Charter Sailboats Bareboat or Crewed

Charter Sailboats Bareboat or Crewed

When using a charter company's boat, you have the choice of having a paid captain and/or crew either allowing them to do all of the work, or mixing your skills in with their skills – this is called a Crewed Charter, or if you are qualified (check with the charter company for qualifications), you may take the boat out on your own without supervision – this is called a Bareboat Charter.  These boats commonly have keels for stability and commonly heel, but don't flip over.  Boats are probably from 22' to 80' long.

Maybe you just wish to enjoy a sail, take clients or friends out on the Lake for a sail, choices may include completely provisioned with food and beverage, fueled up and ready.  All you have to do is step on and go!  Can it get any easier to go sailing?

Maybe you would like to live on the lakefront for a week, enjoying a staycation, go swimming, fishing, learn to sail, or sail to some ports up and down the lake.  Maybe you’re coming into Chicago and want to charter a boat for the day or week.

The following offer bareboat or crewed charter sailboats, call them, tell them what you want to do, how you want the boat provisioned and set sail.

The purpose of this blog is to break the myth that sailing is exclusive and expensive.  You don't have to pay the winter and summer storage fees, insurance, maintenance, cleaning, etc.  Just pay for the days you use a boat.  It may be in the hundreds of dollars or thousands (not tens of thousands) of dollars depending how often you go out.  Again, I have succeeded to introduce sailing in the hundreds or low thousands of dollars. The door is wide open, check them out and join in the fun -

LAKE MICHIGAN

INDIANA

Hammond Harbor, IN
Not yet!

Michigan City, IN

Michigan City Sailboat Charters
Bareboat or Crewed

ILLINOIS

Jackson Park Harbor, IL 
Not yet!

31st Street Harbor, IL

Next Level Sailing - IACC America's Cup Boats
Crewed

Olson’s Classic Yacht’s Sail Share
Crewed

Burnham Park Harbor, IL

Fairwind Sail
Crewed

Red Witch Tall Ship
Crewed

Monroe Harbor, IL

Chicago Yachting
Bareboat or Crewed

3rd Coast Cruising
Crewed

Go Sailing Chicago
Crewed

Ahoy Chicago Sailing
Crewed

Offshore Adventures
Crewed

Sailboats, Inc.
Bareboat

Seabreeze Charter
Crewed

Island Sailing Boat
Crewed

Come Sailing
Crewed

Just Sailing
Crewed

Olson’s Classic Yacht’s Sail Share
Crewed

Sloop City Sailing
Crewed

Aegir Expeditions
Crewed

DuSable Harbor, IL
3rd Coast Cruising
Crewed

Lakeshore Sail Charters
Crewed

Go Sailing Chicago
Crewed

Phenix Sailing Charters - Catamaran
Crewed

Party on Boats in Chicago
Crewed

Navy Pier, IL

Tall Ship Windy
Crewed

Belmont Harbor, IL

Go Sailing Chicago
Crewed

Chicago Sailboat Charters
Crewed

Windy City Sailing
Crewed

Chicago Yacht Shares
Bareboat or Crewed

Sea Safaris
Crewed

Chicago Match Race Center
Bareboat – Open to highly skilled sailors.

Montrose Harbor, IL

Two Brothers Sailing
Crewed

Radiance Charters
Crewed

Evanston, IL

Not Yet!

Wilmette, IL

Free At Last Charters
Crewed

Kenilworth, IL
Not Yet!

Winnetka, IL
Not Yet!

Glencoe, IL
Not Yet!

Highland Park, IL
Not Yet!

Lake Bluff, IL
Not Yet!

Lake Forest, IL
Not Yet!

Great Lakes, IL
Not Yet!

Waukegan, IL

Not Yet!

Northpoint / Zion, IL
Not Yet!

MICHIGAN

New Buffalo, MI

Come Sail Away Sailing Charters
Crewed

New Buffalo Sailing Excursions
Crewed

St. Joseph, MI

Come Sail Away Sailing Charters
Crewed

South Haven, MI

Cat's Meow Charters
Crewed

Sailing South Haven
Crewed

Douglas / Saugatuck, MI

Sailing on Desire
Crewed

Seasun Sailing Charters
Crewed

Sweetwater Sailing
Crewed

Holland, MI

Deeplake Ventures
Crewed

Nancy Anne Sailing Charters
Crewed

Grand Haven, MI

 

Muskegon, MI

Not yet!

White Lake, MI

Not yet!

Pentwater, MI

Not yet!

Ludington, MI

Autonomous Sailing Charters
Crewed

Lets Go Sail / Freedom Enterprise
Bareboat or Crewed

Manistee, MI

Not Yet!

Frankfort, MI

Not yet!

Leland, MI

Not yet!

Northport, MI

Big Boat Sailing
Crewed

Suttons Bay, MI

Not yet!

Traverse City, MI

Grand Traverse Gourment Cruises
Crewed

Great Lakes Sailing Company
Bareboat or Crewed

Nauti-Cat Cruises
Crewed

Traverse City Sailing Charters
Crewed

Boyne City, MI

Not yet!

Charlevoix, MI

Charlevoix Yacht Charters
Crewed

Hunter 35 Cruising Sailboat
Bareboat

Pure Mish Charter
Crewed

Sunshine Charters
Crewed

Petoskey, MI

Not yet!

Harbor Springs, MI

Not yet!

Beaver Island, MI

Not yet!

WISCONSIN

Pleasant Prairie, WI
Not Yet!

Kenosha, WI

Red Sails Charter

Racine, WI

Lake Michigan Sailing Trebor
Crewed

Great Lakes Sailing Charters
Crewed

Lake Geneva, WI

Elmers Lake Geneva Boat Line - Catamaran

Milwaukee, WI

Sea Dog Sailing

Sea Safaris

Sturgeon Bay, WI

Cruise Diver Sailing Vacations

Door County Boat Rental

Door County Sailing Charters

SimpleSail

Talisman Sailing Charters 

Ephraim, WI

Bella Sailing Cruises

Stiletto Sailing Cruises

Sister Bay, WI

Sail Door County

Fish Creek, WI

Friendly Charters

All of Lake Michigan Peer to Peer

BoatSetter

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Updated 2/7/2016

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