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Top San Diego Sailing Trips

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

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 …More

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...

2 hours Free Cancellation
from
$1,200
Private Sunset Sail on San Diego Bay with Champagne

What makes this experience truly unique is the combination of refined European luxury and a relaxed, intimate atmosphere. You will be sailing aboard a beautifully …More

What makes this experience truly unique is the combination of refined European luxury and a relaxed, intimate atmosphere. You will be sailing aboard a beautifully...

2 hours 30 minutes Free Cancellation
5.0 (1)
from
$975
San Diego Private Yacht Charter on a Classic Sailboat

Book the entire boat for your group — no strangers, no shared space, just your crew and Captain Phil on San Diego Bay. Liberty is …More

Book the entire boat for your group — no strangers, no shared space, just your crew and Captain Phil on San Diego Bay. Liberty is...

2 hours 30 minutes Free Cancellation
5.0 (4)
from
$810
Sailing Charter on san diego bay for up to 6 guests

While sailing on your private boat tour on the San Diego bay, enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarines, …More

While sailing on your private boat tour on the San Diego bay, enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarines,...

2 hours
5.0 (2)
from
$800
Bachelorette Sailing Party on San Diego Bay up to 6 Guests

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 6 guests. Enjoy breathtaking views of downtown, the naval base, aircraft carriers, …More

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 6 guests. Enjoy breathtaking views of downtown, the naval base, aircraft carriers,...

2 hours
5.0 (1)
from
$800
Sunset Sailing Tour of San Diego Bay up to 6 Guests

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers …More

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers...

2 hours
5.0 (1)
from
$800
Sailing Charter Sightseeing Cruise on San Diego Bay up to 6 Guests

A Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several …More

A Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several...

2 hours
4.0 (3)
from
$800
Deluxe private Sunset & Day Sail

Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling voyage takes you through breathtaking waters, past iconic landmarks, …More

Likely to Sell Out
Likely to Sell Out

Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling voyage takes you through breathtaking waters, past iconic landmarks,...

2 hours 30 minutes Free Cancellation
5.0 (3)
from
$714
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

Likely to Sell Out
Likely to Sell Out

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 (188)
from
$675
San Diego Wild Life Sailing Adventure Private

Join GoSailing San Diego for a private 4-hour wildlife sail aboard Wolf, a classic 1967 Cal 34 sailboat, with Captain Sal and First Mate Sharon. …More

Likely to Sell Out
Likely to Sell Out

Join GoSailing San Diego for a private 4-hour wildlife sail aboard Wolf, a classic 1967 Cal 34 sailboat, with Captain Sal and First Mate Sharon....

4 hours Free Cancellation
5.0 (2)
from
$503
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
Sunset Sailing Cruise on San Diego Bay | Champagne Included

What makes this experience truly special is the blend of refined European luxury and a relaxed, intimate atmosphere without the feel of a large group …More

What makes this experience truly special is the blend of refined European luxury and a relaxed, intimate atmosphere without the feel of a large group...

2 hours 30 minutes Free Cancellation
5.0 (1)
from
$199
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 (638)
from
$127
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
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
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 (371)
from
$119
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 (370)
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 (82)
from
$119
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
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 (114)
from
$119

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These answers are based on answers previously given to Cool Shore Excursions customers' questions.

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