To limit the spread of the coronavirus, attractions may be closed or have partial closures. Please consult government travel advisories before booking. The WHO is closely monitoring the coronavirus and more information can be found here.
Watch the sun set over San Diego during an all-inclusive small-group cruise aboard a classic sailboat. Pass landmarks such as the Maritime Museum, Coronado Bridge, and USS Midway, and look for sea lions, dolphins, and other wildlife around San Diego Harbor on the 2.5-hour cruise.
Harbor Sailing Experience | Private Sailing Tour in San Diego
From $299.00 per group
25th Birthday Party
, Jan 2020
This sailing cruise was exactly what we were looking for as a group of 5! We celebrated a 25th birthday down in San Diego and were looking for a casual sailing trip that had sight seeing and a great skipper! We all loved Russ - our skipper (i think that's his name). He was so fun!! He offered to take group photos and was very knowledgeable about the city and naval museums around the SD harbor. He had snacks and we were allowed to bring our own on board. OH AND HERE IS THE BEST PART - anytime we came by trash articles in the ocean our skipper would turn the sail boat around to go and get it out of the water!! We loved how conscious he was about the environment and we had tons of fun searching for and spotting trash for him to grab LOL. All in all a great trip and would HIGHLY recommend to others!! next time i'm in SD and want to sail I will be using the same company! :)
Rus was awesome from meeting to stepping back off the boat. The boat was incredibly clean. You can move around, relax and listen to all his knowledge. Nice guy, great price and totally worth every penny. Already want to book again!
We booked this sailing trip for a birthday surprise and it was absolutely perfect! The captain was awesome - he responded in a timely manner to all my questions before our sailing trip and when the day arrived he had thought of everything - snacks, drinks, blankets (it was a chilly day) and even had a captain’s birthday hat for my Dad! We had so much fun checking out the sights and enjoying the day together. We had two little ones on board and they loved it too! Overall - great experience that I would highly recommend! I’d love to do it again!
Go sailing on San Diego Bay with up to six friends on this private 2.5-hour sailboat charter. Pass by sights such as the Maritime Museum, USS Midway, Star of India, Coronado bridge, and more. Your captain shares commentary and provides refreshments such as white wine and fruit. You might see Navy ships near the Navy base, and glimpse marine life such as seals and seabirds.
This was the most wonderful whale watching experience ever. The boat was gorgeous, the crew absolutely spectacular and the wells were stunning… Just 20 yards off the side of our boat. Everything was simply perfect.
Crew and especially the tour guide were terrific, professional, helpful, and very entertaining. It's a beautiful ship and we had a truly wonderful time. Best cruise on the high seas, with good views of whales, dolphins, and sea lions.
Go whale watching from San Diego aboard a replica of a historic sailing schooner that won the world’s first America’s Cup sailing competition in 1851. Throughout your cruise, your expert guide shares informative commentary about gray whales, dolphins, and other marine animals, along with details about the US Navy sites you pass as you head out on the Pacific Ocean.
Meet your skipper at H & M Landing on Shelter Island, a well-known area of San Diego where some of the best seafood restaurants are located. The captain will meet you there & walk you to the yacht "Green Flash" After brief safety instruction, we'll set sail.
Complimentary wine & beer will await you (you are welcome to bring your favorite food & drinks, too - no red wines please). We'll depart from America's Cup Harbor & cruise on San Diego Bay along Point Loma while enjoying the city’s magnificent skyline.
You will enjoy a relaxing sail with a glass of good local wine & pleasant company along with a sense of unity with nature that comes with being under sail.
Affordable Luxury Sailing Tours of San Diego's Bay and Coastal Waterways!
You won't regret!
, Sep 2019
By far the best thing I did while in San Diego for work. The views from the water are amazing and Mike made the whole experience so great. This didi not disapoint at all. I can't wait to come back and sail again one day!
Sail into the setting sun aboard a Catalina style sailboat during this intimate cruise with a small group. Feel like you have the ship all to yourself on this trip that’s limited to just 12 total guests, watching as the last rays of the sun drop into the glistening waves. Enjoy the included beer, wine, soft drinks and snacks during the ride, as well as jackets and wind gear in case you get cold. You can even plug in your own music to add to the fun. Departure times vary throughout the year. Guest must contact Sail San Diego after purchase for the exact departure time.
We booked this excursion because we wanted to do something we had never done before to celebrate our 27th Wedding Anniversary. Well, Happy Captain Greg delivered an amazing sailing experience for us! He pointed out special sightings and provided us with explanations for each. He was friendly, experienced, and gave us great service. The vessel was beauful and fully equipped with more snacks and spirits than we could possibly finish in a 3-hour period. Binoculars and blankets on board added another convenient touch to our experience. Highly recommend them!
Enjoy a sailing adventure on a Catalina-style sailboat with just six people for a comfortable, semi-private experience (or, find five friends and fill up the whole boat). Sail in San Diego Harbor during the day. Sit back and relax to enjoy the water views while enjoying complimentary beer, wine, soft drinks and snacks.
Cruise around San Diego bay aboard an authentic 1992 America’s Cup racing yacht and travel at twice the speed of the average sailboat. The Stars and Stripes USA-11 is one of the fastest and best known America’s Cup racing yachts. It was designed and built to be raced in San Diego, and has been restored to pristine condition. Take a turn at the helm and join in grinding the winches to raise and trim the sails.
A Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several different types of sailing charters and boat tours. Sail San Diego with us.
Our sailing charters and boat tours take you on an exciting tour of San Diego Bay. Book a sailing boat charter and stretch out in the San Diego sunshine with a trusty skipper at the helm, Choose from several types of yacht charters, catamaran cruises, sailboats, and powered luxury yachts. A sailing boat tour on San Diego Bay with Pacifica Sailing Charters is the perfect sailing experience for you and your guests. .
With over 20 years of boating on San Diego Bay and the waters surrounding the San Diego harbor, our boat charters and sailing boat tours are rated #1 on Google, Yelp, and TripAdvisor...
Embark on your very own private 3, 4, or 6 hour extended San Diego sailing adventure. Enjoy an intimate sail with friends and family.
Take in the coastal sights of famous San Diego landmarks from a different vantage aboard a "classic" Slocum styled vessel. She is from an era where sea-going was for exploration of new worlds. These boats were used in the popular "Captain Ron" or "50 FIRST DATES" movies due to their classic lines. Beautiful hand carved old growth Burmese teak, and bronze accents throughout.
Great vessel for spectacular photo opportunities, or to venture to times long past. If you choose the open ocean route with a longer duration, you may even get to see some dolphins, whales or other unsuspecting sea-life along the way.
Embark on your own "private" 2-4 hour San Diego CLASSIC sailing Experience. Enjoy an intimate sail with friends and family. Take in the coastal sights of famous San Diego landmarks from a different vantage aboard a "classic" Slocum styled vessel. She is from an era where sea-going was for exploration of new worlds.
These boats were used in the popular "Captain Ron" or "50 FIRST DATES" movies due to their classic lines. Beautiful hand carved old growth Burmese teak, and bronze accents throughout.
Great vessel for spectacular photo opportunities, or to venture to times long past.
If you choose the open ocean route with a longer duration, you may even get to see some dolphins, whales or other unsuspecting sea-life along the way.
San Diego's best kept secret awaits aboard your private SUNSET cruise on San Diego Bay. See the beauty of downtown cityscape, Embarcadero, Maritime Museum from the ocean which offers a different vantage.
Sip cocktails, share a romantic moment, drop a proposal for engagement, or just enjoy a one of a kind San Diego sunset. Flexibility to customize your itinerary to your own preferences, perfect for couples.
Enjoy intimate moments with friends and family aboard a "classic" Slocum styled sailing vessel. She is from an era where sea-going was for exploration of new worlds and becoming a rare experience today.
These classic designs were used in the popular "Captain Ron" or "50 FIRST DATES" movies due to their classic lines. Beautiful hand carved old growth Burmese teak, and bronze accents throughout. Great vessel for spectacular photo opportunities, or to venture to times long past.
A Once-in-a-Lifetime Experience!
Set sail at one of the best times of day—sunset—during this San Diego Bay cruise. Board a comfortable sailing yacht and cruise along San Diego's coastline, taking in views of the scenic waterfront, military vessels, and historical landmarks. Catch sight of marine life and enjoy spectacular photo ops. Gorgeous sunset views and Champagne makes this tour a great choice for couples or travelers celebrating a special occasion.
Sail the lovely waters off San Diego on a private yacht charter. The itinerary is up to you, or your captain can suggest some places to go. You can opt for a whale watching tour (seasonal), or lay anchor and go for a swim. If you prefer, choose a bay tour; seeing the sights like the Hotel del Coronado, Point Loma Lighthouse, Tijuana, and the San Diego skyline.
Head out onto the waters off the coast of San Diego for a private sailing adventure. Charter your own boat and bring your group of up to six to take in San Diego’s sights from the water. Enjoy a fully customizable experience—just chat with your skipper about your preferences for your sail. Feel free to bring your own wine without worrying about a corkage fee and enjoy complimentary refreshments onboard.
Set sail from San Diego on your own private sailboat cruise that can accommodate up to 12 people. Depart from the Hyatt Regency Mission Bay and glide out to the Pacific Ocean, passing landmarks like Sunset Cliffs Natural Park, Pacific Beach, La Jolla, and Ocean Beach Pier. Get great views of southern California’s landscape and wildlife, and feel free to bring your own refreshments and music to customize your cruise.
Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 12 guests. Enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarines, not to mention an incredible abundance of sea life including Sea Lions, Dolphins and Whales. Whether you need a classic sailboat or catamaran for your Bachelorette Party, we can provide a private catamaran that is roomy, comfortable and stable. Much heavier than traditional boats today, Sea Esta will provide a steady, smooth sail no matter what the conditions. This large and stable catamaran is perfect for sightseeing around San Diego Bay and the perfect bachelorette party yacht for you and your guests.
A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several different types of sunset sailing charters and boat tours. Our sunset sailing charters and boat tours take you on an exciting tour of San Diego Bay. Book a sunset sailing boat charter and stretch out in the San Diego sunshine with a trusty skipper at the helm, A sunset sailing boat tour on San Diego Bay with Pacifica Sailing Charters is the perfect sailing experience for you and your guests. With over 20 years of boating on San Diego Bay and the waters surrounding the San Diego harbor, our sunset boat charters and sunset sailing boat tours are rated #1 on Google, Yelp, and TripAdvisor.
Sail the magnificent San Diego Bay on this private cruise aboard a restored 1934 sailboat. A personalized alternative to crowded group outings, the cruise can be tailored to you; help sail the boat, or just relax on deck enjoying included drinks and snacks. With service from a captain and two crew members, you’ll cruise past San Diego landmarks from the Coronado Bridge to the Embarcadero.
Weather great, Captain Max was great. Highly recommend this vendor. Captain Max was friendly and informative. Nice boat with lots of character. Vendor worked around our schedule and made it easy to get out on the water. This charter was well worth the money and would gladly do it again.
This 2 to 2.5 hour small-group sail seats up to 6 people. You can relax comfortably or invite a group of friends to sail along Point Loma in San Diego. Your guide will gracefully glide passed beautiful views and landscapes near San Diego's skyline for you to enjoy the breath talking scenery.
If interested, you can also learn the basics of sailing while gazing at the glistening water and SD's spectacular scenes.
Come relax and enjoy with your choice of white wine or beer, (pls specify when booking).
Although it says only 15 guests upon check out, we actually can take up to 27 guests on this cruise, and the pricing reflects this amount of guests.
Sailing San Diego Bay is an awesome way to spend an afternoon in beautiful San Diego. Whether you want to go on an exciting adventure where you take the wheel, or if you just prefer to stretch out in the San Diego sunshine with a trusty skipper at the helm, Pacifica Sailing Charters provides fun and exciting boat tours for the perfect sailing experience for you.
There’s plenty of room to explore sailing san diego and everyone gets a chance at the wheel if they feel adventurous on these sailing charters located in san diego.
With over 20 years of boating and sailing on San Diego Bay and the waters surrounding the San Diego harbor, we excel at ensuring each sailing tour, boat charter and catamaran cruise and sailing lesson is a memory you will cherish for a lifetime.
A fully restored 70 foot private sailing ship for your own private group of upto 12. We can comfortably accommodate 12 passengers, we have a bluetooth stereo, and a immaculate interior belowdecks. There is a clean restroom belowdecks and we have a tremendous crew. You will have a Captain and two crew on board to assist with all the sailing, answer any questions, and to assist you in anything needed. If you would like you can assist in hoisting and trimming sail, or, you can sit back and enjoy a cold beverage and some salami, cheese, and crackers.
This is a combination lesson & tour of the bay which gives guests the unique opportunity to learn about sailing and see the sights. It's perfect for someone who has considered learning how to sail but also wants to take friends or family members on a sightseeing tour.