Top Rated San Diego Sunset Sail Classic Yacht 6 Guests
Description
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.
Tour Options
Itinerary
The Maritime Museum of San Diego, established in 1948, preserves one of the largest collections of historic sea vessels in the United States. Located on the San Diego Bay, the centerpiece of the museum's collection is the Star of India, an 1863 iron bark.
The San Diego–Coronado Bridge, locally referred to as the Coronado Bridge, is a prestressed concrete/steel girder bridge, crossing over San Diego Bay in the United States, linking San Diego with Coronado, California. The bridge is signed as part of State Route 75.
The USS Midway Museum is a historical naval aircraft carrier museum located in downtown San Diego, California at Navy Pier. The museum consists of the aircraft carrier Midway. The ship houses an extensive collection of aircraft, many of which were built in Southern California.
Naval Air Station North Island or NAS North Island is located at the north end of the Coronado peninsula on San Diego Bay and is the home port of several aircraft carriers of the United States Navy
Seaport Village includes more than 50 places to shop, for items including men’s and women’s clothing, souvenirs, books, original art, toys and more. Shoppers also can enjoy a meal at one of the four fine-dining restaurants, which serve everything from fresh seafood to burgers, or they can grab a quick snack at the many casual dining stops.
North Embarcadero, the Public Art Collection includes more than 30 pieces of art along the waterfront. You’ll see A National Salute to Bob Hope and the Military, which includes 16 larger-than-life bronze statues. There’s also the Urban Trees Artwork display, which is a yearly exhibit that features tree-size art pieces representing the San Diego landscape from local artists.
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.
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.
Highlights
What's included
Traveller Ratings
Important Information
- Infants and small children can ride in a pram or stroller
- Infants are required to sit on an adult’s lap
- Suitable for all physical fitness levels
- Traditional sailboat with wooden mast, gaff rigging, classic decor
- Restroom on board
Reviews(357)
Captain Philip is a very experienced and down to earth captain that made our trip very enjoyable. From the stories of his travels, to how he restored his boat, to the tour of the bay, he was top notch all the way.
We had a great time on Captain Phillip’s sailboat! Very relaxing and great views! We would choose to do this again!
Thank you so much — relaxing and great views is exactly what San Diego Bay delivers from the deck of Liberty, and I'm so glad you felt it! There's nothing better than hearing that guests would come back, and we will absolutely be ready when you do. See you out on the water! — Captain Phil
Food was terrible. Tour was terrible. I would never recommend this to anyone don’t go Unless you want terrible food and crummy places
Captain Phil's Response: For clarity: this guest cancelled within 24 hours of departure (non-refundable per Viator's policy, which we honor) and did not show up for the sail. We have no record of this guest boarding Liberty or experiencing any food or service. Our 24-hour cancellation policy is clearly stated at booking. We stand behind it and apply it consistently to all guests. If you have questions about what's actually included on a sail with us, feel free to reach out directly. We're happy to answer them. Fair winds, Captain Phil
We had a fantastic sail. The boat is beautiful and captain Phil was charming.
It was a pleasure having you aboard. Thank you for coming out for a sail. Captain Phil
Capt Phillip was knowledgeable everywhere we went on the bay. A pleasant experience to chill and sail in such a fast paced world. I highly recommend this adventure. James
Thank you for the wonderful review, James! It was a pleasure having you aboard Liberty. I'm glad you enjoyed the opportunity to slow down and experience San Diego Bay under sail. In today's fast-paced world, there's something special about unplugging for a couple of hours, feeling the wind in the sails, and simply taking in the beauty of the harbor. I'm also happy you enjoyed learning about the bay along the way. Thank you for your recommendation and for choosing Sail Liberty. I hope to welcome you back aboard for another relaxing San Diego Bay sailing experience. Captain Phil
Our sailboat adventure in California was absolutely unforgettable. Captain Phillip made the experience extraordinary — he was warm, knowledgeable, and shared so many fascinating details throughout the ride. The entire trip was both beautiful and relaxing, easily my favorite part of our vacation. His boat is the real deal — classic, gorgeous, and clearly cared for with pride. And the Bay Area he guided us through was nothing short of breathtaking, with views that felt straight out of a postcard. Truly an experience we’ll treasure.
Thank you for such a thoughtful review! It was a pleasure having you aboard Liberty, and I'm honored that your sail became the favorite part of your California vacation. I truly appreciate your kind words about the experience and the boat. Liberty is a classic sailboat that I take great pride in maintaining, and it's always rewarding when guests notice the care that goes into preserving her character. My goal is to provide an authentic San Diego Bay sailing experience where guests can relax, enjoy the scenery, and learn a little about the harbor along the way. Thank you for sharing your experience and for recommending Sail Liberty. I hope your travels bring you back to San Diego someday, and I'd love to welcome you aboard for another memorable sail. Captain Phil
It was a beautiful time on the water. The Captain is great! Very friendly, the boat was clean and comfy. Definitely worth the money you pay! Very relaxing!
Thank you for the incredible review! It was a pleasure having you, your parents, and your girlfriend aboard Liberty for a sunset sail on San Diego Bay. I’m so glad the experience became one of the highlights of your time in San Diego. One of the things I love most about sailing is giving guests a chance to see the city from a completely different perspective. The views of Coronado Island, the skyline, and the historic ships around the bay are always special when experienced from the deck of a classic sailboat. I appreciate your kind words about the sailing, history, and the relaxed atmosphere aboard Liberty. Creating a fun, comfortable, and memorable small-group sailing experience is exactly what I strive for on every trip. Thank you again for choosing Sail Liberty. I look forward to welcoming you back aboard for another beautiful San Diego Bay sailing experience in the future. Captain Phil
Fun time on the water, we sailed around the bay and took in the sights. The boat was cool and the Captain was friendly.
Thank you for taking the time to leave such a thoughtful review. It was my pleasure to be your captain, and I'm honored that you would recommend the experience to others. I hope to welcome you back aboard Liberty for another unforgettable sail.
This was such a beautiful and chill experience. The sailboat is such a stunner and Phillip’s telling of the history of the boat was really fun. My husband and I ended up meeting 2 other lovely couples on our sail, it was a great group and I would 11/10 do this again.
I'm glad you enjoyed the scenery, the company of the other guests, and the personal experience aboard our classic sailboat. Thank you again for sailing with Captain Phil, and I hope your next visit to San Diego includes another afternoon on the bay. Fair winds! Captain Phil
Captain Philip was wonderful! He is so knowledgeable and had the best snacks and drinks. We enjoyed our trip and the beautiful boat, it had had amazing woodwork done by the captain himself! We met another couple on the boat, just the perfect amount of people so much more enjoyable than a large dinner boat. If you want a semi private and memorable sail. This is the one to choose!!
Thank you for such a wonderful review. I'm honored that your San Diego sailing experience aboard Liberty was part of the perfect ending to your vacation. One of the things I enjoy most is creating a relaxed small-group sailing charter on San Diego Bay, where guests can connect with both the harbor and fellow travelers. Captain Phil
