Two Hour Charters on Lake Michigan

Come aboard the 37 foot Margaret Ann and embark on an unforgettable escape. Whether you are a morning person looking for an exciting way to start your day, a sun worshiper working on your tan, or an old fashion romantic who enjoys the company of a glass of wine and the sunset, you will find yourself in a state of bliss out on the water of the great lake.


Times & Prices

10% discount on all 10am trips for 2019!

Morning & Afternoon Cruises
$55 per person
10:00am -12:00pm
2:00 – 4:00pm
5:00 – 7:00pm

Sunset Cruise
$65 per person
7:30 – 9:30pm
(Time will vary slightly with the season.)

All cruises are BYOB.
Max capacity of 6 passengers.

Private Charters available!

Are we sold out or is your group more than 6?
Come sail with us on the Tall Ship Serenity in Saugatuck, new in 2019! Public and private charters for groups of all size up to 25.


Our Story:

Sailing South Haven is a family owned business located in historic downtown South Haven, Michigan. Established in 2010, we have become one of Southwest Michigan’s leading charter businesses. We take pride in offering a high quality, laid back, unpretentious and unique experience to every guest that sails with us.

The Boat:

Margaret Ann is a 37 foot blue water cruiser perfect for getting out on the lake, setting the sails, kicking back and enjoying the ambience of being surrounded by water.

Built in Florida, Gulfstar yachts are known for their stability, safety and comfort— and are most often spotted island hopping in the Caribbean Islands. Margaret Ann has a fiberglass hull with teak trim and a cabin area down below with cozy port and starboard settees.

A Few Reasons To Sail With Us:

Small group size.  Groups are limited to just six passengers so you’ll have plenty of space to spread out once we set sail.

BYOB. Many of our guests bring a bottle of wine or a 6-pack to enjoy while on the lake. We also have an ice filled cooler on board for you to keep your beverages cold.

Comfort and safety.  The Margaret Ann is outfitted with all essential safety gear. We are also certified by the United States Coast Guard and do regular inspections to make sure everything is in top shape.

Flexibility.  Pitch in and help handle the sails or just kick back, relax and enjoy the scenery.  Whether you’re a seasoned pro or a first-timer, our crew will help ensure a memorable experience for your entire group!


“If you are planning a visit to South Haven during the boating season, please add this sunset cruise to your list of things-to-do. You won’t be disappointed!”

~Martian273 from Grass Lake, MI via Tripadvisor

“Amazing! This was our first time sailing, and it was one of the most relaxing and amazing things we have ever done! ”

~Cincicat2000 from Cincinnati, OH via Tripadvisor

“We took the morning sail and it was a very relaxing and fun time. The waves were about 1.5 feet which made for just a little more adventure! Very professional staff who really know their stuff!”

~EBH59 from Rochester Hills, MI via Tripadvisor


“Great time sailing! Crew was friendly, fun, and professional. Went on the beautiful sunset sail. Would definitely recommend to anyone who loves sailing and wants a more intimate experience. ”

~John from Akron, NY via Google Reviews

“Wonderful Lake Michigan sailing experience! All four of us are ready to go again — I highly recommend this!”

~Gail from Alton, IL via Tripadvisor

“Beautiful boat, excellent customer service! I take a trip with this company every time I visit the area; I can’t wait to go again! ”

~Kevin from Davenport, IA via Google Reviews



Captain Erin

Captain Erin grew up sailing the Great Lakes but really got her sea legs in her twenties while crewing the 171 foot three-masted Schooner Mystic from Mystic, CT. Setting sail on the Atlantic Ocean along the east coast to the Bahamas, she learned the broader aspects of sea life – from helming the ship to rigging the sails and even a little bit of food prep too.

After her love for the sea was solidified, Erin set her sights on finally becoming a Captain. Many classes, inspections, and hours logged at sea later she had her USCG certification in hand. Captain Erin returned to the Great Lakes to share with others her passion of the wind and water by starting Sailing South Haven in 2010.

Captain Andy

Captain Andy has been sailing the Margaret Ann for 8 years. He’s a world traveler, wine maker and photographer, among many other things. Captain Andy has no shortage of stories to tell and he’s happy to share them.


What Should I Bring With Me?

It can be a bit colder out on the water than it is on shore. We recommend bringing a sweater or light jacket with you. And though we do provide light snacks and non-alcoholic drinks, please feel free to bring a bottle of wine and any other food items you will want.

Where is the boat dock?

You will be looking for Old Harbor Inn waterfront hotel at 515 Williams St.
It is at the intersection of Williams and Center street.

The dock is located on the lower level of the outdoor shopping area just to the left of the Idler Dockside Bar and Grille.

You will see a sign that says:
Private Property. Do Not Enter. KWN Boaters Only.
You can ignore this sign, open the rope gate, and walk down the 3 stairs to the dock. There will be a Sailing South Haven flyer attached to the picnic table in front of the boat.

What is your maximum capacity?

We have a maximum capacity of 6 guests. This is a USCG rule so unfortunately we cannot accommodate larger groups.

What happens if the weather is bad on the day of the trip?

The Captain will be in touch with you on the day of your trip if the weather is looking too rough to go out. We’ll never go sailing if the forecast is looking like it could be dangerous in any way. You will get a full refund if we cancel the trip for any reason.

Is my child too young to go sailing?

We welcome people of all ages! We have sailed with kids of all ages, though we do require children under the age of 10 to wear a life vest at all times.

Can my group bring a bottle of wine to enjoy on the boat?

Absolutely! We don’t provide or sell any alcohol but please feel free to bring your own to enjoy while on board. Beer and wine only, please.

What’s your cancellation policy?

If we have to cancel the trip due to weather or any other reason your credit card will be FULLY refunded automatically.

Can I book just one ticket?

Right now our online booking system only allows parties of 2 or more. But if you’d like to go out for a solo sail, just give us a call.

Do you sell gift certificates?

Sorry, we don’t sell gift certificates at this time.


Say Hi.

Email us directly at or use the contact form on this page. We’ll respond as quickly as we can.

Boat Dock
In front of Old Harbor Inn
515 Williams St
South Haven, MI 49090