Set Sail in San Diego
A sailing tour of our beautiful bay will be the highlight of your trip to San Diego!
Welcome Aboard
Sailing tours & sailing lessons
on San Diego Bay
Relax while a Coast Guard–licensed captain shows you the bay, or take the wheel and learn to sail yourself. Lucky Sol is a veteran-owned sailing club that does both.
Beautiful Yachts
Our yachts have exceptional sailing characteristics & comfortable cruising accommodations for up to 6 guests.
Affordability
We offer very competitive pricing on our tours and private charter options. Like our Facebook page for last minute deals.
Location
We are located at Marina Cortez on Harbor Island – minutes from Gaslamp downtown with easy access to the airport.
Comfort
Our yachts have all the amenities of home, including bluetooth stereo, comfy seating, bathroom, and kitchen with refrigerator.
Sailing Tours
Your perfect day on the bay
The breeze picks up, the skyline slides past, and the city noise disappears behind you. Whether it’s a golden-hour sail for two or an afternoon out with your whole crew, your captain handles everything — all you have to do is be aboard.
Sailing Lessons
Start your journey today!
Whether you’re just getting started or planning to embark on a cruising adventure, we can help prepare you for the challenges you’ll face on the water.
Get 2 free online sailing courses from NauticEd!
Start learning before you ever step on the boat, free with our partner sailing school.
As a NauticEd affiliate, we may earn a commission when you enroll through our links, at no extra cost to you.
“Booked the private sailing trip when my (adult) kids and I got together in San Diego. Captain Jason was wonderful! Great experience! Highly recommend!”
“sailing with them was a blast, the staff was friendly, knowledgeable, and made the whole experience unforgettable. the views of the San Diego skyline were stunning!”
“We went out for a sunset tour with my Dad and Step Mom. It was amazing. Jason is such an expert and was such a pleasure to chat with. So accommodating. We had the best time. Thanks Jason!”
“I surprised my wife with a lil sail boat cruise in the SD bay, and I decided to go with Lucky Sol cruise. We met with captain Jason on the dock, the owner of the boat. Jason went over and behind for us, his boat was beautiful and very well keep up! Would definitely come back and recommend to family and friends”
“I booked a 2.5 hour sail with my husband and son. Booking and communication were solid. Jason was knowledgeable about the bay and pleasant. The boat was well maintained. We would definitely use Lucky Sol again.”
“Jason was incredibly responsive and professional. We could not have had a better experience with Lucky Sol. Will definitely sail again with them next time in San Diego!”
“I booked a sail for my wife and her friends for her 30th birthday this past weekend and they had a great time. In addition, we've sailed with Jason on our anniversary and once just for fun. The boat is very clean, Jason is very friendly and professional, and the trip is enjoyable and relaxing all at a great price. We'll continue to support Lucky Sol every time we head out on the water!”
“We have used Lucky Sol Sailing twice now and have had such a wonderful, effortless experience each time. Jason is knowledgeable, safe and really gave us the freedom to enjoy his boat with our friends. I will keep coming back to book with him anytime we are in need of some time on the water! Can't say enough about what a kind guy he is and what a great company he runs!”
“Booked a private sail for 6 people for my dad’s birthday. I was an absolute blast! It was a great experience. The boat is very clean, well kept, and comfy. Snacks and drinks were provided for a private sail. Jason (the Captain) is so friendly and a joy to be around! We will definitely be doing a sail again during the summer. Thank you, Jason! :)”
“Perfect day. Perfect Sail, Perfect Captain (Brent) & Crew (Son of Brent - Kent)”
“Booked the private sailing trip when my (adult) kids and I got together in San Diego. Captain Jason was wonderful! Great experience! Highly recommend!”
“sailing with them was a blast, the staff was friendly, knowledgeable, and made the whole experience unforgettable. the views of the San Diego skyline were stunning!”
“We went out for a sunset tour with my Dad and Step Mom. It was amazing. Jason is such an expert and was such a pleasure to chat with. So accommodating. We had the best time. Thanks Jason!”
“I surprised my wife with a lil sail boat cruise in the SD bay, and I decided to go with Lucky Sol cruise. We met with captain Jason on the dock, the owner of the boat. Jason went over and behind for us, his boat was beautiful and very well keep up! Would definitely come back and recommend to family and friends”
“I booked a 2.5 hour sail with my husband and son. Booking and communication were solid. Jason was knowledgeable about the bay and pleasant. The boat was well maintained. We would definitely use Lucky Sol again.”
“Jason was incredibly responsive and professional. We could not have had a better experience with Lucky Sol. Will definitely sail again with them next time in San Diego!”
“I booked a sail for my wife and her friends for her 30th birthday this past weekend and they had a great time. In addition, we've sailed with Jason on our anniversary and once just for fun. The boat is very clean, Jason is very friendly and professional, and the trip is enjoyable and relaxing all at a great price. We'll continue to support Lucky Sol every time we head out on the water!”
“We have used Lucky Sol Sailing twice now and have had such a wonderful, effortless experience each time. Jason is knowledgeable, safe and really gave us the freedom to enjoy his boat with our friends. I will keep coming back to book with him anytime we are in need of some time on the water! Can't say enough about what a kind guy he is and what a great company he runs!”
“Booked a private sail for 6 people for my dad’s birthday. I was an absolute blast! It was a great experience. The boat is very clean, well kept, and comfy. Snacks and drinks were provided for a private sail. Jason (the Captain) is so friendly and a joy to be around! We will definitely be doing a sail again during the summer. Thank you, Jason! :)”
“Perfect day. Perfect Sail, Perfect Captain (Brent) & Crew (Son of Brent - Kent)”
“One of the best trips one can do in SD .... lovely boat awesome captain ! More like sailing with a friend than a stranger...”
“Awesome sail - best views of the city and sunset from the harbor! Jason is a perfect captain, offering fun facts when elicited and knowing when to give you your space. Highly recommend!”
“We are novices to sailing and Captain Brett was fantastic, and our sailing was wonderful.”
“Thank you Jason for a beautiful and peaceful sail yesterday. Sailing with Lucky Sol Sailing is a perfect way to have a calm and relaxing get away from the daily grind of work and chores. We would recommend a sail with Lucky Sol Sailing any time of the year! Gary and Kandy”
“Booked a sunset sail with my girlfriend for my birthday and Captain Jason was amazing. He was friendly and professional and we learned a lot about San Diego. I never had been sailing before and he made our experience one to remember. I would highly recommend him and this tour company to anyone and I will defiantly book with him again!”
“I'd highly recommend a cruise with Luck Sol Sailing. We had a fantastic time. Every thing was top notch. We did the sunset trip. The boat & Captain were both outstanding. It was fun, relaxing and beautiful. Best SD excursion to splurge on... We would definitely do it again! I'd like to try a day trip too.”
“I highly recommend Lucky Sol Sailing for locals and tourists looking for an unforgettable sailing experience. We've been sailing with Lucky Sol Sailing several times now and always have an amazing time. Jason makes everyone feel welcome and safe, and goes above and beyond to ensure a fun, smooth sail. Looking forward to many more sails with you!”
“Jason was an excellent captain and we all loved the sunset cruise on his boat!”
“Lucky Sol Sailing was awesome! We had a great guide and ran a great tour of the San Diego Bay! I highly recommend this business if you want to see the Bay and surrounding parts of the city!”
“Amazing! Jason is an awesome captain and host. This was our second trip with Jason and we look forward to coming back again next year. Words can not fully describe the beauty of the area. See if for yourself!”
“One of the best trips one can do in SD .... lovely boat awesome captain ! More like sailing with a friend than a stranger...”
“Awesome sail - best views of the city and sunset from the harbor! Jason is a perfect captain, offering fun facts when elicited and knowing when to give you your space. Highly recommend!”
“We are novices to sailing and Captain Brett was fantastic, and our sailing was wonderful.”
“Thank you Jason for a beautiful and peaceful sail yesterday. Sailing with Lucky Sol Sailing is a perfect way to have a calm and relaxing get away from the daily grind of work and chores. We would recommend a sail with Lucky Sol Sailing any time of the year! Gary and Kandy”
“Booked a sunset sail with my girlfriend for my birthday and Captain Jason was amazing. He was friendly and professional and we learned a lot about San Diego. I never had been sailing before and he made our experience one to remember. I would highly recommend him and this tour company to anyone and I will defiantly book with him again!”
“I'd highly recommend a cruise with Luck Sol Sailing. We had a fantastic time. Every thing was top notch. We did the sunset trip. The boat & Captain were both outstanding. It was fun, relaxing and beautiful. Best SD excursion to splurge on... We would definitely do it again! I'd like to try a day trip too.”
“I highly recommend Lucky Sol Sailing for locals and tourists looking for an unforgettable sailing experience. We've been sailing with Lucky Sol Sailing several times now and always have an amazing time. Jason makes everyone feel welcome and safe, and goes above and beyond to ensure a fun, smooth sail. Looking forward to many more sails with you!”
“Jason was an excellent captain and we all loved the sunset cruise on his boat!”
“Lucky Sol Sailing was awesome! We had a great guide and ran a great tour of the San Diego Bay! I highly recommend this business if you want to see the Bay and surrounding parts of the city!”
“Amazing! Jason is an awesome captain and host. This was our second trip with Jason and we look forward to coming back again next year. Words can not fully describe the beauty of the area. See if for yourself!”
Good to Know
Common questions
Where do tours depart from?
All sails depart from Marina Cortez at 1880 Harbor Island Drive, minutes from downtown San Diego and the airport, with convenient parking on site.
Do I need any sailing experience?
None at all. Your Coast Guard–licensed captain handles everything. Just relax and enjoy the bay. Want to participate? Book the Intro to Sailing Lesson & Tour and take the wheel.
How many people can come aboard?
Private charters host up to 6 guests per yacht. Prefer to join others? The public group sail is priced per person.
How long is a sail?
Tours run 2.5 to 3 hours depending on the trip, long enough to see the bay properly without eating your whole day.
Can we celebrate a special occasion on board?
Absolutely. We regularly host proposals, birthdays, anniversaries, and celebrations of all kinds. Tell us what you're planning and we'll make it happen.
How do I book?
Book online anytime through our secure booking page, with live availability. Questions first? Call (619) 431-1415 or send us a message.
Ready to set sail?
San Diego Bay is waiting. Book your sail today, or reach out and we’ll plan something special together.