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Private All-Day Sailing with Complimentary Drinks, Snacks & Wildlife Viewing image 1
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Private All-Day Sailing with Complimentary Drinks, Snacks & Wildlife Viewing

About this Experience

What you'll do:

Six hours on the water? Now you’re talking.

Maybe a few hours on the Bay just isn’t enough. With six hours on the water, you’ve got time to do it all – sail the coast, catch the wildlife, drop anchor, and take a swim. Depart when you want and sail on your schedule. This is all about slowing down, stretching out, and giving you and your crew the time to relax. No rushing allowed.

Why we love it for your party:

  • Six hours to just unwind (No rush, no schedules, just you and your crew soaking in the bay at your own pace)

  • Captains who keep it easy (Friendly, funny, and super chill, making sure everyone feels right at home on the water)

  • Drinks and snacks on hand (A relaxed mix of beers, seltzers, and tasty bites to keep the good vibes flowing)

  • Best seat in the house (Lounge on our cozy bean bag up front and watch the wildlife glide by)

  • Bathroom onboard, no worries (Clean and convenient, so you can stay comfy and keep the day going smoothly)

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.

Additional information:

  • Please check in at our sailing lounge 15-30 minutes before departure. A physical boarding pass is required to board your assigned sailboat.

  • Little sailors under 13 must follow USCG rules and wear a lifejacket—but don’t worry, we’ve got plenty of comfy, fun ones ready for them!

  • What included:

    • Experienced, fun, and laid-back captains! Funny, laid-back, and great with smaller sailors (and their grown-ups).

    • Complimentary drinks - Tecate, Coors Light, Budweiser, Hard Seltzer, Coke, Diet Coke, Sprite, Ginger Ale, Water Bottle, Honest Juice Boxes

    • Complimentary snacks - SunChips, Pop Chips, Hawaiian Kettle Chips, Rice Crips, Kind Bars, Fruit Bars

    • Comfy bean bag on bow - Our favorite seat to spot wildlife.

    • Bathroom onboard - Spacious, spotless, and meticulously cleaned before and after every trip for your comfort

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)

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!

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.

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.

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.

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!!

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.

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!

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.

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

Can we bring our own drinks?

Yep! We’ve got drinks onboard, but if you’ve got a favorite bottle of bubbly, bring it along.

Is there music on the boat?

Oh yeah. Each boat has a Bluetooth speaker, so bring your playlist and turn it up. This is your party.

What should we wear?

Whatever you’ll be comfy in. Sundresses, swimsuits, matching bride squad outfits—go for it. Just bring a light outer layer in case the breeze kicks up.

Will we get seasick?

Most guests don’t, but if you’re worried, stick to the morning or sunset sails when the water’s calmer. And maybe don’t pre-game too hard before.

What if we have more than 10 people?

No problem! We’ve got bigger boats for groups up to 22. And if you book a Custom Sail, we can anchor and swim, stay out as long as you want, and even curate a bar package for your group.

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What about food? Can we do lunch?

Light snacks and drinks are included, but you can bring your own or go all out with catering. We’ve got some solid local vendors we can recommend. Just let us know what you’re thinking!