SAN DIEGO
The 15 best san diego sailing tours you can book right now, with the price a head, how long each one runs and whether the sails go up. Number one is first for a reason.
Review of San Diego’s small-group sunset sail, with skyline views, sea lions, practical tips, pricing, comfort, and honest drawbacks.
“Captain was totally disengaged. Experience did not match description. Skyline of San Diego was never even acknowledged. Engine was on the entire trip with unpleasant diesel odor on deck.”
Sail San Diego at sunset aboard a six-person Catalina-style boat with skyline views, drinks, snacks, music, and a relaxed bay cruise.
“Beautiful experience sailing on this state of the Art sailboat. The captain is the best and we highly recommend this Sunset small group Sailing on the San Diego Bay.”
Review of Sail San Diego’s small-group afternoon sail, with harbor views, drinks, snacks, wildlife, practical tips, and honest value advice.
“Best San Diego “field trip” ever! Captain Dave was the ultimate host sharing his knowledge of the area as we sailed on sparkling seas…the boat is roomy and had a great variety of snacks and drinks, both alcoholic and non-alcoholic. We enjoyed listening to our favorite music while we sailed ( really sailed-not motored) … so fun! it was a top tier day on a top tier boat with a top tier captain. We will definitely sail with Sail San Diego again.”
Sail San Diego Bay aboard the restored Liberty with sunset views, naval landmarks, sea lions, beer, wine, and a six-person group.
“The sunset sail with Captain Phillip is the highlight of our trip so far. Well worth every penny and highly recommend”
Review of San Diego’s small-group sunset sail, with bay views, drinks, marine life, practical tips, price advice, and booking details.
“We enjoyed our boat ride for our birthdays. Ann was amazing and very attentive, she definitely made the boat ride even more amazing! We were first time visitors to San Diego and enjoyed every bit of it!”
Review of San Diego’s 2.5-hour small-group sunset catamaran sail, with harbor views, drinks, wildlife, practical tips, and honest value advice.
“Best sail ever, Capt Ryan was excellent, informative and good guy to sail with, took many pictures if us. Highly recommend.”
Sail San Diego Bay aboard a Catalina 34 with a local captain, skyline views, snacks, and room for only six guests.
“Let me start by saying, I booked this experience specifically because so many reviews spoke so highly of Captain Mike. They were right! Couldn’t have asked for a better captain. Sunscreen, sodas, waters, and a variety of chips weRead more”
Sail San Diego Bay for two hours with skyline, USS Midway views, wine, small groups, sunset light, and chances to spot sea lions or dolphins.
“It was such an amazing time!! Love the experience and the breathtaking views!”
Review of Sterling Sails’ private San Diego Bay cruise, with Captain Liz, sunset views, sea lions, USS Midway, snacks, and pricing.
“We were selebratin my mother's 90 birthday one day as we were walking in Coronado she commented that one day she will like be on a sailing boat ⛵ so I surprise her with it she loved capitan Liz was excelente very accommodating we have a perfect afternoon my mother was very happy. Carlos Guadarrama.”
Review of San Diego’s 150-minute sunset sailing cruise, with bay views, drinks, local insight, wildlife watching, and practical booking tips.
“We had an amazing time with Captain DJ! What a beautiful and relaxing way to spend a few hours sailing the harbor in San Diego! We sipped on wine and beer, listened to great music, and had fun conversing with DJ. We also saw lots of seals and pelicans! If you’re hesitating, just do it, you won’t regret it!”
Sail San Diego Bay aboard the hand-restored Liberty, with drinks, snacks, wildlife, harbor landmarks, and Captain Philip’s personal touch.
“If you are looking for a very nice sailing boat trip on a Classic Sailboat with no more than six total passengers, and a Captain that over delivers with any refreshments as well as His one to one sincere treatment, this adventure is a Must. Captain Phillip is a World Class sailer with a pedigree that is only surpassed by his engaging and accommodating personality and his beautiful sloop, Liberty. Thank You for a fabulous tour Captain Phillip. Chad and Janet”
Sail San Diego Bay on a 40-foot yacht with city views, naval ships, wildlife, drinks, snacks, and a small six-person group.
“Great sailing in a beautiful boat manned by very profesional captain! Very relaxing and high end service”
Sail San Diego Bay aboard a classic yacht with skyline views, Navy ships, wildlife, and a small six-person group.
“I was looking to actually sail. It was a boat ride and historic guided tour of San Diego bay.”
Sail San Diego aboard the historic Californian, help work the rigging, hear sea tales, and explore the Maritime Museum in one four-hour outing.
“This was a pirate adventure for my nine year old great grandson. He was enthralled. He especially enjoyed the firing of the cannons and seeing the nuclear submarines. Four generations of my family were aboard. There was something of interest for each generation. It was a wonderful time!”
Sail San Diego aboard a 16th-century galleon replica, then explore the Maritime Museum, HMS Surprise, and Star of India.
Pick a rig, a coast or an afternoon.
