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Top San Diego Sailing Trips

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
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
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

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
Tall Ship Adventure aboard the Schooner Californian with General Admission

Californian was built from the ground up in 1984 at Spanish Landing in San Diego Bay. She was launched with great fanfare for the 1984 …More

Californian was built from the ground up in 1984 at Spanish Landing in San Diego Bay. She was launched with great fanfare for the 1984...

4 hours
4.3 (6)
from
$85
San Salvador Spanish Galleon Adventure Day Sail with General Admission

Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step on board this 16th century Spanish galleon. …More

Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step on board this 16th century Spanish galleon....

4 hours
4.1 (7)
from
$85
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
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
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
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

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