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Midday Sailing Adventure: Best Wind, Wildlife & Views on a Catalina 400

About this Experience

What you'll do:

Set sail right when the wind’s at its best! Our Midday Sail is all about real-deal sailing, wide-open views, and maybe even a dolphin or two. Cruise aboard our spacious Catalina 400 with snacks, drinks, and room to relax—then still make it back in time for happy hour.

Why we love it for your party:

  • Peak sailing conditions (The wind’s up, the boat’s moving, and you’re getting the real sailing experience)

  • Wildlife in action (Midday is prime time for spotting dolphins, sea lions, and maybe even a whale)

  • San Diego at Its best (Clear skies, wide-open water, and views you won’t get shoreside)

  • Plenty of time for more (A solid adventure without killing the rest of your day)

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

  • Cold drinks included (Beer, hard seltzer, soft drinks, and snacks — all on the house)

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)

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!

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.

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.

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.

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.

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!!

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!!! 🙌 …

Frequently Asked Questions

What happens if the weather is bad?

San Diego’s got great sailing weather most days, but if conditions aren’t safe, we’ll reschedule or refund you. Easy as that.

Is this just a slow cruise?

Not even close. Midday is when the wind picks up, so you’ll feel the boat move. It’s real sailing, not just a float around the Bay.

Will it feel too touristy?

Nope. No packed boats, no canned tour guide speeches. Just a small group, a great captain, and plenty of space to enjoy the water. That’s why locals love to come sailing with us.

What if I've never been sailing before?

Perfect! This is a great intro! You’ll get to experience real sailing with an expert captain, and if you’re up for it, we’ll even show you the ropes (literally).

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

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