Sailing Sailing Tipsy Gypsy Travels

The Joys of Mackinaw Island

We’ve finally left Mackinaw City and went to Mackinaw Island for a few days! On our way out, it was a very blustery day so we did not pull out the sail as of yet but did enjoy the cold ride over. If you’ve ever been to Mackinaw Island,  you know there are many ferries driving by constantly from Mackinaw City and causes quite a bumpy trip. It was still exciting because it was our first official trip with Tipsy Gypsy!!

We’ve both been to Mackinaw Island growing up but haven’t been in quite a while. It was a great maiden voyage and since we got here at the beginning of May, we beat the crowds as the island was just starting to liven up. It also allowed us a complimentary slip at the Mackinaw Island State Harbor. We’re thankful for that! This place has so much to offer – Scenic Views, Delicious Restaurants, Exceptional Accommodations, Unique Transportation, and Great Shopping!

A Brief History

The island is located in Lake Huron between Michigan’s Upper & Lower Peninsulas. Most of it is preserved as Mackinaw Island State Park but is also considered a National Historic Landmark due to the extensive background in culture. Second National Park, just three years after Yellowstone and Michigan’s first state park. Native Americans, specifically the Ojibwa tribes first inhabited the island using it for fishing and a local gathering place for surrounding tribes. In the 17th century, a French-Canadian named Jean Nicolet developed a mission for them and later was moved to St. Igance by explorer Jacques Marquette. It became a French fur trading location and before long was taken control by the British where Fort Mackinaw was built. It went back and forth between British and American ownership to finally give back to Americans in 1815. After the Civil War and all the battling was over, was when most of the tourist locations were formed. The Grand Hotel was built alongside other Victorian architecture, Souvenir Shops sprung up for many of the residents to profit from, and became one of the nation’s most favorable Summer resorts.

Unique Transportation & Outdoor Adventuring

The main attraction to the island are its high cliffs, beautiful coastline, abundance of activities, Victorian architecture, and Fort Mackinaw. One of the most impressive parts of Mackinaw Island is the lack of motor vehicles. They allow for emergency/construction vehicles but most people ride bikes or use horse drawn carriages. It’s pretty awesome.

We mostly rode our bikes around as we enjoyed the island’s offerings but thoroughly enjoyed watching the carriages too. Jake & Elwood especially liked taunting the horses but gave them no attention. The terrain is quite hilly but did end up making it around the island pretty easily. It is an 8-mile bike ride and provides great access to the island’s architecture, scenic views, and wildlife. They do guided tours but we typically enjoy the self-guided tours best.

We explored much of the island by walking and riding our bikes.

Attractions Along the Way

Restaurants/Pubs – Every restaurant we went to was a good one. We first checked out The Pink Pony & Horn’s Bar due to our appreciation for them sponsoring many of the regattas around the island. We also checked out Seabiscuit on a cold afternoon and their Whitefish Chowder had to be my most favorite meal in a very long time. We found awesome place called Mary’s Bistro & Draught House where they had an excellent selection of Microbrews. One of the best places we enjoyed was the Chuckwagon for breakfast. A simple, delicious, & fun place to eat. It’s a very small restaurant but service was fast. Their kitchen was open over the counter and gave us a small show as we were waiting too. They had a toy megaphone to holler down their small prep hallway. Very happy to have made time to eat there. There are so many places to enjoy but we’ve mostly been cooking at the boat to save money and make sure the groceries we do have do not go bad. Plus cooking in the cabin helps to warm up the place!

CoffeeLucky Bean was by far our favorite. In fact, we went there to work almost every day of our stay. There were a few places not open yet for the season but probably would have still ended up at the Lucky Bean. There’s also a Starbucks on the island which was a bit weird but ended up meeting Tharon there after my day of shopping. while we there, a lost dog ended up coming in and running all around the coffee bar. Some girls working on the island for the Summer ended up taking the dog to the local police to help find  Such a cute dog!

Shopping – A must when you visit Mackinac. Seriously, go into EVERY store! Although I did not spend much money, I definitely could have done some damage if not being on our sailing budget. My favorite shops include: Little Luxuries – charming gift shop & clothing boutique, Crazy Horse – showcasing fine Native American jewelry, and Poppins – unique papery collection.

Fort Mackinaw – The bugle sounds at 9am with Reveille and 10pm with Taps. We also noticed that the cannon would sound most hours during the day. The scenery from the Fort was fun and it’s always Tharon’s favorite to enjoy the historical side of our travels. We learned lots on our jaunt around and took lots of fun pictures to commemorate the fun evening.


Okay, so our accommodations were at the Mackinaw Island State Harbor and did not cost us anything but there are some very extravagant places to stay. There are many options to choose from including camping for an affordable rate to staying at the Grand Hotel for $700+ per night. It all depends on your budget and comfort specificity. Although it was a bit chilly at times, we enjoyed our accommodations just fine. Here’s a look at the Grand Hotel –

Some Aerial Shots

Well that was our trip in a nutshell. So much fun and never a boring moment with the boat to care for, activities to enjoy, and people to meet along the way. If anything, we’re already planning another part of our Summer to make it back but look forward to visiting Les Chenneaux Islands for a few days! Until then, cheers & thanks for reading!

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