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

Since 1998, members in our renowned fractional yacht leasing program have had the pleasure of cruising a magnificent new Sea Ray Powerboat or Jeanneau Sailboat without the cost and obligation of ownership.

From Burnham, Monroe, DuSable, Belmont and 31st Street Harbors in Chicago, Dinner Key Marina in Miami, and Annapolis Landing Marina, members have season-long access to a fabulous new sail or power boat in the wonderful waters near their home.

Pinnacle members enjoy:

  • A Single-Season Lease That Covers Every Expense
  • No Mortgage, No Down Payment, No Maintenance Costs
  • Use of Your Personal Yacht Across the Entire Season
  • Day, Weekend and Week Long Cruising In Local Waters
  • The Best Harbors in Chicago, Annapolis & Miami
  • Sail & Powerboat Lessons By U.S. Coast Guard Instructors
  • Concierge & Professional Captain Services

For a low annual lease fee, Pinnacle members have season-long access to a new sail or power yacht valued as much as $600,000. With private, day-to-day use of their boat, members can cruise for a week, get away for several days, or head-out for just a few hours.

The Pinnacle Fleet is comprised of new sail and power yachts by acclaimed international builders Sea Ray and Jeanneau. These are high-end yachts that sport sleek, fast hull designs, state-of-the-art instrumentation, and finely appointed interiors.

Pinnacle offers sailing lessons and powerboat lessons for members new to yachting or who wish to enhance their skills prior to taking the helm on their own.

For members that would like to hand the helm to others so they may focus on their family, guests and business associates, Pinnacle offers U.S. Coast Guard Licensed Captains and Concierge Services for superb entertaining aboard your yacht.

Quite different than a conventional sailing club, boat charter or boat rental company, Pinnacle has created a sophisticated boat leasing program that serves as a surrogate to yacht ownership. We do not accept walk-up day charters; we do not rent boats for day sailing or bareboat charters. Rather, we establish a small group of members that share exclusive, private access to a fabulous sail or power yacht in our fleet across the entire season. Members know the boat and each other, treating the yacht it as if they own it, and treating each other with respect and friendship.

Pinnacle Members are an astute and fun group, mostly in their 40s, 50s, and 60s, including corporate executives, entrepreneurs, financial professionals, physicians, attorneys, management consultants, government officials, educators, contractors, and real estate developers. Most are capable of owning their own boat but choose Pinnacle instead for convenience and camaraderie more so than financial reasons.

Now entering our seventeenth season with hundreds of delighted Members, Pinnacle Yachts is the world's most successful shared yacht leasing organization. Since our inception in 1998 in Chicago, our fleet has been sold-out every season. Because of the popularity of the program, it is best to act well in advance of the season to secure a spot.

We invite you to join us!

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"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, Illinois

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