San Diego’s sailing scene delivers reliable year-round conditions and well-organized tour options. Local operators run daily trips from the harbor, with most tours lasting 2-3 hours.
The most worthwhile outings include small-group wildlife watches (perfect for spotting dolphins and whales) and the historic Tall Ship adventures aboard traditional sailing vessels. For a special splurge, private yacht charters on 42-foot boats offer the freedom to design your own route.
I especially love the sunset cruises along the downtown waterfront – they combine great photo opportunities of the skyline with surprisingly reasonable prices. The afternoon trips work better for families with young children.
Check out these top-rated sailing tours, all led by Coast Guard-certified captains:
Key Points
- Small-group sailing tours with a maximum of 6 travelers, offering comfortable amenities, wildlife sightings, and high traveler recommendation rates.
- Catamaran and yacht tours providing scenic views of San Diego landmarks, with options for private sailing and luxury experiences.
- Customizable private sailing tours on a 42ft yacht, catering to special occasions and offering flexible cancellation policies.
- Educational sailing and maritime experiences on the Californian Tall Ship, including hands-on activities and historical insights.
- Afternoon and evening sailing excursions with complimentary drinks and knowledgeable crew to enhance the sailing experience.
Small-Group Sunset Sailing Experience on San Diego Bay
The Small-Group Sunset Sailing Experience on San Diego Bay offers a unique opportunity to witness the city’s stunning waterfront from the comfort of a private yacht.
With a maximum of 6 travelers, you’ll enjoy a personalized and intimate setting as you sail during the golden hour.
Marvel at the scenic views of military vessels, historical landmarks, and marine life, while taking advantage of the comfortable bean bags, cushions, and blankets provided.
The knowledgeable captains ensure a smooth and memorable experience, making this the perfect choice for special occasions or gatherings.
With 99% traveler recommendation and a Badge of Excellence, this sunset sail isn’t to be missed.
Read our full review: Small-Group Sunset Sailing Experience on San Diego Bay Review
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5 Hour Bay Tour on the Largest Catamaran in San Diego
Explore San Diego’s stunning harbor aboard the largest catamaran in the bay on this 2.5-hour cruise.
You’ll sail past iconic landmarks like the USS Midway, Coronado Bridge, and Star of India, all while enjoying the modern decor, plentiful seating, and dance floor of this comfortable vessel.
The U.S. Coast Guard-certified crew will serve you custom cocktails from the 13-seat bar, allowing you to sip signature drinks like the Tritons Anchor or Port’s Mistress.
With a capacity designed for groups, this cruise is ideal for both locals and visitors looking to experience the best of San Diego’s waterfront.
Small-Group San Diego Afternoon Sailing Excursion
Set out on a small-group sailing excursion in San Diego’s picturesque harbor aboard a Catalina-style sailboat.
This intimate experience is limited to six passengers, allowing you to enjoy complimentary beer, soft drinks, and light snacks as you sail for three hours.
Bring your own music to play through the surround-sound speakers. The meeting point is 2720 Shelter Island Dr, and you’ll need a boarding pass from the Sail San Diego office.
Complimentary wind gear and binoculars are available, and the activity is wheelchair and stroller accessible.
With 478 reviews and a 5.0 rating, this tour is highly recommended for its knowledgeable captains and scenic views.
Read our full review: Small-Group San Diego Afternoon Sailing Excursion Review
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San Diego: Private Sailing Cruise With Optional Extras
Interested in a private sailing cruise in San Diego? For €500.08 per group (up to 6 people), you can embark on a 2.5-hour private sailing excursion.
Choose from various options, including day sails, sunset sails, and offshore excursions. The cruise departs from the San Diego Harbor and includes an experienced USCG skipper, safety equipment, and complimentary water, beer, and wine.
While not suitable for those prone to seasickness or mobility issues, the cruise offers a customizable experience with scenic views and optional extras like snorkeling.
Remember to arrive 15 minutes early, dress comfortably, and bring a camera to capture the beautiful San Diego coastline.
Read our full review: San Diego: Private Sailing Cruise With Optional Extras Review
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Small-Group San Diego Sunset Sailing Excursion
For an intimate sunset sailing experience in San Diego, consider the Small-Group San Diego Sunset Sailing Excursion.
This 3-hour evening cruise aboard a Catalina-style sailboat accommodates just 6 guests, offering a personalized adventure. Enjoy the glistening waves, city lights, and stunning sunset views.
Complimentary light beers, hard seltzers, non-alcoholic beverages, and snacks are provided, and you can even bring your own music. The knowledgeable captains share their expertise if asked.
With 99% traveler recommendation and a Badge of Excellence, this sunset sail is a top-rated activity.
Wheelchair accessible and near public transportation, it’s an experience most travelers can enjoy.
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San Diego: Californian Tall Ship Sailing and Maritime Museum
Sail aboard the Californian, the Official Tall Ship of California, and explore San Diego’s rich maritime history. This 4-hour experience lets you participate in sailing activities, learn from the crew, and gain admission to the Maritime Museum.
For $119 per person, you’ll journey on a replica gold rush-era revenue cutter, haul lines, man the helm, and observe the crew rigging sails.
Afterward, explore historical ships like the Star of India and H.M.S Surprise, and engage with exhibits on San Diego’s naval history and the Age of Sail and Steam.
Just remember to wear comfortable shoes, bring sun protection, and avoid mobility restrictions.
With 5/5 reviews, this is an educational and interactive way to experience San Diego’s seafaring past.
Read our full review: San Diego: Californian Tall Ship Sailing and Maritime Museum Review
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Luxury Catamaran Sailing Charter of San Diego
Travelers seeking a luxurious sailing experience in San Diego can embark on a private catamaran charter that offers stunning vistas of the city’s coastline.
This 5-star rated service boasts 99% traveler recommendations and rave reviews for its accommodating crew and enjoyable atmosphere.
During your private tour, you’ll enjoy amenities like bottled water and ice-filled coolers, and may even spot dolphins along the way.
The charter departs from a convenient location with free and metered parking options.
With a flexible cancellation policy and the option to reserve now and pay later, booking this exceptional sailing experience is a breeze.
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San Diego: Classic Yacht Sailing Experience
Experience the thrill of classic yacht sailing in San Diego’s scenic harbor. For $109 per person, you’ll set sail for 2.5 hours aboard a hand-restored 1914 replica sailboat.
Spot wildlife like sea lions and dolphins as you navigate past the USS Midway and other landmarks. The all-inclusive tour offers beer, wine, soft drinks, and snacks.
Arrive 20 minutes early and call the captain to confirm your readiness. Not suitable for babies or young children, but bring sunglasses, a jacket, and sunscreen.
With free cancellation and reserve-now-pay-later options, this classic sailing experience is an excellent way to enjoy San Diego’s waterfront.
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2-Hour Private Sailing Experience in San Diego Bay
A 2-hour private sailing experience in San Diego Bay offers an unparalleled opportunity to explore the city’s stunning waterfront from the comfort of your own chartered yacht.
With 140 rave reviews and a 100% recommendation rate, this excursion promises a truly memorable outing.
You’ll enjoy a customizable itinerary, a knowledgeable and accommodating captain, and a clean, spacious vessel with amenities like bottled water, snacks, and even a bottle of champagne.
Whether you’re looking for a relaxing sunset cruise or a celebratory occasion, this private sailing experience in San Diego Bay is sure to deliver an unforgettable adventure.
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San Diego Bay: Signature 2-Hour Sailing Tour
Set out on a captivating 2-hour sailing tour of San Diego Bay and witness the city’s iconic landmarks from a unique vantage point.
Cruise on a classic sailing yacht with a small group of up to 6 participants, enjoying views of the San Diego skyline, Coronado Bridge, and harbor.
Keep an eye out for wildlife like harbor seals, pelicans, dolphins, and whales.
The tour costs ₹11,007 per person and departs from Cabrillo Isle Marina, with options to reserve your spot and cancel up to 24 hours in advance.
Reviewers praise the engaging captains and informative nature of these tours, making it a must-do activity for your San Diego adventure.
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Small-Group Yacht Sailing Experience on San Diego Bay
Elevating your San Diego sailing experience, the Small-Group Yacht Sailing Adventure on San Diego Bay offers an intimate and luxurious outing.
Aboard a 40-foot yacht, you’ll enjoy cozy bean bags, cushions, and blankets as you sip on a complimentary glass of wine. With a maximum of 6 travelers, you’ll receive personalized attention from the experienced yacht captains who’ll help you spot local wildlife and naval ships.
The private experience caters to special occasions, while the free cancellation policy up to 24 hours prior provides flexibility.
Whether you’re seeking a relaxing afternoon or a memorable adventure, this small-group sailing tour delivers an unforgettable experience on the waters of San Diego Bay.
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San Diego: Sunset and Day Sailing Excursion With Drinks
Immersed in the tranquil waters of San Diego Bay, the San Diego: Sunset and Day Sailing Excursion with Drinks promises an unforgettable experience.
Set out on a 2.5-hour sailing adventure, with the option to set sail from two convenient locations. Sip on wine, beer, and soft drinks as you witness the stunning sunset or explore the bay during the day, accompanied by knowledgeable guides who’ll share insights into San Diego’s history and culture.
Spot dolphins, capture breathtaking views of iconic landmarks, and create lasting memories on a comfortable, well-maintained yacht.
With a 5/5 rating and free cancellation up to 24 hours in advance, this excursion is an absolute must-do for your San Diego itinerary.
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Luxury Sailing Tour of San Diegos Bay and Coastal Waterways
Discover the beauty of San Diego’s bay and coastal waterways on a luxurious sailing tour. Aboard a 34-foot Catalina sailboat, you’ll embark on a small-group excursion with a maximum of six travelers.
Enjoy stunning views of the city skyline, Maritime Museum, naval base, and Coronado Bridge as your knowledgeable local captain shares interesting facts and stories.
With morning, afternoon, and evening departures available, you can tailor the experience to your preference. Relax and unwind with provided snacks and bottled water, or bring your own drinks if you’re 21+.
With a 97% traveler recommendation rate and a Badge of Excellence, this tour is a must-do for anyone seeking a peaceful and memorable sailing adventure in San Diego.
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San Diego: San Diego Bay Sailing Tour
If you’re seeking a tranquil and awe-inspiring way to experience San Diego’s picturesque bay, the San Diego Bay Sailing Tour is an exceptional choice.
Aboard a private 42ft yacht, you’ll embark on a 2-hour journey, with a maximum of 6 people in your group. Enjoy complimentary refreshments, including bottled water, soda, snacks, and a bottle of champagne, all while taking in stunning views of the downtown skyline, USS Midway, and Coronado Bridge.
With flexible cruise options, including daytime, sunset, and nighttime sails, you’re sure to create lasting memories. The tour’s personalized experience and knowledgeable guides make it an ideal activity for special occasions like birthdays, anniversaries, or family vacations.
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5 Hours of Fun: Catamaran Sunset Sail
Set out on a captivating 2.5-hour sunset sail aboard a comfortable catamaran as you explore the stunning waters of San Diego Bay.
This small group tour, limited to just 6 travelers, is highly recommended, with 98% of past guests praising the experience.
Relax and enjoy the iconic San Diego skyline, as well as possible sightings of sea lions and dolphins.
Complimentary beverages, including beer, wine, and soft drinks, are provided, and you’re welcome to bring your own food and drinks.
Blankets ensure comfort as you sail, and facilities like a small galley and bathroom are available onboard.
Arrive early at the designated meeting point to ensure a smooth start to your sunset adventure.
San Diego: Private 2-Hour Sailing Tour for 3-6 People
Enjoy a private 2-hour sailing adventure on the stunning waters of San Diego Bay.
For a group of 3-6 people, you’ll embark on a private tour starting at $694.84 per group. Relax as you learn to sail and take turns at the helm, enjoying scenic views of the Coronado Bridge, Maritime Museum, and naval ships.
Keep an eye out for wildlife like sea birds, sea lions, and dolphins. Onboard, you’ll savor light snacks, complimentary white wine and beer.
With a live tour guide, a captain, and a crew member, this customizable tour promises an unforgettable sailing experience in San Diego.
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San Diego’s Finest Private Sailing Tours
Explore San Diego’s picturesque bay aboard a luxury private yacht with San Diego’s Finest Private Sailing Tours. Rated 5.0 stars with a Badge of Excellence, this 2.5-hour tour offers an exceptional experience.
Enjoy soda, water, and even alcoholic beverages as you take in the stunning views. The friendly and knowledgeable crew, including Captain Rob and First Mate Claire, ensure a comfortable and memorable outing.
Though not wheelchair accessible, the tour is stroller-friendly and welcomes service animals. Ideal for couples, families, and small groups, this tour is perfect for special occasions like birthdays and anniversaries.
Guests rave about the relaxing atmosphere and beautiful scenery, making it the best way to experience San Diego’s waterfront.
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San Diego: 2 Person Private Sailing Cruise With Snacks
Departing from Harbor Island, this 2-hour private sailing cruise allows you to admire the captivating San Diego skyline.
You’ll have the opportunity to spot local wildlife, including seagulls, seals, and sea lions, while the captain shares stories about the bay’s history.
Relax and enjoy light snacks, sodas, and water, with the option to purchase beer, white wine, or champagne.
Enhance your experience with a boxed sandwich lunch for an additional $15.
Safety is paramount, with life preservers provided.
Reserving now and paying later is an option, and you can cancel up to 24 hours in advance for a full refund.
Read our full review: San Diego: 2 Person Private Sailing Cruise With Snacks Review
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Small-Group San Diego Sailing Trip
Set out on a small-group sailing adventure in San Diego with this captivating 2-hour tour.
Departing daily from Cabrillo Isle Marina, this classic yacht accommodates up to 6 passengers, ensuring an intimate and personalized experience. An experienced skipper guarantees a safe and enjoyable sail, while you take in stunning views of the city’s coastline, including downtown, Point Loma, and the nearby islands.
Onboard, savor a selection of cheese, salami, and crackers as you relish the peaceful ambiance. With free cancellation and rescheduling options, this sailing trip is perfect for special occasions or a leisurely afternoon on the water.
Regardless of your reason, this small-group adventure promises an unforgettable maritime experience in San Diego.
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San Diego: San Diego Bay Sunset & Daytime Sailing Experience
Set sail on an unforgettable San Diego Bay adventure with the San Diego: San Diego Bay Sunset & Daytime Sailing Experience.
Likely to sell out, this 2-hour sailing trip offers stunning views of the San Diego skyline, USS Midway, and Coronado Naval Station.
Depart from Sunroad Resort Marina and spot sea lions and dolphins as you sail.
Enjoy complimentary white wine, soft drinks, and water, or bring your own food and beverages.
With an overall 5/5 rating based on 159 reviews, this sailing experience promises excellent customer service and memorable sights.
Arrive at least 20 minutes early, as sailings leave on time.
Private group options are available for a more exclusive experience.
Read our full review: San Diego: San Diego Bay Sunset & Daytime Sailing Experience Review
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The Sum Up
You’ll find a variety of sailing experiences in San Diego, from small-group sunset sails to private cruises. Whether you want a quick trip or a longer tour, there’s an option to suit your preferences. Explore the bay, take in the city views, and enjoy the peaceful serenity of being on the water. With knowledgeable captains and well-maintained vessels, you’re sure to have a memorable sailing adventure in San Diego.