Pedal. Sip. Repeat. – A Lakeside Escape to Boat Drinks, Chicago

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Pedal. Sip. Repeat. – A Lakeside Escape to Boat Drinks, Chicago

Every city needs a secret harbor. For us, on our final morning in Chicago, that harbor came in the form of folding bikes, a lakefront trail, and a breezy outdoor patio serving BBQ and vodka tonics. Welcome to our accidental masterpiece of a day, starring Boat Drinks Bar & Grill in Burnham Harbor.

It was our last day in the city — bags packed, AirBNB cleaned, bikes charged and folded. But we still had hours before our Amtrak train. What began as a simple “let’s ride south and see what’s down there” evolved into a full-circle journey, ending in the best kind of way: on a dock, cold drink in hand, sandwich dripping with sauce, city skyline off in the distance.

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Southward Bound: From Wicker Park to the Edge of the City

We left our AirBNB in Wicker Park by 11 a.m. and immediately hit the bike lanes heading east, crossing through Humboldt Park and down to the lake. From there, we joined the South Shore Trail, a lesser-known offshoot of the lakefront path that hugs the shoreline all the way to the far South Side of Chicago.

It’s a different vibe than the North Side: quieter, more industrial at times, but with unexpected beauty. Rail yards give way to nature preserves. Warehouses sit beside tiny beach access points. We rode past anglers casting lines, murals fading on old buildings, and the occasional cyclist who looked like they’d done this route a thousand times.

The trail eventually ends in South Chicago, near Rainbow Beach. We paused, took a few deep breaths, and looked at each other: “Now what?”

The answer was obvious: back north… but with purpose. We had seen a place on the map — Boat Drinks — that sounded too perfect to pass up. Marina-adjacent. Open patio. Kitchen still serving.

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Docking at Boat Drinks, Burnham Harbor

Backtracking felt easier, probably because the destination now had food and vodka attached. We cruised up to Boat Drinks Bar & Grill just before 1 p.m. The outdoor patio sits just off the marina, with sailboats bobbing gently, flags flapping overhead, and the unmistakable sound of lake gulls blending with classic rock from the speakers.

We locked up our Portola folding e-bikes, grabbed a shaded table, and sighed the collective sigh of travelers who found exactly what they didn’t know they needed.

The vibe? Think Jimmy Buffett meets Chicago grit. It’s nautical, casual, and incredibly friendly. Staff in boat-logo t-shirts, laminated menus with faded corners, and a drink list that leans heavily into citrus, rum, and clear spirits. Yes, please.

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Food Review: The BBQ Chicken Sandwich

We both ordered the same thing — and no regrets.

The Sandwich: Pulled BBQ chicken stacked high on a soft bun with crispy onions and housemade slaw spilling over the sides.

The Sauce: Tangy with a bit of brown sugar sweetness, not too smoky. Perfectly messy.

The Sides: A handful of kettle chips and a pickle spear that actually snapped when bitten. Respect.

There’s something magical about eating BBQ with a view of masts and sails. Maybe it’s the juxtaposition — meat and marina, bourbon and boat fuel — that makes it feel like a secret spot even when it’s busy.

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Drinks on Deck: Vodka Tonics Done Right

As for drinks, we kept it simple: vodka tonics with lime. Crisp, cold, and refreshing. They came in tall plastic tumblers perfect for a patio, condensation dripping down the side as the lake breeze kicked in. It was the drink of the day, no question.

Bonus: reasonably priced, even with a view. No Chicago mark-up madness here — just fair pours and a wink from the bartender when you say, “Make it strong.”

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Why It Matters: The Beauty of “Found” Moments

This wasn’t a planned stop. We hadn’t circled it on a map or bookmarked it on Yelp. But it turned into the highlight of our entire last day. There’s something about wandering your way into a great meal — especially when it happens on two wheels and ends at the water’s edge.

It reminded us that the best travel moments aren’t always scripted. They happen in the gaps between schedules. They show up when you leave room for adventure.

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Travel Notes for Future Riders

Location: Boat Drinks Bar & Grill, Burnham Harbor, Chicago, IL

Hours:

Monday–Thursday: 11 AM–11 PM

Friday–Sunday: 8 AM–11 PM

Best Time to Go: Midday or sunset — less crowded and easier to grab a patio seat.

Pro Tip: Bring cash just in case. While cards are accepted, marina spots sometimes have intermittent Wi-Fi.

Nearby Landmarks: Shedd Aquarium, Northerly Island, Soldier Field.

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Sidekick Moment: The Russian Blue Cat Cameo

No Deep Dive story is complete without our editorial mascot. Sure enough, while we sipped our drinks, a chunky gray cat — maybe stray, maybe staff — padded across the dock and settled into the shade under a mooring post. Kellie said it looked just like our cartoon cat mascot in real life. We named him “Tonic.”

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Gear Check: What Helped Us Get Here

If you’re looking to replicate this route, here’s the gear that helped make it possible:

ROCKBROS Bike Phone Bag: https://amzn.to/3HPuzY0

Osprey Daylite Plus Backpack: https://amzn.to/45wB5N4

Kryptonite Mini-7 U-Lock: https://amzn.to/400SREH

Anker Power Bank: https://amzn.to/4e6GIUi

Frogg Toggs Rain Suit: https://amzn.to/45uXZV5

Affiliate links help support our travel, tunes, and tips — thanks for clicking!

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Final Thoughts Before the Train

With full bellies and a slight buzz, we rode back toward Union Station, the city stretching out behind us like a postcard. We didn’t just ride to a bar — we turned a blank afternoon into a lakeside memory. And that, to us, is the whole point of traveling by bike.

“Pedal. Sip. Repeat.” It’s more than a motto — it’s a roadmap for adventure.

— Jason & Kellie, Deep Dive AI