San Diego
The sunset sails: the sun dropping behind Point Loma while the skyline lights come up across the bay. Sailboats and motor yachts work the same golden window from different decks.
Experience San Diego’s stunning sunset from a small, intimate sailing yacht with great views, knowledgeable guides, and comfortable amenities for $112.50.
Most Popular“our captain was fantastic :) we got really close to some sea lions which was awesome! also the pinot grigio was a nice touch.”
Enjoy a private, 3-hour sunset sailing in San Diego with limited groups, stunning views, drinks, snacks, and your own music for a personalized experience.
“An incredible, relaxing, and peaceful experience! Captain Kenley made it truly memorable with his insights about the surroundings, pointing out landmarks, and making sure we spotted some sea lions. The weather was perfect, with great winds and clear skies that set the stage for an…”
Experience San Diego’s stunning sunset from a vintage sailboat, with wine, wildlife sightings, and iconic landmarks onboard a small, intimate cruise.
“A wonderful anniversary sunset cruise with Captain Phillip. The scenery including two aircraft carriers, The Coronado Bridge, a yacht confiscated from a Russian Olegard, and the gorgeous San Diego skyline was truly magical”
Discover San Diego’s coastline on a small-group sunset or day sail. Enjoy stunning views, marine life sightings, onboard drinks, and an authentic sailing experience.
“Ann was a fantastic captain and host! She is skilled and a lot of fun! The boat was very comfortable and we had a great time.”
Experience San Diego’s stunning sunsets on a relaxing 1-hour 15-minute cruise from Mission Bay, passing SeaWorld and Ocean Beach Pier with drinks and great views.
“Staff was very friendly and helpful. Was surprised to see how full the boat was. The cruise was smooth sailing.”
Enjoy a 2.5-hour sunset sail on a spacious catamaran in San Diego, with drinks, stunning skyline views, and chances to spot sea lions and dolphins.
“💯 worth it! We had a great experience with Captain Ryan. He was so knowledgeable and friendly. We did the sunset Catamaran Sail and had such an amazing night!”
Experience stunning San Diego views on a 2-hour daytime or sunset sailing cruise. Relax with wine, spot sea lions, and enjoy personalized guidance.
“Thank you so much Corinne for making this experience super memorable! ❤️”
Discover San Diego's bay on a 1.5-hour sunset cruise featuring complimentary appetizers, drink specials, and onboard entertainment—perfect for relaxing evenings.
“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…”
Discover San Diego on a private sunset sailing tour with stunning bay views, friendly crew, snacks, and the chance to see iconic landmarks up close.
“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!”
Experience stunning San Diego sunsets aboard a private sailboat with drinks, snacks, and scenic views—perfect for a romantic evening or special outing.
“Fabulous cruise with a fabulous Captain! A wonderful experience I would certainly recommend.”
Experience stunning San Diego sunsets aboard a scenic cruise with drinks, appetizers, and lively music—perfect for a relaxed, scenic evening on the water.
“The sunset was beautiful! But the boat needed some work - looked like it was old and needed painting, renovating, updating. The drinks were terrible - had a bad flavor”
Experience San Diego’s beauty with a 2.5-hour sunset or day sailing cruise. Enjoy drinks, stunning views, and insider insights from knowledgeable guides.
“It was the perfect amount of people and extremely relaxing.”
Experience San Diego’s highlights on a self-guided GoCar tour, exploring Sunset Cliffs, beaches, and historic sites with stunning views and flexible pacing.
“Must do! It was very fun. It brought us around to many places and things we didn’t have time to see otherwise!!”
Enjoy a 3-hour luxury sail in San Diego Bay, taking in iconic sights, wildlife, and coastal scenery—perfect for relaxing, sightseeing, and making memories.
“Our torn with Greg was amazing. He was super nice and funny and my husband even got to steer for a while. We had always wanted to go sailing, and it was a wonderful experience for us. We can 100% recommend it. Thank you, Greg!”
Experience stunning San Diego sunsets with a 2-hour sailing on the bay, perfect for families, couples, or groups seeking adventure and scenic views.
“Everything for our trip went just as planned. Aiden was a spectacular host, and I would recommend this trip to anybody and everybody. Parking can be difficult during high season. I recommend using the valet service at The Monsaraz for $15.”
Sea caves, sails and a zoo that set the standard, all in shirtsleeve weather.