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Top 10 Best San Diego Sailing Trips

Found 31 Sailing Trips activities in San Diego. Sort by Popularity.
 

Small-Group Sunset Sailing Experience on San Diego Bay

(4.9 of 437 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 $119.00
 
Small-Group Sunset Sailing Experience on San Diego Bay

Small-Group Sunset Sailing Experience on San Diego Bay

  • San Diego
  • Superb437 reviews4.9

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

    Free Cancellation
    Start From $119.00
 
 

Small-Group San Diego Afternoon Sailing Excursion

(5 of 422 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
Start From $116.00
 
Small-Group San Diego Afternoon Sailing Excursion Likely to Sell Out

Small-Group San Diego Afternoon Sailing Excursion

  • San Diego
  • Superb422 reviews5

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

    Free Cancellation
    Start From $116.00
 
 

Small-Group San Diego Sunset Sailing Excursion

(4.9 of 471 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
  • Superb471 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
 
 

2.5 Hours of Fun: Catamaran Sunset Sail

(4.9 of 83 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
  • Superb83 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
 
 

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

(4.9 of 169 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
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
  • Superb169 reviews4.9

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

    Free Cancellation
    Start From $119.00
 
 

San Diego's Best Sunset Sail

(4.9 of 244 reviews)

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 v... More

Free Cancellation
Start From $124.00
 
San Diego's Best Sunset Sail Likely to Sell Out

San Diego's Best Sunset Sail

  • San Diego
  • Superb244 reviews4.9

Sail liberty sunset cruises offer an exclusive small group sailing adventure for up to six individua....

    Free Cancellation
    Start From $124.00
 
 

2-Hour Private Sailing Experience in San Diego Bay

(5 of 121 reviews)

Spend time with the people you love most, on a boat! Whether you're throwing a special event or you just want to get back to nature, the sea is the place to be. 42 foot sailing yacht 'Mojave' is the perfect place for birthday part... More

Free Cancellation
Private Tour
Start From $650.00
 
2-Hour Private Sailing Experience in San Diego Bay Likely to Sell Out

2-Hour Private Sailing Experience in San Diego Bay

  • San Diego
  • Superb121 reviews5

Spend time with the people you love most, on a boat! Whether you're throwing a special event or you ....

    Free Cancellation
    Private Tour
    Start From $650.00
 
 

Small-Group Yacht Sailing Experience on San Diego Bay

(4.9 of 124 reviews)

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

Free Cancellation
Private Tour
Start From $99.00
 
Small-Group Yacht Sailing Experience on San Diego Bay Likely to Sell Out

Small-Group Yacht Sailing Experience on San Diego Bay

  • San Diego
  • Superb124 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Private Sail Yacht Experience on San Diego Bay

(5 of 7 reviews)

Join us on San Diego Bay for a memorable sailing aboard a private sailing yacht. Our sail yacht can accommodate up to 6 of your friends and family while we enjoy a peaceful daytime sailing experience. Set sail on San Diego Bay whi... More

Free Cancellation
Private Tour
Start From $475.00
 
Private Sail Yacht Experience on San Diego Bay Likely to Sell Out

Private Sail Yacht Experience on San Diego Bay

  • San Diego
  • Superb7 reviews5

Join us on San Diego Bay for a memorable sailing aboard a private sailing yacht. Our sail yacht can ....

    Free Cancellation
    Private Tour
    Start From $475.00
 
 

San Diego Sunset Sailing Excursion

(5 of 61 reviews)

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

Free Cancellation
Private Tour
Start From $115.00
 
San Diego Sunset Sailing Excursion Likely to Sell Out

San Diego Sunset Sailing Excursion

  • San Diego
  • Superb61 reviews5

Experience the stunning beauty of San Diego Bay at sunset! Our boat charter mono hull is the perfect....

    Free Cancellation
    Private Tour
    Start From $115.00
 
 

Day Sail Aboard a Classic Yacht : San Diego's Best-Kept Secret:

(5 of 54 reviews)

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

Free Cancellation
Private Tour
Start From $109.00
 
 Day Sail Aboard a Classic Yacht : San Diego's Best-Kept Secret: Likely to Sell Out

Day Sail Aboard a Classic Yacht : San Diego's Best-Kept Secret:

  • San Diego
  • Superb54 reviews5

Sail Liberty offers topnotch sailing for up to six passengers. Enjoy an unforgettable harbor tour on....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

2.5-Hour Catamaran Sail Adventure

(4.9 of 19 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
  • Superb19 reviews4.9

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 Sailing Trip

(5 of 43 reviews)

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

Free Cancellation
Private Tour
Start From $130.00
 
Small-Group San Diego Sailing Trip Likely to Sell Out

Small-Group San Diego Sailing Trip

  • San Diego
  • Superb43 reviews5

Leave the streets behind as you cruise the San Diego Bay and marvel at the cityscape. The vibrant wa....

    Free Cancellation
    Private Tour
    Start From $130.00
 
 

Private Sailing Tour -2 Hour (Up to 12 Passengers)

(5 of 43 reviews)

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

Free Cancellation
Private Tour
Start From $1,200.00
 
Private Sailing Tour -2 Hour (Up to 12 Passengers) Likely to Sell Out

Private Sailing Tour -2 Hour (Up to 12 Passengers)

  • San Diego
  • Superb43 reviews5

Christened in 1934, Cloudia is a beautifully restored, rare example of a classic Norwegian double en....

    Free Cancellation
    Private Tour
    Start From $1,200.00
 
 

San Diego Sailing Yacht Excursion Private Charter

(5 of 43 reviews)

WE PROVIDE A True Sailing Experience Our goal is to give you, your family, friends, and loved ones an amazing experience that you’ve never had before. We do this by showing what it is like to truly sail. You’ll go underway to ... More

Free Cancellation
Private Tour
Start From $679.00
 
San Diego Sailing Yacht Excursion Private Charter Likely to Sell Out

San Diego Sailing Yacht Excursion Private Charter

  • San Diego
  • Superb43 reviews5

WE PROVIDE A True Sailing Experience Our goal is to give you, your family, friends, and loved ones a....

    Free Cancellation
    Private Tour
    Start From $679.00
 
 

2-Hour Morning Sail in San Diego

(5 of 1 review)

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

Free Cancellation
Private Tour
Start From $95.00
 
2-Hour Morning Sail in San Diego Likely to Sell Out

2-Hour Morning Sail in San Diego

  • San Diego
  • Superb1 review5

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

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

San Diego Half-Day Marine Wildlife Tour with Lunch

(4.8 of 24 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
  • Superb24 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
 
 

San Diego Sunshine Sailing Excursion

(5 of 32 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 $115.00
 
San Diego Sunshine Sailing Excursion Likely to Sell Out

San Diego Sunshine Sailing Excursion

  • San Diego
  • Superb32 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 $115.00
 
 

Sunset Sailing Tour of San Diego Bay up to 6 Guests

(5 of 1 review)

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several different types of sunset sailing charters and boat tours. Our sunset sailin... More

Free Cancellation
Private Tour
Start From $600.00
 
Sunset Sailing Tour of San Diego Bay up to 6 Guests Likely to Sell Out

Sunset Sailing Tour of San Diego Bay up to 6 Guests

  • San Diego
  • Superb1 review5

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautifu....

    Free Cancellation
    Private Tour
    Start From $600.00
 
 

Bachelorette Sailing Party on San Diego Bay up to 12 Guests

(5 of 1 review)

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 12 guests. Enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarines, not to mention an incredible abundance of sea... More

Free Cancellation
Private Tour
Start From $1,500.00
 
Bachelorette Sailing Party on San Diego Bay up to 12 Guests Likely to Sell Out

Bachelorette Sailing Party on San Diego Bay up to 12 Guests

  • San Diego
  • Superb1 review5

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 12 guests. Enjoy breathtaki....

    Free Cancellation
    Private Tour
    Start From $1,500.00
 
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