Windward Sailing

Rented a boat and captain for an afternoon sail. They were able to accomodate us the next day (late May), whole transaction was smooth, boat was fine enough, Captain was awesome — personable, experienced, professional, efficient. (He was a South African transplant who teaches sailing there on the weekends.)
Just a great experience all around. Highly recommend!

We have belonged to Windward Sailing Club for almost 20 years. We are so pleased with their boats and their help. Everyone we have ever dealt with have been most pleasant and helpful, from making our reservations, meeting us at the dock going or coming, as well as the cleaning and maintenance folks. Thank you Windward owners and workers for making sailing such a pleasurable experience.

These guys are solid, super easy to do business with and helpful, even if you’re not a member. Rented a duffy from them last weekend and it was smooth sailing. Thanks!

SO HAPPY WE FOUND THESE GUYS!
I purchased a groupon for Pirates Life Boat Rentals in February and when I called to use it, they had a recording saying they were closed until June. I call in July and book a birthday duffy for September 20^th. I called to confirm on ⁹⁄₁₅ and they have another recording saying they are closed and not taking reservations. However, nobody had called to let me know. Imagine if I had showed up with my group of friends and nobody was there to greet us. My entire birthday would have been ruined! I called and texted them numerous times and to this day they have not responded.
THEN, I find Village Boat Rentals and call them and Ali answers right away and is willing to get me scheduled last minute for a decent price. I let her know I will confirm with everyone and call her back. When I call back 30 minutes later, nobody answers and I leave a message. Two days go by of me calling and no answer or no call back from them. AWFUL.
Finally, I go onto Unilocal to read the reviews on the two above places and they are the worst reviews. I’m not sure how they are still in business.
THANKFULLY, someone left Windward Sailing’s name. I called them and they were very professional and extremely helpful! They booked a duffy for me on very short notice. When we got to Windward Sailing, every single employee there was very cordial and wanted to make sure we were good to go. One of my friends was running a little late and they weren’t pushy with us. They let us hang out on the boat and didn’t start our two hours until we pushed away from the dock.
We had an absolute blast and Windward saved the day! We will definitely be using them for all of our duffy adventures in the future!

This review is not for the business but for an employee. I was on a walk, and walked up into the parking lot to get a view of the bay. While standing there, I noticed an employee smoking a cigarette on the dock which I thought was odd because children sail here. When he was done, he flicked it into the bay. Kind of strange to treat the bay like that when the bay is what pays your bills…

There’s a lot of competition in the Duffy rental business these days, with GroupOn deals flooding the market. The price for these social media promotions may be good, but Buyer Beware. Because they are promoting so heavily, it can be very difficult to book for the day and time you want, even planning weeks ahead.
That’s why I’m a loyalist to Windward Sailing Club (formerly Lido Sailing Club). You guys do such a great job and are so accommodating that I’m a little bit reluctant to let the world know about you. But good businesses should be rewarded, so here goes. Five stars to you!

We rented a duffy to celebrate my daughter’s 1^st anniversary and my son’s birthday. We took a 2 hour sunset cruise that was beautiful — we were so fortunate to have beautiful weather and a gorgeous sunet. The duffy rental was reasonable — $ 130 for 2 hours. The staff for Windward Sailing were extremely nice and helpful — the duffy was well maintained.
We had a great time cruising the harbor and seeing the beautiful homes and boats. I would highly recommend Windward Sailing for an enjoyable tour of the harbor and islands.

I’m not a member but I have crewed their boats for a couple friends who are members and this seems like a great value for access to a cruising sailboat fleet and a Duffy fleet. Good selection of boats, member dues and rental rates appear quite reasonable compared to boat ownership or other rental options. If you really, really like to go out on Duffy booze cruises with your friends, a membership might make sense as the Duffy rental rates for members are a fraction of the a la carte rates at Duffy of Newport Beach or other rental outfits. They have a pretty good location on the harbor but the downside is parking, which is almost nonexistent even for members; unless you are heading out at the crack of dawn, expect to park on Lido Island and make the walk across the Via Lido bridge. I’ve considered joining but I’m not a member because I have very affordable access to daysailing boats via UCI’s sailing club as a UC alum, so I would only need Windward’s boats for a weekend Catalina cruise and prefer to bandwagon with my friends for that.