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Top 10 Best San Diego Sailing Trips

Found 33 Sailing Trips activities in San Diego. Sort by Popularity.
 
-10% Small-Group Sunset Sailing Experience on San Diego Bay

Small-Group Sunset Sailing Experience on San Diego Bay

(4.9 of 514 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 $98.10
(Saving 10% ) $109.00
 
-10% Small-Group Sunset Sailing Experience on San Diego Bay

Small-Group Sunset Sailing Experience on San Diego Bay

  • San Diego
  • Superb514 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 $98.10
    (Saving 10% ) $109.00
 
 

2-Hour Sunset Sail from San Diego

(4.9 of 67 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
Start From $130.00
 
2-Hour Sunset Sail from San Diego

2-Hour Sunset Sail from San Diego

  • San Diego
  • Superb67 reviews4.9

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

    Free Cancellation
    Start From $130.00
 
 

Small-Group San Diego Sunset Sailing Excursion

(4.9 of 536 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
  • Superb536 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
 
 

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

(4.9 of 183 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

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

  • San Diego
  • Superb183 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 Aboard a Classic Sailing Yacht

(4.9 of 272 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 a... More

Free Cancellation
Start From $125.00
 
San Diego's Best Sunset Sail Aboard a Classic Sailing Yacht

San Diego's Best Sunset Sail Aboard a Classic Sailing Yacht

  • San Diego
  • Superb272 reviews4.9

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

    Free Cancellation
    Start From $125.00
 
 

Small-Group San Diego Afternoon Sailing Excursion

(5 of 477 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
  • Superb477 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 139 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 $526.50
(Saving 10% ) $585.00
 
-10% 2-Hour Private Sailing Experience in San Diego Bay Likely to Sell Out

2-Hour Private Sailing Experience in San Diego Bay

  • San Diego
  • Superb139 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 $526.50
    (Saving 10% ) $585.00
 
 

2.5 Hours of Fun: Catamaran Sunset Sail

(4.9 of 129 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
  • Superb129 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
 
 

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

(4.9 of 129 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
  • Superb129 reviews4.9

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
 
 

Deluxe Sunset Sail in San Diego

(5 of 97 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
 
Deluxe Sunset Sail in San Diego Likely to Sell Out

Deluxe Sunset Sail in San Diego

  • San Diego
  • Superb97 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
 
 

Deluxe Day Sail in San Diego

(5 of 46 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 $109.00
 
Deluxe Day Sail in San Diego Likely to Sell Out

Deluxe Day Sail in San Diego

  • San Diego
  • Superb46 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 $109.00
 
 

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

(5 of 66 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 $115.00
 
 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
  • Superb66 reviews5

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

    Free Cancellation
    Private Tour
    Start From $115.00
 
 

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
 
 

San Salvador Spanish Galleon Adventure Day Sail with General Admission

(4.5 of 2 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

Free Cancellation
Private Tour
Start From $119.00
 
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
  • Exellent2 reviews4.5

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

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

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
 
 

Tall Ship Adventure aboard the Schooner Californian with General Admission

(4.3 of 4 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
  • Exellent4 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 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
 
 

2.5 Hour Catamaran Sail Adventure

(5 of 39 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
  • Superb39 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 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 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 $109.00
 
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 as we....

    Free Cancellation
    Private Tour
    Start From $109.00
 
 

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
 
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