Chicago sailing, Detroit sailing, instruction, sailboat lessons, an innovative sailing timeshare program and more.

Online Reviews

If you don't want to own the boat, just looking for summer fun - Pinnacle Yachts would be the right choice for you. No experience necessary. Last summer I was leasing a 37ft sail boat and it was a blast. Learning to sail was on my bucket list and I finally did it with the help of this fine organization. Everything is well organized, any problems or needed repairs were done swiftly. I want to thank Pinnacle Yachts owners once again for the wonderful experience - greatly recommended!

Lee N.
Romeoville, IL

If you're wondering whether or not to lease a boat with Pinnacle, stop thinking and just do it. Out of the four summers I've lived in Chicago, summer 2014 was the most fun thanks to our 37' sailboat rental through Pinnacle. Here's the story- being a power boater growing up I've always wanted to get out on Lake Michigan but didn't want to deal with the hassle of buying a slip and having to store a boat over winter. After spending some time googling boat rentals Chicago, I decided to contact Pinnacle. Their owner Gary called me back right away and explained the program to both me and my friend. I originally thought we wanted a power boat, but Gary sold us hard (in a good way) on signing up for a sailboat (even though we had no prior sail experience). I recommend doing it with a friend because it created calendar flexibility, splits the cost, and was safer. After a fun kick-off lunch at the club and a 7 day intensive training course (which we had to pay separate for) we pretty much felt comfortable with the boat and could easily throw up the sails and get around the lake. Hardest part is actually pulling in and out of slip, not sailing. You essentially own the boat all summer along with 9 other owners, and don't pay for gas or maintenance. We were worried about the slot draft (like a fantasy football draft that lasts all day- can draft ~20 time slots either 9am-5pm or 5pm-9am), but with careful planning we secured all the weekend dates we wanted, including Memorial Day, Labor Day, Lolla Sunday, air and water show, and a few Wed firework nights. Throughout the season we picked up a bunch of random free slots too because most other boat owners were from the suburbs. Season runs from end of May to end of October. I think we ended up using it approx 30 times. The boat is awesome with a super nice cabin, two bedrooms, kitchen, and a bathroom. I even slept on the boat a couple of times. Most other owners respected the cleanliness and treated it with respect. Our wind gauge kept breaking which was annoying, but that was only problem we had with maintenance. We found that on weekday nights when we'd take a couple friends out on the lake we would usually sail. On weekends when we'd max out the boat (12 person max), and hang out at the playpen we rarely sailed and just used the motor. Motor maxes out at around 7 knots, which is the same top speed we hit with the sails up. One word of caution- there is an evergreen clause in the contract which automatically signs you up for the next season if you don't tell them otherwise by August...kind of rubbed me the wrong way but was the only negative in entire experience. Pinnacle seems to have this yacht rental business down to a science...and is a very efficient company. I highly recommend.

Nick M.
Chicago, IL

This company is great. We used them and had some excellent experiences. They are very responsive as well if you do have an issue, and will solve it fast. I recommend!

Genevieve T.
Chicago, IL

Clean, beautiful boats. Knowledgeable, friendly training staff (especially Capt. Leo). If you're looking for a way to spend some time on Lake Michigan, I highly recommend looking into Pinnacle.

Gyi T.
Chicago, IL

The experience we had last season with Pinnacle Yachts was outstanding. My husband and I had been trying to find a fun activity the whole family could enjoy, and we decided to lease a share on a 37ft Jeanneau with Pinnacle. It was the best decision we made all summer.

The boat was always clean and maintained. I felt very safe having our younger children aboard, because Pinnacle really makes safety a priority.

We came into the program with no sailing experience, but the training we recieved from our licensed captain was amazing. She was so friendly and professional and really made us feel like sailing pros by the end.

Sailing with Pinnacle was the highlight of my family's summer! Can't wait for next season!

Linda R.
Naperville, IL

I owned a sailboat of my own for about three years, but finally got tired of all the maintanence and I didn't have much time to go out so I sold it. Two years later I came across Pinnacle Yachts and knew that it was perfect for me. It has all the perks of owning a boat without any of the work.

I have been a member for two years, and am I thrilled for the upcoming season. The boat (a 45foot Jeanneau) is in pristine condition whenever I arrive. If there is ever a problem the on call maintanence staff is just a phone call away to fix the problem. They are friendly, professional and quick.

Pinnacle's scheduling system is genius. It is fair and I was able to pick timeslots that fit into my schedule.

My experience with Pinnacle has been great. Can't wait for another season.

Robert W.
Chicago, IL

I have been in a sailing club and a power boat club, and have used charter boat rental companies in Chicago numerous times. Pinnacle Yachts is radically different. As a member you are one of only a few people who lease the boat and sail it privately all season. The boats are built by Sea Ray and Jeanneau, two luxury brands, are in perfect condition and loaded to the hilt. But most impressive is Pinnacle's scheduling software which avoids the "not-available" problem that boat clubs have because of their first-come nature.

Peter F.
Chicago, IL

I have been a member of Pinnacle Yachts since 2004. I have always been impressed by their attention to detail, professionalism, and their beautiful fleet. The timeshare experience has been very rewarding. The boats are very well maintained and whenever I have my time ,it is like having my own sailboat without any of the outside responsibilities and costs. The scheduling system allows for trading and communication between captains. Evening sails are beautiful and add to a great experience.

I would recommend Pinnacle Yachts to anyone who loves to sail.

Elgin, IL

I have been sailing with Pinnacle every summer since 2003 when my wife gave me a season's lease as a Christmas present. They offer a program that more then meets my desire for sailing beautiful, well-equipped yachts on short day long sails with all the convenience of Monroe Harbor in Chicago and with none of the headaches of ownership. A few comments:

PROFESSIONALISM: At the time i joined in 2003, Pinnacle had just a few yachts in Chicago. I was initially overwhelmed with the caliber of the personal, professional attentiveness of the staff to every question, concern and need. Remarkably, as Pinnacle has grown considerably with hundreds of captains now in the program on the east coast and in Florida in addition to expanding in Chicago, the level of personal responsiveness is absolutely undiminished. The Pinnacle team is a class act.

The SHARED LEASE EXPERIENCE: I fully expected that sharing a yacht with 9 other captains would sometimes result in finding the boat a bit messy or in some disrepair on occasion when showing up with friends and family for a day on the water. To the contrary - the yachts are meticulously maintained with a weekly once-over by the staff. And the captains in the program are extremely attentive to leaving the yacht in pristine condition for the next captain on the schedule. In 8 years, I have never boarded my Pinnacle yacht and found any evidence of someone else having been on it; OK, one time i arrived and found a cold sixpack of Blue Moon Ale left in the cooler and a Jimmy Buffett cd in the deck - - - woe is me. The respectfulness of the captains in the program for each other is a real asset - and leaves you with an experience that this is really your yacht and yours alone.

The SYSTEM : Managing the sailing schedule is a piece of cake, thanks to an extremely usable website with features that easily support the occasional trading of scheduled sailing days between and among the captains. For the most part, you only know the other captains on your yacht via email exchanges through the website - and their courtesy and responsiveness to each other is always evident. The Pinnacle group goes out of its way to ensure an equitable balance of sailing days across weekdays/weekends, days/evenings, and over the entire sailing season. It's all smooth as butter.

The YACHTS: Beautiful Jeanneau yachts - - over the years, I've sailed their 34', 37' and 45' yachts out of Monroe Harbor. All are well rigged, fully equipped and fitted, and well-stocked below with all the supplies one needs. More of a boat than I would ever or could ever afford owning on my own - - all for one lease price. They are spectacular.

Overall, can't beat it. I have friends who own sailboats and who hardly ever get out on the Lake as often as I do on my leased Pinnacle yacht. Those who truly enjoy the maintenance, the upkeep and the wintering of a sailboat - - well they have a leg up on me, because i get none of those pleasures. I just enjoy sailing on a beautiful yacht with none of those other headaches - and the Pinnacle option allows exactly that!

David K.
Hinsdale, IL

They make it all so easy. Newer fleet. Outstanding service. Perfect for someone who wants to experience the luxury of very nice boats/yachts without the hassle. Unless you are VERY experienced, their instruction is well worth the price. Patient instructors and excellent depth of knowledge. The best in the business.

D P.
Chicago, IL

This program is THE BEST !!  I have been a member since their founding year (13 years now I think) and have never been disappointed in the quality of the boats nor the service of the staff.  I started out on a 37 foot sailboat on now use the 42 foot sailboat.  These boats are rigged to the hilt; bow thrusters, heavy weather gear, flares, cookware, cool plastic glasses for wine and everything you need to host a great outing for one special guest or a group of fun friends.

This is how good they are.  This summer I had scheduled the boat  for a week straight and was living on the boat.  I love the smell of a clean boat and called the 800 maintenance line one morning to say the Murphy's wood soap was running low and could they have somebody drop off a bottle one day this week.  I also noted that the jib lines seemed to be slipping on the winch clutch and asked if somebody could look at them soon.  I went into the yacht club for breakfast, and 45 minutes later I returned to find a full bag of cleaning supplies (with a note that the spare bottle was under the stove), and get this..... the jib lines were already swapped out with new ones.  I was floored.

This is not the next best thing to owing a boat; it is so much better.

If you are considering this program and want some tips on how to get the most out of the program (best scheduling tips, sunrise sails, overnights in the harbor etc.)  fell free to call me anytime.

Chicago, IL

My wife and I joined Pinnacle almost three years ago with one share, four years later here we are having committed to, at our peak, three shares. Not only are the Pinnacle boats kept in outstanding condition, but the logistical efficiency of the broader company is truly impressive. Boats are washed, well maintained, scheduling is easy and user friendly, and fellow-participants go above and beyond to sort out scheduling (via their online based platform for trading and claiming slots) to fit respective time desires. In fact, I can think of few companies which possesses the ability to simultaneously offer outstanding customer service, logistical efficiency, and value. Most importantly, however, Pinnacle is run by hard working, honest, fair business people who aim to serve their client. It is that fact, more than all their other strengths, which makes Pinnacle a winner.

Justin D.
Chicago, IL

First rate, professional experience. Magnificent yachts, meticulously maintained. I have been sailing my whole life and this is the only way to go. Why would you own a boat when they take care of everything!

Jim B.
Lake Zurich, IL

Absolutely a top-notch organization. I have a Pinnacle timeshare in a 34-foot motor vessel (a SeaRay Sundancer 340) this summer (2010) in Burnham Harbor, Chicago. Pinnacle has a sail program too. They maintain the boats meticulously and have a program that ensures fairness in allocating time slots with your fellow captains. The pricing is very, very reasonable compared to the cost of owning a top of the line boat like the Sundancer.

Edward R.
Oak Park, IL

We have been sailing with Pinnacle Yachts for six years now and could not be happier. Our boat is fantastic with every option and is kept in near perfect condition. The only other people that use the boat are members that we have come to know over the years, with a new person or two joining each season. They are all really good people who care for the boat and respect each other. Pinnacle has a professional staff that maintains and cleans the boat on a regular schedule. These guys are "Johnny On The Spot" whenever you need anything. Having leased a yacht from Pinnacle; we would never go back to owning a boat ourselves again. Overall a great experience and a great value for the money. Highly recommended!

Jeff J.
Chicago, IL

We had a 'timeshare' with Pinnacle Yachts in Chicago during the 2011 sailing season. (The have locations in Annapolis, and Miami as well, I think.) The boat was a 2006 Jeanneau Sun Odyssey 40 berthed in Belmont Harbor. It was a terrific experience given our situation. It worked so well for us because our schedules are very flexible - sailing on weekdays is as convenient as sailing on weekends. If I were living in Chicago now, I would definitely go with Pinnacle again: they keep the boat in top condition, their on-line scheduling system is fair and easy to use, and the cost was very reasonable. Our share gave us 27 sailing times (either 9:00 am - 5:00 pm or 5:00 pm - 9:00 am) during the season for about $7500 - and that's a bargain; the slip alone would cost over $5500 for six months. With haul out, storage, and routine maintenance and repairs, it's like paying the ongoing costs of sailing but getting a free boat!

"Sharing" a sailboat - say by a partnership - is a different thing entirely. In a timeshare the expensive decisions and the dirty work are handled by the organization, e.g., Pinnacle or Sailtime. (Example: we noticed a small tear in the jib. We reported it to Pinnacle; when we returned for our next sailing session there was a new, crisp jib in place.) When sharing, all that falls to the partners and differences in preferences and resources can mean unhappy sailors.

Chicago, IL

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