San Diego Sailing Trips

San Diego Sailing Trips

Cruises, Sailing & Water Tours See all

Only Show: Day Cruises | Dinner Cruises | Dolphin & Whale Watching | Duck Tours | Sailing Trips | Sunset Cruises

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Small-Group San Diego Afternoon Sailing Excursion

5 star rating: Highly Recommended 36 Reviews

Set sail from San Diego on this small-group sailing tour! This three-hour adventure on a Catalina-style sailboat is limited to just six people, ...  Read more

Location: San Diego, California
Duration: 3 hours

From USD $88.99

Small-Group San Diego Sunset Sailing Excursion

5 star rating: Highly Recommended 5 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-style sailboat ...  Read more

Location: San Diego, California
Duration: 3 hours

From USD $88.99

Private Day Sail for 4-6 People

5 star rating: Highly Recommended 4 Reviews

Set out on a private, relaxing 2-hour sailing excursion from San Diego on a fully restored, 36-foot (11-meter) Cal Jensen yacht. Sail past the Maritime Museum ...  Read more

Location: San Diego, California
Duration: 2 hours

From USD $323.64

San Diego Sunset Sail

5 star rating: Highly Recommended 1 Review

This guided tour is driven by a licensed captain and is limited to a small group of up to 6 passengers, making it an intimate experience. Watch as the sun dips ...  Read more

Location: San Diego, California
Duration: 2 hours

From USD $103.24

Classic Sailboat Harbor Tour

Small group sailing tours on San Diego Bay on a unique 1914 replica Friendship Sloop. All boat tours circle the harbor using traditional sailing methods for ...  Read more

Location: San Diego, California
Duration: 3 hours

From USD $90.00

3 Hour San Diego Sunset Sail

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego tha tyou can only get from the water.  Our San ...  Read more

Location: San Diego, California
Duration: 2 hours

From USD $85.00

Small-Group San Diego Sailing Trip

This guided tour is driven by a licensed captain, and only takes up to 6 passengers at a time, which allows for an intimate experience.

Location: San Diego, California
Duration: 2 hours

From USD $91.64

Classic Sailboat Sunset Sail

5 star rating: Highly Recommended 1 Review

This unforgettable 3-hour tour will circle you around the San Diego harbor during the most dramatic part of a California day. The multi-colored sky is the ...  Read more

Location: San Diego, California
Duration: 3 hours

From USD $107.00

3 Hour San Diego Sailing Adventure

Take in the sights, sounds and stories of the bay on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from the water.  ...  Read more

Location: San Diego, California
Duration: 3 hours

From USD $85.00

4 Hour Private Sail for up to 6 people

This private sailboat cruise allows up to 6 guests to enjoy the sailboat all to themselves. With a Captain at the helm, serving you and your guests’ every ...  Read more

Location: San Diego, California
Duration: 4 hours

From USD $637.42

3-Hr Private Endless Summer Special

This is a 3-Hour Private Sailing Charter that can accommodate up to SIX passengers.  A Licensed Captain will navigate your group around the San Diego Bay and ...  Read more

Location: San Diego, California
Duration: 3 hours

From USD $578.84

Private San Diego Tour on Classic Sailboat

Small group sailing tours on San Diego Bay on a unique 1914 replica Friendship Sloop. All boat tours circle the harbor using traditional sailing methods for ...  Read more

Location: San Diego, California
Duration: 3 hours

From USD $500.00

Half Day Local Fishing Trips in San Diego

Fishing is a first class fun and thrilling way to spend your vacation time while in San Diego. With twenty plus years’ experience locally and offshore, we ...  Read more

Location: San Diego, California
Duration: 5 hours 30 minutes

From USD $690.00

Private San Diego Sailing Adventure

Embark on your very own private 3-hour San Diego sailing adventure and enjoy an intimate sail. Take in the coastal sights and famous San Diego landmarks from ...  Read more

Location: San Diego, California
Duration: 3 hours

From USD $299.00

Private Sunset Sail for Two

A Romantic Private Sail for Two on the San Diego Bay offers a Beautiful Sunset and Downtown City Skyline.

Location: San Diego, California
Duration: 2 hours

From USD $346.84

San Diego Half-Day Marine Wildlife Tour with Lunch

Join this guided whale watch tour on a classically restored sailing yacht. Come see marine wildlife in their natural habitat. This is a small group tour, with ...  Read more

Location: San Diego, California
Duration: 4 hours

From USD $172.84

Private Sunset Sail for 4-6 People

A Private Sailing Tour for you and your closest friends.  Let us show you the sunset from the San Diego Bay!

Location: San Diego, California
Duration: 2 hours

From USD $520.84
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Only Show: Day Cruises | Dinner Cruises | Dolphin & Whale Watching | Duck Tours | Sailing Trips | Sunset Cruises

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