SAILING WORLDWIDE
The best days on the water.
The 11 most popular san diego sailing trips. 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“It was my boyfriend and I 10 years anniversary so we wanted to try the sunset sailing experience and let me tell you it was so much fun will do it again”
Small-group San Diego sunset sailing from Shelter Island with beer, snacks, blankets, and big views of Point Loma, USS Midway, and Coronado.
“Unbelievable experience! Rhys was an incredible captain and guide … perfect way to cap off our trip!”
Small-group San Diego harbor sailing with just six aboard a Catalina-style yacht. Beer, snacks, and your music on the water.
“Great time on the sail boat. Dave was an awesome captain and shared a lot of knowledge with us along the way. Highly recommend to couples just looking to relax and soak in San Diego’s views.”
San Diego Bay sunset sail on Liberty, a 1904-style yacht. Beer, wine, snacks included on a small-group 2.5-hour ride.
“Captain Phillip was top notch! Clean yacht, well stocked with snacks and refreshments, great stories. ABSOLUTELY AMAZING!! THANK YOU CAPTIAN PHILLIP!!!!”
Deluxe Sunset & Day Sail in San Diego Bay. Small-group cruise with drinks, blankets, and landmark views past USS Midway to Coronado.
“It was a great experience! Relaxing and chill…loved the smaller boat & it being more intimate with just 6 people”
A 2.5-hour small-group catamaran sunset sail in San Diego with drinks, warm blankets, and quiet wind time around harbor icons.
“Capt. Ryan gave us the best of all worlds! The sunset was beautiful, but the speed this unique boat travels at was exciting. I highly recommend and will do this again when I come back to SD!”
Luxury 2-hour small-group sailing on a 34-foot Catalina in San Diego Bay. Skyline views, snacks, BYO drinks, local captain.
“My parents and I had a beautiful time sailing the San Diego Bay through Viator. Our captain Peter was wonderful! He had years of sailing experience, was very knowledgeable (and easily answered my parents million questions hahRead more”
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.
“It was a very relaxing and entertaining excursion. Bree was very knowledgeable and enlightening regarding the surroundings as well as the boat we were on. I would highly recommend the trip to anyone looking at a sunset cruise.”
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 was a fun and insightful captain. We had great winds and weather making our experience amazing. We toasted with champagne to a beautiful trip to see family living in the area.”
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.
“We were having a mommy/daughter weekend and wanted to sail…this was the perfect experience! It was a typical June day in SD. A little sun, lots of clouds and lots of wind! Our Captain was fantastic - we felt well informed, safe and entertained. I would highly recommend this adventure!”
The sailing ports worth the trip, grouped by the sea they sit on.
