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Sunset Sailing Cruise on a Catalina 400 with Complimentary Drinks & Stunning Coastal Views

About this Experience

What you'll do:

End your day with a breeze, a drink, and front-row seats to San Diego’s legendary sunset. Hop aboard our spacious Catalina 400 sailboat for a two-hour cruise filled with good vibes, great views, and complimentary drinks and snacks. Whether it’s a romantic date night or a golden hour hang with friends, this is the kind of sunset you’ll actually slow down for.

Why we love it for your party:

  • A sunset worth slowing down for (No traffic or noisy bars, and nothing between you and the horizon)

  • Perfect for date night, or any night (Anniversaries, birthdays, or just an excuse to sail with your crew)

  • Small groups, big skies (There’s no such thing as a bad view from the deck of our premium sailboats)

  • Captains who know their stuff (USCG-certified, super experienced, and actually fun to hang out with)

  • Start your evening with a toast (We’ve got beer, hard seltzer, soft drinks, and snacks waiting on board for you)

About this experience partner:

Sail San Diego is a boutique, family-run sailing company and one of San Diego’s tenured operations. Over nearly four decades, Sail San Diego has grown to become the city’s premier sailing provider, offering corporate outings, private events, whale watching tours, and our daily signature sails.

Provided by Sail San Diego

Joined November 2022

Book This Experience

Visit the experience booking site to check availability and book your experience.

Reviews

See All

5 (10 Ratings)

RP

Rhondi P.

December 2025 • Other Party

We had a wonderful time on our private sail with Captain Frank. We were even lucky enough to see some dolphins. Highly recommend.

JL

Jake L.

December 2025 • Group-Trip Party

I definitely recommend this to anyone visiting San Diego. The sailing experience was wonderful and the sights were absolutely amazing. We set out with Captain Rich who was very kind, stress-free and made the experience for our group one to remember. He had a great selection of music and provided some snacks and drinks for the ride.

KP

Kimy P.

December 2025 • Other Party

We had a great time for a great price. The boat was large, with snacks, drinks, and two bathrooms. Our captain was friendly and knowledgeable. I highly recommend this company and plan to sail with them again in the future.

AL

Andy L.

December 2025 • Other Party

We had an absolutely amazing experience with Sail San Diego! Captain Dave was hands down the best—super friendly, professional, and incredibly knowledgeable. He used to work on a sightseeing tourist boat, so he gave us tons of great info about the San Diego coastline, landmarks, and local history while we sailed. The boat was clean, comfortable, and the whole experience was smooth and relaxing. Highly recommend this to anyone looking for a fun, memorable time on the water!

JA

JARG A.

December 2025 • Other Party

Cannot rave enough about our experience with Sail San Diego! January greeted us with a huge smile and was extremely helpful and Captain Rhys was awesome! The sail boat was immaculately kept and the snacks were on point. 100% recommended!!! 🙌 …

TG

Terry G.

December 2025 • Other Party

We had a blast on the morning sail with awesome Captain Greg last weekend. He is a wealth of knowledge about the San Diego area, an amazing captain and also funny! We saw lots of cool things and learned so much. Highlights included seeing the Navy dolphin and sea lion training center and also seeing the trees where Dr Seuss got his inspiration for the fun trees in his books!!! Thanks for a great trip Captain Greg!!

KD

Kirk D.

December 2025 • Other Party

Relaxing ~3 hour excursion in the bay. Intimate setting with only six passengers total plus the capitain. Nice selection of snacks and beverages, and you can bring your own snacks and beverages to supplement what they have / ensure you have something you will like.

JM

Jennifer M.

December 2025 • Other Party

We celebrated our 28th wedding anniversary on Aug 2nd with Sail San Diego on their sunset sailboat cruise. Our captain was knowledgeable and showed us the beauty of the ocean and San Diego. The only bummer was my husband lost his ball cap when we were sitting on the beanbag at the front of the boat. It’s one we got on an Air Force base while with our son. Other than that, it was the perfect way to celebrate our anniversary.

JA

Joseph A.

December 2025 • Group-Trip Party

We booked a three hour tour with sail San Diego and it was amazing. We went to the edge of the bay and to downtown. The views were amazing and captain Reese made the whole trip very enjoyable. We will definitely sail again with this crew!

JG

Jaskirat G.

December 2025 • Group-Trip Party

Took a sail with my husband with them last week. It was such a great experience. They’re so accommodating and called me ahead to give me all the heads up info. The group was only 6 people plus the captain. Captain was so well versed and experienced. It was such an easy sail and we had such a good time. Couldn’t recommend them enough.

Frequently Asked Questions

What happens if the weather is bad?

San Diego sunsets almost always deliver, but if the weather isn’t safe for sailing, we’ll reschedule or refund you. No hassle, no worries.

Will it feel too touristy?

Not at all. No packed decks, no scripted tour guide speeches. Just a small group, a great captain, and the perfect spot to see San Diego’s famous sunset.

What if I have more than 6 people in my family or group?

For bigger groups, check out our Private Sunset Sail. You’ll get the whole boat to yourselves, with space for up to 10 guests.

Will it be too cold after the sun sets?

It cools down, but we’ve got blankets onboard, and the drinks are on us. A light jacket is a good call, and if the views will keep you warm, you can cuddle up with your boo.

Will I make it to my dinner reservations?

Yep! Our Sunset Sail wraps up early enough to get you back in time for dinner. You just might want to make your reservations on the later side to be sure you get there with plenty of time.