Top Rated San Diego Sunset Sail Classic Yacht 6 Guests

Recommended by 98% of travelers

Badge of Excellence

San Diego, USA

Great choice

20+ bookings last month.

2 hours 30 minutes (approx.)
Mobile ticket
Offered in: English

Why travelers loved this

4.9

· GeorgeB ·

May 2026

Phil took us on a wonderful sunset cruise. The boat was in great shape, and well stocked. Interesting conversation and fabulous visuals from the water. Highly recommended.

· Sarah_P ·

Jun 2026

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.

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Overview

Watch the sunset over San Diego and admire the city and ocean views during a small-group cruise on a classic 1904-styled sailboat. Pass landmarks such as the Maritime Museum, Coronado Bridge, and the USS Midway. Look out for sea lions, dolphins, and other wildlife around San Diego Harbor while relaxing and sipping on the provided wine, beer, or non-alcoholic drinks.

Includes wine, beer, and light snacks so don't pack a picnic
Snap photos of the San Diego sky at sunset from a different angle
Sail on a hand-restored reproduction of a 1904 sailboat
Ideal for couples seeking a romantic evening activity

What's Included

Water, soft drinks and packaged snacks.
Alcoholic Beverages

Beer IPA and Larger, White Wine

Gratuities
Parking

Meeting and Pickup

Meeting point

Safe Harbor Sunroad
955 Harbor Island Dr, San Diego, CA 92101, USA
Our departure point is located at: Safe Harbor Sunroad Marina 955 Harbor Island Drive, San Diego, 92101. Gate #1 Docks A-D

End point

This activity ends back at the meeting point.

Itinerary

After making your way to your sailboat, "Liberty," at the Sunset Resort Marina, step on board the handsome boat, modeled after a 1904 vintage sailboat.

Your captain uses traditional sailing techniques to power your vessel, which has gaff rigging, a wooden mast, and handsome decorative details. If you want to try your hand at sailing, participation is encouraged. During the 2.5-hour tour, you might spot sea lions and dolphins, and ride alongside grand ships such as the USS Midway or the USS Carl Vinson.

The cruise includes beer, white wine, soda, water, and light snacks. Pass close to landmarks such as the Maritime Museum and its flagship Star of India and the Coronado Bridge, and snap photos of the San Diego skyline as it lights up for the evening.

Maritime Museum of San Diego (Pass By)

Coronado Bridge (Pass By)

USS Midway Museum (Pass By)

Coronado Island (Pass By)

Seaport Village (Pass By)

Embarcadero Marina Park North (Pass By)

The Rady Shell At Jacobs Park (Pass By)

San Diego Convention Center (Pass By)

Additional Info

Confirmation will be received at time of booking
Traditional sailboat with wooden mast, gaff rigging, classic decor
Restroom on board
Not wheelchair accessible

Stroller accessible
Infants must sit on laps
Most travelers can participate
This tour/activity will have a maximum of 6 travelers

Supplied by

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

Traveler Photos

Gallery picture 1 (from a traveler's review)

Gallery picture 2 (from a traveler's review)

Gallery picture 3 (from a traveler's review)

Gallery picture 4 (from a traveler's review)

Gallery picture 5 (from a traveler's review)

Featured review

Michael_S

Philip was great very personable, and the boat/ship was awesome! Great view of the San Diego skyline. Highly recommend this trip.

Reviews

4.9

based on 357 reviews

Total reviews and rating from Viator & Tripadvisor

We perform checks on reviews

Sort by: Most insightful

Wind in my Sail

Carolyn_L, Aug 2026

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 have a great time on...

John_P, Aug 2026

We had a great time on Captain Phillip’s sailboat! Very relaxing and great views! We would choose to do this again!

Response from Host, Aug 2026

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

Twrrible

Joe_R, Aug 2026

Food was terrible. Tour was terrible. I would never recommend this to anyone don’t go Unless you want terrible food and crummy places

Response from Host, Aug 2026

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

Fun on the water!

Jonathan_L, Jul 2026

Fun time on the water, we sailed around the bay and took in the sights. The boat was cool and the Captain was friendly.

Response from Host, Jul 2026

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.

A highlight of our San Diego weekend

Sarah_P, Jun 2026

Response from Host, Jun 2026

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

Perfect sunset sail

Vanessa_H, Jun 2026

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!!

Response from Host, Jun 2026

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

Sunset Cruise with Phil

GeorgeB, May 2026

Phil took us on a wonderful sunset cruise. The boat was in great shape, and well stocked. Interesting conversation and fabulous visuals from the water. Highly recommended.

Response from Host, Jun 2026

Thank you for the wonderful review! I'm delighted you enjoyed the sunset sail and appreciated both the boat and the unique views of San Diego from the water. It was a pleasure having you aboard, and I enjoyed our conversation as well. Thank you for your recommendation, and I hope to welcome you back for another sail in the future. Captain Phil

Captain Phillip totally delivers a wonderful sail around SD bay!!

Teri_D, May 2026

GPS is tricky!! Go to Sheraton by the airport then it’s down the street! Easy once you’re there. GPS was a total mistake

Response from Host, May 2026

Thank you for the kind words. It was a pleasure having you aboard. I’m glad you enjoyed the sailing, the stories, and the different perspective of San Diego from the water. You’re always welcome back on Liberty.

Amazing Experience

Chuck_L, May 2026

Enjoy a relaxing sailing experience in San Diego Harbor. The boat and the captain are amazing.You won’t regret spending Tim with Captain Phillip.

Response from Host, May 2026

Thank you for noticing the details — from the clear directions to the refreshments aboard. I work to keep the experience simple, authentic, and unhurried. Hope to sail with you again.

Sunny and pretty sail

Deana_M, May 2026

A wonderful way to spend a sun-filled afternoon in San Diego! Captain Philip creates a genuinely personable, fun and scenic tour of the highlights along the waterway. The sailboat is a quaint and lovely restored boat. You can really tell he enjoys hosting guests on his lovely ship. We also appreciated other little touches like the choice of packaged snacks and beverages. A fun little excursion if you're in the area and would recommend.

Response from Host, May 2026

Thank you so much for the thoughtful review. It was truly a pleasure having you aboard. I’m glad the afternoon delivered on sunshine and scenery — San Diego Bay really does show off on days like that. I especially appreciate you noticing the spirit of the boat and the small details. Liberty has a lot of history in her lines, and sharing her with guests who enjoy the experience makes it all worthwhile. You were wonderful company, and I’m grateful you chose to spend part of your time on the water with me. If you find yourselves back in San Diego, I’d be delighted to welcome you aboard again. Fair winds, Philip

Amazing Sunset Sail

Karen_H, Apr 2026

If you’re looking for a quiet, intimate sail in a classic sailboat with a low key and very friendly captain, this is the one! We saw dolphins, sea lions, cormorants and pelicans…and this boat sails so beautifully. Captain Phil also had snacks, seltzer, wine and beer, as well as blankets! He passionately restored his boat in 2020. This is THE BEST sunset sail in San Diego!

Response from Host, Apr 2026

Thank you for the kind words — I really appreciate you taking the time to share this. I’m glad you enjoyed the calm, small-group feel and got to see some of the wildlife out on the bay. Liberty has been a labor of love, so it means a lot to hear you noticed how she sails. It was a pleasure having you aboard. Hope to see you again next time you’re in San Diego. — Captain Phil

Captain Phil was...

Deborah_S, Apr 2026

Captain Phil was informative and a skilled captain. The boat is beautiful and the bay was outstanding!

Response from Host, Apr 2026

I work hard to make a sail aboard Liberty a memorable experience. Thanks for sailing with me. Capt . Phil.

Awesome small group sunset cruise

Lisa_N, Mar 2026

Wonderful experience. Relaxing sunset cruise. Loved the small group. Philip was pleasant and keep the group safe.

Response from Host, Mar 2026

Thank you for the kind words—we’re really glad you enjoyed the sunset and the small-group atmosphere. It means a lot to hear you felt relaxed and well taken care of out on the water. We’d love to have you sail with us again.

Couples celebrating anniversary and birthday

Mary_M, Mar 2026

Phil is an expert captain—been sailing since childhood in Maine. He’s very personable, and his authenticity put my anxieties at ease. The trip through the bay was smooth and offered beautiful views of the city. We saw lots of seals sunbathing on a deck and barking at each other. Lots of relaxing fun and beauty everywhere.

Response from Host, Mar 2026

Thank you for the thoughtful review. I appreciate the kind words. I’ve been sailing most of my life, and it’s always rewarding when guests are able to relax and feel comfortable once we get out on the water. San Diego Bay has a way of surprising people with its calm sailing and wildlife, and the seals along the docks always seem to put on a show. It was a pleasure having you aboard Liberty, and I’m glad you were able to enjoy a peaceful sail around the bay. — Captain Phil

Captain Phillip’s sailing...

Mikaela_H, Feb 2026

Captain Phillip’s sailing tour was beautiful! My husband and I went out along the bay with our two other friends and it was an incredible experience! The views, the sailboat, everything was top tier. Will definitely be doing this again in the future and I recommend if you want an intimate personal experience, this is the tour to do! Thank you again!

Response from Host, Mar 2026

Thank you for the kind words. I’m glad you and your friends had a good time out on the bay. It was a pleasure having you aboard Liberty, and I appreciate the recommendation. You’re always welcome back for another sail. — Captain Phil

Was a wonderful evening...

Stephanie_H, Oct 2025

Was a wonderful evening sail. Had the sail up almost the entire time- which is not common for other ‘sailings’ I’ve had in the past. Captain Philip has a love for sailing and is very knowledgeable.

Response from Host, Oct 2025

Thank you kindly! I’m happy the cruise was everything you hoped for. It was great having you aboard.

Best evening with beautiful view!

Angela_H, Oct 2025

Amazing experience! The captain was so much fun. The views were amazing. The group was so much fun that we went to dinner together afterwards. Would definitely recommend! And will do it again when we're in San Diego.

Response from Host, Oct 2025

Thank you so much for your wonderful review! I’m thrilled to hear you had such a great time on the sail and that the group hit it off so well—dinner afterward sounds fantastic! I really appreciate the recommendation and look forward to welcoming you back next time you’re in San Diego.

Best Sunset Cruise in San Diego!

Dayna_T, Sep 2025

This experience is peaceful, intimate, and serene. The experience is filled with Great San Diego Bay history and amazing views given by Captain Phillip.

Response from Host, Sep 2025

Thank you for your great review .

Great sunset cruise

Aiden_C, Sep 2025

Had an amazing time! The small group made the cruise feel really cozy and personal. Drinks and snacks were great, and the sunset views were beautiful. Definitely recommend captain Philip is a good dude

Response from Host, Sep 2025

Thanks !

Great night on the water, lot's of fun

Walkman_W, Sep 2025

San Diego Bay is a beautiful area with great views of the sky line, sailing racers, and the local sea lion posing on a buoy. The evening was topped off with a sunset over the water. Captain Phil is very knowledgeable about the area, also single handed the Liberty with all sails up and gave a tutorial of the Bay area. All in all, a fantastic night on the water.

Response from Host, Sep 2025

Jimmy the sea lion is always on buoy # 22 . He loves to pose for pictures ! Thanks for sailing with me.

Philip was great very...

Michael_S, Aug 2025

Philip was great very personable, and the boat/ship was awesome! Great view of the San Diego skyline. Highly recommend this trip.

Response from Host, Sep 2025

People do not realize that the San Diego Skyline is very beautiful from the water. Thanks for supporting our small business .

Great sailing

annette_p, Aug 2025

The boat was beautiful and the cruise was great. Max 6 folks was great. We enjoyed the other guests and laughed for 2 hours. Of course the wine helped!! Would so again!

Response from Host, Sep 2025

It is always fun to have people meet on our tours.

The sunset sail with...

Sheryl_D, Aug 2025

The sunset sail with Captain Phillip is the highlight of our trip so far. Well worth every penny and highly recommend

Response from Host, Sep 2025

I am glad that you had a great sail.

Perfect sailing experience!

RachelPiercy, Aug 2025

This was a wonderful experience! Captain Philip is very experienced, and sailed us all around the bay area to see the naval base, ships, the walk along downtown San Diego, the kissing statue, the USS Midway, and more. We took the 6 PM tour in early August, and the sunset at 7:45 PM, and was absolutely beautiful. It does get quite a bit cooler immediately after sunset, but he had blankets to provide just in case. He also provided some beverages and snacks, and answered all of our questions about the area. My only critique is that it was a bit lengthy at 2 1/2 hours, but I know that’s because he wants to ensure his passengers are getting the best experience and their money’s worth. If it were up to me, I would’ve cut it back by 30 minutes. Overall, this was a wonderful experience, and I would highly recommend it!

Response from Host, Sep 2025

Thanks for your great review . Most sailing tours are 2 hours long. I like to give my clients more time on the water to experience the city lights at night .

Phillip was terrific

Kevin_O, Aug 2025

A wonderful anniversary sunset cruise with Captain Phillip. The scenery including two aircraft carriers, The Coronado Bridge, a yacht confiscated from a Russian Olegard, and the gorgeous San Diego skyline was truly magical