Ruby Sailing Yacht

Our department did a team off-​site with Ruby Sails. There was 7 of us and 3 crew members. It was a lot of fun and such a nice day to sail. We ended up bringing our own food and set it up on the boat. The bartender Mark, was very helpful with setting things up and keeping our glasses full. Definitely recommend wearing a snug hat and non slip shoes on the boat. If you’ve never sailed this is a fun thing to do. Josh the captain was very good at giving me all the details and made it so easy to set up!

The Captain and his crew are fantastic. Laid back and fun. My husband swore he wasn’t getting back on a boat after we went whale watching in Boston in a storm (long story) but he loved our little excursion on the Bay. It was easy to reserve, a decent price and you got everything promised including a long, beautiful relaxed sail. The boat has been sailing quite awhile and the crew know what they’re doing but more importantly the kind of experience they want to offer. They set the tone of chill relaxed fun and don’t get too worked up over much. They want everyone to have a good time. We will go back as they make it very easy to get out on the water with no fuss and that’s a huge bonus in living in San Francisco. We’ve actually been out on a lot of different boats but this one is the only one we will go back to (not counting ferrys). Combine a sail with brunch at the Ramp and you’ve got a great day!

Captain Josh and crew are awesome! We had our wedding aboard the Ruby and it was perfect. Very relaxed and unique. Everyone loved being out on the Bay with the great views and fresh air. 28 passenger max was just the right size for us, with other charters being too big or too small. The pricing for the Ruby is very fair as well. The Captain was an excellent officiant and very easy to communicate with prior to the Big Day. I’ve also been sailing on the Ruby for birthday parties and more casual events… each time unique depending on the skies and sea, and super fun.

Just happened to get invited along on the Ruby for a public sail, and I get super sea sick. I took my anti-​seasick meds as directed, boarded the Ruby and had a great day.
You’re not required to work, it’s so casual and with the size of the boat (63 feet?), I felt very safe. A very attractive buffet of sandwiches, fruit and other snacks was set out in the cabin, this was included in the price. Beer/​wine extra.
I talked with many of the guests, everyone was friendly, and I also enjoyed a very tasty sandwich and a cold beer while hanging out a while near Sausalito. It was a real treat to see San Francisco from a boat, feel the boat under sail and just be out on the water. I’m not a sailor, I don’t have friends who own boats, so now I get why you’d sail on the Ruby.

I have booked with a few friends Ruby sailing every year for the last 5 yrs to
celebrate my Birthday, and this year is no different. It is the highlite of the whole
year for me, the best day of the year, can’t wait for Labor Day when i always book
with Capt Josh… but don’t go, i want it all to myself…
leigh M. Napa Valley

There is no better way to see the bay or the sky line of San Francisco than from Josh’s boat. This is a gem of a find for us and we go sailing at least 5 – 6 times per year. We do not go anywhere else but to the Ruby because we know that we are in for an amazing time. Thanks Josh.

I really don’t want people to know about Ruby Sails, but it deserves the credit.
While I’m sure Ruby Sails can accommodate the stiff, corporate crowd just fine — they graciously welcomed our whack-​pack group and easily morphed into our friends for the day. Worth every penny.

I booked the Ruby for my 25^th birthday extravaganza and Captain Josh was extremely helpful and attentive to my needs. There were about 21 of my closest friends aboard the ship and we had a fantastic time. The boat is quite large and we all fit comfortably with room to spare. I brought a few beverages on the boat: boxed wine and 4 magnum champagne bottles. There is a corkage fee of $ 25 for each bottle BUT boxed wine and magnum bottles = 2 bottles. I had a memorable birthday bash and would recommend this to anyone! :)

If I had only one day to spend in San Francisco I would highly recommend an outing on the Ruby Charters. «She» is a 64′ double-​hulled steel yacht built by Captain Josh Pryor and sailing the bay for thirty years. Conveniently located near public transportation (both the 22 Fillmore and the Metro T line will drop you at Mariposa Street.) Her berth is tucked behind The Ramp Restaurant where you can have brunch before you embark or have drinks and listen to salsa upon your return. If the weather’s nice or it’s baseball season or the Fourth of July or Kaboom book your spot well in advance.
For $ 40 one can go out individually during a public sail on a seaworthy vessel and take in sights along the waterfront, under the Bay Bridge, get up close with Alcatraz and soak up some rays in Sausalito. Captain Josh has a great music collection and is an amazing storyteller.
The price of admission includes lunch, unforgettable views and sea fresh air. Beer and wine are available for purchase and are reasonably priced. Private parties for birthdays, weddings as well as memorial services are just three examples of the types of events that take place aboard the Ruby and can accommodate thirty passengers. You are in good hands and the staff is great.
Like I said, if I only had one day to spend in San Francisco, I would highly recommend a Ruby adventure. Money very well spent!!!

Really, really fantastic experience for a super reasonable price.
Captain Josh is super friendly and laid-​back as well. Every one of my friends on board had a complete blast. The atmosphere was chill, but the ride was exciting and fun because of the occasional rocky wave.
I wanted to host a sailing excursion out into the SF Bay for my birthday, and also catch a bit of the Red Bull flugtag happening that Saturday. Captain Josh made sure to take us out to McCovey Bay to watch the festivities, then take us further out to the Golden Gate Bridge, around Alcatraz, then back for the flugtag. We saw seals and dolphins out in the water as well. Perfect day for a perfect sail.
Before finding Ruby Sailing, I researched a ton of places that were really expensive and overpriced. But with Ruby, their hourly rates are much more reasonable. You can find more info on their website.
Beer and wine downstairs, served up by Mark for $ 4 (didn’t give a discount to the birthday girl, but that’s OK :) We had such a blast we all ended up tipping the Captain generously after the ride.
I’ll definitely be calling up Ruby Sailing again! Thanks Captain!

My first sailing adventure on the Bay and it was worth every dime. The Captain and his crew remind me of a bunch of laid back hippies that are truly connected to the Sea. They were safe, professional and extremely friendly. Captain Josh kept in constant contact with me regarding the weather etc. if you are looking for a great sailboat and crew, CHOOSE Ruby Sailing! Thanks guys!

I took my entire staff on a trip this summer and it was a blast. Capt Josh healed the boat over to the edge which someone said was a bit unnecessary (a fellow sailor of mine) but I understand the point that this ride is entertainment as well as just a sail.
Rock on Capt. Josh

BEST PARTY IDEA EVER! I wanted to do something different for my Bachelorette Party. My awesome friend who works at The Ramp suggested trying a sail cruise around the Bay on The Ruby. The sail boat itself is clean, spacious (looked smaller in pics but with about 15 to 20 girls we were very comfortable), very maintained, crew is amazing and helpful, reasonable priced drinks ($ 4 starting price), Cap. Josh lets you play your music, and was SO SO SO MUCH FUN! As a SF native I was lucky enough to book the boat during the Americas Cup Race, got to spend a little time in The Cove during the Giants game, and parade around on this beautiful boat all around the sights and landmarks in my hometown. Its really a must see from the water on this sail boat.
We all though we were going to be cold too. It was windy but in heels and a super short dress (mind that it was my bach party) I was totally comfortable. At 60 to 65 degrees outside, a nice layering coat is perfect. They do offer extra jackets on hand if you don’t have one. After, The Ramp is a nice way to end you day or to start more fun too. :)
A HUNDRED TIMES, I WOULD RECOMMEND THIS SAILING BOAT FOR ANY OCCASION! Super fun and great views and times that anybody can appreciate. Do it again in a heat beat. THANK YOU Captain Josh, Terry and Mark for making my Bach Party wonderful and unforgettable! Cheers sailors!

The Ruby sailed me into my 30s this year with quite the bang! 24 of us headed out on the bay this last saturday and it was one seriously magic birthday. The crew was all so much fun and was really great at keeping everyone happy. We did a 3-​hr. bay cruise and honestly I wished we had done more. Everyone won’t stop talking about what a great idea it was!!! We will definitely be heading out on more adventures with these guys in the near future.

The Ruby is AMAZING. I chartered this sturdy boat, built by Captain Josh with his very own two hands, for my birthday party in September. This party is one I will never forget.
We started with appetizers and drinks at The Ramp and waited for 25 of my closest friends to join me. Captain Josh is a stickler for timeliness so I made sure to give friends a 2 hour window to show up, have a snack and a libation and board the glorious Ruby.
I decided on a sunset cruise and by law of the Bay you can’t sail after dark so we motored instead. This was actually preferable because a lot of people were worried about sea sickness. We got really lucky with a warm and calm night on the water. I definitely recommend going out as the sun goes down! We got to watch the city light up and it was stunning. We sailed along the coast for 2 hours. The view was amazing as was the company!
You can opt to have a beer and wine bar, a full bar and/​or appetizers. You can opt to pay for everything in advance or just pay as you go. I opted for just a beer and wine bar where everyone paid as they went. The bar is downstairs and the bartender is friendly as can be and happy to help. He even set out a bowl of gold fishies. There was a good selection of beer and wine and prices were very reasonable.
Captain Josh was a great sport. He was safe but not at all anal. He let us play our own music which made the experience one-​of-​a-​kind.
I would recommend the Ruby for any event. Its very affordable if you can gather a decent sized group. Everyone on my trip threw in cash and it was a great deal!
Upon exiting the ship, tear, Captain Josh did an amazing jig and sent us on our way :) I went back to get something that was left behind and we invited him to the after party. Captain Josh rode his bike all the way to the Castro, stopped in, drank a beer and was on his way again.
Captain Josh and the Ruby are amazing, I cannot reccommend this experience enough!

Great little 63 foot boat hidden behind a bunch of fences and «do not trespass» signs on Terry Francois Street. We came here for a team outing celebrating our company’s 10^th anniversary. I was so stressed out at not being late … but we ended up just hanging out with the boat docked for an hour and a half.
Finally around 11:30 we ventured into the fog, which appeared to be burning off and staying close to the shore, motor boated over a bit past pier 44. It was a gorgeous day and we got great views of the SF skyline, the Bay Bridge, Alcatraz, Treasure Island … we even caught about 2 swells.
It’s not really sailing when you don’t hoist the sails, but it was a fun trip nonetheless.

I went to write my review and saw that the «First to Review» Ruby’s was someone called Travis W. I was disappointed to discover that this was NOT me, and that I’d have to re-​write the review I never wrote in the first place. (Mental note: Do more Unilocaling while asleep/​blackout drunk/​hypnotized.)
Anyhow, the boat is a schooner or a sloop or a galleon or something. I don’t know – something with a sail on it. Captain Josh is a salty old tar who will regale your women with dirty jokes and keep the party hyphy with his hip-​hop mixtapes not quite «bumping» out of his mini boom box. Think Beatnuts and Leaders of the New School, and then wonder how the hell Capt. Josh got his hands on these tapes. His «first mate» Elizabeth (the nature of their relationship is a little murky, and she would not divulge details when pressed) is a quirky bat who is more than ready to show you how to dance on the floor of a boat that is tilted at 45 degrees. Her duties seem to consist of slangin’ the booze and warning you not to walk backwards down the ladder into the cabin. They’re a hell of a team, completely laid back and fun to party with.
The boat was rented for my friends thirtieth birthday, and when her imitation Captain’s hat flew into the water, irretrievably lost, Captain Josh had a spare to immediately console the distraught birthday girl. (You must’ve misread; I said it was a THIRTIETH b-​day party, not third.) Well played Josh, the crankypants were about to come out.
You can rent the boat in two or three hour increments, which is just about the perfect amount of time to get a good drunk started and give your face a sufficient wind-​thrashing. Fair warning: you can get pretty wet if you’re not aware. Stay on your toes if you care about staying dry.
Dudes: You might have to pee sitting down when the boat is hauling ass and the water is choppy. It’s incredibly emasculating, and makes you feel like your dear old dad getting up in the middle of the night and not wanting to turn to bathroom light on.
Also, Captain Josh totally did a solid and agreed to donate his services to my sister’s boyfriend’s charity auction. 5 stars fo sho. Ahoy, mateys!

When your good friend is sailing away on a new adventure to New York, and you want to wish her a bon voyage, what better way to do so then on an actual sail boat around the city that she enjoyed for almost 5 years.
Captain Josh made for a fine day on the open seas, and with some pretty intense wind through the bay, it made for quite an adventure. At one point I thought I’d fall off the boat around Angel Island, but when Mrs. Captain was sitting on the lower end of the boat, inches from the water, not scared… i got my confidence back and just enjoyed the ride.
Ruby is a sweet ride. Its even a better ride when you know everyone on the boat. Its even a BETTER ride with a few beers in you, a belly full of sandwich, and the smell of open water in your nostrils. I know this much…2 hours is enough for me. I will never be a lifer… but a few hours got me going.

Berthed behind the outdoor patio of the Ramp restaurant (foot of Mariposa, east of 3^rd). Gangway is down just behind (stage left) of the bandstand.
Ruby is fine girl. 60′ steel hulled Sloop designed, and a greater part built by Capt. Josh himself. Certified Capt. on the Bay. Won’t find a more experienced sailing charter! Your safety, and enjoyment are assured. Very stable and smooth, she’ll drag a rail just fine too! Hang on.
Just get on board and enjoy. Perfect escape on a weekday if you can pull that off. Looking towards shore at all of the working folks bustling around whilst you just cruise along… thats the Best!
And weekends of course she is available. Often 3 cruises a day weather permitting. Plan aprox. 3hr. cruise time. (sound familiar?)
Sandwiches, Beer & Wine available from the galley for a nominal fee.
You can bring your own spread if you prefer, just share. 8-​)
Blue Angels for Fleet Week (Book EARLY), KaBoom Fireworks show (Book EARLY), Memorial Services can also be performed. I think Weddings too.
Capt. Josh is a true SF character. What do you want to know? He knows it.
Ahoy Josh!
(Yes. Excellent Tip: Don’t Be Late!!)

Do you have an extra $ 35? If so I can tell you how to spend it and have the best time. Just get yourself down to the Ruby (next to the Ramp) and Josh and his crew will take you out for a 2 ½ hour sail on the bay, provide you with lunch and drink and a very memorable day! I have been on this boat so many times and each time I bring new guests and each and every one of them walk away smiling. (ok so a few have thrown up but that wasn’t my fault!)
Yesterday the weather was perfect. The sun was out the wind was strong, the boat was leaning and guests were having fun. The next time you have an event book the Ruby or better yet forgo the typical tourist spots with your out of town guests and show them a view of the city from the bay.
Just be sure to call ahead and bring cash to pay as your board. No doubt if you have special requests Josh will do his best to accomidate you as long as it is legal.