Skip to content

Popping the Question

As many different ways as there are to say, “I do,” on Mackinac Island, there are even more romantic options when it comes to proposals. From rustic to elegant and...

As many different ways as there are to say, “I do,” on Mackinac Island, there are even more romantic options when it comes to proposals. From rustic to elegant and everything in between, here are some of our suggestions for popping the question in Mackinac style.

Anne’s tablet trail leading to Somewhere in Time Gazebo

Nestled along the Anne’s Tablet Trail — which namesake come from an Art Nouveau tablet commemorating local author, Constance Fenimore Woolson — you’ll find the infamous Somewhere in Time gazebo. Overlooking Haldimand Bay and Downtown Mackinac Island, the view is a great distraction while you get down on one knee. The 1980 film, Somewhere in Time, was shot almost exclusively on Mackinac Island and has developed a strong following. The gazebo was constructed specifically for the film and was the setting for a romantic scene between stars Christopher Reeve and Jane Seymour. Be the star of your own day and hire Mackinac Films to capture the moment.

Take a private carriage ride to The Woods restaurant

This one is as much about the journey as it is the destination. Arrange for a carriage to pick you up through Mackinac Island Carriage Tours. Good to know: pre-paid reservations are available through their business office. Then enjoy the sights as you make your way through the annex toward Stonecliffe Inn. The secluded property was built in 1904 as a family escape by Michael Cudahy. The since converted mansion’s grounds are enchanting and home to The Woods, a restaurant filled with charm and whimsy. Request a table in a romantic semi-private alcove for two.

Garden at Harbour View Inn

Get away from the hustle and bustle of main street in the gardens of the historic Harbour View Inn. Strolling around the gardens you’ll feel miles away from everyone else on the island, when actually you’re still in the heart of downtown. Try and time it for sunset, the orange and pink hues are irresistible and come dusk the garden turns into a midsummer night’s dream fantasy.

Windermere Point


Walk along the boardwalk and pop the question shore-side at Windermere Point. Located at Mackinac Island’s most southern point, this pebble beach is a hidden gem on Mackinac Island and a classic setting for quiet, romantic proposal. Layout a blanket in the grass, pour a little champagne, and let the waves crashing against the shore be the soundtrack for a moment you’ll never forget.

Charter a Sailboat

If Windermere Point isn’t close enough to the water for you, there’s only one other option: set sail. There are a few different ways to get out in the water on Mackinac Island — Sip N’ Sail Cruises — but, by far the most intimate experience is available through Mackinac Island Sailing Charters. Captain Dave and his crew will lead the way as you enjoy a private boating experience around Mackinac Island. Tours are available morning and afternoon, but we recommend going just before sunset. There’s truly nothing like being on the water during one of the most magical hours on Mackinac Island, when the light reflects off the sparkling Straits of Mackinac. It’s a #puremackinac moment.


Your cart is currently empty.

Start Shopping

Select options