San Diego Sailing Sunset and Afternoon Classic Yacht
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
Select a highlighted day to see live departure times and the exact price for your group.
Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
5.0/5
Based on 8 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is San Diego Sailing Sunset and Afternoon Classic Yacht worth booking?
San Diego Sailing Sunset and Afternoon Classic Yacht is a 2.5-hour experience in La Jolla, United States, from $125 per person. It scores 61 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 5/5 rating across 8 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 61 / 100
- Rating
- 5/5 (8)
- Duration
- 2.5 hours
- From
- $125 per person
Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with Captain Phil, a USCG-licensed captain with 55 years of sailing ex
What you get
About this experience
Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with Captain Phil, a USCG-licensed captain with 55 years of sailing experience. Whether you choose an afternoon sail or stay for sunset, the experience is calm, unhurried, and genuinely personal — less like a tour, more like being invited onto a private yacht. Take in the San Diego skyline, Coronado Bridge, and USS Midway from the water — no narration script, no rushing, just the bay at its best. Afternoon sail — open skies, warm sun, and the city in full view. Sunset sail — watch the sky change over the water as the city lights come on. Ideal for couples and travelers who want an authentic, uncrowded San Diego sailing experience. All sails are 2.5 hours. Included: craft beer, California white wine, soft drinks, and packaged snacks. Paid marina parking available. Gratuity for the captain is appreciated and not included.
What's included
Included
- Beer, wine and soft drinks
- Bottled water
- Alcoholic beverages
- Snacks
Not included
- Gratuities
- Parking
What you'll see and do
San Diego Convention Center
The San Diego Convention Center is a striking waterfront venue known for its modern architecture and iconic sail-like rooftop. Located in the heart of downtown along San Diego Bay, it hosts major events like Comic-Con International, trade shows, and conventions. Spanning over 2.6 million square feet, it features expansive exhibit halls, meeting rooms, and a scenic outdoor terrace with panoramic bay views. Its prime location offers easy access to the Gaslamp Quarter, making it a vibrant hub for both business and entertainment.
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San Diego Bay Walk
The San Diego Baywalk along North Harbor Drive is a scenic waterfront promenade perfect for a relaxing stroll after your sailing excursion. Lined with palm trees, public art, and stunning bay views, it offers a lively atmosphere with street performers, waterfront dining, and landmarks like the USS Midway Museum and the Maritime Museum of San Diego. Visitors can unwind at outdoor cafés, watch boats glide by, or simply take in the beautiful coastal sunset.
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Cabrillo National Monument
The Cabrillo National Monument offers breathtaking panoramic views of San Diego Bay, the Pacific Ocean, and downtown San Diego. Located at the southern tip of the Point Loma Peninsula, this historic site commemorates Juan Rodríguez Cabrillo, the first European to explore the West Coast in 1542. Visitors can explore scenic coastal trails, tide pools, and the iconic Old Point Loma Lighthouse, making it a perfect post-sailing adventure for history and nature lovers alike.
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Coronado Island
Coronado Island offers a perfect mix of relaxation and adventure after your sailing excursion. Visitors can stroll along the famous Coronado Beach, known for its sparkling sand, explore the historic Hotel del Coronado, or browse charming shops and cafés in Coronado Village. Outdoor enthusiasts can bike along scenic paths, kayak in the bay, or take in stunning skyline views from Centennial Park. Whether you’re looking to unwind or explore, Coronado provides a picturesque coastal escape.
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Shelter Island
Shelter Island is a peaceful waterfront retreat known for its marinas, parks, and stunning views of San Diego Bay and the city skyline. Visitors can enjoy a relaxing walk along the Shoreline Park promenade, dine at waterfront restaurants, or watch boats sail by from scenic picnic spots. The island is also a popular spot for fishing, kayaking, and stand-up paddleboarding. With its laid-back atmosphere and picturesque setting, Shelter Island is a great place to unwind after a day on the water.
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Coronado Bridge
The Coronado Bridge is an iconic 2.1-mile-long curved bridge connecting downtown San Diego to Coronado Island. Rising 200 feet above the bay, it offers breathtaking panoramic views of the San Diego skyline, bay, and naval ships. A striking architectural landmark, it provides a scenic drive and serves as the gateway to Coronado’s beautiful beaches, charming shops, and the historic Hotel del Coronado.
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The Rady Shell At Jacobs Park
The Rady Shell at Jacobs Park is a stunning open-air concert venue on the San Diego waterfront. With its futuristic, seashell-inspired design, it offers breathtaking bay and skyline views while hosting performances by the San Diego Symphony and world-renowned artists. Located in Embarcadero Marina Park South, it provides a unique outdoor music experience with premium seating, picnic areas, and top-tier acoustics, making it a must-visit destination for live entertainment lovers.
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Seaport Village
Seaport Village is a charming waterfront destination in downtown San Diego, featuring boutique shops, waterfront dining, and live entertainment. With its cobblestone pathways, scenic bay views, and vibrant atmosphere, it’s a perfect spot for a leisurely stroll, shopping for unique souvenirs, or enjoying fresh seafood with a view. Located along the Embarcadero, Seaport Village offers a relaxing and picturesque escape by the bay.
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USS Midway Museum
The USS Midway Museum, located in downtown San Diego along the Embarcadero, is a maritime museum housed aboard the USS Midway (CV-41), the longest-serving U.S. Navy aircraft carrier of the 20th century. Commissioned in 1945, the Midway served for 47 years, participating in significant military operations including the Vietnam War and Operation Desert Storm, before being decommissioned in 1992. The ship was transformed into a museum and opened to the public on June 7, 2004. Visitors to the museum can explore over 60 locations throughout the ship, including the engine room, galley, sleeping quarters, bridge, and flight control areas. The museum features more than 30 restored aircraft spanning 80 years of naval aviation history, interactive exhibits, and flight simulators. A self-guided audio tour, narrated by former Midway sailors, enhances the experience by providing personal insights into life aboard the carrier
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Where it starts and ends
Meeting point
La Jolla
Safe Harbor Sunroad Marina – Gate #1 Docks A–D sign.
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
Safe Harbor Sunroad Marina – Gate #1 Docks A–D sign.
Options you can book
Sunset Sail
Sunset sail aboard a classic yacht.
Afternoon Sail
Enjoy an afternoon sail aboard a classic sailing yacht.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 6 travelers per booking
- Operated by
- Sail Liberty
Know before you go
- Infants are required to sit on an adult’s lap
- Suitable for all physical fitness levels
- Restroom on board
- Traditional sailboat with wooden mast, gaff rigging, classic decor
Photos
What travelers are saying
Outty’s summary of the themes that recur across 8 traveler reviews. Written by us, not quoted from reviewers.
Knowledge and storytelling
2 mentionsReviewers describe the commentary as informative rather than scripted.
Traveler reviews
8 verified traveler reviews for San Diego Sailing Sunset and Afternoon Classic Yacht. Ratings and reviews provided by Viator and Tripadvisor.
Great boat...Capt. Phil...
Great boat...Capt. Phil was a fantastic host! Saw everything in the harbor as well as a spectacular sunset..We will definitely go again...
Response from the operator: Thank you for the wonderful review! I’m so glad your sunset sail aboard Liberty added something special to your San Diego trip.
via Viator
Sailing into the sunset...
Sailing the bay with Captain Philip was an absolute delight. An experienced, knowledgeable and friendly sailor, Captain Philip took us out on an old sailing boat that he personally restored and that is now in pristine condition. We really enjoyed the fact that the group was limited to 6 people (including us). We did the sunset sail, and we would highly recommend it to locals and tourists alike.
Response from the operator: Thank you for the wonderful review! I'm so glad you enjoyed your sunset sail aboard Liberty. I'm especially happy the small-group experience stood out to you. Limiting each sail to just six guests creates a relaxed, uncrowded atmosphere where everyone can enjoy authentic sailing and the beauty of San Diego Bay. Thank you for your kind words about Liberty. Restoring and maintaining this classic sailboat has been a labor of love, and I'm grateful you appreciated her character. I truly appreciate your recommendation and hope to welcome you back aboard for another sail. Captain Phil
via Viator
Beautiful
Lovely evening on a beautiful boat.
Response from the operator: Thanks for sailing with me . The wind was just right to see all of the sights on San Diego Bay
via Tripadvisor
Best way to see San Diego bay⛵️
Captain Philip is a great host. My wife and I throughly enjoyed the experience. It was our first time on sailboat and we want to do it again. I will recommend this experience to all my family and friends.
Response from the operator: I'm so glad your first time sailing was such a memorable one. Thank you for joining Captain Phil aboard Liberty for a true San Diego sailing experience.
via Tripadvisor
Girl's trip in San Diego....
Girl's trip in San Diego. Had a wonderful sunset sail! Enjoyed the sites and learning about the area.
Response from the operator: Greta fun was had by all . Thanks for sailing with me.
via Viator
Good to know
- Duration
- 2.5 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 3
- Verdict
- Solid Choice
Why this scores 61
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
San Diego Sailing Sunset and Afternoon Classic Yacht: questions travelers ask
Practical detail on this experience, plus the wider planning questions for La Jolla.
How much does San Diego Sailing Sunset and Afternoon Classic Yacht cost?
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Prices start at $125 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in La Jolla usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does San Diego Sailing Sunset and Afternoon Classic Yacht take?
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Plan for about 2.5 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in La Jolla is not rushed.
Is San Diego Sailing Sunset and Afternoon Classic Yacht worth it?
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It holds an Outty Ranking of 61 out of 100, which we label "Solid Choice". That score blends traveler sentiment (5/5 across 8 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in La Jolla, and how flexible the cancellation terms are.
Can I cancel or reschedule San Diego Sailing Sunset and Afternoon Classic Yacht?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is San Diego Sailing Sunset and Afternoon Classic Yacht suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 2.5-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book San Diego Sailing Sunset and Afternoon Classic Yacht?
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Around 3 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in La Jolla can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in La Jolla and add a light layer if any part of the 2.5-hour experience runs outdoors or after sunset.
Where does San Diego Sailing Sunset and Afternoon Classic Yacht start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central La Jolla within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in La Jolla?
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La Jolla is San Diego's best water day: kayak tours into the sea caves, snorkelling with leopard sharks in the ecological reserve, coastal walks with sea lions and sunset sails. On Outty we rank every La Jolla experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Cali Dreaming Electric Bike Tour of La Jolla and Pacific Beach, Incredible Slot Canyons to the Pacific, SoCal Riviera Electric Bike Tour of La Jolla and Mount Soledad. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit La Jolla?
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June to September for warm water, year-round for kayaking. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in La Jolla?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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