SAILING WORLDWIDE
The best days on the water.
The 15 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“Bring whatever you want to drink but they did supply white wine and water and pepsi but no ice Derick the captain was awesome”
Small-group San Diego sunset sailing from Shelter Island with beer, snacks, blankets, and big views of Point Loma, USS Midway, and Coronado.
“We had an incredible time! Captain Dave was very knowledgable about the area and engaging! Stunning sunset, fun fellow travelers, and a captain who caught the wind ... couldn't ask for more! Would go sailing with him and Sail San Diego again!”
Small-group San Diego harbor sailing with just six aboard a Catalina-style yacht. Beer, snacks, and your music on the water.
“The entire trip was so fun! Captain. Dave was great and made our trip so much fun! Can’t wait to do another sailing!”
San Diego Bay sunset sail on Liberty, a 1904-style yacht. Beer, wine, snacks included on a small-group 2.5-hour ride.
“This experience is peaceful, intimate, and serene. The experience is filled with Great San Diego Bay history and amazing views given by Captain Phillip.”
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.
“This is such a fun activity in San Diego! We did the sunset cruise for our birthdays on a girls trip and it was the perfect way to see all the sea sites without the pressure of walking thru all of them. Captain Ryan was the best and is so educational about sailing. He will…”
Luxury 2-hour small-group sailing on a 34-foot Catalina in San Diego Bay. Skyline views, snacks, BYO drinks, local captain.
“This was a great time on the water with a beautiful ship, relaxing bay, very informative captain, very interesting sites. I would do this tour again and highly recommend to those interested in getting on the water in San Diego.”
2-hour San Diego Bay sailing from Harbor Island with skyline views, USS Midway sights, and frequent sea lions. Wine included.
“This was such a beautiful boat ride around San Diego”
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.
“It was a perfect trip from start to finish. Captain Liz was very friendly and made us feel very welcome on her sailing boat. We were able to play our music from her speakers.. The trip was beautiful and it was a great way to end our day. I would highly recommend this excursion.”
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.
“Captain Nick made my Mom and I feel so welcome. My Mom is a bit afraid of water and he made her feel safe and calm. He's a great guide and seemingly effortlessly made sure the whole boat was enjoying their time. Highly recommend. I'll be back ☺️”
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 very lucky to have Eric all to ourselves ! He was so pleasant & informative. Delightful 2 hours .”
Private luxury catamaran sailing from Mission Bay to the Pacific with onboard crew service, coastal sights, and wildlife—2 to 8 hours.
“We had an amazing sunset cruise thru the bay with Maddie and Jake. Our family of 12 enjoyed the evening on the boat. Maddie and Jake were so accommodating and welcoming. Would highly recommend this tour!!”
San Diego small-group catamaran sail with beer, wine, soft drinks, and 2.5 hours of harbor views from downtown to Midway.
“Relaxing Day on the water. Celebrated my anniversary sailing this was the relaxing day that we needed to take time out Of our lives to truly take in the beauty of San Diego”
Sail San Diego Bay on a classic 1904-style yacht with Captain Philip, snacks and drinks, plus close looks at Star of India, Midway, Coronado.
“It was such a wonderful experience to be on this beautiful boat with only my family. It was such a personal, intimate experience to have the experience all to ourselves. Captain Phil was extremely hospitable and was happy to answer all of our questions.”
A private 2.5-hour sunset sail from Harbor Island. Up to 12 guests, warm blankets, snacks, and the best chance at a Coronado Bridge sail-under.
“Great experience to see the harbor and the San Diego Skyline! Beautiful views and lots of fun! We had a group of 13 girls on the sail for a bachelorette party and we were well taken care of!”
The sailing ports worth the trip, grouped by the sea they sit on.
