Two years ago, our sailing journey began with sailing school, and now, three seasons in, we’re still learning and loving every minute! I’m amazed at how much we’ve experienced in such a short time.
Want to catch up on our sailing school saga? Check out our videos:
Our Sailing School Adventure – Part 1
Our Sailing School Adventure – Part 2
Our Sailing School Adventure Part 3
Just six months after completing sailing school, we took the plunge and chartered our first sailboat in beautiful Grand Traverse Bay, Michigan. This maiden voyage – our first time without an instructor – was a true test of our skills and a fantastic adventure filled with challenges and triumphs. It solidified our love for sailing and taught us valuable lessons about working together as a team, living in the moment, and the magic of the Great Lakes.
I’ve been meaning to share the story of this unforgettable trip, so here it is:
July 2023 found us in the turquoise waters of Grand Traverse Bay. GTB is actually two bays – East and West – separated by the Old Mission Peninsula. This unique geography creates varied sailing conditions and breathtaking scenery.

Day 0: Settling In
We chartered a sporty 31-foot Marlow Hunter, Dark Horse, from Great Lakes Sailing Company. After stocking up on provisions at a local grocery store, we settled in for the night. A lovely evening with family (❤️❤️❤️❤️ Jack and Emily!) and a glass of wine on the deck made for the perfect start to our adventure. (Pro-tip: If you are planning a trip like this, arrive a day early! We realized we had forgotten a few things, so we did a quick grocery run the next morning.)


Day 1: Setting Sail
After a thorough briefing from Captain Chris, we cast off and motored out of the marina, headed north. The wind was light, so we motored for a couple of hours before finally hoisting the sails.
Under sail, we enjoyed a fantastic 5-7 knots to our first destination: Ingles Bay. There we dropped anchor, whipped up some tacos, and enjoyed sundowners while recapping our day on video (see recap links below).
Daily recap 1: The First Test: WE PASSED!!!
Day 2: Calm Waters and Leelanau Peninsula Views
Day two brought a different experience. We woke up in peaceful Ingles Bay… to discover a thick swarm of bugs in the bathroom (lesson learned: don’t leave the bathroom light on overnight with open hatches!). After a leisurely breakfast and coffee, we set off again, headed north again. Unfortunately, the wind was practically non-existent, so we spent most of the day motoring. We tried to catch some wind a couple of times, but the conditions were not cooperating. As we rounded the tip of the Leelanau Peninsula, known for its cherry orchards and vineyards, we anchored off Cathead Bay Beach, where we could see the greater waters of Lake Michigan to the west.
Kent dared to brave the chilly water for a quick exploration of the beach. Famous for its Petoskey stones and crystal-clear water, Cathead Bay didn’t disappoint. Kent returned with a pocket-full of rocks which was a suitable souvenir. 😊

I should note, we toyed with the idea of sailing to Beaver Island, a 30-mile jaunt out into the Northern-most waters of Lake Michigan, but as it was our first time out on our own, it felt like a pretty big undertaking. Plus, we knew it would eat up a lot of time, and with the weather being a bit unpredictable, we decided to play it safe.
When we had our fill of Cathead Bay, we turned back to the south, motored to Northport Harbor in Northport, MI and enjoyed tacos and cocktails at a charming spot called Fingers Crossed. 🤞


Daily recap 2: Day 2 Grand Traverse Bay: Sailing Without Wind = Motoring
Day 3: Rain Sailing and Mooring Balls
Northport Harbor Marina provided the perfect opportunity for hot showers and a chance to recharge. We also took care of essential tasks like pumping out and refueling. The day’s weather, however, had other plans. As we motored south, rain poured down for hours. While one of us stayed cozy in the cabin (Becca 😬), the other of us (Kent 💪) manned the helm.
Seeking shelter, we found ourselves in Omena Bay. It is a small bay known for its tranquil waters, and a good spot for boaters seeking a more seclusion. There we experienced another first: picking up a mooring ball! We had anticipated that picking up the mooring ball was going to be an ordeal but we were pleasantly surprised to accomplish that task in short order. We fixed ourselves a delicious hamburger dinner and reflected on our provisioning strategy. We had planned to eat out half the time, and found it more efficient to prioritize breakfast and lunch onboard, having stocked up on Michigan goodies like cherries and strawberries. That afternoon, we opted to stay on the mooring ball, rather than go into the marina, for a quiet, more peaceful night.
Daily recap 3: Day 3 Grand Traverse Bay: RAIN SAILING and other firsts!!
Day 4: Glorious Views and Anchor Troubles
After a good night’s sleep at Omena Bay, we motored to Sutton’s Bay for brunch at the 45th Parallel. Suttons Bay, just 6 miles south of Omena Bay, is a charming village with a variety of shops, restaurants, and art galleries. A cute hand-painted illustration of the Great Lakes, an art work from the Laughing Fish Gallery, hangs in my office as a sweet reminder of our trip.


After our meal, we made our way east to the other side of GTB, to Power Island, also known as Fox Island. It is a public island with hiking trails, picnic areas, and a popular spot for swimming. There we would anchor for the night. The beach was beautiful and we were able to relax and enjoy the day. Initially, we had some anchor trouble due to a steep drop off. We decided to reset the anchor and add a stern ANCHOR. After we dove under the boat to check the anchor, we decided we were satisfied with the situation.
The water was crystal clear, and we enjoyed the beautiful scenery after all the rain the day before. We took a moment to reflect, noting that the time was flying by. At the same time, all the tasks involved in keeping yourselves afloat on a sailboat tend to take longer than you expect. We realized that flexibility and a “zen” attitude were essential for enjoying this kind of trip. We were down for it.
Daily recap 4: Day 4 Grand Traverse Bay GLORIOUS!!!
Day 5: The Final Day
Our final day arrived too quickly. Our night at anchor at Power Island was eventful. We had given our anchor situation a lot of thought. What would be the best way to ensure that we didn’t drag our anchor off the cliff? Our stern anchor definitely kept us from drifting, however, the winds shifted overnight. Waves hit us on the beam and the lines rattled on the mast all night, resulting in a very noisy, sleepless night. (Remember that “zen” attitude?)
We sluggishly packed up and motored south back to the marina, feeling sad that the trip was already coming to an end. We loved getting to know Dark Horse and found her adequate for our needs. This trip was truly magical and affirmed our love for sailing.
Reflections
Our Grand Traverse Bay adventure was a whirlwind of learning experiences. We faced challenges with anchoring, provisioning, and navigating varying weather conditions, but every hurdle taught us something new. We learned the importance of patience, flexibility, and teamwork, and landed on the perfect balance between the tranquility of anchoring and the convenience of marinas. We were able to fine-tune our provisioning strategy and learned just how much time sailing tasks can take. This trip was an unforgettable experience that we’ll cherish forever.
Have questions or comments about chartering a boat in northern Lake Michigan? Hit me up! I’ve got recs!
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