I’ve Always Loved Being on the Water. Sailing Was Something New.
I’ve spent countless days on the water fishing, boating, and exploring Wisconsin, but somehow I’d never experienced sailing on one of the Great Lakes. When my friend Julia (part of duo @thatwisconsincouple) invited me aboard All Hands Sailing in Bayfield for a trip to Raspberry Island, I couldn’t pass up the opportunity. By the end of the day, I was already thinking about when I could do it again.
I’ve known Julia for a couple of years through the content creation world. Her sister was originally supposed to join her on this sailing trip, but after an unfortunate recent ankle injury, she wasn’t able to make it. Julia invited me a week before, and I immediately said yes.
Not only would this be my first time sailing on Lake Superior, but I’d soon find out it would also be my first visit to Raspberry Island.
While I’ve visited Bayfield more times than I can count, I’d somehow never explored the Apostle Islands beyond Madeline Island. Between weekend getaways, my bachelorette party, watching family run the Madeline Island Marathon, and countless ferry rides, Madeline has always been my go-to island. This trip reminded me that there is so much more waiting to be discovered just beyond Bayfield’s shoreline.
If you’re looking for one of the most unique things to do in Bayfield, Wisconsin, here’s what you can expect from sailing with All Hands Sailing.
Why Choose a Sailing Adventure in Bayfield?
Bayfield is known as the gateway to the Apostle Islands, and there are countless ways to experience Lake Superior. You can kayak the sea caves, hop aboard a sightseeing cruise, or take the ferry to Madeline Island. Sailing, however, offers something entirely different.
Instead of rushing from one destination to the next, sailing encourages you to slow down. You notice the wind, the waves, the changing shoreline, and the quiet moments that often get overlooked aboard a larger boat. The journey becomes just as memorable as the destination.
Before our scheduled departure, Julia and I had time to enjoy downtown Bayfield. We grabbed coffee, wandered through a few local shops, and soaked in the charm that makes Bayfield one of my favorite Wisconsin towns. If you have extra time before or after your sail, I highly recommend doing the same.
Pictured above are Wonderstate Coffee, Honest Dog Books, and All Hands Sailing at the City Docks.
What to Expect with All Hands Sailing
We met Sarah, Captain Alec, Bronte, and Sarah (and their four-legged friend Milo) at the marina before boarding the Raptor.
My first impression? This was a much larger sailboat than I expected.
There was plenty of room to move around, comfortable seating, and space to simply sit back and enjoy Lake Superior. As someone who had never sailed before, I honestly didn’t know what to expect, but Captain Alec immediately made the experience feel approachable.
After a quick safety briefing, we left the dock and made our way out of Bayfield Harbor.
One thing I appreciated learning was that the sailboat is equipped with a motor as well. Sailing depends entirely on the wind, so on calmer days, the motor helps keep the trip on schedule while still allowing guests to experience sailing whenever conditions cooperate. We didn’t have a lot of wind during our trip, but we still had the opportunity to raise the sails and experience what makes sailing so special.
One of the things I really enjoyed about All Hands Sailing is that they truly welcome everyone. If you’ve sailed your entire life or have never stepped aboard a sailboat, the experience is designed to be relaxing, educational, and enjoyable. Guests can simply sit back and take in the views or learn more about sailing from the captain throughout the trip. All Hands Sailing offers everything from shorter day sails to overnight adventures around the Apostle Islands, making it easy to find an experience that fits your schedule.
Sailing on Lake Superior
Leaving Bayfield Harbor and heading out onto Lake Superior felt different than any boating experience I’ve had before.
I’m used to fishing boats where the destination is usually the focus. Sailing slows everything down. We spent the morning talking, laughing, snacking, sipping Diet Coke Limes, and enjoying the company while Captain Alec worked the sails whenever the wind allowed. Watching him manage the lines and adjust the sails gave me an entirely new appreciation for the skill behind sailing.
Unfortunately, wildfire smoke had settled across northern Wisconsin that day, limiting visibility. On a clear day, you can see several of the Apostle Islands from the water, but even through the haze, the views were beautiful.
It was peaceful. Relaxing. Exactly the kind of pace that Lake Superior deserves.
Exploring Raspberry Island
Our destination for the day was Raspberry Island, a place Julia had wanted to visit for years because of its historic lighthouse. She loves lighthouses.
As we approached the dock, the lighthouse slowly appeared through the smoky skies, and it was every bit as picturesque as I had imagined.
We were welcomed by one of the volunteer guides, who shared the history of the lighthouse and the families who once lived there. Hearing stories about the keepers made the buildings feel much more than just another historic landmark, then were handed off to National Park Service representative Frank, and eventually the earlier volunteers wife at the top of the lighthouse.
Raspberry Island Light was first placed into service in 1863 to guide ships traveling through the western channel of the Apostle Islands. The original keeper’s quarters were expanded in the early 1900s, and today the beautifully restored station is cared for by the National Park Service. During the summer, visitors can tour the lighthouse and learn about the people who kept the light burning long before modern navigation existed. (National Park Service)
One detail I thought was especially interesting was learning that the original Fresnel lens is no longer in the lighthouse. Today, a much smaller Coast Guard beacon serves as the navigational light while the original historic lens has been preserved elsewhere. (National Park Service)
If you’re someone who collects National Park passport stamps, don’t forget your book. Raspberry Island has a passport stamp available, making it another fun stop for anyone working toward filling their collection.
Is All Hands Sailing Worth It?
Absolutely.
Whether you’re visiting Bayfield for the first time or have been coming here for years like I have, sailing offers an entirely different perspective of the Apostle Islands.
You don’t need sailing experience. You don’t need to know the terminology. You don’t need to help sail the boat unless you want to.
Instead, you simply get to enjoy being out on one of the most beautiful lakes in the world.
I think this experience would be perfect for couples, families, photographers, solo travelers, or anyone looking to celebrate a special occasion. If you’re hoping to slow down for a few hours and experience Lake Superior in a way that’s both peaceful and memorable, this is absolutely worth adding to your Bayfield itinerary.
Tips Before You Go
- Dress in layers. Even on warm summer days, Lake Superior can be surprisingly cool.
- Bring your camera. You’ll want it.
- Arrive early and spend some time exploring downtown Bayfield.
- Be flexible. Sailing depends on the weather, and every trip is a little different.
- Don’t worry if you’ve never sailed before. All Hands Sailing makes the experience approachable for everyone.
Final Thoughts
Even though I spend countless hours on the water every year, sailing on Lake Superior was something entirely new for me.
It reminded me that no matter how familiar a destination feels, there’s always another way to experience it.
For me, that new perspective came from the deck of the Raptor, sailing toward Raspberry Island with great company, a knowledgeable captain, and a fresh appreciation for one of Wisconsin’s most beautiful places.
If you’re planning a trip to Bayfield and looking for something beyond the typical tourist attractions, I’d wholeheartedly recommend adding an All Hands Sailing adventure to your itinerary. I know I’ll be back!
Thank you sincerely to Julia for the invitation and to All Hands Sailing for an excellent experience.
