Trip Tales | A Family Travel Podcast

Kelsey chats with Jamie from @jamie.travel.tips on Instagram about her August 2024 trip to Disneyland California with her two young boys, mother-in-law, and best friend. Jamie shares exactly how she made this magical trip budget-friendly—using points to stay at the Hyatt House Anaheim Convention Center (family room with bunk beds!) and even booking park tickets on points! Tune in for favorite ride...

Kelsey sits down with Stephanie Howard from Traveling Ears Vacations ( @travelingearsvacations ) on Instagram, who got an exclusive preview of Epic Universe in May 2025! Stephanie takes us through the portals, explores the brand‑new lands, rides the incredible attractions, and samples the amazing food - including charcuterie boards and cocktails at the swanky rooftop bar atop the Helios Grand Hote...

In this episode, Joe joins me on the pod as we share every detail of our July 2025 trip to Cabo San Lucas, including how we stayed at The Cape, A Thompson Hotel, for $0 using points. We talk through our trip budget, why we prioritize couples trips, and the adventures that made this getaway unforgettable: Hiking Mt. Solmar with the legendary dog trainer Enrique Snorkeling and jumping off a catamara...

Ryan is back on the podcast! After sharing his couples trip to Costa Rica last year on Episode 15 , he returns with another couples summer getaway, this time to Placencia, Belize. The best part - this fabulous trip started as a school auction prize! In June 2025, Ryan and three other couples headed to a stunning vacation home in Belize complete with a private chef, daily laundry service, and even...

Kelsey sits down with Theme Park Journalist and Disney expert Carlye Wisel from the Very Amusing podcast to dive into everything you need to know about the Disney Treasure cruise ship. From the brand-new Haunted Mansion Parlor to the immersive Plaza de Coco restaurant, this episode covers it all!  This episode is presented by Level 8 Luggage . Use code PreAS20 for 20% site-wide in July! I'm l...

In this special episode, Kelsey's kids take over to share their favorite trips, dream destinations, and honest thoughts about life with a travel content creator mom! From waterslides and connecting rooms to Summit One and the Jellycat Diner in NYC, they spill all the details on their favorite adventures — and yes, they roast Mom along the way. They talk about the best parts of: Skiing in Park City...

In this episode, Kelsey sits down with Martha from The Next Chapter Travel , a company that curates small luxury trips for women. Martha shares all the details of their unforgettable 5-star journey across Ireland — from spa treatments to falconry, fine dining to pub hopping, castle stays and countryside views in October 2024, Their itinerary highlights include Adare, Killarney, Kenmare, Cork, and...

Join Kelsey as she chats with Angie from @angies.travel.tips , a mom of 4 boys, about their unforgettable island-hopping adventure across Oahu, Kauai, and Maui in March 2025! From snorkeling with sea turtles and cliff jumping to cage diving with sharks, this trip was full of epic moments—and Angie paid for their Hilton and Hyatt stays entirely with points. Hear about their favorite beaches, must-t...

Kelsey is recapping her family of five’s trip to Arizona in May 2025 where they used Chase Ultimate Rewards points to cover nearly all their hotel stays! From insane views at the Grand Canyon and Horseshoe Bend to exploring Antelope Canyon and spotting animals at Bearizona, this trip was packed with adventure. And of course, it ended just right at a luxury Scottsdale resort with poolside food and...

Kelsey has been to Marco Island a dozen times and in this episode, she’s sharing everything you need to know to plan the perfect trip! From the best hotels and cost-saving tips to her favorite restaurants, sunset spots, and can’t-miss activities, this is your complete guide to one of the most beautiful beach destinations in the U.S.  Follow Kelsey on Instagram Buy Me a Coffee to support the T...

Kelsey sits down with Raya from the Travel Party of 5 podcast to hear all about her and her husband’s much-needed couples getaway to the stunning Kimpton Seafire in Grand Cayman. From swimming in glowing bioluminescent waters to experiencing Starfish Point, their July 2024 escape was the perfect reset. They loved it so much, they’re already planning to return with the kids. If you're dreaming of t...

Kelsey sits down with Katie from Katie’s Travel Tricks and the Points for Normal People podcast to break down two of the most popular family-friendly, all-inclusive resorts: Hyatt Ziva Cancun vs. Hyatt Ziva Cap Cana in Punta Cana. Katie has visited both properties with her kids and gives a detailed comparison of everything from the pools and food to the beaches and waterslides. Which one reigns su...

In this episode, Kelsey sits down with Nikki from @PackinPoints to hear all about her family of 6's (4 kids ages 9 - 18) epic adventure across Italy and Switzerland in June 2024 — much of it paid for with points and miles! Nikki shares how they fell in love with the rolling hills of Tuscany, gives a hot take on Florence, and describes rock-jumping into crystal-clear waters in Cinque Terre. Plus, t...

Kelsey is joined by longtime St. John visitor Christy, who has been traveling to this Caribbean gem for years with her family of four and often with a full crew of extended relatives. From the timeshare villas at The Westin to iconic beach bars like the Soggy Dollar, Christy shares her go-to beaches, can't-miss restaurants, and the boat day tradition that always steals the show. Plus, hear about t...

In this episode, Kelsey sits down with Katie from KG Travel Co. to hear all about her spring break trip with her family of four to Las Vegas, Zion National Park, and Bryce Canyon. From transforming Vegas into a kid-friendly adventure with a scavenger hunt, to avoiding the infamous three-hour shuttle lines in Zion with a genius e-bike rental hack - Katie shares practical tips and heartwarming momen...

Kelsey sits down with guest Kristen, who just returned from an unforgettable 8-night trip sailing through the British Virgin Islands in February 2025. Kristen’s family of four teamed up with another family—both with kids ages 8 to 12—to charter a fully crewed catamaran called Wanderlust ( photos of catamaran , and Wanderlust on Instagram ) departing from the island of Tortola. With a captain and p...

In this episode, Kelsey sits down with expat mom Brittani, who moved from Phoenix, Arizona to the Netherlands with her family of five. As a long-time Disneyland California fan, Brittani has now visited Disneyland Paris twice (Spring 2024 and December 2024) - and she’s sharing everything you need to know before you go. From the decadent breakfast spread at the Disneyland Paris Hotel to must-ride at...

In this episode, Kelsey chats with Mary Ellen from the Wonderland on Points podcast and @familytravel4thewin on Instagram to hear all about her family of 5's 4-night getaway to the Grand Hyatt Baha Mar in the Bahamas. Traveling in January 2025, Mary Ellen shares how she booked both flights and hotel entirely on points, plus her tips for saving on food while still enjoying the best the resort has t...

In this heartfelt episode, Kelsey sits down with Giovanna Silvestre, author of Confused Girl and @confusedgirlla on Instagram, to talk about her unforgettable month living on the Amalfi Coast. From mid-October to mid-November 2023, Giovanna stayed in an AirBNB with panoramic views of the Mediterranean Sea, immersing herself in the beauty and rhythm of local life. She opens up about how this magica...

I'm back from an amazing spring break in New York City with my family of 5 and I'm sharing all the details! In this episode, you’ll hear how we made the most of 4 nights and 5 days in the Big Apple (March 2025), from iconic sights like the Statue of Liberty and Summit One to navigating the subway and seeing SIX on Broadway. I break down how I planned the itinerary, found a hotel room that fit all...

In this episode, Kelsey welcomes Katie Kinley from @katiekinleytravels to share about her experience on the Disney Wish cruise ship. Katie and her family of 5 recently sailed on the Disney Wish for a 4-night Halloween on the High Seas cruise to Nassau and Castaway Cay, and she’s here to break down their experience. From ship highlights and what it’s really like to cruise Disney with three kids, to...

In this episode, Kelsey sits down with Annie from @letstraveltalk on Instagram to hear about her family of 5's adventure to Costa Rica in November 2024. From beach days at the Hyatt Andaz Peninsula Papagayo to the rainforest surrounding Tabacon Thermal Resort & Spa, Annie shares how Costa Rica delivered the perfect blend of adventure and nature. The family’s trip included rappelling down water...

Kelsey's Chase Sapphire Preferred Referral Link In this episode, I’m sharing exactly how I’ve been booking incredible vacations for my family without spending a dime on hotels. It all comes down to: transferring Chase Ultimate Rewards points to Hyatt . I’ll walk you through the step-by-step process, explain why Hyatt is the best transfer partner, and show you how to maximize your points for free s...

Kelsey sits down with Erika to chat about her family of five’s December 2024 ski trip to Copper Mountain , just outside of Denver, CO. Having skied at many of the top U.S. ski resorts, Erika shares why Copper Mountain stood out as a hidden gem. From its family-friendly vibe, fun restaurants, and wide-open slopes with no lift lines, to unique activities like ice skating on a real pond under Edison...

In this Trip Fails Minisodes episode, we’re diving into three mini Trip Fails stories that didn’t quite go as planned. First, Katie shares her experience at The Kingsley in Bloomfield Hills, MI in November 2024 - a hotel that gives off swanky boutique vibes but, surprise… it’s actually a DoubleTree by Hilton in disguise. Spoiler: the experience didn’t match the luxury look. Next, Tali recounts how...