The bustling San Diego harbor delivers excellent sailing opportunities year-round. Small-group tours on sleek catamarans provide the most intimate experience, while historic Tall Ships offer hands-on sailing adventures perfect for maritime history buffs. Families particularly enjoy the dual-helm sailing excursions, which allow guests to try their hand at steering. Our favorite outings are the sunset cruises on modern luxury vessels – they combine comfort with spectacular views and typically include light refreshments. Most tours maintain generous cancellation policies and keep groups small, maxing out at 12 passengers. Let’s explore San Diego’s most outstanding sailing tours.
Key Points
- Sunset sailing adventures on catamarans with complimentary drinks and snacks, accommodating up to 6 guests for personalized experiences.
- Educational and family-friendly sailing tours on tall ships and private yachts, offering hands-on sailing activities and scenic views.
- Classic yacht sailing experiences with knowledgeable captains, offering wildlife sightings and iconic landmark views.
- Highly rated sailing tours with flexible cancellation policies and consistent 5-star reviews from satisfied customers.
- Accessible and unique sailing features, including complimentary amenities, dual helms for hands-on steering, and private tours for a personalized adventure.
Small-Group Sunset Sailing Experience on San Diego Bay
A popular sunset sailing experience on San Diego Bay, this small-group tour offers travelers a personalized and scenic adventure.
Accommodating a maximum of 6 people, the experience provides comfortable bean bag seating and opportunities to spot marine life and take photos of San Diego’s waterfront, military vessels, and historical landmarks.
Captained by experienced yacht captains, the 521 five-star reviews highlight the knowledgeable and accommodating crew, smooth sailing, and beautiful views.
With a 99% traveler recommendation, this sunset sail is ideal for special occasions. Guests can take advantage of the free cancellation and rescheduling policy up to 24 hours before the experience.
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San Diego: Californian Tall Ship Sailing and Maritime Museum
Sailing the Californian, the Official Tall Ship of California, offers visitors a unique hands-on experience exploring San Diego’s maritime heritage.
For $119 per person, guests can embark on a 4-hour adventure to engage in traditional sailing activities and learn historical facts from the crew.
The experience includes admission to the Maritime Museum of San Diego, where visitors can discover exhibits on the Navy, the Age of Sail, and the Age of Steam.
With a 5/5 rating based on 3 reviews, this sailing tour is highly recommended for families seeking an educational and interactive way to experience San Diego’s seafaring past.
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Small-Group San Diego Afternoon Sailing Excursion
Off the shores of San Diego, travelers can embark on a relaxing yet invigorating 3-hour sailing excursion aboard a small group tour.
Limited to just six passengers, the Small-Group San Diego Afternoon Sailing Excursion offers a personalized experience as you sail the harbor. Complimentary non-alcoholic beverages, light snacks, and alcoholic options like beers and hard seltzers are provided.
The tour also includes cold-weather gear and a surround-sound system for your music. With consistently high ratings and excellent reviews, this sailing adventure is perfect for vacations, celebrations, or simply enjoying the scenic Southern California days.
The tour departs from Shelter Island and returns to the same location, with flexible departure times to suit your schedule.
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San Diego: Classic Yacht Sailing Experience
Travelers seeking a classic sailing experience in San Diego can embark on a 2.5-hour tour aboard a hand-restored 1914 replica sailboat.
Priced from $109 per person, the all-inclusive experience offers scenic views of the USS Midway Aircraft Carrier and California coast landmarks, as well as the opportunity to spot wildlife like sea lions, dolphins, and sea birds.
The tour includes beer, white wine, soft drinks, and snacks, and is led by a live guide available in English.
Participants must sign a liability release and are subject to weather-dependent scheduling, with rescheduling or full refunds offered for weather-related cancellations.
With a 5/5 rating based on 40 reviews, this classic yacht sailing experience is a wonderful way to see downtown San Diego from the water.
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Small-Group San Diego Sunset Sailing Excursion
This 3-hour evening sailing cruise in San Diego offers a small-group experience limited to just 6 passengers, providing a cozy and intimate setting to watch the sunset over the Pacific Ocean with the city lights in the distance.
The cruise includes complimentary light beers, hard seltzers, non-alcoholic beverages, and light snacks.
Blankets and binoculars are provided for chilly weather and wildlife viewing, while passengers can bring their own music to enjoy on the boat’s surround-sound system.
With over 500 positive reviews and a 99% recommendation rate, this sunset sailing excursion is a memorable way to experience the scenic beauty of San Diego.
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San Diego Bay: Signature 2-Hour Sailing Tour
Embarking on a 2-hour sail around San Diego Bay, guests can soak in the city’s iconic skyline and keep an eye out for local marine life. Priced at Kč 3,087 per person, this small-group tour accommodates up to 6 participants and is conducted in English.
Highlights include sightings of harbor seals, pelicans, dolphins, and whales, as well as notable landmarks like the Coronado Bridge and aircraft carriers.
Booking is flexible, with a reserve-now-pay-later option. Participants should arrive 15-20 minutes early and park in a nearby secure lot.
While food and drinks aren’t included, guests are encouraged to tip their engaging and informative captains at the end of the 2-hour experience.
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Luxury Sailing Tour of San Diegos Bay and Coastal Waterways
For those seeking a luxurious sailing adventure in San Diego, the Luxury Sailing Tour of San Diego’s Bay and Coastal Waterways is a must-try experience.
Aboard a 34-foot Catalina sailboat, this small-group tour takes you on a journey through the city’s scenic waterways, led by a knowledgeable local captain.
With a 97% recommendation rate and a Badge of Excellence, the tour offers stunning views of landmarks like the Maritime Museum and Coronado Bridge.
Guests can enjoy snacks, bottled water, and even bring their own alcohol.
While not wheelchair-accessible, the tour is suitable for most travelers, except those with certain medical conditions.
Priced from $119 per person, this experience is a great way to explore San Diego’s coastal beauty.
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San Diego: Sunset and Day Sailing Excursion With Drinks
Visitors to San Diego can enjoy a captivating Sunset and Day Sailing Excursion that showcases the city’s breathtaking coastal landscapes. Priced from $101.15 per person, this 2.5-hour tour departs from Harbor Island and offers activities like sailing, sightseeing, and marine life viewing.
Guests can savor complimentary wine, beer, and soft drinks while admiring the skyline, Coronado Bridge, and Gaslamp Quarter. With knowledgeable guides providing local insights, the experience emphasizes creating unforgettable memories.
Suitable for small groups, the tour operates rain or shine and features a safety briefing. Reviewers praise the captains’ hospitality and the excursion’s overall positive experiences.
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Small-Group Yacht Sailing Experience on San Diego Bay
Travelers seeking a luxurious sailing adventure on San Diego Bay can experience the Small-Group Yacht Sailing Experience.
This 40-foot yacht cruise offers stunning views of the city’s skyline in comfort and privacy. With a maximum of 6 guests, the private experience provides the opportunity to spot dolphins, sea lions, and naval ships.
Onboard amenities include cozy bean bags, cushions, and blankets, as well as an included glass of wine. Experienced yacht captains ensure a memorable outing, and guests can bring their own food and drinks.
With 99% positive reviews, this sailing excursion is a highlight for many visitors to San Diego.
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San Diego: San Diego Bay Sunset & Daytime Sailing Experience
Explore the scenic San Diego Bay aboard a 2-hour sailing experience, offering either daytime or sunset voyages. Priced from $95 per person, this sailing tour departs from the Sunroad Resort Marina and sails along the San Diego skyline.
Guests may spot sea lions and dolphins, and private options are available for groups of 6. Onboard, enjoy white wine, soft drinks, and water, and bring your own food and drinks.
Hotel pickup and drop-off are provided, though gratuity isn’t included. With a 5/5 rating from 159 reviews, guests praise the personal attention from captains and the stunning views, making this a must-try activity in San Diego.
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Luxury Catamaran Sailing Charter of San Diego
For a private luxury sailing experience in San Diego, guests can charter a catamaran that accommodates up to 12 people.
The catamaran departs from San Diego Bay, passing by iconic landmarks like Sunset Cliffs, Pacific Beach, La Jolla, and Ocean Beach Pier.
The charter offers personalized service from the crew and includes bottled water, two ice-filled coolers for personal food and beverages, and the option to bring your own refreshments and music.
Priced from €1,129.89 per group, the experience has received 87 reviews with a 5.0 overall rating, and 99% of travelers recommend it, highlighting the excellent crew and memorable sunset views.
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San Diego: 2 Person Private Sailing Cruise With Snacks
San Diego’s tranquil harbor sets the stage for a private sailing adventure tailored to couples or small groups.
Lasting two hours, this cruise departs from Harbor Island, where a live English-speaking guide provides historical insights about the bay. Guests can take in scenic views of the San Diego skyline and spot local wildlife like seagulls, seals, sea lions, and dolphins.
Light snacks, sodas, and water are included, while optional beer, wine, and boxed lunches can be purchased.
With a flexible reservation policy and no upfront payment required, this €570.46 per group cruise offers a relaxing way to experience San Diego’s picturesque waterfront.
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5 Hours of Fun: Catamaran Sunset Sail
Offering a captivating sunset experience, the 2.5-hour Catamaran Sunset Sail in San Diego allows visitors to soak in the city’s picturesque waterfront.
Operated by Fun Cat Sailing Catamaran Adventures, this highly-rated tour boasts a 98% recommendation from travelers and a Badge of Excellence.
With a maximum of 6 guests, the intimate sailing experience features complimentary beer, wine, and snacks. Passengers can choose to participate in sailing tasks or simply relax and enjoy the smooth ride and stunning sunset views.
The tour departs from the Safe Harbor Sunroad marina, with convenient parking available nearby. Travelers are encouraged to dress for the cooler evening temperatures and bring their own additional refreshments if desired.
San Diego: Private 2-Hour Sailing Tour for 3-6 People
Explore San Diego Bay’s picturesque waterfront on a private 2-hour sailing tour for groups of 3 to 6 people. Priced at €657.34 per group, this experience offers the flexibility of free cancellation up to 24 hours in advance.
Along the way, you’ll learn to sail and take a turn at the helm, while enjoying views of landmarks like the Coronado Bridge and Maritime Museum. Keep an eye out for sea birds, sea lions, and maybe even dolphins.
Complimentary light snacks, soft drinks, white wine, and beer are included, along with the captain and crew’s services. Conveniently located at Cabrillo Isle Marina, this tour provides a memorable sailing adventure in San Diego.
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2-Hour Private Sailing Experience in San Diego Bay
Set out on a memorable 2-hour private sailing adventure in the picturesque San Diego Bay.
You’ll sail aboard a clean, spacious yacht, accommodating up to six passengers. Captain Liz, with her expert knowledge, will provide engaging commentary on the sights, including the USS Midway, Seaport Village, and harbor seal hideaways.
Enjoy complimentary bottled water, snacks, soda, and even a bottle of champagne. The experience can be tailored to your group’s preferences, with free cancellation and rescheduling up to 24 hours before.
Reviewers praise Liz’s friendliness and the boat’s comfort, often describing the sailing as relaxing, fun, and unforgettable.
Set sail for an exclusive 2-hour escape on the tranquil waters of San Diego Bay.
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San Diego: San Diego Bay Sailing Tour
The San Diego Bay Sailing Tour provides a remarkable opportunity to explore the picturesque waterfront of San Diego from a unique perspective.
Aboard a 42ft yacht, up to 6 guests can embark on a 2-hour guided tour, with options for daytime, sunset, or nighttime cruises. The tour showcases the city’s iconic landmarks, including the downtown skyline, Point Loma, USS Midway, and the Coronado Bridge.
Guests can enjoy complimentary bottled water, soda, snacks, and a bottle of champagne, and they’re welcome to bring their own food and drinks.
With a 5/5 rating based on customer reviews, this sailing experience is ideal for various occasions, from birthdays and anniversaries to team-building events.
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Day Sail Aboard a Classic Yacht : San Diegos Best-Kept Secret:
While the San Diego Bay Sailing Tour showcases the city’s iconic landmarks, there’s another sailing experience that’s often overlooked – the Day Sail Aboard a Classic Yacht.
This intimate, 6-person cruise aboard the restored vintage sailboat, Liberty, offers a unique and peaceful outing on the water. Guests can expect a comfortable setting with complimentary snacks, drinks, and knowledgeable commentary from Captain Philip, who shares insights about the bay and local history.
With excellent reviews, wheelchair accessibility, and flexible cancellation policies, this day sail is a must for those seeking a personalized and relaxing time on the water in San Diego.
Read our full review: Day Sail Aboard a Classic Yacht : San Diegos Best-Kept Secret: Review
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5-Hour Catamaran Sail Adventure
Travelers seeking a unique and exhilarating experience can enjoy the 2.5 Hour Catamaran Sail Adventure in San Diego Bay.
With a 100% traveler recommendation and a maximum of 6 passengers, this small group tour offers a personalized and relaxing atmosphere.
Complimentary beer, wine, and soft drinks are provided, and the option to sunbathe, observe sea life, or assist in sailing adds to the experience.
The captains are friendly and knowledgeable, and the overall feedback from customers highlights the smooth sailing, historical insights, and wildlife sightings.
Early reservations are recommended, as this experience is likely to sell out quickly.
Small-Group San Diego Sailing Trip
For those seeking a more intimate sailing experience in San Diego, the Small-Group San Diego Sailing Trip offers a 2-hour excursion through the harbor.
With a maximum of 6 guests per vessel, this tour provides a personalized outing to observe local wildlife and take in scenic views of downtown, Point Loma, and the surrounding islands.
Aboard a classically restored yacht, guests can enjoy complimentary snacks, wine, beer, and soft drinks while sailing under the guidance of an experienced skipper.
With 100% traveler recommendation and a perfect 5.0 rating, this small-group sailing adventure is a must-do for those seeking an intimate and picturesque experience on the waters of San Diego.
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Private Day Sailing for Couple
Couples seeking a private and picturesque sailing adventure in San Diego can embark on a 2-hour day sail aboard a classically restored yacht.
This exclusive tour accommodates a maximum of 2 passengers per charter and is recommended by 90% of travelers. Passengers will enjoy scenic views of San Diego’s coastline, including Downtown, Point Loma, Harbor Island, Shelter Island, and Coronado Island.
An experienced skipper ensures a safe and smooth sailing experience, and onboard amenities like cheese, salami, crackers, snacks, and bottled water are provided.
The charter departs from Cabrillo Isle Marina, and guests must arrive 15 minutes prior to the 2-hour tour.
Priced at $519 per group, this private sailing experience offers a unique way to explore San Diego’s beautiful waterfront.
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San Diego’s Finest Private Sailing Tours
Those seeking a private and serene sailing experience in San Diego won’t be disappointed with the city’s Finest Private Sailing Tours.
Boasting 27 stellar reviews, a 100% recommendation rate, and a coveted Badge of Excellence, this tour operator offers a 5-star rated sailing adventure aboard a beautiful 40-ft sailboat.
Guests can enjoy complimentary drinks and snacks while taking in the stunning harbor views and learning about San Diego’s history from the knowledgeable captain.
With dual helms that allow for hands-on steering, this tour is perfect for couples and families looking to escape the crowds and enjoy a tranquil, personalized sailing experience.
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Catamaran Sailing Cruise on San Diego Bay for up to 12 Guests
Adventurers can embark on a captivating Catamaran Sailing Cruise on San Diego Bay for up to 12 guests. Priced from $1,500 per group, this private tour offers a unique opportunity to sail the bay in style.
Guests will meet at the designated location, where they’ll be escorted to the boat. During the cruise, they’ll enjoy snacks and bottled water, while taking in the breathtaking scenery.
While moderate physical fitness is required, the experience isn’t recommended for those with certain medical conditions. After the tour, guests will return to the initial meeting point.
With a 5-star rating, this sailing adventure promises an unforgettable experience on the waters of San Diego Bay.
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Harbor Cruise on the Largest Catamaran in San Diego Bay
For a captivating harbor cruise in San Diego, visitors can embark on the largest catamaran in the bay. Operated by Triton Charters, this 22-review, 5.0-rated experience is recommended by 100% of travelers.
The cruise departs from the Commercial Dock next to Intrepid Boatworks, with free parking available. The 85-passenger vessel is staffed by a captain, crew, and bartender, offering a full bar (drinks not included) but no food or snacks.
While not wheelchair accessible, the spacious layout and scenic views make this a popular choice, though some suggest adding non-alcoholic options for kids.
With a lowest price guarantee starting at $55 per person, this is an excellent way to explore San Diego’s picturesque harbor.
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Private Luxurious Sailing Cruise in San Diego Bay
Embarking on a private luxurious sailing cruise in San Diego Bay, travelers are treated to an unparalleled experience.
Operated by Sail Riviera San Diego, this exclusive cruise offers a personalized and indulgent journey along the picturesque coastline. Accommodating up to six guests, the cruise includes a selection of alcoholic beverages, customized charcuterie boards, and panoramic views of the bay.
Conveniently located at the Sunroad Marina, the meeting point provides easy access, with parking available on-site. Lasting approximately three hours, the cruise departs at 3:30 PM, ensuring a memorable and relaxing afternoon for all participants.
With a 5.0 overall rating from 12 reviews, this private sailing experience is a must-try for those seeking a luxurious and unforgettable adventure in San Diego.
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San Diego Private Sailing Adventure
With the sun gleaming over the harbor, travelers can embark on a private sailing adventure aboard a classic yacht in San Diego.
This 3-hour excursion provides a unique opportunity to experience the city’s coastline from the water, with a price tag of $625 for up to 6 guests. The experience includes beer, wine, soft drinks, snacks, and gratuities.
Departing from the Safe Harbor Sunroad, the sailboat features a wooden mast, gaff rigging, and classic decor, offering a traditional nautical atmosphere.
While not wheelchair accessible, the tour is stroller-friendly and near public transportation. Moderate physical fitness is required, and infants must sit on laps.
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Frequently Asked Questions
Can I Bring My Own Food and Drinks on the Sailing Tour?
You can typically bring your own food and drinks on sailing tours. Most companies allow this, as long as you don’t bring anything that could spill or damage the boat. It’s a good idea to check with the tour operator beforehand.
What Is the Minimum Age Requirement for the Sailing Experiences?
The minimum age requirement for sailing experiences varies by operator, but is typically around 5-8 years old. Many tours welcome children and families, so check with the specific company for their age policies before booking.
Are There Any Restrictions on the Number of Passengers Allowed?
The number of passengers allowed on sailing experiences varies by provider. Many operators have limits on group size, often capping at around 6-12 passengers for a more intimate and personalized outing. Specific passenger restrictions should be confirmed with each sailing company.
Do I Need Any Prior Sailing Experience to Participate?
No, prior sailing experience is generally not required for most sailing tours and rentals in the area. Companies typically provide instruction and guidance to ensure a safe and enjoyable experience for first-time sailors.
Can I Customize the Sailing Route or Duration of the Tour?
Customers can often customize the sailing route and duration of tours, though options may be limited. Many providers offer some flexibility, but it’s best to inquire about specific customization possibilities when booking to ensure the desired experience.
Recap
With a diverse range of sailing experiences, San Diego offers something for every traveler. From sunset cruises and tall ship adventures to private luxury charters, visitors can enjoy the city’s rich maritime heritage. Whether seeking a group excursion or a personalized sailing journey, San Diego’s waterfront provides an unparalleled opportunity to create lasting memories on the waves.