San Diego’s sailing scene is simply terrific – I love it. These Pacific waters offer some of the best views of the city skyline and marine life you’ll find anywhere. Small-group afternoon cruises are my favorite, especially the sunset tours that provide close-up views of sea lions and the naval base. For a splurge, private charters deliver wonderful personalized experiences – the crews really know their stuff and the complimentary drinks are a nice touch.
I’m particularly fond of the classic yacht tours aboard restored vessels, where you get a real sense of maritime history along with your sightseeing. The family-friendly catamarans are another solid choice, offering stable rides and plenty of space to move around.
Let’s look at my recommended sailing tours in San Diego, ranked from best value to pure luxury.
Good To Know
- For a sunset sailing experience with stunning views, consider the Deluxe Sunset Sailing Excursion, which is rated 5.0 stars and 97% recommended.
- The Deluxe Day Sail Experience offers a full-day sailing adventure with a 100% recommendation rate, 5.0 overall rating, and complimentary alcoholic beverages.
- For a private sailing experience, the Private Luxurious Sailing Cruise provides a 3.5-hour cruise for up to 6 guests, including charcuterie boards.
- The San Diego Private Sailing Adventure offers a 2.5-hour sunset tour for up to 6 guests, with complimentary beer, wine, and snacks.
- While most tours are not wheelchair accessible, stroller-friendly options are available, and the proximity to public transportation enhances accessibility.
Small-Group San Diego Afternoon Sailing Excursion
The Small-Group San Diego Afternoon Sailing Excursion offers a unique opportunity to experience the city’s beautiful harbor from the comfort of a sailing yacht.
This 3-hour cruise, limited to just six passengers, provides an intimate sailing experience. Guests can enjoy complimentary non-alcoholic beverages, light snacks, and even bring their own music to play on the boat’s surround-sound system.
The captains share their knowledge upon request, allowing passengers to learn about the notable landmarks they pass, such as the Coronado Bridge and the USS Midway Museum.
With the provided gear and the chance to spot wildlife, this sailing excursion is a must-try for those seeking a relaxing and scenic outing in San Diego.
Read our full review: Small-Group San Diego Afternoon Sailing Excursion Review
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Small-Group San Diego Sunset Sailing Excursion
As the sun begins to dip below the horizon, visitors embark on the Small-Group San Diego Sunset Sailing Excursion, a 3-hour evening cruise that offers an intimate and relaxing way to experience the city’s vibrant waterfront.
Limited to just 6 guests, the sailboat cruise provides stunning views of the sunset and city lights. Guests can bring their own music to enjoy through the surround-sound speakers and savor complimentary beer, soft drinks, and light snacks.
Blankets are provided for warmth, and binoculars are available for wildlife viewing. With a 5.0-star rating and 99% of travelers recommending the experience, this sunset sailing excursion is perfect for special occasions or casual outings.
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Small Group Sunset Sailing Experience on San Diego Bay
Departing from Gate 1 Docks A-D on Harbor Island Drive, the Small Group Sunset Sailing Experience on San Diego Bay invites visitors to embark on an intimate 3-hour journey across the tranquil waters.
With a maximum of 6 travelers per tour, this highly-rated experience (99% traveler recommendation) provides a comfortable and personalized setting. Guests can relax on the boat’s bean bags and cushions while experienced sail yacht captains guide them through the bay, sharing local insights and knowledge.
The tour includes stunning sunset views, sightings of sea lions, and a hassle-free end back at the meeting point. Priced at $98.10 per person, it’s the perfect activity for romantic outings, celebrations, and small group adventures.
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2-Hour Private Sailing Experience in San Diego Bay
Tailored to the preferences of up to six travelers, the 2-Hour Private Sailing Experience in San Diego Bay invites guests to embark on a customized journey across the tranquil waters.
The clean, spacious sailing vessel boasts room for the entire group and comes equipped with bottled water, snacks, soda, and a complimentary bottle of champagne.
Guests can relax and enjoy the stunning views while sipping on provided alcoholic beverages, as a dedicated captain navigates the yacht.
With a 5.0 overall rating from 140 reviews and a Badge of Excellence, this private sailing excursion offers an unforgettable experience, complete with an accommodating captain and a comfortable, well-appointed boat.
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Affordable, Luxury Sailing Tour of San Diegos Bay and Coastal Waterways
Offering an affordable, yet luxurious sailing experience, the Sailing Tour of San Diego’s Bay and Coastal Waterways invites guests aboard a 34-foot Catalina sailboat for a small-group adventure.
With 97% of travelers recommending the tour, it boasts a Badge of Excellence and an impressive 5.0 overall rating.
Captained by a local expert, the tour provides informative commentary and the opportunity to steer the vessel, all while guests enjoy stunning views and a relaxing atmosphere.
Complemented by snacks, bottled water, and a BYOB policy for those 21 and over, this experience caters to most travelers, though it’s not recommended for those with back problems or serious medical conditions.
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San Diegos Best-Kept Secret: Sunset Sail Aboard A Classic Yacht
For those seeking a more intimate and authentic sailing experience, the Sunset Sail Aboard A Classic Yacht offers a hidden gem in San Diego.
Modeled after a 1904 vintage sailboat, this 2.5-hour tour aboard the classic yacht Liberty provides a personalized and relaxing journey.
Sail past iconic landmarks while learning about traditional sailing techniques with the knowledgeable Captain Philip.
Enjoy the serene atmosphere, free of loud music or party crowds, and keep an eye out for wildlife like sea lions and dolphins.
With a maximum of 6 travelers, this sunset sail is perfect for couples and families looking to create lasting memories on the water.
Read our full review: San Diegos Best-Kept Secret: Sunset Sail Aboard A Classic Yacht Review
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5 Hour Catamaran Sunset Sail. Catamarans Are More Fun!
A 2.5-hour Catamaran Sunset Sail takes travelers on a captivating journey along the San Diego coastline.
At $119 per person, this activity offers excellent value with its inclusiveness – beer, wine, soft drinks, and bottled water are provided.
With a maximum of 6 travelers, the experience promises an intimate and exclusive atmosphere. Guests can relax on blankets while taking in the breathtaking views and listening to music.
The knowledgeable and friendly captains contribute to the overall enjoyment.
While some minor issues with beverage temperature have been noted, the vast majority of reviews highlight the relaxing ambiance, stunning sunsets, and the fun of sailing aboard a catamaran.
Small-Group San Diego Sailing Trip
Travelers seeking a more intimate sailing experience in San Diego will find the Small-Group San Diego Sailing Trip an excellent choice.
This 2-hour excursion accommodates a maximum of 6 guests, allowing for a personalized and scenic adventure. Aboard the sailboat, guests can search for local wildlife like harbor seals, pelicans, and sea lions, while taking in the beautiful views of the San Diego coast.
The experienced skipper ensures a safe and enjoyable sail, and the included snacks, beverages, and friendly service make for a well-rounded experience.
With free cancellation up to 24 hours prior and a 5.0 rating from 47 reviews, this small-group sailing trip is a great option for those looking to explore San Diego’s harbor.
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San Diego’s Finest Private Sailing Tours
Situated at the Safe Harbor Sunroad marina, San Diego’s Finest Private Sailing Tours offers an unparalleled sailing experience for groups and couples seeking a personalized adventure on the city’s stunning waterways.
With a 5.0 overall rating and a Badge of Excellence, this highly-recommended tour boasts a comfortable yacht, knowledgeable captain, and top-notch amenities.
Guests rave about the relaxing atmosphere, beautiful views, and excellent hospitality provided by Captain Rob and Claire.
Whether celebrating a special occasion or simply seeking a peaceful outing, this private sailing tour is an ideal choice for those wanting a memorable experience on the San Diego Bay.
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Day Sail Aboard a Classic Yacht : San Diegos Best-Kept Secret:
Tucked away in the heart of San Diego’s bustling harbor, Day Sail Aboard a Classic Yacht offers a unique and intimate sailing experience that’s been dubbed the city’s best-kept secret.
With a maximum of 6 travelers per tour, this classic yacht cruise provides a relaxing and personalized outing on the water. Guests can savor complimentary drinks and snacks while Captain Phillip shares his extensive knowledge of the bay.
The restored vintage sailboat, Liberty, offers stunning views of the harbor, sea lions, and potential dolphin sightings. Consistently earning 5-star reviews, this experience is a must-do for anyone seeking a truly memorable sailing adventure in San Diego.
Read our full review: Day Sail Aboard a Classic Yacht : San Diegos Best-Kept Secret: Review
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San Diego Sunset Sailing Excursion
What better way to cap off a day in San Diego than with a deluxe sunset sailing excursion? Boasting a 5.0-star rating, the Deluxe Sunset Sail in San Diego offers an exceptional small-group experience.
Guests can enjoy stunning views of the Coronado Bridge, Point Loma, and San Diego Bay as the sun dips below the horizon. Sightings of dolphins, seabirds, and sea lions are common.
The knowledgeable and friendly captains enhance the experience, engaging with guests and sharing local insights. With complimentary drinks, including alcoholic beverages, this 97% recommended tour is perfect for celebrating special occasions or simply taking in the beauty of San Diego’s coastline.
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San Diego Sunshine Sailing Excursion
For those seeking a delightful daytime sailing experience in San Diego, the Deluxe Day Sail offers a hidden gem.
With a 100% recommendation rate and a perfect 5.0 overall rating, this tour provides an exceptional value at ₹9,979.61 per person.
Accommodating up to 6 travelers, the experience features complimentary alcoholic beverages, bottled water, and soda.
Guests rave about the beautiful scenery, attentive service, and personal touches from the various captains.
Although not wheelchair accessible, the tour’s central meeting point and easy parking make it accessible.
With free cancellation up to 24 hours in advance, the Deluxe Day Sail is a must-try for those looking to bask in San Diego’s sunshine on the open waters.
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San Diego Small Group Catamaran Sailing Excursion
The San Diego Small Group Catamaran Sailing Excursion offers a unique and intimate way to experience the city’s picturesque harbor. This 2.5-hour adventure aboard a catamaran is highly recommended by travelers, boasting a perfect 5.0 rating based on 39 reviews.
Guests can relax and soak up the sun while observing local marine life and Navy ships. The small group size (max 6 travelers) ensures a personalized experience, and complimentary beer, wine, and soft drinks add to the enjoyment.
With free cancellation up to 24 hours in advance and a Reserve Now and Pay Later option, this sailing tour provides flexibility and convenience. Customers consistently praise the captain’s hospitality and the overall smooth, memorable experience.
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Private Day Sailing for Couple
On a private 2-hour sailing tour for couples in San Diego Bay, guests can embark on a memorable experience aboard a classically restored yacht.
Recommended by 90% of travelers and boasting a perfect 5.0 rating from 10 reviews, this tour offers an intimate setting with a maximum of 2 passengers per charter.
Guests will sail past iconic landmarks, including Downtown San Diego, Point Loma, Harbor Island, Shelter Island, and Coronado Island, while enjoying complimentary appetizers, a glass of wine or beer, and bottled water.
Gratuities and parking fees are covered, and the tour departs from Cabrillo Isle Marina with a flexible, customizable itinerary based on guests’ interests.
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Harbor Cruise on the Largest Catamaran in San Diego Bay
Triton Charters offers travelers the opportunity to experience the largest catamaran in San Diego Bay.
With a 100% traveler recommendation rate and a Badge of Excellence, this 1.5-hour cruise is a must-do for visitors. At $55 per person, the tour accommodates up to 85 travelers, providing a peaceful and relaxing atmosphere.
The crew, including a captain, crew, and bartender, enhances the experience with their fun and engaging presence. While no food or snacks are available, the full bar offers drinks for purchase.
Travelers rave about the scenic views, especially during sunset cruises, making this a great outing for a reasonable price.
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Private Luxurious Sailing Cruise in San Diego Bay
If you’re looking for an exclusive and indulgent way to experience San Diego’s picturesque bay, Sail Riviera San Diego’s Private Luxurious Sailing Cruise is an exceptional choice.
This 12-reviewed, 100% recommended tour accommodates up to 6 guests and offers a range of alcoholic and non-alcoholic beverages, as well as customized charcuterie boards.
Departing from the Sunroad Marina, the 3.5-hour cruise ends back at the same location. While not wheelchair accessible, the tour is conveniently located near public transportation. Guests can take advantage of the available paid parking or use ride-share apps.
With free cancellation and unlimited rescheduling up to 24 hours before the tour, this private sailing experience is a luxurious and flexible way to enjoy San Diego’s stunning bay.
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Private Sail Yacht Experience on San Diego Bay
Situated within the stunning San Diego Bay, the Private Sail Yacht Experience invites guests to embark on a leisurely and personalized sailing adventure.
Priced from $599 for up to 6 people, this private tour boasts an impressive 5.0 rating across 7 reviews. Guests will enjoy the services of a private guide, as well as complimentary white wine, soda, water, and chocolates.
Visitors are welcome to bring their own food and drinks, and can relax aboard the yacht as it navigates the picturesque harbor.
With free cancellation up to 24 hours in advance and a convenient meeting point, this sailing experience offers a truly unforgettable way to explore the beauty of San Diego Bay.
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San Diego Private Sailing Adventure
Guests embark on a captivating 2.5-hour sunset tour aboard a hand-restored 1914-styled sailboat in San Diego.
This intimate experience accommodates a maximum of 6 guests, offering the opportunity to participate in sailing the boat. Complimentary beer, wine, and snacks are included, allowing guests to savor the moment as they pass by landmarks like the USS Midway and Pt Loma lighthouse, spotting sea lions and other wildlife along the way.
With a traditional sailboat equipped with a wooden mast, gaff rigging, and classic decor, this private sailing adventure provides a unique and memorable experience in San Diego.
Moderate physical fitness is required, and infants must sit on laps.
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Catamaran Sailing Cruise on San Diego Bay for up to 12 Guests
Aboard a spacious catamaran, guests embark on a captivating sailing cruise along the picturesque San Diego Bay.
This private tour accommodates up to 12 people, providing an intimate and personalized experience.
With 2 positive reviews, the 2-hour cruise departs from the Marina Cortez building, where guests can access paid parking.
The tour includes snacks and bottled water, and tipping the captain and crew is customary.
However, it’s not recommended for travelers with back problems or serious medical conditions, as a moderate level of physical fitness is required.
Children are welcome but must be accompanied by an adult, and luggage restrictions apply.
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Sunset Sailing Tour of San Diego Bay up to 6 Guests
Set out on a captivating Sunset Sailing Tour of San Diego Bay, accommodating up to 6 guests.
You’ll sail past downtown, aircraft carriers, and submarines, with the potential to spot marine life like sea lions and dolphins.
The tour is led by a professional captain and includes snacks and bottled water. Tipping is customary at 18-20% of the charter fee.
Meet at the designated location, call for an escort, and enjoy the activity ending back where you started.
While not wheelchair accessible, the tour is stroller-friendly and near public transportation.
However, it’s not recommended for travelers with certain medical conditions.
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Sailing Charter Sightseeing Cruise on San Diego Bay up to 6 Guests
Adventurous travelers can embark on a private sailing charter sightseeing cruise around San Diego Bay.
The cruise offers beautiful views of beaches, navy outposts, and abundant sea life, including sightings of sea lions, dolphins, aircraft carriers, and submarines.
Options include catamarans, sailboats, or powered luxury yachts, with morning, afternoon, or sunset trips available.
The starting price is $600 per person, and tipping the captain and crew is customary.
While the tour isn’t wheelchair accessible, it’s stroller-friendly and near public transportation.
Travelers should note the non-refundable policy and that the cruise isn’t recommended for those with back problems, pregnant women, or those with serious medical conditions.
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Private Sailing Tour -2 Hour (Up to 12 Passengers)
Travelers seeking a more intimate sailing experience can consider the Private Sailing Tour – 2 Hour, which accommodates up to 12 passengers.
Located in San Diego, this private tour departs from the Hyatt Regency’s cafe and returns to the same meeting point. Priced at $1,200 per group, the tour is wheelchair and stroller accessible, and allows service animals.
Passengers can enjoy the sailing experience from 9:30 AM to 8:00 PM, with various schedule options available. Guests can reserve the tour now and pay later, and cancellations are free up to 24 hours before the start.
This private sailing tour offers a personalized sightseeing adventure on the waters of San Diego Bay.
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San Diego Sailing Yacht Excursion Private Charter
The San Diego Sailing Yacht Excursion Private Charter offers a deluxe sailing experience on the waters of San Diego. Priced at $543.20 per group of up to 6 people, this 2-hour tour provides a private sunset and day sail.
Included are alcoholic beverages like beer, wine, and seltzers, as well as non-alcoholic options. Guests must arrive 20 minutes early and meet the captain at Gate 1 in the Sunroad Safe Harbor Marina.
While the tour isn’t wheelchair accessible, most travelers can participate. Reviews praise the breathtaking views, luxurious boat, and the captain’s expertise, making this a memorable outing for any group.
Read our full review: San Diego Sailing Yacht Excursion Private Charter Review
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Private Catamaran Cruise Through San Diego Bay
For an unforgettable experience on the waters of San Diego Bay, the Private Catamaran Cruise offers a delightful excursion.
Setting sail from the Triton Charters and Yacht Rental dock, guests will enjoy a private cruise through the picturesque bay. With all fees and taxes included, and alcoholic beverages provided, this 5-star rated activity is perfect for those seeking a relaxing and scenic journey.
Although not wheelchair accessible, most travelers can participate, and infants are welcome to sit on laps.
After the cruise, the activity concludes back at the meeting point, leaving guests with lasting memories of their time on the water.
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Frequently Asked Questions
Can I Bring My Own Food and Drinks on the Sailing Tour?
Yes, you can typically bring your own food and drinks on a sailing tour. Most companies allow passengers to bring their own snacks and beverages to enjoy during the sailing experience.
What Is the Minimum Age Requirement for the Sailing Excursions?
The minimum age requirement for sailing excursions typically ranges from 6 to 12 years old, depending on the company. Many offer family-friendly options with appropriate safety measures for younger participants. It’s best to check with each provider for their specific age guidelines.
Do the Sailing Tours Accommodate People With Disabilities?
The sailing tours generally accommodate people with disabilities, but it’s best to check with the specific tour operator to understand their accessibility options and any necessary accommodations. They’ll work to ensure everyone can enjoy the sailing experience.
How Do I Get to the Departure Location for the Sailing Trip?
To get to the departure location, you can drive and park nearby or use public transportation. Most sailing tour companies provide detailed directions and transportation information on their websites to help visitors easily access the departure point.
Can I Book a Private Sailing Tour for a Special Occasion?
Yes, you can book a private sailing tour for a special occasion. Many tour companies offer customizable private charters, allowing you to enjoy a personalized sailing experience on your own schedule and with your desired group size.
The Sum Up
San Diego offers a variety of sailing experiences to suit different preferences and budgets. From small-group excursions to private charters, visitors can enjoy stunning views of the city’s coastline and bay. Whether it’s an afternoon or sunset sail, these tours provide an unforgettable way to experience the beauty of the city from the water.