San Diego Sailing Trips - Page 2

32 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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4.55

San Diego Catamaran Sailing Cruise

From $800

1 provider live

Sail through San Diego Bay

Bottled water

4.55

San Diego Sailing Party on the Bay

From $800

1 provider live

Sail across the stunning San Diego Bay

Bottled water

4.55

San Diego Sailing Charter

From $475

1 provider live

Sail the stunning San Diego Bay

Bottled water

4.55

San Diego Bay Sunset Sailing Tour

From $800

1 provider live

Sail through San Diego Bay at sunset

Bottled water

4.54

San Diego Private Sailing Tour

$599-$1100

3 providers combined

Relax on a private sailing tour of San Diego Bay

Light snacks

4.54

San Diego Tall Ship Sailing Adventure

From $85

2 providers combined

Sail on a replica Gold Rush era tall ship

Sailing trip

4.54

San Diego Sailing Charter Sightseeing Cruise

From $800

1 provider live

Sail through scenic San Diego Bay

Bottled water

4.53

San Diego Catamaran Sailing Cruise

From $800

1 provider live

Sail on a private catamaran

Bottled water

4.53

San Diego Catamaran Sailing Charter

From $1100

1 provider live

Sail the stunning San Diego Bay

2 ice-filled coolers with bottled water

4.52

San Diego Private Sunset Sail

From $669

1 provider live

Sail along San Diego Bay

Experienced skipper for a safe and smooth sailing experience

4.52

San Diego Morning Sailing Tour

From $95

2 providers combined

Sail past iconic San Diego landmarks

2-hour sailing experience

4.51

San Diego Sailing Cruise for Two

From $12140

1 provider live

Sail the San Diego Bay on a private yacht

Captain/guide