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Sailing Trips

Whale Watching Season Begins Tomorrow!

We are fired up here at Sail San Diego for one of our favorite times of the year… San Diego’s whale watching season, which officially begins tomorrow, December 15!! Sail San Diego is the only San Diego charter company to offer multiple ways to see the Pacific Gray Whale migration. For power & speed enthusiasts,…

New 4K Sunset Sail Video!

For over 30 years, Sail San Diego has been the #1 sailboat charter in San Diego, and we’re still going strong as #1… just ask TripAdvisor! We’ve recently been expanding our YouTube channel here at Sail San Diego, and that with 4K Ultra High Definition video: (Use the gear icon, and select 2160p 4K to…

2 Options for San Diego’s 2018 Whale Watching!

Sail San Diego is proud to offer our guests two options, each with departures twice daily, for viewing the Pacific Gray Whale migration of 2018 – up close and personal! First, we offer 3.5-hour whale watching tours aboard our 40-foot modern-day sailing yachts. Second, we offer 2.5-hour whale watching excursions aboard our 34-foot walk-around dual-engine…

Did Someone Say “Christmas Eve Whale Watching”??

Sail San Diego is offering whale watching aboard our 40-foot sailing yachts on Christmas Eve 2017. Several seats have already been sold & availability is very limited due to the holiday, so make sure to secure your family’s spot on an amazing sailing cruise with the Pacific Gray Whales during their annual migration. Spend Christmas…

A lesson Of A Lifetime

         My years of preparation for this epic journey began in San Diego at a little one-boat sailing company. It was my 23rd birthday and my girlfriend of the time had purchased two tickets for a sailing lesson. Other than something to do, we didn’t think it would spark an everlasting love for the ocean…

The Action On The Water Has Been Fantastic!

Our whale watching excursions have been the best ever this year! Not one day has gone by that we haven’t seen grey whales & humpback whales. Today a group of guests went out for a three and a half hour whale watching tour and they came back with the biggest smiles on their faces. The…

Whale Watching On The Power Boat

Today we went whale watching on the power boat. The day started out with high visibility even though it was a bit foggy. We drank hot coco as we accelerated towards the open ocean in search for the beasts of the deep. Traffic on the water was almost non existent because of the low wind…

Why We Chose Our Yachts

Our boats are built for ultimate comfort and ease of use to create the best sailing experience. In the sailing world there are a whole lot of options to chose from when it comes to picking the right boat. The Catalina 400 was the boat of choice for us because of its wide body spacious…

The Joy of Spacious Sailing

So you made reservations to go sailing, you contacted all your family members, prepared yourselves to spend a couple hours on the water, and then you get there, and there are 5 other families, crying babies, and you forgot your earplugs next to the aspirin at home.. The mistake you made was not booking your…

We Love Your Feedback!

For those of you who have already made it down to Shelter Island Marina to enjoy a day on the water with us, we would love to hear about your experience! From Bachelorette Parties, Family Reunions, Date night, Anniversary’s, Corporate Events, we have had a lot of fun with our guests and enjoy the stories they…