Classic Sunset Sail in San Diego

29 Reviews | San Diego, USA

Loading Options

2 hours 30 minutes (Approx.)
Mobile Ticket
Instant Confirmation

Keeping you safe during COVID-19
What you can expect during your visit
Face masks provided for travelers
Face masks required for guides in public areas
Face masks required for travelers in public areas
Gear/equipment sanitized between use
Guides required to regularly wash hands
Paid stay-at-home policy for staff with symptoms
Regular temperature checks for staff
Regularly sanitized high-traffic areas
Transportation vehicles regularly sanitized


We offer a premium sailing experience aboard the vintage sailing yacht “Liberty”. Our vessel is a work of art unlike any boat on the bay. She is flawlessly maintained with high standards of pride and craftsmanship. You will fall in love with her mirror-finish wood accents, beautiful cozy cabin and clean facilities. This is an all-inclusive 2 ½ hour experience with beer, wine, soft drinks and snacks. Play some music and relax on cushioned seats as we sail the scenic waters of San Diego Bay. Feel free to steer the boat and feel the power of the wind in the sails. Our sailing experience is limited only to 6 guests. You can sail with other travelers or select a private cruise for just you and your friends and family.


  • Small-group tour
  • See the sights illuminated at night
  • Romantic experience, perfect for couples
  • Snacks and Beverages included



What's Included

What To Bring

Additional Info


Average 4.86 out of 5 stars based on 29 verified reviews from Cool Destinations and TripAdvisor

5 stars
4 stars
3 stars
2 stars
1 star
Kim, Oct 2020 Verified
The trip was wonderful, very relaxing. A magnificent boat, that’s been cared for with pride! Small group 6 people. Captain very personable
Randy, Oct 2020 Verified
Really enjoyed seeing San Diego from the water! Phillip did a great job and his boat is beautiful. The trip was fun and the sunset was perfect!
John, Oct 2020 Verified
The sunset cruise was awesome. Captain Phillip was great and the two other couples that were on the boat with us were a lot of fun. Beautiful views of downtown and Coronado. Awesome, relaxing time. Would def do it again!!
Shannon, Oct 2020 Verified
Had a great time! Highly recommend sailing with captain Phil. Felt like we were a group of friends out for a joy ride.
Scott, Sep 2020 Verified
The boat was great, captain was great, the weather was great. What an amazing day on the water. A good amount of stocked beer, wine and snacks.
Wesley, Sep 2020 Verified
Phil was great, great couples activity. Smooth and quiet evening and nice to meet some folks as well!
Allyson, Sep 2020 Verified
Captain was great, lovely vintage sailing boat, perfect weather and a great sunset! We would recommend this excursion to others!
Casey, Sep 2020 Verified
Our experience was amazing, we took an Uber to the location and were able to find the docks pretty quickly. After check in we went straight to the boat and sailed for 2 hours. The views and conversations were amazing- not to mention he let my Fiance' steer the boat for some time (one of his lifelong dreams too!-So thank you Phillip!) There was wine and I believe beer being offered. Prior to booking, we spoke with a lady through a third party booking agency (I think) and she mentioned that there would be soft drinks, food and white wine/beer. I did not see any food, maybe there was or maybe there wasn't I'm not too sure if the captain mentioned it or not (maybe I did not hear him). She also told us that the company would take us pretty much anywhere we would like and that we would have the choice to swim or not, which even though we didn't have that option upon arrival, i'm not sure we would have wanted to anyway so it didn't bother us too much. In addition to this, the lady also told us that we would be sailing for 4 hours and that it was a private sunset sail - i really don't know where she got this information because when we arrived there was another couple with us, and the sail was only 2 hours. I usually don't mind, but we chose this cruise mostly because we wanted to have a private party plus with COVID-19 still happening we wanted to ensure that our interactions with strangers were limited. In fact, I was very surprised that they would book another couple with us during a pandemic. We dressed up for our sail because we were celebrating and taking some photos, but the guys did have to take their dress shoes off (no biggie- the captain is responsible for any damages made to the vessel therefore he would have to pay to fix it if there were.) and Overall the captain was certainly amazing as well as the views, which is why I am rating this experience at 5 stars. I personally would not book through Cool Destinations again just because it seems that they do not have all of the correct information. Next time, I will probably call the docks directly and do it that route. As a side note- I noticed that the other couple didn't thank or even tip the captain, so please be sure to tip! they work really hard and just like any other service industry, you should consider tipping.
MELANIE C, Sep 2020 Verified
What a great way to see San Diego! Captain Philip made the experience relaxing and fun. My girls and I loved it!
Daniel, Sep 2020 Verified
It was amazing! Beautiful sunset on SD Bay while Captain Phil worked his magic with the sails. Toss in a couple cold beers, my beautiful wife and you have the makings of a perfect night!

Still have questions?

We’re here to help. Call (800) 814-2665 to speak with a Cool San Diego specialist!
Product code: COOL-37126P3

Similar Tours & Activities

Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

San Diego Harbor Cruise

 2 hours  Instant Confirmation

Customers Who Bought This Tour Also Bought

San Diego Harbor Cruise

 2 hours  Instant Confirmation

San Diego Whale Watching Cruise

 4 hours 30 minutes  Instant Confirmation

Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.