Sail and Sip: The Ultimate Private Sailboat and Winery Tour in San Diego
Difficulty
easy
Duration
5 hours
Fitness Level
Suitable for most fitness levels as walking is moderate and the sailing involves little physical exertion
Overview
Discover San Diego from sea to shore with this exclusive private sailboat cruise paired with a curated wine tasting at a chic urban winery. Perfect for special occasions or a stylish afternoon on the bay.
San Diego Sailboat & Winery Private Tour (Private)
Savor the sea and sip the vine — all in one unforgettable experience.
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Adventure Photos
About This Adventure
Embark on a unique 5-hour private tour that combines a scenic sail across San Diego Bay with a delightful wine tasting experience. Enjoy breathtaking views of the skyline and iconic landmarks, followed by a curated tasting of local wines paired with light bites at a stylish urban winery. Perfect for any special occasion!
Embark on a unique 5-hour private tour that combines a scenic sail across San Diego Bay with a delightful wine tasting experience. Enjoy breathtaking views of the skyline and iconic landmarks, followed by a curated tasting of local wines paired with light bites at a stylish urban winery. Perfect for any special occasion!
Adventure Tips
Dress in layers for changing weather
San Diego Bay can get breezy on the water; bring light jackets or sweaters to stay comfortable.
Wear flat, non-slip shoes
Safety on the sailboat requires stable footing—choose comfortable, flat shoes with good grip.
Arrive early for smooth check-in
Plan to arrive 15 minutes before your tour to allow time for any orientation and boarding procedures.
Notify dietary restrictions in advance
For a personalized wine tasting, inform the operator of vegetarian or other dietary needs beforehand.
Local Insights
Wildlife
- Brown pelicans soaring over the bay
- Harbor seals occasionally spotted near the shoreline
History
San Diego Bay has a rich naval history, home to the USS Midway Museum and significant military heritage.
Conservation
Local operators prioritize sustainable boating practices and encourage wine tasting venues to support regional vineyards using eco-friendly methods.
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Adventure Hotspots in San Diego
Frequently Asked Questions
Recommended Gear
Light jacket or windbreaker
Protects against chilly breezes on the water during spring afternoons.
spring specific
Sunscreen
Important for sun protection during the daytime sail and winery stop.
summer specific
Hat or cap
Keeps sun off your face during afternoon light and potential glare off the water.
fall specific
Comfortable flat shoes
Supports safe movement aboard the sailboat and walking at the tasting room.