Midwest USA

Explore the Great Lakes and enjoy tranquil river boating in Illinois Michigan and Ohio

Boating the American Midwest


Who needs the sea to go sailing? Explore Lake Michigan on a Chicago yacht charter, or enjoy the beautiful scenery of Lake Erie with one of Sailo’s boat rentals in Detroit. Set sail with friends or family for an unforgettable experience.

The Great Lakes are a unique location to enjoy boating in the Midwest USA, with plenty of things to keep sailors of any level enthralled. If you’re the type who enjoys hoisting the sails and feeling the fresh air in your face as you cut through the waves.. Or, if your style is more relaxing on deck with a cool beverage and a matching soundtrack, you’ll find lots to choose from for your boat rental with Sailo.

When looking to go sailing in the Midwest USA, you’ll find the best choice of sailboats, fishing boats and party boats in Chicago, Detroit and Cleveland. From these great city bases you’ll be able to go fishing, throw an unforgettable party or simply enjoy the great outdoors.


Summer in the city

If the heat gets too much, jump aboard one of our beautiful boat rentals in Detroit or a Chicago yacht charter, which is the perfect way to cool down. Get away from the hustle and bustle of downtown by taking a trip on board your own private boat rental.

When choosing your boat charter with Sailo, you’ll be able to select either a captained boat, where the crew takes care of the technical side. Or go for a bareboat, perfect for experienced sailors looking to take friends and family for a thrilling day out.

If you’re thinking about heading to the infamous Chicago playpen, choose a Sailo yacht charter to bring all your friends to the party. Most motor yachts come with a great sound system and usually include some extras like a complimentary drink or watersports equipment.

Over in the north of Michigan state, the Torch Lake sandbar is one of the most popular places to head to in the summer months to experience a wild party on board your private boat. Choose your Michigan yacht charter and explore the lakes with Sailo.


The wind in your sails


Those summer winds are made for jumping on board your own private sailboat and heading out across the lake for an awesome day trip. Set sail from the windy city with your choice of monohull or catamaran sailboats. Boating the Midwest USA is a popular activity and you’ll find plenty of options for boat rentals in Detroit and Chicago yacht charters.

Take in those city views from the lake and experience the joys of the open water. Whatever your plans for enjoying the lakes and rivers of the Midwest USA, choose your perfect boat rental with Sailo.


A party to remember


Bachelors and bachelorettes will love the opportunity to party on the water like a true rock star. Take a look at our boat rentals, perfect for a day splashing about at the wild Chicago playpen, or head to Michigan and the Torch Lake sandbar. With a captain helming your boat, you’ll be able to focus on having a good time and enjoying the music and the company of friends. Plus, you’ll be able to snap some unique selfies to make your friends jealous on the deck of your party boat rental in Chicago and Michigan.


Celebrate in style


Charter your own private party boat with Sailo for a day to remember! If you’re looking for a venue that will wow your guests, perhaps for a birthday, a wedding reception or even a corporate event for your company, you’ll find some great opportunities for a Chicago motor yacht charter to cruise Lake Michigan or Lake Erie. Choose from a paddle steamer boat rental in Detroit, to a luxury yacht charter in Chicago, just two examples of the incredible choice you’ll find on Sailo.


Get away from it all with a fishing trip


Both Lake Michigan and Lake Erie are excellent fishing spots, ideal for a day trip away from the noise and pollution of the city. Cast your line from the deck of your fishing boat charter and relax on deck with a cool drink in hand. A private boating trip on the Great Lakes is one of the best things to do in the Midwest USA in the summer. Who knows, perhaps you’ll catch your dinner, just in time to barbecue on the beach. At the very least you’ll have some great stories to tell and the pleasure of enjoying a day on the water...


Enjoy the city at sunset


Experience the city in a different light with a sunset boat trip. Both Chicago and Detroit are cities that are great when enjoyed from the water, and what better way to take in their impressive skylines than with a private yacht charter. A sunset cruise makes a great gift for your loved one, or the perfect way to wow friends or guests from the deck of your captained boat rental. If you’re looking for a unique thing to do, and to get away from the crowds, enjoy an unforgettable sunset boating trip with your Sailo yacht charter.

Find Your Dream Yacht Charter in Chicago, Detroit and Cleveland