 reviews4.9

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on ....

    Special Offer
    Free Cancellation
    Start From $99.00
    (Saving inf% ) $0.00
 
 
-inf% 2.5-Hour Small-Group Catamaran Sail with Drinks

2.5-Hour Small-Group Catamaran Sail with Drinks

(4.9 of 237 reviews)

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your choice of a relaxing daytime sail or a breathtaking sunset sail. Designed for comfort and stability, these modern catamarans featu... More

Special Offer
Free Cancellation
Start From $119.00
(Saving inf% ) $0.00
 
-inf% 2.5-Hour Small-Group Catamaran Sail with Drinks

2.5-Hour Small-Group Catamaran Sail with Drinks

  • San Diego
  • Superb237 reviews4.9

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your ....

    Special Offer
    Free Cancellation
    Start From $119.00
    (Saving inf% ) $0.00
 
 

Small-Group San Diego Sunset Sailing Excursion

(4.9 of 601 reviews)

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

Special Offer
Free Cancellation
Start From $127.00
(Saving inf% ) $0.00
 
-inf% Small-Group San Diego Sunset Sailing Excursion Likely to Sell Out

Small-Group San Diego Sunset Sailing Excursion

  • San Diego
  • Superb601 reviews4.9

Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This th....

    Special Offer
    Free Cancellation
    Start From $127.00
    (Saving inf% ) $0.00
 
 

2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks

(5 of 92 reviews)

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

Special Offer
Free Cancellation
Start From $119.00
(Saving inf% ) $0.00
 
-inf% 2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks Likely to Sell Out

2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks

  • San Diego
  • Superb92 reviews5

With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepare....

    Special Offer
    Free Cancellation
    Start From $119.00
    (Saving inf% ) $0.00
 
 

Spectacular Sunset Sail on San Diego Bay

(5 of 22 reviews)

A rare sunset sailing adventure aboard our 35-foot sailboat, Luna: small group, local captain sharing hidden stories, hands-on sailing, wildlife encounters, and unforgettable vistas of San Diego Bay. Participate or sit back and en... More

Special Offer
Free Cancellation
Start From $120.00
(Saving inf% ) $0.00
 
-inf% Spectacular Sunset Sail on San Diego Bay Likely to Sell Out

Spectacular Sunset Sail on San Diego Bay

  • San Diego
  • Superb22 reviews5

A rare sunset sailing adventure aboard our 35-foot sailboat, Luna: small group, local captain sharin....

    Special Offer
    Free Cancellation
    Start From $120.00
    (Saving inf% ) $0.00
 
 

Small-Group San Diego Afternoon Sailing Excursion

(5 of 536 reviews)

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

Special Offer
Free Cancellation
Start From $116.00
(Saving inf% ) $0.00
 
-inf% Small-Group San Diego Afternoon Sailing Excursion Likely to Sell Out

Small-Group San Diego Afternoon Sailing Excursion

  • San Diego
  • Superb536 reviews5

This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing....

    Special Offer
    Free Cancellation
    Start From $116.00
    (Saving inf% ) $0.00
 
 

Deluxe Day Sail in San Diego

(5 of 64 reviews)

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

Special Offer
Free Cancellation
Start From $95.20
(Saving 20% ) $119.00
 
-20% Deluxe Day Sail in San Diego Likely to Sell Out

Deluxe Day Sail in San Diego

  • San Diego
  • Superb64 reviews5

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our person....

    Special Offer
    Free Cancellation
    Start From $95.20
    (Saving 20% ) $119.00
 
 

Private Sailing Charter on San Diego Bay

(4.9 of 42 reviews)

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

Special Offer
Free Cancellation
Private Tour
Start From $475.00
(Saving inf% ) $0.00
 
-inf% Private Sailing Charter on San Diego Bay Likely to Sell Out

Private Sailing Charter on San Diego Bay

  • San Diego
  • Superb42 reviews4.9

San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. W....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $475.00
    (Saving inf% ) $0.00
 
 

2-Hour Private Sailing Experience in San Diego Bay

(5 of 170 reviews)

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

Special Offer
Free Cancellation
Private Tour
Start From $675.00
(Saving inf% ) $0.00
 
-inf% 2-Hour Private Sailing Experience in San Diego Bay Likely to Sell Out

2-Hour Private Sailing Experience in San Diego Bay

  • San Diego
  • Superb170 reviews5

Our unique sail displays a peace sign because that is exactly what we share with our customers, peac....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $675.00
    (Saving inf% ) $0.00
 
 

Daytime Sailing Along San Diego's Skyline

(4.9 of 146 reviews)

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

Special Offer
Free Cancellation
Private Tour
Start From $99.00
(Saving inf% ) $0.00
 
-inf% Daytime Sailing Along San Diego's Skyline Likely to Sell Out

Daytime Sailing Along San Diego's Skyline

  • San Diego
  • Superb146 reviews4.9

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on th....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $99.00
    (Saving inf% ) $0.00
 
 

San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included

(4.9 of 336 reviews)

Experience a San Diego sailing charter unlike any other aboard Liberty, a classic Friendship sloop replica inspired by a 1904 yacht. Our intimate San Diego sunset sail and afternoon sailing tours on San Diego Bay are limited to ju... More

Special Offer
Free Cancellation
Private Tour
Start From $135.00
(Saving inf% ) $0.00
 
-inf% San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included Likely to Sell Out

San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included

  • San Diego
  • Superb336 reviews4.9

Experience a San Diego sailing charter unlike any other aboard Liberty, a classic Friendship sloop r....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $135.00
    (Saving inf% ) $0.00
 
 

Spectacular Afternoon Sail on San Diego Bay

(5 of 15 reviews)

A unique small group two-hour sailing experience aboard our 35-foot sailboat, Luna. Enjoy spectacular views as your fun-loving, informative Captain shares his knowledge of sailing and San Diego. Get hands-on or sit back and enjoy ... More

Special Offer
Free Cancellation
Private Tour
Start From $120.00
(Saving inf% ) $0.00
 
-inf% Spectacular Afternoon Sail on San Diego Bay Likely to Sell Out

Spectacular Afternoon Sail on San Diego Bay

  • San Diego
  • Superb15 reviews5

A unique small group two-hour sailing experience aboard our 35-foot sailboat, Luna. Enjoy spectacula....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $120.00
    (Saving inf% ) $0.00
 
 

2-Hour Morning Sail in San Diego

(4.9 of 27 reviews)

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

Special Offer
Free Cancellation
Private Tour
Start From $95.00
(Saving inf% ) $0.00
 
-inf% 2-Hour Morning Sail in San Diego Likely to Sell Out

2-Hour Morning Sail in San Diego

  • San Diego
  • Superb27 reviews4.9

Set sail from America's Cup Harbor on your morning sailing tour, and enjoy the sights of Point Loma,....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $95.00
    (Saving inf% ) $0.00
 
 

San Diego Small Group Classic Sail Includes Craft Beer and Wine

(5 of 4 reviews)

Experience a San Diego sailing charter unlike any other aboard Liberty, a classic Friendship sloop replica inspired by a 1904 yacht. Our intimate San Diego sunset sail and afternoon sailing tours on San Diego Bay are limited to ju... More

Special Offer
Free Cancellation
Private Tour
Start From $125.00
(Saving inf% ) $0.00
 
-inf% San Diego Small Group Classic Sail Includes Craft Beer and Wine Likely to Sell Out

San Diego Small Group Classic Sail Includes Craft Beer and Wine

  • San Diego
  • Superb4 reviews5

Experience a San Diego sailing charter unlike any other aboard Liberty, a classic Friendship sloop r....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $125.00
    (Saving inf% ) $0.00
 
 

San Diego Sunset or Afternoon Sail on Classic Yacht

(5 of 80 reviews)

Experience a San Diego sailing charter unlike any other aboard Liberty, a classic Friendship sloop replica inspired by a 1904 yacht. Our intimate San Diego sunset sail and afternoon sailing tours on San Diego Bay are limited to ju... More

Special Offer
Free Cancellation
Private Tour
Start From $135.00
(Saving inf% ) $0.00
 
-inf% San Diego Sunset or Afternoon Sail on Classic Yacht Likely to Sell Out

San Diego Sunset or Afternoon Sail on Classic Yacht

  • San Diego
  • Superb80 reviews5

Experience a San Diego sailing charter unlike any other aboard Liberty, a classic Friendship sloop r....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $135.00
    (Saving inf% ) $0.00
 
 

Deluxe private Sunset & Day Sail

(5 of 3 reviews)

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

Special Offer
Free Cancellation
Private Tour
Start From $571.20
(Saving 20% ) $714.00
 
-20% Deluxe private Sunset & Day Sail Likely to Sell Out

Deluxe private Sunset & Day Sail

  • San Diego
  • Superb3 reviews5

Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $571.20
    (Saving 20% ) $714.00
 
 

2.5 Hour Private Sunset Sailing Tour in San Diego up to 12 guests

(5 of 73 reviews)

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

Special Offer
Free Cancellation
Private Tour
Start From $260.00
(Saving inf% ) $0.00
 
-inf% 2.5 Hour Private Sunset Sailing Tour in San Diego up to 12 guests Likely to Sell Out

2.5 Hour Private Sunset Sailing Tour in San Diego up to 12 guests

  • San Diego
  • Superb73 reviews5

Sea Monkey Adventures is San Diego’s first family-friendly sailing tour company, dedicated to help....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $260.00
    (Saving inf% ) $0.00
 
 

San Salvador Spanish Galleon Adventure Day Sail with General Admission

(4.8 of 4 reviews)

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

Special Offer
Free Cancellation
Private Tour
Start From $119.00
(Saving inf% ) $0.00
 
-inf% San Salvador Spanish Galleon Adventure Day Sail with General Admission Likely to Sell Out

San Salvador Spanish Galleon Adventure Day Sail with General Admi....

  • San Diego
  • Superb4 reviews4.8

Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step o....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $119.00
    (Saving inf% ) $0.00
 
 

Tall Ship Adventure aboard the Schooner Californian with General Admission

(4.3 of 6 reviews)

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

Special Offer
Free Cancellation
Private Tour
Start From $119.00
(Saving inf% ) $0.00
 
-inf% Tall Ship Adventure aboard the Schooner Californian with General Admission Likely to Sell Out

Tall Ship Adventure aboard the Schooner Californian with General ....

  • San Diego
  • Exellent6 reviews4.3

Californian was built from the ground up in 1984 at Spanish Landing in San Diego Bay. She was launch....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $119.00
    (Saving inf% ) $0.00
 
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