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Top 10 Best San Diego Sailing Trips

Found 38 Sailing Trips activities in San Diego. Sort by Popularity.
 

Deluxe Sunset & Day Sail Small Group

(5 of 201 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

Deluxe Sunset & Day Sail Small Group

  • San Diego
  • Superb201 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 576 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
  • Superb576 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
 
 

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

(4.9 of 200 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
  • Superb200 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
 
 

Catamaran Sailing Adventure Premium 2.5hr Small group w/ drinks

(5 of 71 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
Start From $119.00
 
Catamaran Sailing Adventure Premium 2.5hr Small group w/ drinks Likely to Sell Out

Catamaran Sailing Adventure Premium 2.5hr Small group w/ drinks

  • San Diego
  • Superb71 reviews5

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

    Free Cancellation
    Start From $119.00
 
 

2-Hour Private Sailing Experience in San Diego Bay

(5 of 166 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
  • Superb166 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 35 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
  • Superb35 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
 
 

Daytime Sailing Along San Diego's Skyline

(4.9 of 142 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
  • Superb142 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
 
 

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

(4.9 of 321 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
 
 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
  • Superb321 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
 
 

Deluxe Day Sail in San Diego

(5 of 52 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
  • Superb52 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
 
 

Small-Group San Diego Afternoon Sailing Excursion

(5 of 523 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
  • Superb523 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
 
 

Catamaran Sunset Sail Premium 2.5hr Small group w/ drinks

(4.9 of 195 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
 
Catamaran Sunset Sail Premium 2.5hr Small group w/ drinks Likely to Sell Out

Catamaran Sunset Sail Premium 2.5hr Small group w/ drinks

  • San Diego
  • Superb195 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
 
 

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

(5 of 76 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
  • Superb76 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
 
 

Small-Group San Diego Sunset Sailing Excursion

(4.9 of 578 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
  • Superb578 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
 
 

Spectacular Midday Sail

(5 of 3 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
 
Spectacular Midday Sail Likely to Sell Out

Spectacular Midday Sail

  • San Diego
  • Superb3 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
 
 

San Diego Bay Harbor Cruise: Private 2-Hour Experience

(5 of 3 reviews)

Explore the stunning San Diego Bay on a private 2-hour harbor cruise designed for up to 6 guests. Perfect for special occasions or a relaxing outing with friends and family, this charter offers breathtaking views of downtown San D... More

Free Cancellation
Private Tour
Start From $995.00
 
San Diego Bay Harbor Cruise: Private 2-Hour Experience Likely to Sell Out

San Diego Bay Harbor Cruise: Private 2-Hour Experience

  • San Diego
  • Superb3 reviews5

Explore the stunning San Diego Bay on a private 2-hour harbor cruise designed for up to 6 guests. Pe....

    Free Cancellation
    Private Tour
    Start From $995.00
 
 

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

(5 of 72 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
  • Superb72 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
 
 

San Diego Private Morning Sail up to 12 guests

(5 of 33 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 $80.00
 
San Diego Private Morning Sail up to 12 guests Likely to Sell Out

San Diego Private Morning Sail up to 12 guests

  • San Diego
  • Superb33 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 $80.00
 
 

2-Hour Sunset Sailing on San Diego Bay

(5 of 12 reviews)

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
  • Superb12 reviews5

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

    Free Cancellation
    Private Tour
    Start From $120.00
 
 

San Diego Bay Sailing Tour

(5 of 17 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
  • Superb17 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-Hour Morning Sail in San Diego

(4.8 of 25 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
  • Superb25 reviews4.8

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
 
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