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Top San Diego 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

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 (542)
from
$38
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

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

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
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

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
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

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
2.5-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

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 (357)
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

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
5.0 (637)
from
$127
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

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
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 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
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

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 (41)
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

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
2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks

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 …More

Likely to Sell Out
Likely to Sell Out

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...

2 hours 30 minutes • Free Cancellation
5.0 (112)
from
$119
Deluxe Day Sail in San Diego

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 …More

Likely to Sell Out
Likely to Sell Out

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...

2 hours 30 minutes • Free Cancellation
5.0 (81)
from
$119
Top Rated San Diego Sunset Sail Classic Yacht 6 Guests

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with …More

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with...

2 hours 30 minutes • Free Cancellation
5.0 (359)
from
$125
Daytime Sailing Along San Diego's Skyline

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 …More

Likely to Sell Out
Likely to Sell Out

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...

2 hours • Free Cancellation
5.0 (160)
from
$99
2-Hour Private Sailing Experience in San Diego Bay

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 …More

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...

2 hours • Free Cancellation
5.0 (187)
from
$675
San Diego Sailing Cruise Small Group 6 Guests Classic Yacht

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with …More

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with...

2 hours 30 minutes • Free Cancellation
5.0 (85)
from
$125
Private Day Sail in San Diego up to 12 guests

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 …More

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...

2 hours 30 minutes • Free Cancellation
5.0 (70)
from
$81
San Diego Harbor Cruise on the Largest Catamaran in San Diego

Enjoy a San Diego harbor cruise on San Diego's largest and newest catamaran yacht. We provide our guests with a unique way to splash by …More

Enjoy a San Diego harbor cruise on San Diego's largest and newest catamaran yacht. We provide our guests with a unique way to splash by...

2 hours 30 minutes • Free Cancellation
4.9 (55)
from
$55
Private Sunset Sail in San Diego up to 12 guests

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 …More

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...

2 hours 30 minutes • Free Cancellation
5.0 (73)
from
$85

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