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Top California Sailing Trips

City Cruises San Diego: Scenic 90-Minute Narrated Harbor Tour

Discover the best of San Diego Bay on our expertly narrated harbor tour. Spanning over 13 miles, this journey takes you past iconic landmarks such …More

San Diego, USA

Discover the best of San Diego Bay on our expertly narrated harbor tour. Spanning over 13 miles, this journey takes you past iconic landmarks such...

1 hour 30 minutes • Free Cancellation
4.6 (540)
from
$38
San Francisco Bay Sailing Cruise

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 …More

Likely to Sell Out
Likely to Sell Out
San Francisco, USA

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...

1 hour 30 minutes • Free Cancellation
4.9 (648)
from
$65
Sunset Sail Along the San Diego Skyline

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 …More

Likely to Sell Out
Likely to Sell Out
San Diego, USA

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...

2 hours • Free Cancellation
4.9 (653)
from
$99
San Diego Whale Watching Cruise

Each year approximately 20,000 gray whales migrate from the Bering Sea to the lagoons of Baja California and back again. Come witness this amazing journey off …More

San Diego, USA

Each year approximately 20,000 gray whales migrate from the Bering Sea to the lagoons of Baja California and back again. Come witness this amazing journey off...

3 hours 30 minutes • Free Cancellation
4.6 (681)
from
$54
San Francisco Bay Cruise

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, …More

Likely to Sell Out
Likely to Sell Out
San Francisco, USA

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,...

1 hour • Free Cancellation
4.6 (366)
from
$39
2.5-Hour Small-Group Catamaran Sail with Drinks

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your choice of a relaxing daytime sail or a breathtaking sunset sail. …More

Likely to Sell Out
Likely to Sell Out
La Jolla, USA

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your choice of a relaxing daytime sail or a breathtaking sunset sail....

2 hours 30 minutes • Free Cancellation
5.0 (356)
from
$119
Small-Group San Diego Sunset Sailing Excursion

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 …More

Likely to Sell Out
Likely to Sell Out
San Diego, USA

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...

3 hours • Free Cancellation
4.9 (635)
from
$127
San Diego Whale Watching Cruise

Whale watching season is all year long in San Diego! Our team at Next Level Sailing provides the optimal experience with guides so experienced we …More

Likely to Sell Out
Likely to Sell Out
San Diego, USA

Whale watching season is all year long in San Diego! Our team at Next Level Sailing provides the optimal experience with guides so experienced we...

4 hours • Free Cancellation
4.8 (2,460)
from
$85
2-Hour Sunset Sail on the San Francisco Bay

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 …More

San Francisco, USA

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...

2 hours • Free Cancellation
4.8 (416)
from
$129
Deluxe Sunset & Day Sail Small Group

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 …More

Likely to Sell Out
Likely to Sell Out
San Diego, USA

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...

2 hours 30 minutes • Free Cancellation
5.0 (354)
from
$119
Escape from the Rock! Cruise around Alcatraz

Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and past Angel Island State Park before circling Alcatraz Island for an …More

San Francisco, USA

Embark on a 90-minute cruise along the San Francisco waterfront, under the Golden Gate Bridge and past Angel Island State Park before circling Alcatraz Island for an...

1 hour 30 minutes • Free Cancellation
4.5 (146)
from
$48
Monterey Bay Whale Watching

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 …More

Likely to Sell Out
Likely to Sell Out
Monterey & Carmel, USA

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...

2 to 3 hours • Free Cancellation
4.8 (349)
from
$70
2hr. INTERACTIVE Sailing Experience on San Francisco Bay

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 …More

Likely to Sell Out
Likely to Sell Out
Sausalito, USA

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...

2 hours • Free Cancellation
5.0 (105)
from
$149
1.5-Hour San Francisco Bay Sailing Tour

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 …More

Likely to Sell Out
Likely to Sell Out
San Francisco, USA

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...

1 hour 30 minutes • Free Cancellation
4.8 (396)
from
$99
Catamaran Sailing Cruise in Monterey

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 …More

Monterey & Carmel, USA

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...

1 hour 15 minutes • Free Cancellation
4.8 (42)
from
$65
Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

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 …More

San Diego, USA

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...

2 hours • Free Cancellation
4.9 (204)
from
$119
Spectacular Sunset Sail on San Diego Bay

A rare sunset sailing adventure aboard our 35-foot sailboat, Luna: small group limited to six people, local captain sharing stories, hands-on sailing, and unforgettable vistas …More

La Jolla, USA

A rare sunset sailing adventure aboard our 35-foot sailboat, Luna: small group limited to six people, local captain sharing stories, hands-on sailing, and unforgettable vistas...

2 hours • Free Cancellation
5.0 (40)
from
$96
Small-Group San Diego Afternoon Sailing Excursion

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 …More

Likely to Sell Out
Likely to Sell Out
San Diego, USA

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...

3 hours • Free Cancellation
5.0 (563)
from
$116
Private Sailing Charter on San Diego Bay

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 …More

San Diego, USA

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...

3 hours • Free Cancellation
4.9 (50)
from
$499
Private Therapy Sailing Adventure

Old Plank Adventures: Sail into Deep Tranquility LUXURY SAILING | THERAPEUTIC ESCAPES | GOURMET CUISINE | INTIMATE WILDLIFE ENCOUNTERS Immerse yourself in the timeless Mediterranean …More

Santa Monica, USA

Old Plank Adventures: Sail into Deep Tranquility LUXURY SAILING | THERAPEUTIC ESCAPES | GOURMET CUISINE | INTIMATE WILDLIFE ENCOUNTERS Immerse yourself in the timeless Mediterranean...

2 to 3 hours
4.8 (49)
from
$400

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