San Diego Sailing Trips

10 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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4.71

San Diego Sailing Tour in San Diego Bay

$625-$650

Sail through stunning San Diego Bay

Soda/Pop

4.67

San Diego Bay Sailing Experience at Sunset

From $89

Sail past the USS Midway Museum

White wine

4.64

San Diego Sailing Excursion at Sunset

$95-$101

Sail through San Diego Bay

Yacht captain as a host

4.6

San Diego Sailing Tour on Classic Yacht

$109-$135

Sail past iconic San Diego landmarks

Soda/Pop

4.59

San Diego Private Sailing Tour for up to 12 Guests

$495-$500

Sail between downtown and Coronado

Sailboat rental fee

4.56

San Diego Private Sailing Tour

From $599

Relax on a private sailing tour of San Diego Bay

Private guide

4.54

San Diego Spanish Galleon Day Sail

From $119

Sail aboard a 16th-century galleon

4-hour boat tour

4.52

San Diego Sailing Tour

From $95

Sail past iconic San Diego landmarks

2-Hour or 3-Hour Sailing Experience

4.52

San Diego Tall Ship Sailing Adventure

From $119

Sail on a replica gold rush era revenue cutter

Sailing trip

4.38

San Diego Sailing Tour

From $130

Experience San Diego Bay from a classic yacht

Sailing tour