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Top 10 Best San Diego Sailing Trips

Found 36 Sailing Trips activities in San Diego. Sort by Popularity.
 

Small-Group San Diego Sunset Sailing Excursion

(4.9 of 590 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

Free Cancellation
Start From $127.00
 
Small-Group San Diego Sunset Sailing Excursion Likely to Sell Out

Small-Group San Diego Sunset Sailing Excursion

  • San Diego
  • Superb590 reviews4.9

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

    Free Cancellation
    Start From $127.00
 
 

Deluxe Sunset & Day Sail Small Group

(5 of 244 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

Free Cancellation
Start From $119.00
 
Deluxe Sunset & Day Sail Small Group Likely to Sell Out

Deluxe Sunset & Day Sail Small Group

  • San Diego
  • Superb244 reviews5

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

    Free Cancellation
    Start From $119.00
 
 

Sunset Sail Along the San Diego Skyline

(4.9 of 603 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

Free Cancellation
Start From $109.00
 
Sunset Sail Along the San Diego Skyline Likely to Sell Out

Sunset Sail Along the San Diego Skyline

  • San Diego
  • Superb603 reviews4.9

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

    Free Cancellation
    Start From $109.00
 
 

Private Sailing Charter on San Diego Bay

(4.9 of 41 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

Free Cancellation
Private Tour
Start From $475.00
 
Private Sailing Charter on San Diego Bay Likely to Sell Out

Private Sailing Charter on San Diego Bay

  • San Diego
  • Superb41 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $475.00
 
 

2.5-Hour Small-Group Catamaran Sunset Sail with Drinks

(4.9 of 223 reviews)

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

Free Cancellation
Private Tour
Start From $119.00
 
2.5-Hour Small-Group Catamaran Sunset Sail with Drinks Likely to Sell Out

2.5-Hour Small-Group Catamaran Sunset Sail with Drinks

  • San Diego
  • Superb223 reviews4.9

Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and loungi....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Small-Group San Diego Afternoon Sailing Excursion

(5 of 531 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

Free Cancellation
Private Tour
Start From $116.00
 
Small-Group San Diego Afternoon Sailing Excursion Likely to Sell Out

Small-Group San Diego Afternoon Sailing Excursion

  • San Diego
  • Superb531 reviews5

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

    Free Cancellation
    Private Tour
    Start From $116.00
 
 

San Diego Sunset or Afternoon Sail on Classic Yacht

(5 of 80 reviews)

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

Free Cancellation
Private Tour
Start From $115.00
 
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

Book an unforgettable tour with Captain Phil and sail in style aboard Liberty, a stunning replica of....

    Free Cancellation
    Private Tour
    Start From $115.00
 
 

Private Sunset Sail for 3-6 People

(4.7 of 12 reviews)

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

Free Cancellation
Private Tour
Start From $669.00
 
Private Sunset Sail for 3-6 People Likely to Sell Out

Private Sunset Sail for 3-6 People

  • San Diego
  • Superb12 reviews4.7

Experience a private group charter with up to six passengers while sailing along the San Diego Bay.....

    Free Cancellation
    Private Tour
    Start From $669.00
 
 

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

Free Cancellation
Private Tour
Start From $119.00
 
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....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

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

(4.9 of 331 reviews)

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

Free Cancellation
Private Tour
Start From $115.00
 
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
  • Superb331 reviews4.9

Book an unforgettable tour with Captain Phil and sail in style aboard, Liberty, a stunning replica o....

    Free Cancellation
    Private Tour
    Start From $115.00
 
 

2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks

(5 of 84 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

Free Cancellation
Private Tour
Start From $119.00
 
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
  • Superb84 reviews5

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

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Private Sunset Sail for Two

(5 of 5 reviews)

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

Free Cancellation
Private Tour
Start From $462.00
 
Private Sunset Sail for Two Likely to Sell Out

Private Sunset Sail for Two

  • San Diego
  • Superb5 reviews5

Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise a....

    Free Cancellation
    Private Tour
    Start From $462.00
 
 

2-Hour Private Sailing Experience in San Diego Bay

(5 of 168 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

Free Cancellation
Private Tour
Start From $625.00
 
2-Hour Private Sailing Experience in San Diego Bay Likely to Sell Out

2-Hour Private Sailing Experience in San Diego Bay

  • San Diego
  • Superb168 reviews5

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

    Free Cancellation
    Private Tour
    Start From $625.00
 
 

Daytime Sailing Along San Diego's Skyline

(4.9 of 145 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

Free Cancellation
Private Tour
Start From $89.00
 
Daytime Sailing Along San Diego's Skyline Likely to Sell Out

Daytime Sailing Along San Diego's Skyline

  • San Diego
  • Superb145 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Deluxe Day Sail in San Diego

(5 of 57 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
Private Tour
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
  • Superb57 reviews5

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

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

2-Hour Sunset Sail from San Diego

(4.8 of 72 reviews)

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

Free Cancellation
Private Tour
Start From $130.00
 
2-Hour Sunset Sail from San Diego Likely to Sell Out

2-Hour Sunset Sail from San Diego

  • San Diego
  • Superb72 reviews4.8

Leave your worries behind as you cruise the San Diego Bay and marvel at the cityscape. The vibrant w....

    Free Cancellation
    Private Tour
    Start From $130.00
 
 

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

Free Cancellation
Private Tour
Start From $260.00
 
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....

    Free Cancellation
    Private Tour
    Start From $260.00
 
 

San Diego Half-Day Marine Wildlife Tour with Lunch

(4.8 of 27 reviews)

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

Free Cancellation
Private Tour
Start From $196.00
 
San Diego Half-Day Marine Wildlife Tour with Lunch Likely to Sell Out

San Diego Half-Day Marine Wildlife Tour with Lunch

  • San Diego
  • Superb27 reviews4.8

Experience an exciting adventure while sailing along the San Diego coastline. Venture off into the P....

    Free Cancellation
    Private Tour
    Start From $196.00
 
 

Deluxe private Sunset & Day Sail

(5 of 2 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
  • Superb2 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
 
 

Private Sunset Sail for Two

(5 of 6 reviews)

A Romantic Private Sail for Two on the San Diego Bay offers a Beautiful Sunset and Downtown City Skyline.... More

Free Cancellation
Private Tour
Start From $499.00
 
Private Sunset Sail for Two Likely to Sell Out

Private Sunset Sail for Two

  • San Diego
  • Superb6 reviews5

A Romantic Private Sail for Two on the San Diego Bay offers a Beautiful Sunset and Downtown City Sky....

    Free Cancellation
    Private Tour
    Start From $499.00
 
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