Let’s get one thing straight—we didn’t get into insurance to spend our best weather months stuck behind a desk, watching people live their lives through the office window.
But every summer, like clockwork, agents go into full-on panic mode trying to "keep up" their prospecting while their leads are checked out, their pipeline thins out, and their own motivation takes a nosedive... or they wind up on a golf course convinced theyre prospecting while only talking to the same 3 guys from BNI they always golf with.
It doesn’t have to be like that.
There are ways to keep making real money, keep your pipeline warm, and actually enjoy summer—all without cold calls, chasing people indoors, or sacrificing your sanity.
Below are 5 outdoor-friendly summer prospecting strategies—each one designed to help you be outside, productive, present, and profitable.
1. Hit Up Marinas and Boat Launches—Be the Toy Insurance Expert
Why it works: People are spending money on boats, Jet Skis, and summer homes, and almost none of them are properly covered. You showing up where the toys live makes you look smart, social, and like someone who “gets it.”
How to do it:
Spend a few hours on Saturdays or Sundays walking the marina or hanging near the local boat launch. Bring a cooler, sunglasses, and zero pressure.
Start conversations naturally:
“Hey, beautiful boat. Curious—do you guys insure it through your homeowners or separate?”
Most boat owners are underinsured, overpaying, or exposing themselves without knowing it. That’s your opening.
Offer to do a “Summer Toys Coverage Review” via text or phone later that week.
Bring branded koozies, waterproof phone pouches, or cooling towels to give away with your contact info.
You're in flip flops talking boats—not in a tie cold calling strangers. You’re fishing for business while they’re fishing for fluke.
Sponsor Youth Sports the Right Way—Then Show Up
Why it works: You’re visible, trusted, and part of the community—and you’re hanging out at games instead of stuck in your CRM praying for an inbound lead.
How to do it:
Sponsor a summer sports team (little league, soccer, flag football, lacrosse—whatever’s hot locally).
Don’t just slap your logo on a banner. Be there. Bring water, fruit snacks, fans, or a misting bottle. Be the MVP parent even if your kid isn’t playing.
Set up a shade tent on tournament weekends with a branded table and “Free Coverage Check-Up” signs. Offer cold drinks and conversations, not hard sells.
Use a QR code to collect info and enter people into a raffle for something useful—Yeti cooler, gas gift card, beach gear.
You’re watching a ballgame, not sitting in another boring networking meeting. You’re in the shade making friends and money.
Host a Neighborhood Ice Cream Social for Parents
Why it works: Ice cream brings out the kid in everyone. But here’s the play—you’re not targeting kids. You’re targeting parents, aka the people who actually make insurance decisions.
How to do it:
Hire a local ice cream truck or set up a couple of coolers with frozen treats in your driveway or a local park.
Promote it on your personal Facebook, through neighborhood groups, or by handing out simple flyers.
Let people know it’s “just for fun,” but if anyone wants a quick summer insurance checklist or review, you’ve got ‘em covered.
While the kids go full sugar-coma, the adults chat and get curious.
Have a “5 Summer Insurance Gaps Most Families Miss” handout ready, and a simple sign-up form for reviews.
You’re passing out Bomb Pops, not business cards. You're in the sun, building relationships, and casually collecting leads without pitching.
Get a Booth at the Farmers Market or Summer Fair
Why it works: People come to these events to discover something new. They’re outdoors, in a good mood, and way more open to talking than when you catch them between work emails.
How to do it:
Snag a booth at your local farmers market, craft fair, or outdoor community event.
Create a theme around “Summer Insurance Check-Up” or “Toy Season Coverage Review” (boats, RVs, side-by-sides, etc.).
Offer a simple raffle (cooler, local gift basket, beach chair) in exchange for names, emails, and what they’d like reviewed.
Give away useful stuff—bug spray, mini sunscreen bottles, reusable bags—branded with your info.
Chat casually. Your pitch is simple:
“We’re just helping people double-check their coverage for summer now that everyone’s dusting off their toys and hitting the road.”
You’re under a tent, making eye contact, sipping iced coffee, not chasing leads behind a screen.
Host Firepit Fridays (Trust-Building at Its Finest)
Why it works: People let their guard down around a firepit. No one expects to be pitched, which is exactly why they’ll listen. You're becoming part of their summer rhythm—not their spam folder.
How to do it:
One Friday a month, invite 5–10 people over for s’mores and drinks. Neighbors, clients, friends-of-friends. Doesn’t matter.
You’re not selling. You’re socializing. You’re being memorable. And if someone brings up insurance—which they will—you’re ready to guide the convo naturally.
Keep “Review Later” cards with a QR code that lets them book a time with you after the weekend.
Mention things casually in convo:
“You guys renting that Airbnb this summer? You know you’re liable if the tenants break the pool slide, right?”
“Your daughter driving to her summer job yet?”
Shorts. Firepit. Cold drink. Good people. Zero stress. Leads without the chase.
You can either spend the summer staring out the window from behind your laptop, waiting for people to respond to your fourth follow-up…
Or you can be outside, making money, building relationships, and enjoying the season you wait all year for.
These five methods work because they don’t feel like work. They let you build trust, start conversations, and make sales in environments where people are relaxed and open. And guess what? You’ll feel better, too—because you’re finally blending work and life instead of trading one for the other.
Summer doesn’t have to slow you down. You just have to change the way you move.