San Diego Sailing Trips

7 experiences to discover

Explore the best sailing trips tours and activities in San Diego. Our unbiased ratings help you find the perfect experiences for your trip.

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$109-$115

Sail past iconic San Diego landmarks

Boat trip

From $119

Sail through San Diego Bay

Yacht captain as a host

$599-$615

Relax on a private sailing tour of San Diego Bay

Light snacks

From $95

Sail past iconic San Diego landmarks

2-hour morning sailing cruise

$105-$119

Sail aboard a historic 16th-century galleon

4-hour boat tour

$105-$119

Sail on a replica gold rush era tall ship

Sailing trip

$115-$130

Experience San Diego Bay from the water

Sailing tour