lake michigan sailboat charter

Deeplake Ventures is located on the eastern shore of Lake Michigan in Holland, Michigan and offers sailing charters, sailing instruction and captain services.

Deeplake Ventures is owned and operated by Captain Jeremy Smith, a USCG licensed 100-Ton Master of Motor and Auxiliary Sail Vessels.

Charters depart from Eldean Shipyard, just minutes by boat to Lake Michigan and centrally located on the West Michigan coast, to easily serve visitors to the region including the South Haven, Saugatuck, Grand Haven, Muskegon and Grand Rapids areas.

To learn more explore the site or simply contact Captain Jeremy:

Jeremy@ deeplakeventures.com, (616) 403-5491, customer feedback:.

"I cannot thank you enough for the wonderful evening you showed us.  Our children thought it was the highlight of the trip."

"Thank you again for sharing your boat with us, you made our vacation one to remember."  

"Jeremy was an awesome captain and tour guide!  This was the best part of our trip to Michigan by far.  Thank you!"  

"We really enjoyed our first time sailing.  Weather was great and Jeremy made it so enjoyable and we learned so much at the same time."  

"Everything was great!  My wife and I had a terrific time and would recommend this to our friends and family!!"

"We had a great time with Jeremy. It was a fun way to get out on Lake Michigan. He was very knowledgeable and personable. Would definitely recommend sailing with him!"

"Capt. Jeremy was great to work with! He was very accommodating, knowledgeable, and friendly. I would definitely recommend his services to anyone looking to get out on the lake!"

"What a great way to see Lake Michigan and Lake Macatawa!  Jeremy did a great job accommodating our family of 6 including two small children.  I high recommend this as a must do in Holland.  Jeremy is very knowledgeable of the area and very easy to get a long with."

• Schedule & Rates
• Captain & Vessel

​Sailing Charters & Captain Services

SAIL LAKE MICHIGAN WITH US!

Schedule & rates.

Improve your sailing skills and gain confidence, or have your boat moved to your next destination.

More > 

Contact Captain Jeremy to schedule your day on the water, sunset sail, or special occasion today.

Chartering is a convenient and relaxing way to experience sailing on the Great Lakes.

TO OUR LITTLE SLICE OF PARADISE

At our family-owned sailboat charter, we're not just offering a boat — we're inviting you on an unforgettable journey. Picture yourself cruising under the vast Michigan sky, sails billowing in the cool lake breeze, surrounded by the stunning beauty of nature. Whether you're looking to pick up some handy sailing tips and tricks along the way, or just discovering the allure of the open water; our experienced captain is here to ensure your sailing adventure is nothing short of perfect. So come aboard the sailing vessel Julianna , feel the rhythm of the water beneath you, and let us create lifelong memories together on the shimmering blue of Lake Michigan. We can't wait to share our passion for sailing with you!

CANCELLATIONS & RESCHEDULING If you need to cancel your charter, please inform us at least 1 day (24 hours) in advanc e of your scheduled departure for a full refund. If you cancel within t he 24-hour window, we're unable to offer a refund due to the preparations made for your sail. We appreciate your understanding and cooperation with our policy.

INCLEMENT WEATHER CONDITIONS Safety and enjoyment are our top priorities. If the weather is forecasted to be unsafe for sailing, we will work with you to reschedule your trip to a more suitable date or issue a full refund.

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SUNSET SAIL

3 hr 30 min

Max. 6 guests on board  

In compliance with U.S. Coast Guard regulations, individuals under the age of 13 are required to wear a life preserver. We encourage those who possess their own to kindly bring it for use. However, should it be necessary, we are prepared to provide one.  

Embark on our 3-hour+ sailboat charter, featuring a captivating 30-minute cruise down the channel to the lake and back, promising an unforgettable aquatic experience.  

**Additional time aboard may be permitted if there are no back-to-back bookings  -- $100/hr. Talk to Captain Tim once your journey begins!

Do children count towards the total number of passengers on board?

Yes, according to U.S. Coast Guard regulations, all individuals, regardless of age, are accounted for as souls on board.  

Are we permitted to bring our own food and beverages, including alcohol?

Certainly! We encourage you to bring along any drinks, snacks, or alcohol you'd like to enjoy once we have set sail.

What essentials should we pack for our sailboat charter trip? We recommend bringing closed-toed shoes for safety, layered clothing to accommodate changing weather conditions, sunglasses, sunscreen, towels, hats, and any snacks or drinks you might desire during the trip.

Is it possible to take a swimming break during our sailboat journey? Absolutely, your day is entirely customizable! We can drop anchor for a swimming break, as long as it fits within the allocated time for your charter.

Are there bathroom facilities available on board? Yes, our sailboat is equipped with a marine head, complete with a flushable toilet and sink for your convenience.

What are the safety measures onboard? We prioritize your safety above all. Our boat is equipped with life jackets, fire extinguishers, first aid kits, and other safety equipment. Furthermore, our captain is well-trained in safety procedures and emergency responses.

ABOARD JULIANNA

A day in the life aboard the sailing vessel julianna.

LYNDA WARNER Form Submission 2023

Loved talking about the history of the Douglas Saugatuck area. Was a great time looking forward to going again next year.

EDDIE HARTMANN Google Review 2023

We have sailed on Juliana several times and could not recommend it more, and we plan to stop by for a sail whenever we are in Douglas.

KRISTEN MENNEMEIER Facebook Rev iew 2023

The boat is beautiful and Tim was kind, knowledgeable, and very accommodating. He anchored to let our children swim and even let them sail the boat.

CLAIRE McCORMACK Google Review 2023

We learned so much about sailing during our adventure. We even got to steer the boat! Unforgettable memories were made.

ABOUT THE CAPTAIN

Captain tim.

Captain Tim's love for the water runs deep, beginning back in his teenage years in the quiet lakes and Forest Preserves of DuPage County, Illinois. Alongside his father, he learned to sail small boats such as Sunfishes, Hobie Cats, and sloop-rigged dinghies.

Their boating adventures took a leap when his father bought a larger 25-foot sailboat in the late '70s. It was then that Tim started his journey of sailing on Lake Michigan, spending most weekends with his family enjoying the

waters and the scenery of Chicago.

Fast forward to 2005, when Captain Tim and his wife Julie became the proud owners of "Julianna". With this vessel, they've explored much of Lake Michigan and Huron, taking their children on summer cruises for the last 18 seasons and logging thousands of miles on the water.

In 2012, the Julianna  began participating in the Chicago to Mackinaw race, a tradition Captain Tim plans to continue. Throughout the years, he's ensured the safety of his wife Julie and crew during many challenging passages on the race up the Lake.

In addition to "Julianna", Captain Tim has spent considerable time on other boats on Lake Michigan, serving as a Delivery Captain for several private owners. He's also expanded his sailing experiences to the Southern Atlantic Ocean and the Caribbean.

Captain Tim's passion for sailing is unmistakable. We are confident that his enthusiasm will be contagious during your journey on board the sailing vessel  Julianna , creating a memorable and enjoyable experience for you.

219 North Union Street

Douglas, MI 49406

Tel:  (269) 447-7000

HOURS OF OPERATION:

Tues - Sun: 10am - 10:30pm

(Closed Mondays)​​

Thanks for Your Message!

• Sailing School
• Featured Yachts
• Service & Management

CHARTERS | SCHOOL | SALES

“name your price” sales event.

Be careful… you just may get a great boat at the price you offer!

We have new inventory coming and are motivated to sell the current inventory. “Name Your Price” only applies to existing inventory so once they’re gone, they’re gone.  So go ahead and make that offer!

MICHIGAN’S AUTHORIZED JEANNEAU DEALER

Save up to $47,000 on our in-stock jeanneau’s new models at our docks in st. clair shores and traverse city., yacht charters.

We continue to provide the best sailing charter fleet on Lake Michigan to cruise the harbors of Grand Traverse Bays, Little Traverse Bay, The Straits of Mackinaw, The Manitou Islands, Beaver Island, the Les Cheneaux Islands and beyond!

SAILING SCHOOL

Our passion is sailing and our goal is to share the knowledge and feeling of being under sail. Great Lakes Sailing Co. is an ASA Award Winning Sailing School with a 30 year history of introducing sailing to over 5000 sailors.

FEATURED YACHTS

Check out these new and used boats in-stock now and get sailing this summer! New Jeanneau models in stock and arriving soon. We have most Jeanneau models on display so give us a call to set up a time to meet us at our docks.

2024 JEANNEAU SUN ODYSSEY 440

2024 jeanneau sun odyssey 410, sail northern michigan.

The first thing people notice when arriving in Northern Michigan is the clear, teal and blue Caribbean-esque water . Navigation is very easy due to lack of tides and water depths exceed 700 feet in some areas, and within our sailing grounds are 45 anchorages, harbor towns and marinas available to cruisers.

12935 S. West Bay Shore Drive

Traverse City, MI  49684

[email protected]

231.941.0535

12935 S West Bay Shore Dr

Traverse City, Mi 49684

Lake Michigan yacht charters offering Great Lakes yacht rentals of a lifetime!

Escaping with one of our Lake Michigan yacht charters is awaiting for you aboard our luxury 68′ Chris Craft yacht named “Adeline’s Sea Moose” When you long for nothing more but an escape from it all… Adeline’s Sea Moose and her attentive crew come to the rescue to meet all your needs. You’re about to embark on a Great Lakes yacht rentals experience unlike any other… and best of all it’s absolutely fun-filled! Slipping out of your shoes and onto her deck, you’ll quickly realize there’s going to be something uniquely different about private Adeline’s Sea Moose Great Lakes yacht rentals. With the greeting and handshake of the Captain down to the warm smiles of the gracious crew, you’ll immediately start to know you’re in exceptional hands and headed for an incredible fun-filled time aboard your very own floating playground.

Chicago Lake Michigan   boat   rentals  for parties

Adeline’s Sea Moose Chicago Lake Michigan boat rentals for parties offer a 68-foot luxury Chris Craft yacht and her attentive crew. Adeline’s Sea Moose Chicago Lake Michigan boat rentals for parties also offer a combination of luxury and versatility. It is easy to understand the popularity of the delightful aft-deck salon with a wet bar, whether for open-air dining or merely for the possibility of solitude with a good book. Above, the flybridge offers an ample seating or lounging area. Here, guests can enjoy the sun and cool drinks or gather for a sunset cocktail as a prelude to dinner.

When it comes to Lake Michigan boat rentals, go for our Private Yacht Rental!

There are Lake Michigan boat rentals, and then there is our Adeline’s Sea Moose private yacht rental Our alternative to Lake Michigan boat rentals will truly offer you the best memorable experience in Chicago AND even more, value when you consider… with Adeline’s Sea Moose, can have your extended family and friends aboard “your very own” 68 foot private yacht for food, drink, merriment and what surely will be a unique activity for all. There’s plenty of room to roam for the family for all and when the gathering is over, you and your select guests can continue to enjoy all the amenities the yacht has to offer for the rest of your time aboard.

Best Lake Michigan  Chicago   boat   rental  for company events

Lake Michigan Chicago   boat   rental  for birthday party

Ready for an epic cruise on your special day? Then you’re ready for an Adeline’s Sea Moose Lake Michigan Chicago boat rental for a birthday party. Your Lake Michigan Chicago boat rental for birthday party awaits you at J-Dock in Burnham Harbor. With our Lake Michigan Chicago boat rental for birthday party cruises, you get to combine all of the best elements of other parties and ditch the things that aren’t as great, like the large crowds of intrusive strangers. Take the delicious food, fun drinks, and your friends and relatives and sail away!

(224) 601-0220

Charitable charters.

Cruising into a bright future with Inner Voice Chance to win 3.5-hour Lake Michigan cruise for up to 32 people on Adeline’s Sea Moose.

You will not be disappointed

TEXT Only 312-500-7838

Docking Address: J-Dock Burnham Harbor 1559 South Lake Shore Drive Chicago , IL 60605 at the end of Waldron Drive. The first dock north of the Harbormaster’s office.

Office Address: Chicago Private Yacht Rental, Inc 4751 West Touhy Avenue Suite 101 Lincolnwood, IL 60712

231-547-0266

• View the Schedule
• Reserve a Seat

 231-547-0266

Day Cruise $350

Sunset Cruise $395

2 hour sail in Saugatuck, MI

Free and flexible cancellation

Coast Guard Certified

Free & easy parking

Up to 6 people

What to expect

Embark on a unique adventure on board the Margaret Ann, a 37-foot cruising sailboat, as we set sail on a private charter accommodating up to 6 guests. Our journey begins in the South Haven channel, where you'll enjoy a relaxing 10-minute cruise down the river past the iconic South Haven lighthouse.

Next, we'll head out onto the vast and awe-inspiring Lake Michigan. You can choose to help our experienced crew raise the sails and feel the thrill of the wind and waves, or you can simply sit back and relax while our friendly and professional staff takes care of everything for you.

Our private charter is the perfect way to explore the charming and picturesque region of South Haven, whether you're an experienced sailor or a first-time visitor. You'll discover the natural beauty and captivating scenery of the area while enjoying and laid back and friendly service aboard the Margaret Ann.

$350 + tax for daytime (including morning and afternoon) sailing cruises

$395 + tax for evening sunset sailing cruises

Meeting Point

Please arrive 10 minutes early at the boat dock located on the river side of Old Harbor Inn at 515 Williams St. 

Flexible Cancellation Policy

Age restriction, what to bring, private charter aboard a sailboat.

Sail in comfort and style on a comfortable cruiser and explore the best of Lake Michigan and South Haven.

"Exceeded my expectations"

"100% a Great Experience. My wife, our daughter and myself chartered a 2 hour sailing experience with Captain Andy and we had a great time. Andy and our crew member were very welcoming right off the bat and adjusted our experience to meet our needs. Our daughter is pretty young (3 months old at the time) so we took it easy, didn't go too fast and just enjoyed the ride. It was apparent from the get go that safety is a priority here and at no point did I feel that was compromised. When we come back to South Haven we will definitely be booking again. Thanks Captain Andy!"

Matt Cronel

"Absolutely beautiful."

"This was my third sunset sail out of South Haven, my first with Captain Andy. It was, by far an incredible experience! We had a visit from a cormorant that sat atop the mast. The sunset was vivid and presented a scene suitable for painting with hues of yellow, blue, purple, and red. Andy and Erv were both knowledgeable and the conversation was friendly, informative, and enjoyable."

September 2022

"The best crew. Hands down."

"Absolute must-do in South Haven. Captain Andy and Captain Erin were awesome, and it made for a great afternoon on Lake Michigan. Great idea for an anniversary, birthday, or a date night. Will definitely be re-booking an excursion next year on the Margaret Ann when we are back in town!"

Michelle Fern

"They went above and beyond."

"Our group had a great trip with Captain Andy & Chloe recently. The boat is beautiful and Andy & Chloe couldn’t have been nicer or more professional. It was such a relaxing way to spend an evening with friends - we’ll definitely be back next summer!"

Michael Kern

Free cancellation

There is no designated parking for the boat, but there is typically plenty of parking in the city lots throughout downtown.

Cancellation Policy

Let us know 5 days in advance for a full refund.

In the case of bad weather on the day of the sail

Safety is our number-one priority when taking our guests out on the water. If the weather is dangerous to sail in then we will not go. You will have the option to reschedule or obtain a full refund.

We may still sail if there is light rain in the forecast but will cancel the trip if the weather or conditions are unsafe in any way. 

It can be a little chilly on the water so we recommend bringing a light jacket.

Any food or beverage you want to enjoy during your sail (alcohol is permitted.)

"A Perfect Blend of Relaxation and Excitement!"

"I absolutely loved this sailing tour! The cruise down the Kalamazoo River was a perfect way to unwind and enjoy the beauty of the area, and the sail on Lake Michigan was such an exciting adventure. The crew was amazing - friendly, knowledgeable, and made us feel right at home. This is a must-do experience for anyone visiting Southwest Michigan!"

James Torrick

"Spectacular sailing experience."

"We had the most amazing time on this sailing tour! The cruise along the Kalamazoo River was so peaceful and scenic, and the transition to Lake Michigan was exhilarating. The crew was incredibly friendly and knowledgeable, and the ship was well-maintained and equipped. I highly recommend this adventure to anyone looking for a unique and unforgettable experience in Saugatuck."

Laura Neiman

"An Unforgettable Experience with Amazing People."

"I can't say enough good things about this sailing tour! The crew was fantastic and made us feel like family from the moment we stepped on board. The ship was clean and well-maintained, and the views along the Kalamazoo River and Lake Michigan were breathtaking. This was truly an unforgettable experience that I will cherish forever. Thank you for such an amazing adventure!"

Samantha Harris

"Highly Recommend for Everyone!"

"This sailing tour was absolutely fantastic! The crew was professional and friendly, and the ship was well-equipped and maintained. The views of the river and Lake Michigan were stunning, and the sailing experience was so much fun. I highly recommend this adventure to everyone - it's perfect for families, couples, and even solo travelers. Don't miss out on this amazing experience in Saugatuck!"

William Chen

Private Charter

A great Lake Michigan experience awaits....

Saugatuck's premier sailing charter since 1998

A great activity while in West Michigan is to get out on the water!  You can sail out of the harbor of Saugatuck, Michigan onto Lake Michigan- the Big Lake.  Onboard the sailboat "Drifter", Captain Mort of Sweetwater Sailing will safely make the experience as enjoyable as possible, steering a course down the Kalamazoo River and out the channel.  Past the pier heads, as the engine goes off, the views of the beach and the dunes, the sparkling blue water and the wind in the sails will be part of your experience.  Sit back and relax on your sailing charter, or try your hand steering this sturdy yacht...it's up to you!

Charter with Sweetwater Sailing for an activity you will always remember, or make it the scene of celebrating your special event....a Reunion, Birthday, Proposal, Shower.  Captain Mort welcomes you aboard "Drifter" for a great day.

"Thanks for a great morning wake-up." Lisa, Rhode Island

"What an awesome afternoon! You  gave us an unforgettable anniversary!" Craig & Linda, Michigan

"When the wind blows in a sail, it  makes my heart sing. This was truly  the best time of our getaway." Sue & John, Washington

"Our entire family loved our time on the boat!  The best day of our vacation!" Dawn from St. Louis

"A great relaxing trip - Well Done." Dave and Linda from Jackson, Michigan

"Lake Michigan just like glass...the sail of a lifetime!  Thanks, Mort!!!" Brian and Linda, Lake Orion, Michigan

"Super cruise! First time and definitely will do it again. Thanks!" Danny and Penny, Payne, Ohio

"We had a wonderful time and enjoyed our time on the water. Excellent service. Thanks!" Paul and Valerie, St. Louis

"Nice way to unwind after running the Mt. Baldheaded 15 K! Fun, enjoyable and relaxing ride." Sheila, Plainfield, Indiana

"Bachelor Party! Had a blast, thanks so much for everything! Most memorable." Rick and friends, Holland, California, Illinois

"We schedule a Private Charter with Captain Mort every time we get to Saugatuck. There is a great peaceful feeling out on the Lake, and the scenery is beautiful." Lucie, Ann Arbor, Michigan

"Depending on the day, it could be exciting, or utterly relaxing, or the kind of sail that makes you just want to keep going and travel the lake!" Ellen and Roger, New Mexico

"Thank you so much for a great sail! We five women..Molly (Chicago), Cathy (Albuquerque), Liz ( Columbus), Joan (Charlotte) celebrated our 60th with you! July 2016"    

"A perfect day on the water with Captain Mort. Thanks for all the great info about sailing on Lake Michigan"

"A perfect sunset sail.  Thank you so much for a wonderful experience!"

"Had a great time!  Will do it again!"

" Thank you so much for taking us out on your sail boat!  It was very beautiful and we had an awesome time.  Hope to sail again soon!"

"Your sailboat Drifter is lovely and comfortable.  We enjoyed the trip so much, and appreciate your beautiful boat.  Thoroughly relaxing!"

876 Holland St. | Saugatuck, MI 49453 Shore Harbor Marina Behind The Southerner Restaurant To park/ use driveway at 868 Holland St. and walk around front of big building on your right to our dock and slip #31 616-836-0306 | 269-543-4362

• Captain Mort
• Testimonials

Fresh Coast Sailing

Sailboat Charters in South Haven

Sail the Fresh Coast!

Individual tickets available for the 5 p.m. and sunset sail times,  2 hour sailing charters on lake michigan from the port of south haven, pc: stryd photograpy, sail lake michigan: breathtaking views with captain andy, south haven's most popular sailing charter, searching for a unique summer adventure on beautiful lake michigan, look no further, experienced captain & local crew.

Our licensed captain and professional crew, all local to South Haven, will ensure a safe and unforgettable experience. They're passionate about sharing their knowledge of the Great Lakes, sailing, and the rich history of our community.

Memorable Daytime or Sunset Cruises

Choose from our exhilarating daytime cruises or our magical sunset sails. Each adventure is designed to create lasting memories - we want you to leave with a smile, a newfound appreciation for sailing, and stories to tell!

Luxurious Escape: Unwind in Comfort and Safety on the Mary Grace

We're thrilled to introduce Mary Grace, our beautiful Catalina 36 MK II! This inspected and meticulously maintained vessel offers exceptional comfort, safety, and dependability for your sailing adventure. Relax in the spacious 8-foot cockpit, enjoy the inviting cabin, or take in the views from the roomy bow. Mary Grace is perfect for creating memories that will last a lifetime!

Book Your Dream Sail Today!

Contact us today to reserve your spot on a daytime or sunset sail aboard Mary Grace. Let's make your summer in South Haven unforgettable!

PC: Radiant Landscapes Photography

Unforgettable sailing charters on lake michigan, 2-hour adventures: explore lake michigan with just your group (up to 6 people) and a friendly, us coast guard-licensed captain..

Perfect for all ages : Bring the whole family! Life jackets are available for children under 6.

Create your ideal experience : Whether you crave music and drinks or a peaceful escape, we cater to your vibe.

Bring your own beverages : Beer and wine are allowed (plastic cups and refrigeration provided).

Pack a picnic or enjoy light snacks : We offer light refreshments with your charter.

Use the on-board restroom (head) for your convenience.

Experienced captain : Your captain has over 10 years of sailing charter experience on Lake Michigan, ensuring a safe and enjoyable trip.

Flexible cancellation policy : Get a full refund if the captain cancels due to weather, or cancel anytime up to 48 hours before your trip for a full refund.

Children welcome : All ages are welcome aboard, but swimming is not permitted during the charter.

Ample Shade:  With a large bimini and and dodger, We have plenty of shade to keep you even cooler in the summer heat.  

Spacious and comfortable: Relax and enjoy the views with ample seating for 6 and plenty of extra space.

Set Sail Now! Book Your South Haven Sailing Adventure Online  

Sailing Times and Costs

We offer sailings 7 days a week at 4 different times both daytime and sunset cruises:

Private $350.00

Individual $75.00

10 a.m. to noon

2 to 4 p.m.*

5  to 7 p.m.*  

Sunset Sail:

Private $400.00 

Individual $99.00

8 to 10 p.m.*

*Please note: These times are subject to change as sunset times vary throughout the summer.

Come Sail Away! Where do you want to go?

Is a Sailing Charter on Your Bucket List??

This is your playground. Where do you want to sail?

Starting in the beautiful and protected waters of Lake Charlevoix, with the option of going anywhere in Northwest Michigan, a Pure Mish Sailing Adventure makes a perfect vacation. Where do you want to sail? Compare Ports of Call for your Pure Mish, Lake Charlevoix Sailing Charter or Lake Michigan Sailing Charter. Check out the Charlevoix Visitors Bureau (www.visitcharlevoix.com) and the Petoskey Area Visitors Bureau (www.petoskeyarea.com) for more fun area options

Pure Mish, Catalina 387, Sailboat for Charter on Lake Michigan or Lake Charlevoix

Pure Mish is a very roomy Catalina 387 sailboat with beautiful woodwork, a large cockpit, two private staterooms, a full galley, a head with a shower and much more. Explore this area of the site for more pictures and descriptions of the boat.

Check prices, choose a date and book your Sailing Charter

Click here to view the calendar of available dates and make your selection. Here you will also find prices and other trip options and ideas.

Stories and Photos from past Pure Mish Sailing Adventures

Check out some photos of past trips. Can you picture yourself in this setting? Sailing Lake Charlevoix and Lake Michigan is as good as it gets. Hopefully the photo gallery will give you an idea of how beautiful it is up here. If you are a Pure Mish sailor, please feel free to leave a post and a photo or two from your trip.

A Pure Mish Charlevoix Sailing Charter is a great local getaway for a sailing experience that rivals an expensive vacation in an exotic sea. Dubbed by some as the Caribbean of the north, Lake Charlevoix is spectacular! And, with direct access to Lake Michigan, Pure Mish can take you anywhere your dreams want to go.

Sailing Yacht Charter Lake Michigan Sailboat Charters & Rentals

Top-rated yacht charters in lake michigan - preselected yacht rentals:.

Sailing yacht Catalina 400 available for charter in Belmont Harbour

• Catalina 400 [Yacht Price incl. Taxes]
• Final cleaning
• Yacht Insurance
• Check-in/out

Yacht Hunter 326 - Sailboat Charter Chicago

• Hunter 326 [Yacht Price incl. Taxes]

Sailing yacht J 22 for rent in Belmont Harbour

• J 22 [Yacht Price incl. Taxes]

Sailing boat First 36.7 for charter in Chicago

• First 36.7 [Yacht Price incl. Taxes]

Sailing yacht J 30 available for charter in Chicago

• J 30 [Yacht Price incl. Taxes]

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Best Lake Michigan Charter Excursions

Sailing out of Holland, Saugatuck, or Grand Haven, SuFISHient Charters is your best choice for top-notch fishing or simply enjoying the beauty of Lake Michigan.

We take pride in making your charter boating trip memorable and enjoyable. From a seasoned veteran to a first timer, we strive to create a lasting impression on all who fish with us from the port of Holland, Michigan.

Our Charters

Lake michigan fishing, boat adventures, inland fishing, our difference.

We are set apart because SuFISHient Charters is passionate about creating the best experience possible—whether that’s catching a boatload of fish or a relaxing trip on the waters—and creating a friendly environment for your crew. Whether you are vacationing in the Holland area with your family, having a day out with friends, hosting a corporate outing, giving a gift, or just want to go fishing, SuFISHient Charters is the right choice.

Our Customers

Awesome fishing experience, would definitely recommend suFISHient Charters. We enjoyed fresh baked cookies prepared by Jeff’s wife while heading out. Jeff and his first mate Mark set out multiple lines and my husband, my dad and I were reeling in Salmon in no time! While tending the lines and netting our fish, they gave us great advice and three new Salmon recipes to try. Before we knew it, we had caught our limit and were heading back in feeling like pros. Back at the dock, Jeff filleted our fish while Mark tended the boat. Jeff and his first mate Mark were fun and professional. We will definitely use them again the next time we are in Holland. A couple of photos of the ones we reeled in. Thanks again Jeff and Mark for a wonderful fishing trip!

Went fishing for the first time With my wife and teen boys. Jeff was very knowledgeable and patient with our first timer questions. Our family had an amazing experience. Jeff provided exact instructions on what to expect and what to bring and what to leave behind. He was ready at 6 am on a chilly morning with a big smile. He kept chatting with the boys providing hints and tips on the do’s and don’ts. We ended up catching 9 trouts and were very happy with our catch. To sweeten the experience at the end Jeff brought out a caramel peanut rice cake that his wife had graciously baked. Thanks Jeff! If we had to go fishing in Holland MI, it will be with Jeff’s SuFISHicient Charters.

My son and I went out with SuFISHient last week while on vacation. They have a very nice boat with lots of room to fish. We had a great time with the team. The captain is very good with his boat and works hard to get us into the places where the fish are. He knows a lot about fishing in that area and what is biting and what the fish like. We caught a good number of fish and several of them being quite large. We were right on the brink of great Salmon season and managed to catch a few of these fish. I highly recommend this company for fishing on Lake Michigan.

Jeff did an amazing job on our recent fishing charter trip for a bachelor party. He was friendly and joked around with us the entire trip. Have already talked about returning for another trip with Jeff just for fun. 100% recommend!!

• © 2023 SuFISHient Charters
• Phone: 1-616-886-9143
• Email: [email protected]

The Most Fun You’ll Have With The Sails Up!

The Vagabond | Setting Sail from Montrose Harbor | 601 W. Montrose Dr. – Chicago, IL 60613 | 630-816-1427

Enjoy the awesome Chicago skyline

Take a nice relaxing sunset sail

Chicago Sailing Charters

Group | Private | Corporate Yacht | Event Rentals

At Two Brothers Sailing Adventures Chicago we take great pride in providing a wide selection of sailing charters and adventure options in the Chicago area. Every yacht we charter or sailing package we offer has been designed with safe and fun activities that are also uniquely planned to make the most of your time. If you don’t know about Chicago sailing or yacht rental on Lake Michigan, it is a great getaway in the Spring, Summer and Fall months. Our safety record is impeccable and our charter captains are fully trained and licensed. You are guaranteed to have a sailing adventure with captains and crew that are all accomplished Lake Michigan sailors excited to share their love of adventure sailing and the water, with a passion for entertaining new passengers and friends in Chicago.  It is easy to Charter a sailing adventure by checking our availability . We love seeing our friends return year after year! When you book a Chicago sailing charter or yacht rental adventure with us, you’ll soon see why people love to go ‘sails up’ with us.

We’re Ready to Put Our Sails Up for You

Two Brothers Sailing Adventures is ready to put our sails up for you. It all starts by tailoring the length of your sail within two to three hours, or more. We provide many options and choices including the sites you’ll sail to and see and the fare you’ll be treated to during your trip with us. Each sailing adventure is conducted by one of our licensed captains with the duty of keeping their passengers safe and entertained on beautiful Lake Michigan.

Two Brothers Sailing Adventures is your Chicago sailing destination. We pride ourselves on offering a wide selection of adventure, including small boat rentals, luxury yacht charters and sailing lessons. Whether you’re traveling from the Midwest, or across Lake Michigan, Two Brothers Sailing Adventures is the perfect destination for an adventurous sailing getaway in Chicago. Our licensed charter captains are fully trained, and we guarantee you’ll have a fun, safe sail in the Chicago area. We look forward to welcoming you aboard, and showing you why people love to go “sails up” with Two Brothers Sailing Adventures.

We may be the captain, but when you sail with us, we let you take the helm. Whether you want to sail for two hours or five, see specific sites, or just sit back and enjoy Lake Michigan, we’re committed to providing you with a unique Chicago sailing experience. 

Let’s set sail together and make some great memories!

We encourage you to be yourself unless you want to be a pirate then always be a pirate! We pride ourselves on using ALL of our sails, not just revving an engine and calling it sailing in Chicago. All of our sails fly high barring safety concerns.

Sailing Services in Chicago Include the Following:

Sailing Lessons

Boat Charters

Boat Rentals

Contact us to schedule your next sailing adventure on the Chicago Lakefront. We’re ready to set sail and provide you with adventures of a lifetime for your co-workers, friends and families.

See the beautiful sights – Sail the city front from Museum Row to Navy Pier…

Sail to the historic Chicago Cribs and beyond . You still get the great city views while adventuring a bit further to sea…

Swim Socialize and Sunbathe – Sail over and join the crazy crowds at Chicago’s famous Playpen – a protected anchoring area just off Oak Street Beach where boaters of all kinds park and play…

Sunsets with your sweetheart – This is a couples sail scheduled so that you capture breathtaking views of the sun setting while the city lights are rising – truly a perfect date night…

Sunsets with family and friends – Like the romance sail, you will enjoy the beauty of day turning to night…but on this ride you’ll have to sneak below to get alone because your passengers will be tagging along for the fun…

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Setting Sail From

Montrose Harbor Chicago, IL 60613 630-816-1427 *contact us upon arrival for dock details

Come Aboard “New Adventure”

We are currently not running charters but may plan to do so in the future. Captain John is available for coaching and boat moves. Email Captain John using the contact form to get in touch. See and post reviews on Trip Advisor .

This luxury sailboat has spacious cockpit seating, two staterooms, a full sized bathroom, galley and living room with dining table. Air conditioning, TV, DVD and stereo are just some of the features to make your experience enjoyable. New Adventure is docked in Burnham Harbor, Lake Michigan (near Soldier Field).

Get involved, take the wheel, help with the sails, or just sit back, relax and enjoy. Every adventure is unique, different and tailored to what you want to do:  sail, anchor for a swim, or motor through the harbors. Bring your phone’s playlist and we can pipe the music up to the cockpit area.

It is recommended that you come prepared for all weather conditions. A light jacket that is good in wind, sunglasses, hat, and sunscreen. Warmer days can get quite warm conversely with cool water and wind, it can get quite cool. A covered bimini provides shade, as needed.  Bathroom facilities are on board and also at Burnham Harbor.

A refrigerator is on board and includes ice for storing perishables. You may also bring your own cooler, food, or adult beverages.

Parking is available to the South of the circle at the harbor, across the street at Soldier Field, and also at the Museum campus.  

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Motor Yacht Charter in Gelendzhik

BOAT HOMER ✔ SPECIFICATIONS • Crew: 2 people • Length: 12 m • Width: 4 m • Capacity: 10 people ✔ PRICE • 5000 RUB - per Hour  If you have any questions, we can answer those through GetMyBoat’s messaging platform before you pay. Just hit, “Request to Book” and send us an inquiry for a custom offer.

Starting from

• ₽5,000/hr 1 hr min

Check Availability

Yachting has long been a fairly popular form of tourism, because it is able to provide vacationers with freedom of movement, a high level of comfort, and also an unforgettable romance. Every year, this type of tourism spreads to new countries and cities. We offer to rent a yacht in Gelendzhik through the company Skyline Lineraquo, without additional charges, directly from the owner.

Features & Details

• Life jackets/required safety gear
• Single Engine
• Twin Engine
• Dual Comm-forward seating
• Cuddy Cabin
• Wheel steering
• Inboard Engine

Approximate Location

You’ll get directions to the departure location when you make a booking.

Cancellation Policy

Full refund up to 5 days prior.

Top Destinations Nearby

Krasnodar Krai

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