SAILING WORLDWIDE
The best days on the water.
The 11 most popular san diego tours. What each sail costs, how long you are on the water, and which crews run it well.
A small-group sunset sail on a yacht in San Diego Bay with skyline views, wildlife sightings, and easy deck comfort for about 2 hours.
Most Popular“The captain was excellent. The sailing company was great as they let us sail a day later than scheduled after our flight to San Diego was delayed many many hours. Highly recommend this company.”
Small-group San Diego sunset sailing from Shelter Island with beer, snacks, blankets, and big views of Point Loma, USS Midway, and Coronado.
“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!”
Small-group San Diego harbor sailing with just six aboard a Catalina-style yacht. Beer, snacks, and your music on the water.
“My family and I had such a great time on our sailing adventure. We just wanted to relax with some fun in the sun, and this trip delivered. Captain Greg was fantastic and offered us great recommendations for restaurants and things to do in the area.”
San Diego Bay sunset sail on Liberty, a 1904-style yacht. Beer, wine, snacks included on a small-group 2.5-hour ride.
“Lovely evening with Capt. Phillip and two other couples, sailing through the bay! The captain is a wealth of knowledge… just ask him questions!”
Deluxe Sunset & Day Sail in San Diego Bay. Small-group cruise with drinks, blankets, and landmark views past USS Midway to Coronado.
“We did this as a family for Christmas. We’ve lived in San Diego most of our lives and it was beautiful to see all the sights from the water. It was both calming and fun. Our 8 year old granddaughter loved it as well. Capt. Collin was great! So knowledgeable and very sweet. We enjoyed…”
A 2.5-hour small-group catamaran sunset sail in San Diego with drinks, warm blankets, and quiet wind time around harbor icons.
“Best sail ever, Capt Ryan was excellent, informative and good guy to sail with, took many pictures if us. Highly recommend.”
Luxury 2-hour small-group sailing on a 34-foot Catalina in San Diego Bay. Skyline views, snacks, BYO drinks, local captain.
“Captain Mike was wonderful, knowledgeable about the area and complimented our sail. I recommend this trip 100%”
2-hour San Diego Bay sailing from Harbor Island with skyline views, USS Midway sights, and frequent sea lions. Wine included.
“The sunset cruise was very relaxing, a great experience. Our guide was knowledgeable and low key. which was very appropriate for that setting. We enjoyed it very much.”
Sail San Diego Bay on a small yacht for skyline views, sea lions, and an easy, intimate 2-hour sunset or daytime cruise with wine included.
“SHOUT OUT TO MY MAIN MAN STEW!!!! he really knows how to be a captain, and i would follow this man thru the gates of Point Nemo.”
A private 2-hour yacht sail in San Diego Bay for up to six. Customize your route with Captain Liz, plus snacks, drinks, and champagne.
“Liz made the final night of our family vacation the best night! My family cannot stop talking about the boat ride and how much fun Liz was! We did so many things together this week, and this won the week! Liz was very knowledgeable, professionally fun, and very engaged with our lil family! Thanks for…”
A 2-hour daytime sail in San Diego Bay with a glass of wine, cozy seating, and skyline views plus views of the Midway from the water.
“Relaxing beautiful day on the water! Clean sailboat and friendly captain! We were taken to see the sea lions as well!”
The sailing ports worth the trip, grouped by the sea they sit on.
