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Top 10 Best San Diego Sailing Trips

Found 39 Sailing Trips activities in San Diego. Sort by Popularity.
 

Deluxe Sunset & Day Sail Small Group

(5 of 176 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
  • Superb176 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 566 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 $115.00
 
Sunset Sail Along the San Diego Skyline Likely to Sell Out

Sunset Sail Along the San Diego Skyline

  • San Diego
  • Superb566 reviews4.9

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

    Free Cancellation
    Start From $115.00
 
 

Sunset or Afternoon Sail On A Vintage Yacht Beer & Wine Included

(4.9 of 307 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
Start From $125.00
 
 Sunset or Afternoon Sail On A Vintage Yacht Beer & Wine Included Likely to Sell Out

Sunset or Afternoon Sail On A Vintage Yacht Beer & Wine Included

  • San Diego
  • Superb307 reviews4.9

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

    Free Cancellation
    Start From $125.00
 
 

2.5 Hours of Fun: Catamaran Sunset Sail

(4.9 of 186 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
Start From $119.00
 
2.5 Hours of Fun: Catamaran Sunset Sail Likely to Sell Out

2.5 Hours of Fun: Catamaran Sunset Sail

  • San Diego
  • Superb186 reviews4.9

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

    Free Cancellation
    Start From $119.00
 
 

2-Hour Private Sailing Experience in San Diego Bay

(5 of 158 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
  • Superb158 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
 
 

Private Sailing Charter on San Diego Bay

(4.9 of 34 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 $450.00
 
Private Sailing Charter on San Diego Bay Likely to Sell Out

Private Sailing Charter on San Diego Bay

  • San Diego
  • Superb34 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 $450.00
 
 

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

(4.9 of 196 reviews)

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

Free Cancellation
Private Tour
Start From $119.00
 
Luxury Sailing Tour of San Diego's Bay and Coastal Waterways Likely to Sell Out

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

  • San Diego
  • Superb196 reviews4.9

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Small-Group San Diego Sunset Sailing Excursion

(4.9 of 570 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
Private Tour
Start From $127.00
 
Small-Group San Diego Sunset Sailing Excursion Likely to Sell Out

Small-Group San Diego Sunset Sailing Excursion

  • San Diego
  • Superb570 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
    Private Tour
    Start From $127.00
 
 

2.5 Hour Catamaran Sail Adventure

(5 of 53 reviews)

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

Free Cancellation
Private Tour
Start From $119.00
 
2.5 Hour Catamaran Sail Adventure Likely to Sell Out

2.5 Hour Catamaran Sail Adventure

  • San Diego
  • Superb53 reviews5

With over 35 years of experience sharing our love of sailing with San Diego visitors, we are prepare....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Small-Group San Diego Afternoon Sailing Excursion

(5 of 514 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
  • Superb514 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
 
 

Daytime Sailing Along San Diego's Skyline

(4.9 of 140 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 $99.00
 
Daytime Sailing Along San Diego's Skyline Likely to Sell Out

Daytime Sailing Along San Diego's Skyline

  • San Diego
  • Superb140 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 $99.00
 
 

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 $776.00
 
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 $776.00
 
 

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

(5 of 69 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 $90.00
 
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
  • Superb69 reviews5

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

    Free Cancellation
    Private Tour
    Start From $90.00
 
 

Deluxe Day Sail in San Diego

(5 of 49 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

Free Cancellation
Private Tour
Start From $119.00
 
Deluxe Day Sail in San Diego Likely to Sell Out

Deluxe Day Sail in San Diego

  • San Diego
  • Superb49 reviews5

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

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Sunset and Afternoon Sailing Tours Aboard A Vintage Yacht

(5 of 2 reviews)

This unforgettable 2.5 hour tour will circle you around the San Diego harbor during the most dramatic part of a California day. The multi-colored sky is the perfect backdrop for relaxing and enjoying our complimentary beer and win... More

Free Cancellation
Private Tour
Start From $135.00
 
Sunset and Afternoon Sailing Tours Aboard A Vintage Yacht Likely to Sell Out

Sunset and Afternoon Sailing Tours Aboard A Vintage Yacht

  • San Diego
  • Superb2 reviews5

This unforgettable 2.5 hour tour will circle you around the San Diego harbor during the most dramati....

    Free Cancellation
    Private Tour
    Start From $135.00
 
 

San Diego Afternoon Sail

(5 of 2 reviews)

Join Captain Doyle for an unforgettable 2-hour sailing experience aboard our 35-foot sailboat, Luna. Enjoy wide-open views of the city's skyline and waterfront attractions as we sail among tall ships, mega-yachts, and military ves... More

Free Cancellation
Private Tour
Start From $120.00
 
San Diego Afternoon Sail Likely to Sell Out

San Diego Afternoon Sail

  • San Diego
  • Superb2 reviews5

Join Captain Doyle for an unforgettable 2-hour sailing experience aboard our 35-foot sailboat, Luna.....

    Free Cancellation
    Private Tour
    Start From $120.00
 
 

2-Hour Sunset Sailing on San Diego Bay

(5 of 1 review)

Join Captain Doyle for an unforgettable 2-hour sunset sailing experience aboard our 35-foot sailboat, Luna. Enjoy wide-open views of the city's skyline and waterfront attractions as we sail among tall ships, mega-yachts, and milit... More

Free Cancellation
Private Tour
Start From $120.00
 
2-Hour Sunset Sailing on San Diego Bay Likely to Sell Out

2-Hour Sunset Sailing on San Diego Bay

  • San Diego
  • Superb1 review5

Join Captain Doyle for an unforgettable 2-hour sunset sailing experience aboard our 35-foot sailboat....

    Free Cancellation
    Private Tour
    Start From $120.00
 
 

Afternoon or Sunset Sail On A Vintage Yacht Beer & Wine Included

(5 of 71 reviews)

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

Free Cancellation
Private Tour
Start From $115.00
 
Afternoon or Sunset Sail On A Vintage Yacht Beer & Wine Included Likely to Sell Out

Afternoon or Sunset Sail On A Vintage Yacht Beer & Wine Included

  • San Diego
  • Superb71 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
 
 

San Diego Private Morning Sail up to 12 guests

(5 of 32 reviews)

This private morning sail is a great way to start the day. Mornings are best to go see San Diego's wildlife because there is little wind and few waves, allowing us to easily cross over to Point Loma. The bay will most likely have ... More

Free Cancellation
Private Tour
Start From $235.00
 
San Diego Private Morning Sail up to 12 guests Likely to Sell Out

San Diego Private Morning Sail up to 12 guests

  • San Diego
  • Superb32 reviews5

This private morning sail is a great way to start the day. Mornings are best to go see San Diego's w....

    Free Cancellation
    Private Tour
    Start From $235.00
 
 

Tall Ship Adventure aboard the Schooner Californian with General Admission

(4.2 of 5 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
  • Exellent5 reviews4.2

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
 
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