** Petoskey > Boyne City > Charlevoix > Leland > Frankfort **
The best trips are the ones where nothing goes wrong. Our run from Beaver Island to Petoskey was exactly that – calm waters, gentle breezes, and no drama to slow us down. It was the perfect backdrop for a fresh start, a chance to soak in the Michigan coast’s quiet magic. Tasha, who hadn’t set foot here since her youth, was eager to revisit old memories, while David was stepping onto these shores for the first time.
Now or Never travels from Beaver Island to Frankfort
We booked a slip for a whole week – far longer than we’d imagined when we started this leg of our journey. Michigan’s coastal popularity in the summer meant that finding a spot further down the coast was nearly impossible, and Tasha spent hours each day combing through reservations like a treasure hunter hunting for that elusive prize.
But as with any adventure, challenges crept in. Our trusty water pump, which had started acting up back in Canada, finally gave out – refusing to run unless hooked to shore water. Suddenly, the simple pleasure of running a tap became a luxury. A replacement water pressure switch was on order, shipped to the marina.
Meanwhile, our Starlink internet, essential for staying connected on the water, had been flickering on and off for weeks. Warranty service was excellent, but with a catch – they couldn’t ship the replacement unit to Canada due to contract rules. So here we were, anchored firmly in a U.S. port, waiting for technology to catch up with us.
Petoskey quickly surprised us. Despite being a small town of just 3,500 residents, it buzzed with a lively energy we hadn’t expected. The town’s charm is woven from a tapestry of vibrant flowers, friendly faces, and an active downtown that felt welcoming without being overwhelming.
Petoskey
While waiting for our parts and packages, we dove into the outdoor delights. The Little Traverse Wheelway beckoned – a scenic 26-mile trail hugging the water from Charlevoix to Harbor Springs. We didn’t conquer it all, but the miles we did cover, cycling beside shimmering lakes and under endless skies, were pure joy.
Sights along the Wheelway – Little Traverse Bay
Not far off, the Bear River Recreational Trail led us into a quieter world of waterfalls, winding rivers, and whispering trees. We spotted wildlife flitting through the brush, and the promise of salmon running soon added an exciting edge to our peaceful strolls. Here, the city felt miles away, even as it lay just beyond the trees.
Bear River, Petoskey
Back in town, we found ourselves drawn to cozy watering holes, quirky shops, and hidden gems tucked within easy reach of the marina. We even discovered a charming tunnel beneath the busy US 31 – a daily path for walkers and bikers alike.
TUNNEL
Cool tunnel taking pedestrians under US 31 from waterfront to downtown Petoskey
Our marina neighbors were a lively bunch: a hardworking charter fishing crew running nearly non-stop 4-5 hour trips. Watching their rhythm was exhausting in itself!
When the water pump switch finally arrived, Captain Dave was ready. A quick swap, and we were back in business – water flowing freely, ice maker humming, comfort restored.
A captains work is never done
Soon after, the new Starlink unit showed up – a sleeker, newer model with a different mounting setup. Dave jumped into action, adapting and modifying parts to make it fit perfectly. The upgrade was worth the hassle, and while the warranty took care of shipping, the task of packing up the old unit proved tricky.
New vs. old starlink
Boats and cardboard boxes don’t mix – moisture and pests are a nightmare. Luckily, during a morning walk, Dave spotted a perfect box in a downtown recycling pile. With packing materials salvaged from other deliveries and a roll of tape from a recent grocery order, we sealed up our parcel.
Getting it to FedEx? That was another story. Most might hail a ride, but not us. Using the Bear River trail, we pulled our folding wagon over gravel paths, across rivers (Dave carrying the wagon over stepping stones like a champ), and up a steep stone staircase to reach a Walgreens with a FedEx drop-off.
Over the river and through the woods
Package delivered, we rewarded ourselves with a cold drink nearby, basking in the satisfaction of a job well done before the peaceful walk back.
We also found time to visit a local model railroad club, marveling at their intricate 1913 Petoskey layout. Dave’s eyes lit up – trains and history, a perfect combo.
Reuniting with fellow loopers Cheryl and Rand, aboard Cheryl Ann, whom we first met on the Tennessee River years ago, was a joyful highlight. It’s one of the best parts of this journey – the community, the shared stories, and the friendships that endure.
Petoskey’s bike trails, downtown charm, and blooming gardens had us reluctant to leave, but the call of the road (or water) pushed us onward. Thanks to Tasha’s relentless daily slip-hunting on the DNR website, she scored a precious two-day window in Charlevoix. This reservation system felt like a game of Jenga, constantly shifting with the tides of weather and availability.
We set off a day early, hoping for a last-minute slip in Charlevoix. Timing the narrow harbor entrance and its twice-hourly bridge openings was a test of patience and skill. Captain Dave nailed it, slipping through without delay – unlike a viral YouTube boat trapped during a storm.
Now or Never’s entrance to Round Lake, Charlevoix
June 2025 storm – boater struggling waiting for bridge
With no luck getting a dock in Charlevoix, we cruised Lake Charlevoix all the way to Boyne City. This spontaneous detour stirred up childhood memories for Tasha – skiing down frosty slopes at Boyne Mountain, the rush of cold air and freedom with every turn.
Boyne City
Though we couldn’t visit the mountain or its striking Sky Bridge, this unexpected stop, complete with ice cream and loaner bikes, turned an 18-mile trip into a 31-mile memory we’ll cherish.
Rain showers and thunderstorms chased us back across the lake the next day, sometimes cloaking the waters in mist. Thankfully, the straight route and calm conditions meant we were alone, wrapped in nature’s quiet drama.
Some cruising days are just blah
Arriving in Charlevoix, we found the docks still full but didn’t wait long before securing our spot. The town’s docks hug Round Lake, framed by lavish homes and a welcoming city park – a smaller, equally enchanting sibling to Petoskey.
Our two-night stay stretched to three, as we settled into Charlevoix’s slow rhythm. Evening concerts from the city bandstand floated across the park, serenading us from the back deck of Now or Never. Nearby, a local pub offered a front-row seat to vessels navigating the bridge chute – including the twice-daily Beaver Island ferry. A wonderful farmers market in the park and Tasha found her tees!
Charlevoix
Tasha persuaded Dave to join the official Mushroom House tour, a pricey cart ride we felt could’ve been a self-guided adventure. These quirky homes, crafted over decades by self-taught architect Earl Young, blend seamlessly into the landscape. Massive boulders, fieldstone, cedar shingles – sometimes sourced from beaches or hidden underwater – form whimsical, almost fairytale-like structures.
Mushroom mobile
Their wavy eaves, exposed rafters, and chimney stacks that resemble melted stone make each home a piece of art. Many are private residences, but some welcome visitors as Airbnbs.
Charlevoix mushroom houses
Leaving Charlevoix early to sync with the bridge schedule, we crossed Grand Traverse Bay, aiming to overnight in the bay – but no slips were available. So we pressed on 35 miles to Fishtown and its historic docks in Leland.
Arriving just before lunch, we snagged a balcony table at The Cove, gazing out over a river waterfall and timeworn fishing shanties. Fishtown remains one of the Great Lakes’ last working commercial fishing villages, its weathered shanties now a lively mix of boutiques, galleries, and eateries nestled alongside fishing boats still hauling in the day’s catch.
Fishtown – Leland
After exploring, chores called us back to the boat, but happy hour found us under tiki umbrellas just below our lunch spot, savoring waterfront views and a famous Chubby Mary cocktail -complete with a whitefish garnish. With sidewalks closing early, the quiet evening aboard was the perfect end to a busy day.
Fishtown Chubby Mary
The next morning, a quick check of the weather sent us following the fleet of loopers toward Frankfort, needing a harbor spot for the night.
Frankfort runs a no-reservations policy. Call at 8 a.m., then wait your turn as boats depart. About an hour into the trip, Tasha called to find seven boats ahead of us on the list. They promised to call by 11 a.m. if a slip opened. At 11:20, the call came – we were in! We arrived with four looper boats from Leland.
Passing Sleeping Bear Dunes on way to Frankfort
Frankfort welcomed us with a car show and farmers market right off our stern. We love immersing ourselves in local life, and Frankfort’s lively downtown, nearby beach, and lighthouse kept us happily exploring. We also discovered a fantastic bike trail, pedaling until our legs said enough – only to realize we’d barely scratched the surface.
Frankfort
The next morning, Lake Michigan showed its wild side with big waves. Coordinating with three other looper boats, we planned a departure timed for calmer seas. It was a bit overwhelming for Tasha, but she rose to the challenge, gear on, and ready to roll.
A five-hour, 50-mile cruise awaited, leading us to our next stop—Ludington.
Cheers! David, Tasha,
& Remy forever in our hearts! – Loop Dog for 1 year and 3357 miles
Remy and Jack looking for fish and turtles
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