Sailing trips · SAN DIEGO SAILING TRIPS

6 San Diego Sailing Trips Worth Booking

6 trips  ·  from $109 a head

This is the shortlist you would send a friend: 6 san diego sailing trips worth the money, each with its price, its traveller verdict and the one thing to know before the lines come off.

Sunset Sail Along the San Diego Skyline - Passing the USS Midway and Maritime Museum
Evening Experiences, Sailing Trips, San Diego Sailing Trips, Sunset Sailing Cruises, Sunset Sailing Cruises in San Diego, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Trips

Sunset Sail Along the San Diego Skyline

1.Sunset Sail Along the San Diego Skyline

★★★★★★★★★★5.0 · 603 reviews · 2 hours (approx.) · from $109Our pick

Sail San Diego Bay for about two hours with up to six people, passing the USS Midway and Maritime Museum as the sun sets. Captains such as Aaron, Patrick, Adam, and Derek keep the outing friendly and informative. Bean bags, blankets, cushions, and an onboard bathroom add comfort.

“Fun and scenic activity. Good value. About an hour and a half. Parking at marina $20-$30 in addition.”

Check availability →Read our full review

Small-Group San Diego Sunset Sailing Excursion - Passing the USS Midway and Coronado Bridge
Evening Experiences, Sailing Trips, San Diego Sailing Trips, Sunset Sailing Cruises, Sunset Sailing Cruises in San Diego, Sunset Sailing Cruises in the USA, Tour Reviews, Tours, USA Sailing Trips

Small-Group San Diego Sunset Sailing Excursion

2.Small-Group San Diego Sunset Sailing Excursion

★★★★★★★★★★5.0 · 592 reviews · 3 hours (approx.) · from $127

Set sail from Shelter Island for about three hours with a maximum of six passengers. Expect sunset views of Point Loma, Coronado, the USS Midway, and the skyline, plus beer, hard seltzers, soft drinks, snacks, blankets, binoculars, and Bluetooth music. Captains such as Dave, Greg, and Rhys keep the trip friendly and informal.

“Getting to know the 4 other people on board. Sunset cruise was just what I needed to decrease my asthma symptoms.”

Check availability →Read our full review

Small-Group San Diego Afternoon Sailing Excursion - Leaving Shelter Island for Point Loma
Sailing Trips, San Diego Sailing Trips, Tour Reviews, Tours, USA Sailing Trips

Small-Group San Diego Afternoon Sailing Excursion

3.Small-Group San Diego Afternoon Sailing Excursion

★★★★★★★★★★5.0 · 531 reviews · 3 hours (approx.) · from $116

Sail San Diego takes up to six passengers on a three-hour daytime cruise from Shelter Island. Expect Point Loma lighthouses, Coronado Bridge, naval ships, wildlife, snacks, beer, soft drinks, and Bluetooth music. Captains such as Dave, Greg, Bree, and Chris add local color.

“Captain Bree was amazing. She made all of us very comfortable, single-handedly sailed the boat, and was pleasant and positive throughout. We caught some super fun wind outside the harbor then came back inside to see some sights. Highly recommend Captain Bree to all and sail San Diego as well.”

Check availability →Read our full review

San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included - What the 2.5-hour sailing is like
Bay, Harbour & Coastal Sailing, Drinking Tours, Food & Drink, Luxury Yacht Cruises, Luxury Yacht Cruises in the USA, Sailing Trips, San Diego Sailing Trips, Tour Reviews, USA Sailing Trips, Wine Tours

San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included

4.San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included

★★★★★★★★★★5.0 · 331 reviews · 2 hours 30 minutes (approx.) · from $115

Spend about 2.5 hours aboard Liberty, a hand-restored reproduction of a 1904 sailboat. Captain Phillip guides a maximum of six passengers past the USS Midway, Coronado Bridge, Navy ships, sea lions, and the glowing San Diego skyline. Beer, white wine, soft drinks, water, and snacks are included.

“We had a wonderful time. Captain Philip is very nice and knowledgeable. The pleasures of the bay were fully experienced. From the other ships and boats ( private and commercial and military) to the seals and sea lions and birds and to the aircraft overhead, we enjoyed the quiet sailing and the panoramic views of the San Diego skyline. The gorgeous sunset put the whole experience into another level of spectacular. I’d recommend this trip unconditionally!”

Check availability →Read our full review

Deluxe Sunset & Day Sail Small Group - The USS Midway, Maritime Museum, and downtown waterfront
Evening Experiences, Sailing Trips, San Diego Sailing Trips, Sunset Sailing Cruises, Sunset Sailing Cruises in San Diego, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Trips

Deluxe Sunset & Day Sail Small Group

5.Deluxe Sunset & Day Sail Small Group

★★★★★★★★★★5.0 · 245 reviews · 2 hours 30 minutes (approx.) · from $119

Spend about two and a half hours sailing San Diego Bay with no more than six people aboard. Captains such as Ann, Colin, Billy, and DJ share harbor stories, point out sea lions and dolphins, and guide you past the USS Midway, Coronado Bridge, Seaport Village, and other waterfront sights. Drinks are included, and the cruise returns to the marina.

“The views were amazing, Captain Collin was awesome, and the drinks were complimentary! This was my fiance and I's favorite activity in San Diego, cannot recommend it enough!”

Check availability →Read our full review

2.5-Hour Small-Group Catamaran Sunset Sail with Drinks - Meeting the captain at Harbor Island
Catamaran Cruises, Catamaran Cruises in the USA, Evening Experiences, Sailing Trips, Sailing Trips with Open Bar & Drinks, San Diego Sailing Trips, Sunset Sailing Cruises, Sunset Sailing Cruises in San Diego, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Trips

2.5-Hour Small-Group Catamaran Sunset Sail with Drinks

6.2.5-Hour Small-Group Catamaran Sunset Sail with Drinks

★★★★★★★★★★5.0 · 223 reviews · 2 hours 30 minutes (approx.) · from $119

Spend 2.5 hours sailing San Diego Bay with no more than six people aboard. Captains Ryan, Matt, and Kaya mix local stories with easygoing hospitality as you pass the USS Midway, Coronado Bay Bridge, Point Loma, sea lions, and seabirds. Beer, wine, soft drinks, water, and blankets are included.

“Captain Ryan is very knowledgeable, both about the area and his boat. The sail was a quiet and relaxing few hours with my kids, husband, and friend, with plenty of room to spread out. It is big enough for kids to wiggle around safely, but I wouldn't recommend a catamaran for kids who don't listen well to directions (for safety reasons). We will definitely use this company again next time we come to San Diego!”

Check availability →Read our full review

Scroll to Top

Every kind of sailing day

Pick the boat, the hour on the water or the country.