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Benjamin Mahoney / Yacht Charter Broker / Luxury Concierge

@benlovesboats

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Yacht Charter Broker
Skip searching yacht charter websites - I bring the inventory.
Yacht charters and boat rentals on Lake Michigan + Worldwide.

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There’s a Japanese phrase I recently learned: mono no aware (物の哀れ).
It’s the feeling of realizing something is beautiful while knowing it won’t last forever. That little ache when you can actually feel a season of your life becoming a memory.

And that’s exactly how I feel right now.

My first season as a yacht broker is coming to an end, and I don’t think I was prepared for how much this summer would mean to me.

I started this season hoping I could build something. I knew boats. I knew Chicago. I knew I loved being on the water. And I believed I could create a better, more personal way for people to experience it.

But I had no idea if it would actually work.
Well…it worked.

People trusted me. They booked with me. They came back. They referred their friends.
Owners trusted me with their boats.
Captains became friends.
Clients became friends.
And something that started as an idea became a real business that I’m incredibly proud of.

But weirdly, when I look back on this summer, the bookings aren’t what I think about first.

I think about the people.

I think about friendships I’ve had for years that somehow became even stronger this summer.
I think about bringing old friends into new circles and watching those friendships form without me.
I think about people I met because of this business who I now know are going to be in my life long after the boats are put away.

Somewhere along the way, I stopped feeling like I was just building a client list. I was building relationships. Real ones.

The kind where you realize certain people you met through boating and work are probably going to be sitting at your table 10 or 20 years from now.
That might be the biggest success of this entire season.

I also got to be a tiny part of so many other people’s memories. Birthdays. Families. Old friends reuniting. New friendships starting. People celebrating huge moments and people celebrating absolutely nothing other than a beautiful Saturday in Chicago.

There’s something really special about realizing that your job helped create a day someone else might remember for the rest of their life.

And this summer taught me a lot.

(Continued in comments) taken in Lake Michigan by @benlovesboats

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2 months ago

There’s something about yachts that goes far beyond the water, the design, or the luxury.

For me, it’s about people.

It’s about that moment when someone steps onboard and everything just clicks—the energy, the setting, the feeling that they’re exactly where they’re meant to be. That’s what I chase.

I don’t just love yachts. I love what they create. Connection. Celebration. Escape. The kind of memories that don’t fade.

Finding the right yacht for the right person isn’t a transaction—it’s personal. It’s listening, understanding, and matching someone’s vision with an experience they didn’t even know was possible.

Because at the end of the day, it’s never just about the yacht.

It’s about the people on it.

Wanna charter a yacht or rent a boat on Lake Michigan? (or interested in knowing the difference?) Here when ya need me.

#chicago #lakemichigan #playpenchicago #chicagoboatrental #chicagoboatrental taken in Lake Michigan by @benlovesboats

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6 months ago

When @naiaontheriver is booked up but your Captain isn’t.

Experience NAIA by private yacht.

We’ll make the dock res and @naiaontheriver will provide service and vibes to you dockside.

DM to setup this premium experience.
#naiaontheriver #thingstodoinchicago #chicagoboatrental #chicagoyachts #chicagoboating by @benlovesboats

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4 months ago

Navy Pier Open Air / Final lineup of the season for outdoor shows and they’re going big.

10/16 — Charlotte de Witte
10/17 — Deadmau5
10/18 — Black Coffee

Charter a private yacht. 13 guests. One epic weekend.

Trade the crowd for crew and take the party to Lake Michigan.

DM to book.

@navypiermarina
@navypieropenair

#edm #edmchicago #chicagoedm #thingstodoinchicago #chicagoboating by @benlovesboats

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10 days ago

The endless cycle.

#chicagoboatrental #yachtcharter #yacht #chicago #chicagoboats by @benlovesboats

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12 days ago

Best boating/charter season of my life.
See ya’ll next season. 🤝🛥️

Rippers.

#thingstodoinchicago #chicagoboating #yachtcharter #chicagoboats #chicago taken in Lake Michigan by @benlovesboats

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16 days ago

Make good decisions.
Don’t let the long process of searching tons of websites and apps for the perfect boat rental in Chicago annoy you too. I make it easy by bringing the inventory directly to you and helping you navigate bareboat chartering. All completely free of charge.

@karissakolorist
#chicagoboatrental #chicagoboats #chicagoboating #chicagoboatscene #chicagoboatrentals

Boat rental in Chicago
Yacht rental in Chicago

Yacht: 55’ Sea Ray L550 - available for charter. taken in Playpen Chicago by @benlovesboats

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5 months ago

There is no way we used to be strangers.

Best humans
@karissakolorist
@champagne_sheri

Cannes/Nice/Monaco/Italy(till kicked out)/St. Tropez

Need a yacht charter in South of France? DM Me 🛥️ taken in Nice Côte d'Azur by @benlovesboats

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4 months ago

As this 2026 boating season ends. Be smart out there.

#yacht #yachtcharter #chicagoboatrental #chicagoboating #yachtlife taken in Lake Michigan by @benlovesboats

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20 days ago

My financial advisor hates me.

#thingstodoinchicago #chicagoboatrental #yachtcharter #chicagoboating #yachting

@brad_smith_re
@elevateyacht
@navypiermarina taken in Navy Pier Marina by @benlovesboats

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17 days ago

All in for small group September.

Lotta asks by clients lately for bringing extra passengers.
Plain and simple / Bareboat charters = 13 passengers(Charterer + 12). No way around it.

It’s a beautiful maritime tradition where the Coast Guard forces you to admit who your 14th favorite friend is.

#thingstodoinchicago #chicagoboatrental #chicagoboating #chicagoboat #chicagoyachts taken in Lake Michigan by @benlovesboats

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a month ago

The art of Fall boating season.

#lakemichigan #chicago #chicagoboatrental #yacht #yachtcharter taken in Playpen Chicago by @benlovesboats

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19 days ago