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 Sunset Sailing Excursion

5 star rating: Highly Recommended 9 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 is limited ...  Read more

Location: San Diego, California
Duration: 3 hours

From USD $88.99

Small-Group San Diego Afternoon Sailing Excursion

5 star rating: Highly Recommended 37 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

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

Classic Sailboat Afternoon 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 $107.00

San Diego Sunset Sail

5 star rating: Highly Recommended 2 Reviews

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

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

San Diego Bay Sailing Tour

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 wonder aboard a beautiful sailing ...  Read more

Location: San Diego, California
Duration: 3 hours

From USD $79.00

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

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

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

Nature Cruise and Whale Watching 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: 4 hours

From USD $110.00

Classic Sailboat Harbor Morning Cruise

Experience the bustling activity of the bay, wildlife, and a stunning view of the city skyline on a San Diego harbor cruise on a unique 1914 replica Friendship ...  Read more

Location: San Diego, California
Duration: 3 hours

From USD $90.00

Private Sunset Cruise on San Diego Bay

San Diego's best kept secret awaits on a private sunset cruise of San Diego Bay. See downtown Embarcadero from the water and the beauty of the city from a ...  Read more

Location: San Diego, California
Duration: 3 hours

From USD $150.00

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 have ...  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 a ...  Read more

Location: San Diego, California
Duration: 3 hours

From USD $299.00

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 wonder aboard a beautiful sailing ...  Read more

Location: San Diego, California
Duration: 3 hours

From USD $349.00

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

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

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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