Monday with Maggie Returns: Food, Real Estate & Life on Hilton Head

This week on the Eat It and Like It podcast, Jesse Blanco and Maggie Crenshaw reunite after a busy spring to catch up on everything from business changes and real estate to the best bites around Hilton Head and Bluffton. Jesse shares why it suddenly looks like he’s living on Hilton Head full-time, while Maggie talks about returning to Coast Professionals brokered by eXp Realty and what’s ahead in her real estate career. Of course, there’s plenty of food talk too — including shoutouts to Sunrise Cafe, Cahill’s, Quarterdeck, Charlie’s, Java Burrito, Pomodori and more. It’s a fun, laid-back conversation about island life, restaurant favorites, Heritage week adventures, and what both Jesse and Maggie have planned for the busy summer season ahead.

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Eat It & Like It
Monday with Maggie: A Springtime Reunion
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After a little spring hiatus, Jesse Blanco and Maggie Crenshaw are back together for another edition of Mondays with Maggie on the Eat It and Like It Podcast. And as you’d expect, the conversation bounced everywhere from food and business to Hilton Head real estate and Heritage week adventures.

Jesse opened the episode joking about how long it had been since the two had caught up publicly.

“Where the hell you been?” Jesse laughed.

Maggie quickly fired back.

“Where you been? You’ve been cheating on me with food festivals and whatnot.”

The truth is both of them have simply been busy. Jesse explained that the early part of the year is always packed with restaurant weeks, food festivals, cooking demos and travel. Rather than making big business changes in January like everyone else, he usually waits until after St. Patrick’s Day to regroup and evaluate everything happening with Eat It and Like It.

“When you wake up in the morning and say, ‘Okay, I like how this feels,’ that’s how you know,” Jesse said about the recent updates to his business, podcast and newsletter.

Maggie spent the first part of the year doing some reflection of her own. She shared that she recently rejoined Coast Professionals brokered by eXp Realty, returning to a team she had worked with previously.

“There’s about 70 agents on the team,” Maggie explained. “There’s a lot of support, more opportunity, and just that infectious energy that happens from talking about real estate all the time.”

The pair also talked about the unique nature of Hilton Head’s second-home market, where buyers sometimes spend years searching for the perfect property.

“Some of my buyers I’ve worked with for one year, two years, some five years,” Maggie said. “They come once a year, look at properties, and eventually the right one comes along.”

Of course, it wouldn’t be a Mondays with Maggie episode without plenty of food talk.

Jesse shared that he’d been spending so much time on Hilton Head recently that multiple people asked if he had moved there permanently.

“I was asked three different times if I was moving to Hilton Head Island,” Jesse said. “The funny part is, I wasn’t going there more often. I was just posting about it more.”

That led into a rapid-fire conversation about some of their favorite recent meals around Hilton Head and Bluffton.

Maggie gave a big shoutout to Sunrise Cafe, where she recently stepped outside her normal order and tried the huevos rancheros.

“It was the real deal,” she said. “Really good.”

Jesse countered with praise for Cahill’s in Bluffton.

“The huevos rancheros at Cahill’s are spectacular,” Jesse said. “It should be on everybody’s short list if you haven’t been.”

The food conversation kept rolling from there, including mentions of Pomodori, Java Burrito, Amigos, Quarterdeck and Charlie’s. Maggie also praised the triggerfish dish and house pâté at Charlie’s, while Jesse admitted one of his favorite espresso martinis on the island comes from Quarterdeck.

“You’re paying for that view too,” Jesse joked while talking about dining at Quarterdeck overlooking Harbour Town.

There was also a fun exchange about Jesse dreaming of eventually having a tiny “crash pad” somewhere on Hilton Head to avoid late-night drives back to Savannah after events and dinners.

“I’d love to have a little studio apartment,” Jesse admitted. “Just a bed, a shower, TV — a little crash pad.”

Maggie, naturally, was ready to help make that happen.

“We can work that out,” she laughed.

As the episode wrapped up, both hinted at exciting opportunities ahead professionally, though neither was ready to fully share details just yet. Summer plans remain mostly open, but both agreed they’ll likely spend the season doing exactly what they always do — working, eating, and enjoying life around the Lowcountry.

And honestly, that sounds just about perfect.

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