Posted on August 19th, 2025

 

There’s something about casting off on Lake Michigan with the Chicago skyline in your wake that just hits different.

The combo of city grit and open water calm feels like a summer daydream—until you realize you’ve packed like you’re heading to a brunch, not a boat.

Booking the boat is easy. Knowing what to bring? That’s where things get interesting.

A bareboat charter sounds simple, but the experience you have hinges on how ready you are. Comfort, spontaneity, even a good night’s sleep—all of it comes down to what makes it into your bag.

This isn’t about overpacking or playing it safe. It’s about giving yourself the freedom to enjoy every moment without the “wish I brought that” regret.

Before you chase the horizon, a little planning goes a long way. Keep reading—we’ll help you figure out what deserves a spot on deck.

 

What To Pack for a Bareboat Charter Adventure

What you bring on board will either make your bareboat charter feel like smooth sailing—or send you rummaging through bags for something you forgot.

This isn’t the kind of trip where you can just wing it with a hoodie and a half-charged phone. Packing smart means fewer surprises and more time soaking in the skyline with a cold drink in hand.

Start with the basics. You’ll need ID to confirm your booking, and if you’ve got boating credentials, bring those too. Chicago charters don’t always ask, but better safe than trying to explain your experience mid-dock.

Weather on Lake Michigan likes to keep things interesting, so don’t rely on the forecast alone. Instead, think layers—nothing fancy, just what works.

Plan for the kind of day that can shift from blazing sun to breezy chill in under an hour. The lake doesn’t care if you packed light. That’s why your bag should include:

• A waterproof jacket or windbreaker

• Non-marking boat shoes with solid grip

• Sunscreen with high SPF

• A dry bag for phones, chargers, and wallets

• Polarized sunglasses (the glare is no joke)

These aren’t overkill—they’re the baseline. Trust that skipping any of them can turn a solid day into an uncomfortable one fast.

Gear-wise, don’t assume the boat has everything. Some charters are fully loaded, others not so much. Check in advance, but it never hurts to bring extras: spare lines, a small cooler, and a first-aid kit.

Keep your meals simple and your water supply generous. Think fresh snacks that won’t wilt in the sun and drinks that hold up without a fridge.

A few underrated additions? A multi-tool that fixes what duct tape can’t. A small waterproof notebook—more useful than you’d expect when planning next moves or tracking lake conditions.

And for the sustainably minded, eco-friendly soap and wipes help you leave no trace.

Packing isn’t just a chore. It’s how you shape the kind of day you’ll have out there.

When everything you need is precisely where it should be, you’ll spend less time adjusting and more time enjoying the open water. That’s the goal. Keep it simple. Stay ready. Let the lake do the rest.

 

Preparation Tips for Charter Adventure in Chicago

Getting ready for a bareboat charter in Chicago means planning for a lake that doesn’t obey the rules. One hour it’s calm and sunny, the next you’re wishing you had a fleece. Lake Michigan has its own moods, and your best bet is to pack with that in mind.

Lightweight layers are key—something for the chill in the early hours, something breathable for midday, and a jacket that actually keeps out the rain when it shows up uninvited.

Weather aside, there’s more to prepare than just what you wear. Your time on the water can run a lot smoother when you’re ahead of the curve on safety, food, and gear.

Preparation isn’t about overloading your bag—it’s about avoiding the “wish we’d brought that” moment later.

Here’s where to focus:

• Check the weather the night before and the morning of. Then pack like the forecast is only half right.

• Walk through the boat with the charter operator. Know where the life vests, radios, and emergency gear live.

• Stock food that travels well: think wraps, dried fruit, or anything that won’t fall apart in a cooler.

• Bring backup power. Phones die fast when they’re doubling as maps, cameras, and music players.

These aren’t over-the-top precautions. They’re what let you relax once you’re off the dock.

While you’re sorting safety gear, don’t skip the basics. Know what the boat’s equipped with—PFDs, flares, and extinguishers—and double-check they’re all in working order.

A compact VHF radio is a solid backup even if you’re close to shore, and if you’re exploring beyond the usual routes, a personal GPS or emergency beacon adds peace of mind without taking up much space.

Food and drink deserve more thought than just grabbing a bag of chips. The sun, wind, and motion work together to dehydrate and drain you faster than you'd expect.

Pack more water than you think you’ll need. Throw in a small grill or reusable utensils if you want your meals to feel less rushed and more like part of the experience.

Smart prep makes the difference between just being out on the lake and actually enjoying the ride. Take a little time upfront, and you'll spend the rest of the trip wondering why you didn’t do this sooner.

 

Setting the Scene for Adventure on Lake Michigan

Once you’ve packed the essentials and mapped out the basics, it’s time to think about how to level up your charter experience.

A bareboat adventure on Lake Michigan isn’t just about steering the boat—it’s about what you do with the time between destinations.

This is where the extras come into play. They’re not requirements, but they’re what turn a solid day on the water into a trip you’ll talk about long after you’ve docked.

If your crew leans toward activity, gear that supports the lake’s slower moments can go a long way. A pair of binoculars gives you a front-row seat to the skyline without leaving your spot on deck.

Waterproof cameras or compact action cams make it easy to capture your crew’s highlights without worrying about equipment taking a dive.

Even something as simple as a deck of cards or a small board game can shift the energy when the sails are down and the mood turns mellow.

When planning your route, consider more than just the water. Chicago’s coastline is full of low-key gems that most guides barely mention.

Mooring near places like Northerly Island or the Indiana Dunes can introduce a different pace—a chance to stretch your legs, explore trails, or take in the city from a quieter angle.

If you’re more into museums than nature walks, sailing near the South Side provides you with access to local landmarks without fighting weekend traffic.

The key isn’t to overbook every stop but to stay open to diversions. Flexibility is part of what makes this kind of trip different from a regular vacation.

Food on board doesn’t need to be fancy, but sourcing it well makes a difference. Chicago’s farmers markets and neighborhood bakeries are perfect for stocking up before departure.

A crusty loaf of bread, a wedge of local cheese, and a few bottles from a nearby brewery are the kinds of details that make onboard meals feel less like picnic leftovers and more like something intentional.

The payoff? Better meals, smoother moods, and a stronger connection to where you are.

Every add-on, from fresh food to spontaneous detours, shapes the way your charter unfolds. It’s not about overplanning. It’s about layering in the kind of touches that help you live the lake, not just float on it.

 

Ready to Charter Your Own Lake Michigan Escape?

By now, you've got the essentials: the gear, the game plan, and the mindset to make your bareboat charter something more than just a day on the water.

Sailing Chicago’s lakefront is about perspective—trading concrete for current, traffic for wind, and routine for something a little more open-ended.

Every stop you chart, every meal you pack, and every small detail you prep becomes part of the bigger story you’ll take home.

If you're ready to start your chapter, Lakefront Voyages makes it easy to start.

We help tailor your experience to suit the vibe you're after—be it an easy afternoon cruise with friends or a weekend-long escape anchored in the rhythm of the waves.

Our fleet of well-equipped bareboats gives you the freedom to sail on your terms, backed by support that actually knows the lake.

No matter if you’re plotting your first voyage or returning for a fresh route, we’re here to help you book a bareboat charter in Chicago.

Want to chat about options or get help with planning?

Reach out any time at [email protected] or call us directly at (773) 559-0399.

Set your course. Book your charter. And let Chicago’s shoreline show you something new.