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Top 10 Best California Sailing Trips

Found 60 Sailing Trips activities in California. Sort by Popularity.
 

Small-Group Sunset Sailing Experience on San Diego Bay

(4.9 of 543 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 Likely to Sell Out

Small-Group Sunset Sailing Experience on San Diego Bay

  • California
  • Superb543 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
 
 

2 Hour Sailing Cruise on Lake Tahoe

(4.9 of 681 reviews)

Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing adventure and include complementary local beer and wine, as well as non-alcoholic beverages on all of our daily cruises. Unlike other t... More

Free Cancellation
Start From $140.00
 
2 Hour Sailing Cruise on Lake Tahoe Likely to Sell Out

2 Hour Sailing Cruise on Lake Tahoe

  • California
  • Superb681 reviews4.9

Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing advent....

    Free Cancellation
    Start From $140.00
 
 

Deluxe Sunset & Day Sail Small Group

(5 of 129 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

  • California
  • Superb129 reviews5

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect....

    Free Cancellation
    Start From $119.00
 
 

Sunset Sailing Cruise in Monterey Bay

(5 of 12 reviews)

Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is the most popular (and most romantic!) way to experience Monterey Bay. Departing daily, 90 minutes before sunset, this dreamy 1.5-... More

Free Cancellation
Start From $95.00
 
Sunset Sailing Cruise in Monterey Bay Likely to Sell Out

Sunset Sailing Cruise in Monterey Bay

  • California
  • Superb12 reviews5

Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is....

    Free Cancellation
    Start From $95.00
 
 

San Francisco Bay Cruise

(4.4 of 262 reviews)

You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hour excursion heads underneath the Golden Gate Bridge, around Alcatraz Island, past Angel Island State Park, and alongside the cit... More

Free Cancellation
Start From $38.00
 
San Francisco Bay Cruise Likely to Sell Out

San Francisco Bay Cruise

  • California
  • Exellent262 reviews4.4

You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hou....

    Free Cancellation
    Start From $38.00
 
 

2-Hour Sunset Sail on the San Francisco Bay

(4.8 of 359 reviews)

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour sunset sail is just the ticket. Step aboard the gorgeous traditional vessel to take in the sights at the most bewitching time of d... More

Free Cancellation
Start From $129.00
 
2-Hour Sunset Sail on the San Francisco Bay Likely to Sell Out

2-Hour Sunset Sail on the San Francisco Bay

  • California
  • Superb359 reviews4.8

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour ....

    Free Cancellation
    Start From $129.00
 
 

San Francisco Bay Sailing Cruise

(4.9 of 591 reviews)

Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sail away from bustling city and enjoy photo ops from the vantage point of the water. You’ll coast past the city skyline, the Gold... More

Free Cancellation
Start From $69.00
 
San Francisco Bay Sailing Cruise Likely to Sell Out

San Francisco Bay Sailing Cruise

  • California
  • Superb591 reviews4.9

Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sa....

    Free Cancellation
    Start From $69.00
 
 

2.5 Hours of Fun: Catamaran Sunset Sail

(4.9 of 149 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

  • California
  • Superb149 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
 
 

Small-Group San Diego Afternoon Sailing Excursion

(5 of 499 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

  • California
  • Superb499 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 554 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

  • California
  • Superb554 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 Hour Private Sunset Sailing Tour in San Diego up to 12 guests

(5 of 61 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

  • California
  • Superb61 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
 
 

Sunset Sail On A Charming Vintage Yacht - Beer &. Wine Included

(4.9 of 287 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 Sail On A Charming Vintage Yacht - Beer &. Wine Included Likely to Sell Out

Sunset Sail On A Charming Vintage Yacht - Beer &. Wine Included

  • California
  • Superb287 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
 
 

Monterey Bay Whale Watching

(4.7 of 277 reviews)

Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watching tours depart from Moss Landing, right at the mouth of the Monterey Bay Canyon, one of the largest underwater canyons in the wor... More

Free Cancellation
Private Tour
Start From $69.95
 
Monterey Bay Whale Watching Likely to Sell Out

Monterey Bay Whale Watching

  • California
  • Superb277 reviews4.7

Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watchi....

    Free Cancellation
    Private Tour
    Start From $69.95
 
 

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

  • California
  • 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
 
 

2-Hour Private Sailboat Charter in the San Francisco Bay

(4.9 of 19 reviews)

Imagine sailing underneath the Golden Gate Bridge on your own private yacht and seeing wildlife. Just kick back and celebrate your special event under the romance of sail. Private sailboat charters are a great way to celebrate you... More

Free Cancellation
Private Tour
Start From $695.00
 
2-Hour Private Sailboat Charter in the San Francisco Bay Likely to Sell Out

2-Hour Private Sailboat Charter in the San Francisco Bay

  • California
  • Superb19 reviews4.9

Imagine sailing underneath the Golden Gate Bridge on your own private yacht and seeing wildlife. Jus....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

2hr. SUNSET Sailing Experience on San Francisco Bay

(5 of 15 reviews)

This sailing experience is an Interactive sunset sailing adventure on San Francisco Bay! This Sailing Experience is "interactive" which means we want you to get the full experience of sailing so you'll have an opportunity to tak... More

Free Cancellation
Private Tour
Start From $149.00
 
2hr. SUNSET Sailing Experience on San Francisco Bay Likely to Sell Out

2hr. SUNSET Sailing Experience on San Francisco Bay

  • California
  • Superb15 reviews5

This sailing experience is an Interactive sunset sailing adventure on San Francisco Bay! This Sail....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

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

(4.9 of 187 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

  • California
  • Superb187 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
 
 

2hr. INTERACTIVE Sailing Experience on San Francisco Bay

(5 of 49 reviews)

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a private yacht with a USCG licensed captain and crew where you'll sail beneath the Golden Gate Bridge, across the San Francisco waterfr... More

Free Cancellation
Private Tour
Start From $149.00
 
2hr. INTERACTIVE Sailing Experience on San Francisco Bay Likely to Sell Out

2hr. INTERACTIVE Sailing Experience on San Francisco Bay

  • California
  • Superb49 reviews5

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a priv....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Catamaran Sailing Cruise in Monterey

(4.9 of 11 reviews)

Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage after your captain hoists the sails and catches the wind to make for a peaceful and exciting cruise on the bay. On the way out of t... More

Free Cancellation
Private Tour
Start From $65.00
 
Catamaran Sailing Cruise in Monterey Likely to Sell Out

Catamaran Sailing Cruise in Monterey

  • California
  • Superb11 reviews4.9

Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage af....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

1.5-Hour San Francisco Bay Sailing Tour

(4.8 of 377 reviews)

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a semi-private 90-minute cruise of the bay, complete with beer and wine. This double-masted, teak-decked, bronze-fitted beauty hold... More

Free Cancellation
Private Tour
Start From $99.00
 
1.5-Hour San Francisco Bay Sailing Tour Likely to Sell Out

1.5-Hour San Francisco Bay Sailing Tour

  • California
  • Superb377 reviews4.8

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a....

    Free Cancellation
    Private Tour
    Start From $99.00
 
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