sailboat charter mackinac island

MACKINAC ISLAND PARADISE (LAKE HURON)

COSMOS provides a charter to this famous Mackinac Island Paradise with an advanced booking of 45 days or more. Departure can be from a suitable location to accommodate guests so there is less travel time over the water. Suggested departure locations are Tobermory (Bruce Peninsula), or any port on Manitoulin Island (North Channel). There are airports at both these locations to accommodate guests who wish to fly to the departure location. A minimum one week-long charter would be necessary to allow at least three days touring the island. Guests would sleep aboard the vessel each evening, and explore the island during the day. 

Mackinac Island is located at the eastern end of the Straights of Mackinac where the waters of Lake Huron and Lake Michigan meet. There is a natural harbour at the south end of Mackinac Island where the yacht can swing on anchor, or the vessel can dock at one of the marinas that provide transient slips for seafaring folks that arrive by yacht. Guests can enjoy a superb dinner on shore in many of the fine restaurants and hotels on the island.

The most notable feature of Mackinac Island is the fact internal combustion engines were outlawed on the island in 1898, and so the only way to travel is on foot, by horse-drawn vehicles, by horseback, or on bicycle. There are NO motor driven vehicles on this Island! As a result, everyone arrives by boat, most arriving by commercial ferries that bring passengers from Mackinaw City or St. Ignace.

It is unique for visitors to arrive by private yacht. Once you set foot on the island, you will feel you are stepping back in time. There are many historic buildings to see. Fort Mackinac constructed by British soldiers during the American Revolution. Today the original restored fort is a National Historic Landmark. A visit to this historic place allows visitors to trace the foot-steps of British and American troops as you explore the historic buildings, enjoy the exhibits, and watch lively demonstrations of an era gone by.

There are many attractions on Mackinac Island ! A favorite activity for visitors is to rent a bicycle and tour the 8.2-mile long paved bicycle roadway that follows the shoreline of the entire island. Horse-drawn taxis can be taken on tours on the island including a visit to the infamous Grand Hotel….and yes, even the street cleaning machines are horse-drawn! There are many fudge shops in the downtown area and the sweet aromas of baking fudge are always in the air as you leisurely walk the main streets.

For more information about this ‘out of this world’ charter, please contact us or telephone (905) 715-8795.

[email protected]

231-330-0562.

Our Cruises

Make memories...

Time spent with your family and friends on the water is time well spent. Customize your cruise and create your own adventure - whether you choose a relaxing sightseeing tour or a sun-bathing, swimming excursion, this will be a highlight of your island vacation! Take a look at the cruise options aboard our Sea Ray Sundancer 320.

Priceless memories...

Pricing is for a private cruise and varies on the size of your party. The Brown Eyed Girl II can accommodate up to 6 passengers, in addition to crew members. See pricing and booking information and be sure to reserve your cruise well in advance, as cruises will fill up quickly.   

SAILING & CHARTERS

Brown Eyed Girl Charters offer private powerboat charters for families and small groups. Cruise the Straits of Mackinac aboard the Brown Eyed Girl II with a certified USCG Master Captain. Customize your tour – enjoy sightseeing while viewing the island and surrounding area from a different perspective or simply spend some time swimming and soaking up the sun!

Sip n' Sail Cruises feature live entertainment and breathtaking views. The Isle Royale Queen III is a luxurious 81′ vessel with a large open outdoor deck, heated indoor cabins, restrooms and a cash bar. Tickets must be purchased online at www.sipnsailcruises.com  

Explore the history of the Straits of Mackinac aboard the Ugly Anne , a United States Coast Guard certified charter boat with tours departing from Mackinaw City. Call (231) 436-5094.

Wild Honey Sailing Charters takes you on the magnificent waters around Mackinac Island. Daily cruises available for two hours with up to six passengers. Contact Captain David Rowe at (810) 516-5052.

Spend a day in the Straits of Mackinac, fishing and taking in the beautiful scenery with:

EUP Fishing Charters   or call 251-504-1046. 

North Shore Sport Fishing Charters  or call 906-430-2839.

It's on everyone's list of things to do on Mackinac Island.

Cheers to Unforgettable Memories: Embark on a Sip n' Sail Cruise from Mackinac Island

Cruise Options

Sip n' sail sunset cruise, easy like sunday morning, bloody mary & mimosa bridge tour, michigan craft beer cruise, sip n' sail cruise, great turtle sunset voyage, bourbon under the bridge, history cruise, private charters.

The lsle Royale Queen III and the Robin E are the perfect venues to create a one-of-a-kind event for your special gathering. Our crew and staff will help create a perfect special occasion for your guests. Book early as prime dates fill up quickly.

A popular destination for bachelor/bachelorette parties and birthday celebrations or anyone looking for an upbeat destination before hitting the streets of downtown Mackinac Island. DJs and live entertainers are allowed on board for private events or our state of the art sound system will accommodate your music preference for the occasion. Our vessels are equipped with iPod hookups to play your own music and playlists through our BOSE sound system. Local restaurants available for your catering needs. The Isle Royale Queen III and the Robin E are great ways to reward your employees, entertain clients or surprise your family and friends! 

Charter Options

Wedding functions, corporate events, family, social and celebrations of life.

The "Isle Royale Queen III" is a charming 81' vessel featuring multiple outdoor viewing areas & heated interior cabins, onboard restrooms, a full service interior bar & a state-of-the-art sound system. Read all about the history of our majestic vessel; from the Queen's humble origins to where she stands today from her voyages along the Straits!

“Robin E” is a 55’ glass bottom Vessel featuring a full service interior bar, multiple indoor and outdoor seating and standing areas and a modern sound and communication system. Read more about the history of this beautiful vessel on the Great Lakes.

Reserve Your Private Charter

Call (844) 906-9006 or complete our contact form for additional information.

You are using an outdated browser. Please upgrade your browser to use our website.

Brand New 68′ Sunseeker Manhattan Luxury Motor Yacht

Now available for private charters on the great lakes, explore grand traverse region, lake charlevoix, manitou islands, beaver island, mackinac island and more, the possibilities are endless, fully crewed | daily and weekly charters available.

Send Inquiry

Get the best of both worlds, and in every direction!

Mackinac Island Sailing Charters

• See all photos

Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as waiting time, length of visit, general tips, and location information.

Mackinac Island Sailing Charters - All You Need to Know BEFORE You Go (2024)

Private Charters

Straits of mackinac: where do you want to go.

Private charters are an excellent option for a larger group or family that would like to have the boat to themselves. The most popular charter is to go under the Mackinac Bridge, then cruise the Straits of Mackinac, but we are happy to customize a cruise to whatever experience our guests are looking for.  Our main port of departure is from Mackinaw City, but we can pick up from another location depending on if we can secure dockage. Charters can have up to 30 people, and we do have a cash bar with beer, wine, pop, and water. Feel free to give us a call or email, and we would be happy to discuss how we can customize a trip for you.

Under the Bridge Cruise

Around the island cruise, bois blanc island cruise, customized charters.

Listed in Explore , Tours

If you’re looking for a sailboat charter to explore the beautiful waters around Mackinac Island for up to 6 people, Wild Honey the place.

Sip n' Sail Cruises

Review Highlights

“ . Not too mention, the sunset was beautiful, which they timed perfectly to be under the Mackinac Bridg e to view ” in 3 reviews

“ We had THE BEST service for our bachelorette party ! ” in 2 reviews

“ Just did a sip and sail (June 2019) with three kids in tow (ages 15,13 and 9). ” in 2 reviews

Location & Hours

Suggest an edit

7325 Main St

Mackinac Island, MI 49757

About the Business

Evening boat tour under the Mackinac Bridge to view a sunset with live entertainment and a unique bar …

Ask the Community

Ask a question

Yelp users haven’t asked any questions yet about Sip n' Sail Cruises .

Recommended Reviews

• 1 star rating Not good
• 2 star rating Could’ve been better
• 3 star rating OK
• 4 star rating Good
• 5 star rating Great

Select your rating

Overall rating

Great time and wonderful experience. Awesome and attentive crew! Captain was terrific as was the music!

If you find yourself on Mackinac Island, I highly recommend Sip n' Sail Cruises. This was my first time and it was an unforgettable experience that left me in awe of the breathtaking views it was a very romantic evening. The highlight of the cruise was undoubtedly the stunning scenery as we sailed under the Mackinac Island Bridge during the golden hour. Great photo opportunities! The staff on board were exceptional in ensuring a memorable experience for everyone. They were organized and attentive, making sure guests were well taken care of throughout the journey. What impressed me the most was that I always had a drink in my hand. A hot tip though: The seats on the deck fill up quickly, and most passengers prefer not to sit inside. My partner and I discovered a hidden spot at the front of the boat that no one seemed to check, and we were able to snag a prime seating location. But even so, it was very crowded, not shoulder to shoulder but you were for sure bumping people. That is why I only gave it 4 stars, I wish they limited the number of people a bit more. While you can stand the entire time, having a spot to sit was nice for the 1.5-hour cruise.

We added this to our itinerary on Mackinac Island and we were so glad we did. We chose a tour that fit nicely into our schedule and it was just right. The guitarist was fantastic and made everything enjoyable.

This is an ABSOLUTE MUST when planning your trip to Mackinac!! Molly is simply the best, most kind hostess!! We are from Texas and were told you didn't need to make reservations by someone at one of the hotels. It is best to have reservations. Molly made room for us!! It was one of the highlights of our 5 day trip to the island!! We loved every minute. The music was great. The whole experience was fabulous!! We would go again and again for sure and you are missing out if you do not incorporate this into your travels plans!!

Looking for a fresh take while on Mackinac Island? Why knot try the Sip n' Sail while you're on your Island Adventure! Departs twice daily in the summer around 4 and 8pm for a truly a moment to remember... Set sail for a sunset ride to the Mackinac Bridge with the fun loving crew of the Queen Mary the III. A regal vessel with an historic past celebrating their 5th season on the Straits of Mackinac. Captain and crew greet and welcome you aboard. There was a birthday party as well as a bachelorette party in tow. Special shout outs from the live musician who was rocking out Dave Matthews to John Cougar. Being from Scottsdale Arizona I enjoyed standing on the bow catching some Lake Michigan mist. Plenty of seating below deck and a few seats above. Get there early so you can get one of the captains chairs on the second level. Personally, I didn't sit down the entire trip, but then again I like going to the galley and refilling my cocktail at the well stocked bar. Beer, wine and liquor available. Marinated peaches in Grand Marnier, i i Captain!! You will not be disappointed in your mini adventure within the Mackinac Island experience. A truly unique experience off the shores of Mackinac Island that gives you something to talk about for the rest of your life. Thanks for the memories Captain V. You are an Island Treasure! -Walker

We had THE BEST service for our bachelorette party! The staff and crew were helpful, friendly, and fun. Live music, beautiful views and a little bit of bridge history thrown in. Would definitely do again!

We did a sip and sail cruise for 4th of July. We were there an hour and a half early, just waiting on the dock and they let us board 45 min. early- we got the best seat in the house! We had a wonderful time and would do it again. Beautiful views of the fireworks too!

Just did a sip and sail (June 2019) with three kids in tow (ages 15,13 and 9). It was awesome! The weather absolutely sucked! Raining, windy, cold. Seriously though we had the best time. The drunks stayed towards the front of the boat. We were in the back. The music was a little hard to hear but we spent most of our time on the top deck in the rain with Molly (a crew member). She was awesome. Gave a lot of insights about the island and even got my kids in the wheelhouse and my 9 yr old got to hold the wheel. Great experience for them. So much fun. At the end it was obvious that some passengers had over indulged so good thing they were walking or biking to their hotels. Overall this was a fun experience for my family even though the weather was complete garbage.

Best value on the island! Whether you are staying on the island or just daytripping don't miss the relaxing sunset bridge tour. Fabulous band, attentive service, and a cash bar with reasonable prices and special drinks. Comfortable boat with lots of comfortable seating and wonderful music piped all over the boat. All those photo angles of the Mackinac Bridge are yours for the taking, and sunset on the water is always a romantic treat. Everyone is welcome, from individuals to groups of all kinds. Friendly but professional staff are always there to assist you! Highest recommendation!

We have been vacationing on Mackinac Island for over 16 years and this was the first year we decided to try one of the sunset tours. We chose Sip n' Sail due to the other positive reviews and I would recommend it to others. My wife and I took our 10 year old and 8 year old girls and it was a perfect night. The staff was wonderful, the boat was very clean and the music was great. Not too mention, the sunset was beautiful, which they timed perfectly to be under the Mackinac Bridge to view. We will definitely use them again in the future. I would recommend getting there early to get a seat, although we stood the whole trip and it was still a great time.

2 other reviews that are not currently recommended

Collections Including Sip n' Sail Cruises

The Best of Mackinaw/Mackinac

By Victoria M.

People Also Viewed

Lake View Hotel

Murray Hotel

Nautical North Family Adventures

The Mackinac House

Breakers Resort

Les Cheneaux Distillers

Hotel Iroquois

Metivier Inn

Colonial House Inn

Island House Hotel

Browse Nearby

Restaurants

Things to Do

Romantic Restaurant

Photographers

Boat Charters Cost Guide

Boat Charters Near Me

Boat Rides Near Me

Other Boat Charters Nearby

Find more Boat Charters near Sip n' Sail Cruises

People found Sip n' Sail Cruises by searching for…

Sailing Charter Mackinac Island

Best Boat Cruise in Mackinac Island

Island Tour in Mackinac Island

Related Cost Guides

Boat Charters

Boudoir Photography

Bounce House Rentals

Event Photography

Valet Services

Videographers

• 5 More Cost Guides

Mackinac Island Sailing Charters

• See all photos

Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as waiting time, length of visit, general tips, and location information.

Mackinac Island Sailing Charters - All You Need to Know BEFORE You Go (2024)

• Skip to main content

Great Lakes Charter Cruising

Private charter yacht vacation in great lakes.

An unknown wonderland hidden within the Midwest of America, the Great Lakes cover more than 94,000 square miles and encompass 5 lakes; Superior, Michigan, Huron, Erie and Ontario. Explore the vast expanse of interconnecting lakes by private yacht charter and experience the unique mix of mesmerizing landscapes, diverse wildlife and cosmopolitan cities that make the great inland oceans an enchanting yacht charter destination.

Great Lakes Charter Cruise Itineraries

Great Lakes offers a variety of cruising itineraries including:

• Charlevoix, MI - Traverse City: Beaver Island, Mackinac Island, Round Island, Petoskey, Traverse City.
• Omena Bay/Northport - Traverse City: Charlevoix, Petoskey, Harbor Springs, Oyster Bay, Northport, Elk Rapids
• Power Island - Traverse City: Northport, Charlevoix, Omena Bay/Northport, Elk Rapids, Sutton’s Bay.

Great Lakes Charter Yacht Season

June through September

Great Lakes Charter Vacation Activities

• Hiking - Big Sable Point Lighthouse; Escarpment Trail
• Camp on South Manitou Island
• Cliff Jump at the Grotto (Lake Huron)
• Kayak to Turnip Rock (Lake Huron)
• Water sports
• Two Sisters Vineyard, Niagara-on-the-Lake, Ontario
• Bonobo Winery, Traverse City, Michigan

Questions, Comments, Inquiries?

Contact us today for more information.

Contact Us +1 401.849.0344

Popular Great Lakes Charter Cruising Destinations

Traverse city, marquette michigan, niagara falls, grand marais, minnesota, madeline island, wisconsin, great lakes luxury charter yachts, contact nicholson yachts.

Questions? We're ready to help. Please just contact us today.

Sailboats Mackinac Island

ABOUT OUR ISLAND

The jewel of the Great Lakes. Enjoy beautiful vistas, shopping, and carriage rides during the day, and watch the city transform at night with its happening music and bar scene. Mackinac Island has something for everyone.

Mackinac Island Tourism Bureau 7274 Main Street Mackinac Island, MI 49757 (906) 847-3783 www.mackinacisland.org

Member Resources Job Portal

SUBSCRIBE TO OUR NEWSLETTER

Sign up for our eNewsletter that details seasonal specials and all the latest updates from your favorite Island.

• Address * ZIP / Postal Code

FOR MORE INFO

Call (906) 847-3783, connect with us.

• Privacy Policy

Mackinac Island Sailing Charters

• See all photos

Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as waiting time, length of visit, general tips, and location information.

MACKINAC ISLAND SAILING CHARTERS - All You Need to Know BEFORE You Go

Shepler's Ferry to Mackinac Island postpones plan to add fee, RFID luggage tracking

S hepler's Ferry service to Mackinac Island, which has been exploring the idea of implementing luggage fees for visitors, confirmed this week that the plan is on hold.

Chris Shepler told the Detroit Free Press late Monday that after extensive discussion of the controversial idea with the Mackinac Island Transportation Authority, local elected officials and island hotels, there will be no such fees this year. The cost would have been $4 per bag for visitors and no charge for island residents.

"The idea has been scuttled for the 2024 season" that runs from April to October, said Shepler, president of the company in operation and grandson of its founder who began service in the 1940s.

Start the day smarter. Get all the news you need in your inbox each morning.

The bag fees would pay for technology used to tag and track luggage loaded on and off the ferry boats, which serve an estimated 650,000 passengers annually. The newest ferry, launched in 2020, cost $5 million and carries 210 passengers. Shepler's employs an estimated 200 workers in the summer.

At issue, Shepler said, is that the ferry company for years has spent hours tracking luggage for customers who get frustrated about its location. Luggage is loaded onto the ferry, then unloaded, put onto a courier bicycle or horse-drawn carriage , sent to a hotel and then to a room where the guest is registered, Shepler told the Free Press.

Luggage fees would help offset the costs of radio frequency tracking devices, known as RFID technology, which reads information contained in wireless devices without making physical contact or requiring a line of sight, according to the U.S. Department of Homeland Security website .

Currently, island visitors get little slips of paper that match their luggage and pray everything goes according to plan. As Mackinac Island continues to see increased tourism, challenges grow, Shepler said.

"We want to always try and increase our service to visitors on Mackinac Island, whatever that is," he told the Free Press. "We take that very seriously."

On Monday, Shepler's posted on its Facebook page the latest status of its plans: "Shepler's Ferry has decided to postpone the launch of our luggage tracking system, originally scheduled for April 2024. We are also postponing our new luggage fee schedule. So it's 'business as usual' in 2024. Thank you for your understanding and continued support."

The post had 393 likes by Tuesday morning, 58 shares and 77 comments. Responses ranged from criticism about corporate greed and a desire to travel with competitor Star Line ferry to feedback from a passenger who said she lost a bag and contents worth at least $500 last season while visiting the island.

"We spend 40 to 50 hours a week looking for misplaced bags," Shepler told the Free Press. "Sometimes those bags are merely on the next vessel, but we don't know that, and the concern of the guest comes from having to catch a flight or wanting to get home. So the first phone call goes to St. Ignace, the second call goes to the hotel, the third call goes to Star Line. We’re making 30 phone calls off that one trip."

Being able to track luggage would save Shepler's and their patrons time and help eliminate any angst, Shepler said.

Jason Wiley, Shepler's director of operations, told the Free Press that the company has invested more than half a million dollars in the new technology.

The Mackinac City Council had scheduled a public hearing for late March.

The Mackinac Town Crier newspaper ran the headline recently, "New ferry luggage fees spur backlash." It said Mayor Margaret Doud and Mackinac Island City Council officials opposed the fee plan and would consider its regulatory authority allowed by city charter. The Free Press left messages for the mayor and city council seeking comment.

Council Member Brian Bailey, general manager of the Chippewa Hotel on Main Street, told the Free Press on Tuesday, “We are very happy to hear Shepler’s Ferry has decided not to move forward with their proposed baggage charge as we on City Council felt it is an unnecessary and unsubstantiated fee to our guests of the Island.”

A ferry boat service is a franchise and must pay franchise fees. The city charter grants the city the power to authorize, license and regulate ferries to and from the city and to regulate and prescribe, from time to time, charges and prices for the transportation of persons and property.

The charter says : "No ferry boat company shall make any unjust or unreasonable discrimination in rates, charges ... however, this shall not be deemed to prohibit the establishment of a graded scale of charges and classification of rates to which any customer or passenger coming within such classification shall be entitled."

Island leaders have talked privately and publicly about their concern related to luggage fee costs. Last month, the City Council passed a resolution from Council Member Anneke Myers calling the luggage fee unjustified, saying a $4 fee per bag would impose a "financial burden" on visitors and impose an 11% cost increase on a $36 round trip ferry ticket.

In addition, implementing the proposed fees, "in their current form," would jeopardize the financial stability of lodging facilities, according to a letter signed by the Mackinac Island Convention and Visitors Bureau and the Mackinac Island Tourism Bureau.

Early Tuesday, Tim Hygh, executive director of the Mackinac Island Tourism Bureau, told the Free Press that Shepler's luggage fee postponement "is great news and the timing couldn't be better as we put the final touches on what promises to be another incredible season."

Michigan State Police praise tech tracking system

Meanwhile, Matt Helmkamp, strategic intelligence unit manager at the Michigan Intelligence Operations Center of the Michigan State Police, wrote a letter in support of the luggage tracking system after being consulted by Shepler's.

"Characterized by its ability to monitor luggage in real-time, this system ensures a secure, transparent, and efficient travel experience for passengers and plays a vital role in safety and security," Helmkamp wrote in the letter provided by Shepler's to city officials and hotels, and obtained by the Free Press.

"The role of the Intelligence Operations Center involves thorough assessment of critical infrastructure and proactive measures to ensure the safety of all Michigan residents. This includes identifying vulnerabilities, coordinating with relevant agencies for robust security, and continuously monitoring threats to mitigate risks efficiently," he said. "The adoption of this technology is not merely an enhancement of security measures; it revolutionizes the way luggage is managed and monitored throughout its journey. By providing real-time data on each piece of luggage, the system substantially reduces the risks associated with lost or tampered items and acts as a robust deterrent against potential security breaches."

Data captured by the RFID system can help police if needed, providing detailed logs of luggage movement, Helmkamp said in the letter. "The implementation of this RFID luggage tracking system aligns Shepler’s Ferry with national best practices in transportation security, setting a standard for safety and operational excellence."

Shepler's Ferry has not permanently abandoned the idea of a tracking system, Shepler told the Free Press early Tuesday. "We think the system is the right way to go. We brought it up to the island hotels back in September. I thought we were out in front of it. We're going to continue to work with city officials and hotels to evaluate how this system can be used in the future."

Florida billionaire continues investing in Michigan businesses

Shepler's sold in 2022 to a self-made billionaire from Naples, Florida, who learned his work ethic making early morning deliveries door-to-door with his milkman father in tiny Washington, Missouri.

While David Hoffmann didn't make the highest offer of 40 potential buyers, he runs the multibillion-dollar Hoffmann Family of Companies with his wife, Jerri, and sons Geoff and Greg, and that appealed to the Shepler family. 

The Hoffmann family has a presence in 27 different countries, including Europe, China, Latin America and South America, Hoffmann told the Free Press at the time of the purchase. He is the biggest real estate owner in Naples, Florida, Hoffmann confirmed. His family has renovated downtown Naples, Winnetka, Illinois, on the north shore of Chicago, and Avon, Colorado, the base of Beaver Creek Ski Mountain, Hoffmann said. And their  vineyard investment in Augusta, Missouri, has generated attention . 

Last year, the Hoffmann Family of Companies purchased Maurer Publishing, LLC, publisher of the Mackinac Island Town Crier and the St. Ignace News, and a printing shop in northern Michigan, according to the April 3 edition St. Ignace News . All editors, writers and employees remained amid plans to keep the print products and expand into digital operations.

Mackinac Island is gearing up (and hotel rooms are selling out ) for the 100th consecutive Bayview Mackinac Race in July, from Port Huron to the island. A record number of sailboats, exceeding 316, have already registered, according to a Bayview Yacht Club spokesman.

More: Mackinac Island gets new restaurant on Main Street honoring old Michigan family

More: Longtime customer buys a favorite hotel on Mackinac Island

Contact  Phoebe Wall Howard : 313-618-1034 or [email protected]. Follow her on X at  @phoebesaid

This article originally appeared on Detroit Free Press: Shepler's Ferry to Mackinac Island postpones plan to add fee, RFID luggage tracking