Corporate Membership

Entertain your clients, friends, and vendors with captained charters

Low-cost boat charter

How Captained Boat Membership Works

Looking for a different way to entertain clients and business associates? Forget the golf course, sailing is the best way to make an impression; they’ll always remember their first time sailing along the Chicago lakefront. And sailing gives you plenty of time to talk over deals and connect. 

Beyond entertaining, SailTime is perfect for team-building activities, rewarding high-performing employees, and taking your family out for some needed off time. You’ll spend all summer enjoying your membership boat however you want.

Three people sitting on the trampoline of a catamaran

What it Offers

Easy, Hassle-Free Entertaining

Captained charter is usually an expensive outing. For a large new boat with all the amenities, you could be looking at up to $800/hour plus captain’s cost. But by signing up for SailTime corporate membership, you could reduce that to around $500 per half-day sail for the same quality new boat.

By becoming a member, you pay upfront for a guaranteed amount of sailing that you book yourself via our online scheduler.  Prices vary according to the boat model and the amount of sailing you want.  See below for membership levels and see the fleet for pricing information.

You don’t even have to be present.  With a USCG-certified captain onboard, you can gift a magical evening on the water to whomever you want.  Customers, family, and friends; with how much boat time you’ll have, you can afford to make everyone’s summer more nautical.


Minimum of 7 sail times per month
Additional sail times when reservations are made with 36 hours of the start time
Cloud-based App with scheduler


Minimum of 3 sail times per month
Additional sail times when reservations are made within 24 hours of the start time
Cloud-based App with scheduler
Multiple Locations

Nationwide Company? Sail all over!

SailTime has locations across the United States, in every large sailing city.  Contact us today to setup sailing adventures for your entire company!

Find Your Boat

View Our Fleet

In addition to our downtown Chicago fleet, we also have boats in the north suburban Winthrop Harbor, IL.  Those boats have their location listed in the fleet list.