SAN DIEGO
San Diego’s best days out.
A short guide to the 15 best sunset & sailing cruises, with what each one costs, how long it runs and who you book it through.
Sunset sail on San Diego Bay for up to six people. Bean bags onboard, skyline views, and passes near USS Midway and Maritime Museum.
Most Popular“Great service, beautiful and relaxing. Bring a jacket… even if it’s warm when you set sail. Gets cold quickly.”
Small-group sunset sailing from Shelter Island with views of Point Loma, USS Midway, and Coronado—plus drinks, snacks, and your own music.
“Be aware, the entire sailing adventure stays in the bay. If you want to go out into the ocean, this is not the trip you want. However, it was very relaxing and romantic!”
Six-person San Diego Harbor sailing with beer, snacks, jackets, binoculars, and your own music on board.
“Wonderful and beautiful family outing during spring break! I highly recommend - we even saw a whale in action! This is a must do for sure - also Captain Mike was fabulous!”
Vintage yacht sunset sail on San Diego Bay with beer, wine, snacks, and a small-group cruise under full sail.
“Was a wonderful evening sail. Had the sail up almost the entire time- which is not common for other ‘sailings’ I’ve had in the past. Captain Philip has a love for sailing and is very knowledgeable.”
Sunset whale and dolphin cruise from Mission Bay, San Diego. Spot marine mammals with a certified guide, then watch the coastline glow.
“The crew members were very nice and knowledgeable, but we did not see any whales. We did see a pod of dolphins. We went so far out- about 10 miles in the ocean, and it was very choppy. Bring warm clothing! Be mindful Read more”
Small-group San Diego sunset sail for $119 with onboard drinks, blankets, and dolphin spotting past USS Midway and Coronado Bridge.
“We had a fabulous sunset sail. The wind was great, the scenery and the sunset were beautiful. Our captain was highly skilled and knowledgeable! The giant beanbag and blankets made sitting 4 adults topside cozy. We highly recommend San Diego Sailing Excursions!!”
Mission Bay sunset cruise with views of SeaWorld and Ocean Beach Pier, Mahalo bar drinks, and a relaxed 75-minute sail.
“It is a large boat with about 50 passengers. There is a bar and snacks for purchase. Sunset did not disappoint!”
2.5-hour San Diego sunset catamaran with beer, wine, and soft drinks, minimal motor use, and views of USS Midway and Point Loma.
“WOW!! We had a fabulous time this evening sailing on your catamaran on San Diego Bay with Captain Kaya! She was wonderful!!”
Small-group sail on a 34-foot Catalina from Harbor Island for skyline and coastal views, with local captain stories, snacks, and BYO drinks.
“Captain Mike is a fantastic captain, guide and person. We highly recommend getting out on the bay with Captain Mike!”
Private 2-hour sail in San Diego Bay with Captain Liz. Up to 6, custom route, snacks, drinks, and champagne.
“Very enjoyable. Our family had a great time. The boat and crew were very friendly, knowledgeable and entertaining.”
San Diego Bay sunset or daytime sailing from Harbor Island with included wine, soft drinks, sea lion spotting, and skyline views.
“This was the absolute highlight of our trip! The sailboat was gorgeous, Captain Rick was the best, and overall, we were beyond happy with our experience!”
A 2-hour daytime sail in San Diego Bay with onboard wine, comfy deck seating, and skyline views plus a pass by the USS Midway from water.
“Rick was a great Captain. He answered all our sailing questions and was fully comfortable sailing the cruiser. He made it fun, interacting with us and showing us so many sights around the San Diego Bay. Highly recommend Rick and company for your next charter!”
Private luxury catamaran sailing from Mission Bay with smooth cruising to La Jolla Cove or Sunset Cliffs, crew service, and BYO snacks.
“Captain and staff were very friendly and knowledgeable. Taught was newer and in top condition. The head and galley were very clean. Definitely will see y’all next year.”
Small-group catamaran sailing from San Diego’s Harbor Island with drinks, blankets, and wildlife sightings for about 2.5 hours.
“It was a nice cruise, but it was very busy as there were many boats military, and otherwise in the same harbor. Not as relaxing as I had hoped.”
A 1.5-hour San Diego Bay sunset cruise with happy hour sips, snacks, and views of naval ships and the Coronado Bridge.
“The cruise was not as advertised - the Hours d’oeuvres we’re gone shortly after we Boarded so we didn’t get any - the passed Hours d’ oeuvres never came our way we Finally were able to each get a slider by Literally chasing down the server. If desert Was served it never reached us. I’m…”
Every neighborhood, every stretch of coast, and every way to get out on the water.
