Always On Adventures

Jamie Villamor & Jon Gray
  • 5.0 (7)
  • Places & Travel
  • Updated Weekly

Always on Adventures is a free-wheeling conversation show hosted by entrepreneur, international cover model, and TeamUSA sponsored competitive shooter Jamie Villamor alongside hospitality innovator and experiential expert Jon Gray. Jamie and Jon, each a powerhouse in their own right, also happen to be a couple who spend their days globetrotting across countries and continents. Their conversations always begin previewing or recapping their adventures together, spanning all corners of the earth. Where those conversations end, though, is anyone’s guess. Between their three kids (each!), their b

  1. 3d ago

    New York Fashion Week Has Changed | Ep. 29, Part 1

    Jamie returns from New York Fashion Week with an insider’s perspective on how the industry has changed—from runway standards and the rise of influencers to models working for exposure. Drawing on her own modeling career, she shares what surprised her and why free products don’t pay the bills. Meanwhile, Jon’s outfit gets rejected mid-podcast, Jamie makes her case for sexy grandmas, and a solo trip becomes a New York food tour thanks to Jon’s restaurant recommendations. Next week, the adventure continues in Washington, D.C., where Jamie discovers she’s agreed to more than she realized. ____________________________ FOLLOW US ON SOCIAL MEDIA! Always On Adventures Website: https://alwaysonadventures.world/ Follow Jamie Villamor on Instagram: https://www.instagram.com/jamie_villamor/ Follow Jon Gray on Instagram: https://www.instagram.com/grayjon/ Follow Always On Adventures on Instagram: https://www.instagram.com/alwaysonadventures/ Have a suggestion for the show? Email us: hello@alwaysonadventures.world Producer: George Carmona | IG: https://www.instagram.com/mr_george_carmona/

  2. Oct 9

    The Baby Shower Debrief, Part 2: Candy Wars & Blended Family Drama

    The baby shower is over, but the debrief isn’t. Jamie and Jon pick up with candy-bar drama, disappearing decorations, and a dog accident that turned into a family argument—with 80 guests in the house. Then they get into the realities of blended families: relatives you’d rather avoid, sons-in-law who need a family tree, and why Jon gets along with Jamie’s ex-husband. Plus, a 6:30 a.m. wake-up call proves that grown kids don’t stop needing Mom—or her credit card. ____________________________ FOLLOW US ON SOCIAL MEDIA! Always On Adventures Website: https://alwaysonadventures.world/ Follow Jamie Villamor on Instagram: https://www.instagram.com/jamie_villamor/ Follow Jon Gray on Instagram: https://www.instagram.com/grayjon/ Follow Always On Adventures on Instagram: https://www.instagram.com/alwaysonadventures/ Have a suggestion for the show? Email us: hello@alwaysonadventures.world Producer: George Carmona | IG: https://www.instagram.com/mr_george_carmona/

  3. Oct 6

    80 Guests & Zero Boundaries: The Baby Shower Debrief

    The baby shower is over, the family has flown home, and Jamie and Jon have plenty to unpack. From hosting 80 women and resetting breakers to gift-opening fatigue, candy-bar drama, and a badly timed dog accident, Makenna’s celebration delivered more than a few stories. They also get honest about navigating blended families, whether you should pretend to like relatives, and why grown kids still treat Mom’s house like their own. With two daughters pregnant, Jamie’s next adventure is getting closer—and apparently, nobody is giving up their childhood bedroom.

  4. Sep 5

    We CAN't Plan Our Wedding!

    We were supposed to be planning our wedding. Instead, we spent 30 minutes trying to pick a location and ended up nowhere. Every time Jon and Jamie pick a wedding date, one of their kids gets pregnant, moves out, or has a life event that conflicts. Makenna recently got married and moved to San Jose while pregnant. Cierra is in Nashville, also pregnant. They're planning back-to-back baby showers with an event planner named Mylo and multiple conflicting themes (sweet retreat, soda pop bar, new chapter with books, crepe maker station). Meanwhile, Nash (Jon's oldest at 15) moved to Long Island for hockey and they're texting 24/7 like he's Jon's girlfriend. Jon is doing 75 Hard to get in shape for the wedding but keeps cheating with pancake syrup in his pocket. They're looking at castles in Ireland, Scotland, Italy, Austria, Switzerland, and more—but then found out Sting has a villa in Tuscany that sleeps 33 people, so they're trying to manifest a wedding there. Just the flights to Europe for everyone would cost $13,000. Nixon keeps knocking on their bedroom door at 6:55am even though they posted a "no knocking before 9am" sign. Jon got a vasectomy early in their relationship (he made it clear another baby would be a problem). They're shooting for 2028 for the wedding (8/28/28—the lion's portal), but honestly, at this rate, there'll be three more grandkids by then. ____________________________ FOLLOW US ON SOCIAL MEDIA! Always On Adventures Website: https://alwaysonadventures.world/ Follow Jamie Villamor on Instagram: https://www.instagram.com/jamie_villamor/ Follow Jon Gray on Instagram: https://www.instagram.com/grayjon/ Follow Always On Adventures on Instagram: https://www.instagram.com/alwaysonadventures/ Have a suggestion for the show? Email us: hello@alwaysonadventures.world Producer: George Carmona | IG: https://www.instagram.com/mr_george_carmona/

  5. Aug 28

    Texas Tombstone Ranch: Family Vacation Chaos, Hot Dogs & The Family Photo Drama

    Visit Texas Tombstone: www.texastombstone.com We took the whole blended family to Texas Tombstone Ranch outside Dallas for our first big family vacation where everyone could actually coordinate time off, PTO schedules, and pregnancies. Spoiler: it was chaotic but incredible. The owner Micah has an insane story—he went from a rough upbringing to building a thriving community out there with his family. He built this entire Western town concept (complete with jail, saloon, general store, theater room, outdoor kitchen) originally just for his grandkids to enjoy, and now he rents it out for family reunions, corporate events, and weddings. We stayed for 4 days and it was one of the best family experiences we've had. The kids chose it over the Bahamas when we asked them which trip they wanted to repeat. But the chaos: Makenna refused to be in the family photo without Preston (her husband who couldn't make it), so we had to compromise. Nixon ate two hot dogs in one bun at dinner and Aleeya captured it perfectly on camera. Nixon's priorities at her pep rally were hilarious—she only cared if "Jet" (her school crush) was watching, not about impressing 10,000 people. Then there's the stepmom/stepdaughter dynamics: Nixon claims the flowers Jon brings home are "family flowers" and not Jamie's, tells Jamie "this is my dad's house, not your mom's house," and constantly competes for attention. Harper got stuck sleeping alone while his girlfriend and her sisters chose to sleep together in the jail cell beds. And somehow Jamie is already planning Christmas and coordinating Santa gifts for 10 kids while their grandkids are still being born. This episode is about the beauty of a big blended family actually getting along + the chaos that comes with it. Texas Tombstone is genuinely worth a trip if you have a large family, friend group, or want to do a corporate retreat. ____________________________ FOLLOW US ON SOCIAL MEDIA! Always On Adventures Website: https://alwaysonadventures.world/ Follow Jamie Villamor on Instagram: https://www.instagram.com/jamie_villamor/ Follow Jon Gray on Instagram: https://www.instagram.com/grayjon/ Follow Always On Adventures on Instagram: https://www.instagram.com/alwaysonadventures/ Have a suggestion for the show? Email us: hello@alwaysonadventures.world Producer: George Carmona | IG: https://www.instagram.com/mr_george_carmona/

  6. Aug 21

    We're Grandparents & Not Even 43: Stroller Prices, Peptide Threats & Grandma Rules

    They're becoming grandparents in their early 40s and it's hitting different. Jamie and Jon are grappling with the identity crisis of being young grandparents—he didn't expect to marry a grandma, and now she's jokingly asking for the ring back. They break down the insane stroller market (2,500-3,000 for one stroller) vs. Jon's genius skateboard attachment accessory from 20 years ago that was way cooler. Jon got his Dexa scan results and had a body fat breakdown—he got 7% higher than he wanted and almost drove off an overpass. Now he's threatening 75 Hard, and she's threatening to jab him with GLP-1 peptides if he fails (she's already buying the vial). They're dealing with new grandparent boundaries—they're not allowed to kiss the baby on the face, though Jon plans to sneak cheek kisses when babysitting. Plus: she doesn't understand PTO and keeps trying to get her son-in-law to just take the week off, AARP discounts for grandparents under 45, and the Ring Cam Romance story about Preston showing up with beef sticks and flowers that started it all. ____________________________ FOLLOW US ON SOCIAL MEDIA! Always On Adventures Website: https://alwaysonadventures.world/ Follow Jamie Villamor on Instagram: https://www.instagram.com/jamie_villamor/ Follow Jon Gray on Instagram: https://www.instagram.com/grayjon/ Follow Always On Adventures on Instagram: https://www.instagram.com/alwaysonadventures/ Have a suggestion for the show? Email us: hello@alwaysonadventures.world Producer: George Carmona | IG: https://www.instagram.com/mr_george_carmona/

  7. Aug 14

    Italy Part 2: Walking Through Holy Doors & Why She Stayed (He Left)

    Rome was the grand finale. We met up with her kids (Leah, McKenna, and Harper) and experienced the Jubilee—something that only happens every 25 years. Jamie had walked past the Holy Doors at Saint Peter's Basilica 20 years ago when they were closed, and now they were open for the blessing. We both walked through them (though honestly, it didn't feel different), but it was a cool full-circle moment. Rome was packed, hot as hell, and we walked 30,000 steps to see the Colosseum, Trevi Fountain, and the Basilica. We also discovered why Italian pizza doesn't have pepperoni (it's an American thing), why you can't ask for ranch in Italy, and how every single pizza place makes fresh cheese daily—whatever isn't used that day gets tossed. Jamie ate nothing but pasta and bread the entire trip and somehow came back skinnier, which shouldn't be possible but apparently is. Then Jon went back to work while Jamie extended the trip to Switzerland with McKenna for "naked spa time." This was the first trip in 3.5 years they came home together (besides Hawaii). They're already talking about Positano as a potential wedding venue (even though they still haven't planned their own wedding). Next destination options: Vietnam, Cuba, Bosnia, or Georgia. This trip proved Italy is elite. ____________________________ FOLLOW US ON SOCIAL MEDIA! Always On Adventures Website: https://alwaysonadventures.world/ Follow Jamie Villamor on Instagram: https://www.instagram.com/jamie_villamor/ Follow Jon Gray on Instagram: https://www.instagram.com/grayjon/ Follow Always On Adventures on Instagram: https://www.instagram.com/alwaysonadventures/ Have a suggestion for the show? Email us: hello@alwaysonadventures.world Producer: George Carmona | IG: https://www.instagram.com/mr_george_carmona/

  8. Jul 31

    Italy Part 1: Travel Strikes, Stolen Bags & Rammstein Playing Outside Our Hotel

    Italy was supposed to be a smooth trip. It wasn't. Our flight to Paris got cancelled due to travel strikes, so we rebooked through Boston to arrive on July 4th (fireworks over Europe—wild). When we landed in Milan, trains were cancelled due more strikes—you just show up and hope your train goes. Plus: bags getting stolen left and right on Italian trains, so we had to guard our luggage like it was gold. We split up in Milan—Jon took the train to Lake Como while Jamie went to Tuscany for her daughter's wedding. Lake Como was incredible (heated bathroom floors had her refusing to leave), but we accidentally booked the wrong day thanks to European calendar systems starting on Monday instead of Sunday—a pro tip for anyone traveling to Europe. Then we regrouped in Lucca, a medieval town where we discovered Rammstein (the German metal band) was performing RIGHT OUTSIDE our hotel. We attended the daughter's wedding at a villa in the mountains, then took an insane train ride to Positano with different AC situations (she sat in the no-AC car by herself, he sat in arctic temperatures). We met random people walking through Positano, hired an Airbnb with ocean views, and experienced one of Italy's most beautiful coastal towns. This is Part 1—Rome and the Jubilee coming next.____________________________FOLLOW US ON SOCIAL MEDIA!Always On Adventures Website: https://alwaysonadventures.world/Follow Jamie Villamor on Instagram: https://www.instagram.com/jamie_villamor/Follow Jon Gray on Instagram: https://www.instagram.com/grayjon/Follow Always On Adventures on Instagram: https://www.instagram.com/alwaysonadventures/Have a suggestion for the show? Email us: hello@alwaysonadventures.worldProducer: George Carmona | IG: https://www.instagram.com/mr_george_carmona/

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About

Always on Adventures is a free-wheeling conversation show hosted by entrepreneur, international cover model, and TeamUSA sponsored competitive shooter Jamie Villamor alongside hospitality innovator and experiential expert Jon Gray. Jamie and Jon, each a powerhouse in their own right, also happen to be a couple who spend their days globetrotting across countries and continents. Their conversations always begin previewing or recapping their adventures together, spanning all corners of the earth. Where those conversations end, though, is anyone’s guess. Between their three kids (each!), their b

Information

  • Creator
    Jamie Villamor & Jon Gray
  • Years Active
    2025 - 2026
  • Episodes
    33
  • Rating
    Explicit
  • Copyright
    © Jamie Villamor & Jon Gray
  • Show Website
    Always On Adventures