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Top 10 Best San Diego Sailing Trips

Found 35 Sailing Trips activities in San Diego. Sort by Popularity.
 

Small-Group Sunset Sailing Experience on San Diego Bay

(4.9 of 531 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 $125.00
 
Small-Group Sunset Sailing Experience on San Diego Bay

Small-Group Sunset Sailing Experience on San Diego Bay

  • San Diego
  • Superb531 reviews4.9

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

    Free Cancellation
    Start From $125.00
 
 
-7% Deluxe Sunset & Day Sail small group

Deluxe Sunset & Day Sail small group

(5 of 109 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

Special Offer
Free Cancellation
Start From $101.15
(Saving 7% ) $109.00
 
-7% Deluxe Sunset & Day Sail small group

Deluxe Sunset & Day Sail small group

  • San Diego
  • Superb109 reviews5

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

    Special Offer
    Free Cancellation
    Start From $101.15
    (Saving 7% ) $109.00
 
 

Small-Group San Diego Sunset Sailing Excursion

(4.9 of 548 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

Small-Group San Diego Sunset Sailing Excursion

  • San Diego
  • Superb548 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
 
 

Small-Group San Diego Afternoon Sailing Excursion

(5 of 486 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
  • Superb486 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
 
 

2-Hour Private Sailing Experience in San Diego Bay

(5 of 147 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 $585.00
 
2-Hour Private Sailing Experience in San Diego Bay Likely to Sell Out

2-Hour Private Sailing Experience in San Diego Bay

  • San Diego
  • Superb147 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 $585.00
 
 

2.5 Hours of Fun: Catamaran Sunset Sail

(4.9 of 145 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 Hours of Fun: Catamaran Sunset Sail Likely to Sell Out

2.5 Hours of Fun: Catamaran Sunset Sail

  • San Diego
  • Superb145 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
 
 

An Unforgettable Sunset Aboard A Classic Sailing Yacht

(4.9 of 279 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 $125.00
 
An Unforgettable Sunset Aboard A Classic Sailing Yacht Likely to Sell Out

An Unforgettable Sunset Aboard A Classic Sailing Yacht

  • San Diego
  • Superb279 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 $125.00
 
 

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

(4.9 of 186 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
  • Superb186 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
 
 

2.5 Hour Catamaran Sail Adventure

(5 of 43 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
  • Superb43 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
 
 

San Diego's first ever Family Sailing Tours

(5 of 4 reviews)

We are based in San Diego and we are designed for families. Our whole mission is to bring families closer together. We want to put smiles on everyone’s faces; parents, children, and grandparents alike. Our vessel, the Sea Monke... More

Free Cancellation
Private Tour
Start From $475.00
 
San Diego's first ever Family Sailing Tours Likely to Sell Out

San Diego's first ever Family Sailing Tours

  • San Diego
  • Superb4 reviews5

We are based in San Diego and we are designed for families. Our whole mission is to bring families c....

    Free Cancellation
    Private Tour
    Start From $475.00
 
 

Small-Group Yacht Sailing Experience on San Diego Bay

(4.9 of 134 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
 
Small-Group Yacht Sailing Experience on San Diego Bay Likely to Sell Out

Small-Group Yacht Sailing Experience on San Diego Bay

  • San Diego
  • Superb134 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 Sailing Charter on San Diego Bay

(4.9 of 33 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
  • Superb33 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
 
 

2-Hour Morning Sail in San Diego

(5 of 18 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

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
  • Superb18 reviews5

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
 
 

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

(5 of 60 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
  • Superb60 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
 
 

2-Hour Sunset Sail from San Diego

(4.9 of 70 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
  • Superb70 reviews4.9

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
 
 

San Diego Bay Sailing Tour

(5 of 16 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 group sail is li... More

Free Cancellation
Private Tour
Start From $95.00
 
San Diego Bay Sailing Tour Likely to Sell Out

San Diego Bay Sailing Tour

  • San Diego
  • Superb16 reviews5

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 $95.00
 
 

An Unforgettable afternoon Aboard A Classic Sailing Yacht

(5 of 66 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
 
An Unforgettable afternoon Aboard A Classic Sailing Yacht Likely to Sell Out

An Unforgettable afternoon Aboard A Classic Sailing Yacht

  • San Diego
  • Superb66 reviews5

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
 
 

Small-Group San Diego Sailing Trip

(5 of 47 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
  • Superb47 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 Day Sailing Experience in San Diego up to 12 guests

(5 of 44 reviews)

This private day sail, is a excellent if you are looking for a more exciting sail! Day sailing is best to go see our San Diego landmarks along downtown where we will see the US Midway, Sea port Village, the Rady shell and we might... More

Free Cancellation
Private Tour
Start From $235.00
 
Private Day Sailing Experience in San Diego up to 12 guests Likely to Sell Out

Private Day Sailing Experience in San Diego up to 12 guests

  • San Diego
  • Superb44 reviews5

This private day sail, is a excellent if you are looking for a more exciting sail! Day sailing is be....

    Free Cancellation
    Private Tour
    Start From $235.00
 
 

Deluxe Day Sail in San Diego

(5 of 47 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 $101.15
(Saving 7% ) $109.00
 
-7% Deluxe Day Sail in San Diego Likely to Sell Out

Deluxe Day Sail in San Diego

  • San Diego
  • Superb47 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 $101.15
    (Saving 7% ) $109.00
 
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