Discover San Diego’s coastline aboard the private Sailing Vessel Maile. Customize your trip from a relaxing bay cruise to ocean swims, enjoying local brews and expert captains for a coastal adventure unlike any other.
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Difficulty
easy
Duration
2–4 hours
Fitness Level
Minimal physical fitness required; mobility to board the sailboat is necessary, suitable for most ages and abilities.
Wildlife
History
San Diego’s maritime history dates back to Spanish exploration in the 16th century, shaping the city’s strong connection to the Pacific Ocean.
Conservation
Sail San Diego supports clean ocean initiatives and practices responsible waste management to protect local marine ecosystems.
Sail San Diego
Discover San Diego’s coastline aboard the private Sailing Vessel Maile. Customize your trip from a relaxing bay cruise to ocean swims, enjoying local brews and expert captains for a coastal adventure unlike any other.
Sail San Diego operates a fleet of premium sailboat charters in San Diego Bay and the Pacific Ocean. They offer private and ticketed sails tailored to small groups, bachelorette and bachelor parties, wildlife watching, and full-day charters. Trips include private morning, midday, sunset and all-day sails, ticketed morning, midday and sunset cruises, themed bachelor and bachelorette sails, an Easter Sunday special, and a dedicated whale-watching sail for migrating Grey Whales. Charters accommodate up to twelve guests on private sails and smaller ticketed departures for groups of six or fewer. Options include bareboat charters for experienced sailors or a licensed captain for guests who prefer to relax. Complimentary drinks and snacks are provided on every trip. Safety is prioritized with well maintained vessels, experienced captains, and local knowledge of weather and marine conditions. Sail San Diego emphasizes personalized itineraries, respectful wildlife viewing practices, and clear booking policies, including transparent pricing and duration details. Reviews highlight friendly crews, clean boats, and memorable coastal views. Reservations are available for single tickets or private charters and include flexible time slots for morning, midday, sunset and all-day adventures. Sail San Diego is licensed to operate in San Diego waters and follows local regulations and marine guidelines. Whether guests seek a short family outing, a romantic sunset, a lively celebration, or a focused wildlife experience, Sail San Diego delivers professional service, comfortable boats, and reliable scheduling for memorable time on the water.
Experienced crews provide local commentary, navigation, and attentive service throughout each sailing experience daily.
Max Guests
Up to 12
Private sails seat up to 12 guests
Trips Offered
10 Trips
Morning, midday, sunset, all-day, specials
Duration
2–6 hours
Morning two hour to six hour options
Included
Drinks & Snacks
Complimentary on every trip
Book a private charter or join a ticketed cruise for morning, midday, sunset, or whale watching adventures.
Bring Layers for Changing Conditions
San Diego’s bay can turn breezy and cool quickly, even on sunny days—pack a light jacket or windbreaker.
Arrive Early for Shelter Island Parking
Shelter Island can get busy; arriving early helps ensure you find convenient parking near the dock.
BYOB but No Red Wine
You’re welcome to bring beer and white wine for your trip; red wine is currently not allowed on board.
Stay Hydrated and Snack Ready
Complimentary non-alcoholic drinks and snacks are provided, but bringing extra water is always smart for sunny days on deck.
Windbreaker or Light Jacket
Protects against cool ocean breezes and afternoon chill on the water.
summer
Sunglasses with UV Protection
Essential to shield your eyes from strong reflections off the water.
Non-Slip Boat Shoes or Sandals
Provides safety and comfort while moving around on deck.
Sunscreen with High SPF
Prevents sunburn during extended exposure under open sky.