Trip Tales | A Family Travel Podcast

Kelsey interviews Jenna about her multigenerational family road trip through the Florida Keys in April 2025. Jenna, her husband, their two boys (ages 7 and 9), and her parents hit the road from Miami, making memorable stops in Homestead, Islamorada, Marathon, Long Key, and Key West. From quirky roadside attractions to oceanfront stays and delicious local eats, this episode is packed with fun ideas for your own Florida Keys adventure. Jenna also shares details about their epic (and rocky!) journey to Dry Tortugas National Park.

Mentioned in this episode:
- Best Western Plus Miami Airport North
- Keys Fisheries, Marathon FL for stone crab
- Homestead: The Coral Castle (Edward Leedskalnin), White Lion Cafe, Robert Is Here Fruit Stand
- Overseas Highway
- Lime Tree Bay Resort - Layton / Long Key
- Islamorada: Robbie's of Islamorada (tarpon)
- Keyz Charters - 2 hour private snorkel trip to Alligator Reef Lighthouse
- Habanos oceanfront Cuban restaurant
- Crane Point Hammock Nature Center
- Key West hotels: Best Western Hibiscus Key West, Casa Marina, H2O Suites  
- Seaside Cafe at the Mansion - Lobster Bianca Pizza
- Dry Tortugas National Park & Fort Jefferson
- Key West Conch Train
- Mel Fisher Maritime Museum
- Key West Aquarium
- First Flight Restaurant
- Louie's Backyard
- Blue Heaven Brunch
- Mallory Square Sunset Celebration
- Doc's Diner
- Towne Place Suites Miami AirportTrip Tales is a travel podcast sharing real vacation stories and trip itineraries for family travel, couples getaways, cruises, and all-inclusive resorts. Popular episodes feature destinations like Marco Island Florida, Costa Rica with kids, Disney Cruise Line, Disney Aulani in Hawaii, Beaches Turks & Caicos, Park City ski trips, Aruba, Italy, Ireland, Portugal’s Azores, New York City, Alaska cruises, and U.S. National Parks. Listeners get real travel tips, itineraries, hotel reviews, restaurant recommendations, and inspiration for planning their next vacation.

Trip Tales is a travel podcast sharing real vacation stories and trip itineraries for family travel, couples getaways, cruises, and all-inclusive resorts. Popular episodes feature destinations like Marco Island Florida, Costa Rica with kids, Disney Cruise Line, Disney Aulani in Hawaii, Beaches Turks & Caicos, Park City ski trips, Aruba, Italy, Ireland, Portugal’s Azores, New York City, Alaska cruises, and National Parks like Grand Canyon, Yellowstone, Grand Tetons and Yosemite. Listeners get real travel tips, itinerary recommendations, hotel reviews, restaurant recommendations, and inspiration for planning their next vacation, especially when traveling with kids.

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 rides, must-try food, and practical money-saving tips straight from a former Disney cast member. Buy Me a CoffeeFollow Kelsey on InstagramMentioned in this episode:
- Purchased park tickets through Getaway Today or Undercover Tourist so your purchase codes as "Travel"
- Capital One Venture Credit Card - Travel Eraser
- Disneyland Magic Keys
- Hyatt House at Anaheim Resort/Convention Center (free breakfast)
- ART (Anaheim Regional Transportation) Shuttle to Disneyland
- Oga's Cantina
- Carnation Cafe
- Disney California Adventure Park: Web Slingers, Radiator Springs, Redwood Creek Challenge Trail, Wine Country Trattoria, San Fransokyo Square, Soarin'
- Anaheim Packing District: Food HallTrip Tales is a travel podcast sharing real vacation stories and trip itineraries for family travel, couples getaways, cruises, and all-inclusive resorts. Popular episodes feature destinations like Marco Island Florida, Costa Rica with kids, Disney Cruise Line, Disney Aulani in Hawaii, Beaches Turks & Caicos, Park City ski trips, Aruba, Italy, Ireland, Portugal’s Azores, New York City, Alaska cruises, and U.S. National Parks. Listeners get real travel tips, itineraries, hotel reviews, restaurant recommendations, and inspiration for planning their next vacation.



Trip Tales is a travel podcast sharing real vacation stories and trip itineraries for family travel, couples getaways, cruises, and all-inclusive resorts. Popular episodes feature destinations like Marco Island Florida, Costa Rica with kids, Disney Cruise Line, Disney Aulani in Hawaii, Beaches Turks & Caicos, Park City ski trips, Aruba, Italy, Ireland, Portugal’s Azores, New York City, Alaska cruises, and National Parks like Grand Canyon, Yellowstone, Grand Tetons and Yosemite. Listeners get real travel tips, itinerary recommendations, hotel reviews, restaurant recommendations, and inspiration for planning their next vacation, especially when traveling with kids.

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 Hotel. She’s sharing her best tips, favorite eats, and must‑ride attractions to help you get ready for Universal Orlando’s newest park!Buy Me a CoffeeMentioned in this episode:
- Sapphire Falls
- New hotels: Helios Grand, Stella Luna, Terra Luna
- Epic Universe portals
- Super Nintendo World: Mario Kart - Bowser's Challenge, Yoshi's Adventure, Minecart Madness, Toadstool Cafe
- Dark Universe: Monsters Unchained, Curse of the Werewolf, the Burning Blade Tavern
- Helios Grand rooftop bar, Flora Taverna
- Isle of Berk | How to Train Your Dragon: Viking Training Camp playground, Hiccups Wing Gliders, Fyre Drill
- Harry Potter Ministry of Magic: K. Rammelle candy shop, Café L’air De La Sirène French restaurant
Celestial Park: Constellation Carousel, Stardust Racers
- Valet ParkingTrip Tales is a travel podcast sharing real vacation stories and trip itineraries for family travel, couples getaways, cruises, and all-inclusive resorts. Popular episodes feature destinations like Marco Island Florida, Costa Rica with kids, Disney Cruise Line, Disney Aulani in Hawaii, Beaches Turks & Caicos, Park City ski trips, Aruba, Italy, Ireland, Portugal’s Azores, New York City, Alaska cruises, and U.S. National Parks. Listeners get real travel tips, itineraries, hotel reviews, restaurant recommendations, and inspiration for planning their next vacation.

Trip Tales is a travel podcast sharing real vacation stories and trip itineraries for family travel, couples getaways, cruises, and all-inclusive resorts. Popular episodes feature destinations like Marco Island Florida, Costa Rica with kids, Disney Cruise Line, Disney Aulani in Hawaii, Beaches Turks & Caicos, Park City ski trips, Aruba, Italy, Ireland, Portugal’s Azores, New York City, Alaska cruises, and National Parks like Grand Canyon, Yellowstone, Grand Tetons and Yosemite. Listeners get real travel tips, itinerary recommendations, hotel reviews, restaurant recommendations, and inspiration for planning their next vacation, especially when traveling with kids.

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 catamaran into crystal-clear waters
• A romantic dinner at Esperanza’s Cocina del Mar
• And yes, breakfast burritos every single morning of our trip

Buy Me a CoffeeEarn 150,000 points with Sapphire Reserve or 75,000 points with Sapphire Preferred -> https://www.referyourchasecard.com/19w/Q648OUK4ORMentioned in this episode:
- The Cape, A Thompson Hotel, Hyatt, Cabo San Lucas Mexico
- YNAB app - You Need a Budget
- Sunny Desert Transfer or LOMAS
- Southwest Airlines Upgraded Boarding via Performance Business Credit Card
- San Jose del Cabo vs. Cabo San Lucas
- The Rooftop at The Cape Hotel
- Enrique's Mr. Solmar hike with dogs - Enrique's Facebook Page
- Enrique's hike address: Antigüa Empacadora de Cabo, Blvd. Paseo de la Marina s/n, Centro, San Lucas, 23450 Cabo San Lucas, B.C.S., Mexico
- Brunch at Solomon's Landing
- Esperanza's Cocina del Mar
- Cabo Adventures Snorkel Excursion
Trip Tales is a travel podcast sharing real vacation stories and trip itineraries for family travel, couples getaways, cruises, and all-inclusive resorts. Popular episodes feature destinations like Marco Island Florida, Costa Rica with kids, Disney Cruise Line, Disney Aulani in Hawaii, Beaches Turks & Caicos, Park City ski trips, Aruba, Italy, Ireland, Portugal’s Azores, New York City, Alaska cruises, and U.S. National Parks. Listeners get real travel tips, itineraries, hotel reviews, restaurant recommendations, and inspiration for planning their next vacation.

Trip Tales is a travel podcast sharing real vacation stories and trip itineraries for family travel, couples getaways, cruises, and all-inclusive resorts. Popular episodes feature destinations like Marco Island Florida, Costa Rica with kids, Disney Cruise Line, Disney Aulani in Hawaii, Beaches Turks & Caicos, Park City ski trips, Aruba, Italy, Ireland, Portugal’s Azores, New York City, Alaska cruises, and National Parks like Grand Canyon, Yellowstone, Grand Tetons and Yosemite. Listeners get real travel tips, itinerary recommendations, hotel reviews, restaurant recommendations, and inspiration for planning their next vacation, especially when traveling with kids.

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 a personal boat driver who took them to dinner by sea. From snorkeling adventures to a BBQ on a private island, the group relaxed and enjoyed paradise.This episode is presented by Level 8 Luggage. Use code PreAS20 for 20% site-wide in July! I'm loving the 20-inch Luminous Carry On in Pink.Buy Me a CoffeeEarn free travel by applying for my favorite travel credit card, the Chase Sapphire Preferred, with my link!Mentioned in this episode:
- Gecko Vacation Rentals in Belize
- Island Time Gecko vacation rental home in Placencia, Belize
- Belize City
- Cessna Grand Caravan Turboprop Plane
- Manatees
- Restaurants: Barefoot Bar, Tipsy Tuna, Tutti Frutti Gelato, Omar's, Rum Fish, Placencia Yacht Club
- Turtle Inn - A Francis Ford Coppola Hideaway
- Snorkeling in Belize National Parks
- Global Entry

Trip Tales is a travel podcast sharing real vacation stories and trip itineraries for family travel, couples getaways, cruises, and all-inclusive resorts. Popular episodes feature destinations like Marco Island Florida, Costa Rica with kids, Disney Cruise Line, Disney Aulani in Hawaii, Beaches Turks & Caicos, Park City ski trips, Aruba, Italy, Ireland, Portugal’s Azores, New York City, Alaska cruises, and National Parks like Grand Canyon, Yellowstone, Grand Tetons and Yosemite. Listeners get real travel tips, itinerary recommendations, hotel reviews, restaurant recommendations, and inspiration for planning their next vacation, especially when traveling with kids.

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 loving the 20-inch Luminous Carry On in Pink.Buy Me a CoffeeMentioned in this episode:
- Disney Cruise Line Ship: Treasure
- Disney's Contemporary Resort
- Disney Springs - Summer House on the Lake
- Shiki-Sai: Sushi Izakaya in Disney World's Epcot 
- Disney Wish vs. Disney Treasure vs. Disney Destiny
- Plaza de Coco, Worlds of Marvel, 1923, Enchanté, Palo Steakhouse
- Haunted Mansion Parlor, Skipper Society, Periscope Pub
- Shows: Seas the Adventure, Beauty & the Beast, Moana
- Castaway Cay
- It's a Small World Nursery

Trip Tales is a travel podcast sharing real vacation stories and trip itineraries for family travel, couples getaways, cruises, and all-inclusive resorts. Popular episodes feature destinations like Marco Island Florida, Costa Rica with kids, Disney Cruise Line, Disney Aulani in Hawaii, Beaches Turks & Caicos, Park City ski trips, Aruba, Italy, Ireland, Portugal’s Azores, New York City, Alaska cruises, and National Parks like Grand Canyon, Yellowstone, Grand Tetons and Yosemite. Listeners get real travel tips, itinerary recommendations, hotel reviews, restaurant recommendations, and inspiration for planning their next vacation, especially when traveling with kids.

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, Utah
• Exploring New York City
• Disney Cruise Line
• Walt Disney World
• Universal Studios Orlando

Plus, the kids answer listener-submitted questions, share their bucket list picks (Italy and Paris!), and give real, unfiltered opinions on what makes travel fun (and sometimes not-so-fun) as a kid.Buy Me a CoffeeMentioned in this episode:
- Delta Airlines
- New York City: Sloomoo Institute, Summit One, Ellen's Stardust Diner, Ice Skating at Rockefellar Center, Jelly Cat Diner, Junior's Cheesecake, Statue of Liberty, SIX on Broadway, Trattoria Trecolori, RISE NY museum and ride, Wo-Hop in Chinatown
- Park City, Utah: Skiing at The Canyons
- Disney Cruise Wish Ship
- Disney World, Universal Studios Orlando, Islands of AdventureTrip Tales is a travel podcast sharing real vacation stories and trip itineraries for family travel, couples getaways, cruises, and all-inclusive resorts. Popular episodes feature destinations like Marco Island Florida, Costa Rica with kids, Disney Cruise Line, Disney Aulani in Hawaii, Beaches Turks & Caicos, Park City ski trips, Aruba, Italy, Ireland, Portugal’s Azores, New York City, Alaska cruises, and U.S. National Parks. Listeners get real travel tips, itineraries, hotel reviews, restaurant recommendations, and inspiration for planning their next vacation.


Trip Tales is a travel podcast sharing real vacation stories and trip itineraries for family travel, couples getaways, cruises, and all-inclusive resorts. Popular episodes feature destinations like Marco Island Florida, Costa Rica with kids, Disney Cruise Line, Disney Aulani in Hawaii, Beaches Turks & Caicos, Park City ski trips, Aruba, Italy, Ireland, Portugal’s Azores, New York City, Alaska cruises, and National Parks like Grand Canyon, Yellowstone, Grand Tetons and Yosemite. Listeners get real travel tips, itinerary recommendations, hotel reviews, restaurant recommendations, and inspiration for planning their next vacation, especially when traveling with kids.

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 Dublin, with overnight stays at some of Ireland’s most celebrated properties: Adare Manor, The Park Hotel, and Hayfield Manor. You'll hear about tastings at Jameson and Guinness, views of the iconic cliffs, and how this luxurious, all-female escape delivered the perfect blend of pampering, culture, and connection.This episode is presented by The Next Chapter Travel.
Trip Tales listeners can get $100 OFF a trip curated by The Next Chapter Travel by using code TNCT100 at booking.Buy Me a CoffeeMentioned in this episode:
- ADARE: Adare Manor, Calendar House, falconry, The Oak Room, Cliffs of Moher, Doolin, Gus O'Connor's Pub
- KILLARNEY: Killarney National Park, Ring of Kerry, Ross Castle
- KENMARE: Park Hotel, SAMAS Spa, tea at Sheen Falls Lodge, Cromwell's Bridge, fairy tree, Kenmare Stone Circle, The Quiet Man movie
- CORK: Jameson Midleton Distillery Tour, Hayfield Manor Hotel, Blarney Castle and the Blarney Stone, Saint Fin Barre's Cathedral, The Cork English Market, The Rock of Cashel, The Cashel Palace Hotel, Irish National Stud & Gardens
- DUBLIN: EPIC The Irish Emigration Museum, The Shelbourne Hotel, St. Stephen's Green, Trinity College, The Book of Kells Experience, The Long Room at The Library of Trinity College Dublin, St. Patrick's Cathedral, The Church Cafe Bar
- Ashford Castle in Mayo, Ireland
- Dromoland Castle Hotel in Country Clare, Ireland
- The K Club

Trip Tales is a travel podcast sharing real vacation stories and trip itineraries for family travel, couples getaways, cruises, and all-inclusive resorts. Popular episodes feature destinations like Marco Island Florida, Costa Rica with kids, Disney Cruise Line, Disney Aulani in Hawaii, Beaches Turks & Caicos, Park City ski trips, Aruba, Italy, Ireland, Portugal’s Azores, New York City, Alaska cruises, and National Parks like Grand Canyon, Yellowstone, Grand Tetons and Yosemite. Listeners get real travel tips, itinerary recommendations, hotel reviews, restaurant recommendations, and inspiration for planning their next vacation, especially when traveling with kids.

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-try shaved ice, and magical Hawaiian family moments!This episode is presented by: The Next Chapter Travel
Use code TNCT100 for $100 OFF at bookingBuy Me a CoffeeMentioned in this episode:
- Pro Shot Underwater iPhone Case
- Barrel Point Surf Boogie/Skim Board Bag
- Master Lock Travel Safe
- OAHU: Hilton Hawaiian Village Waikiki Beach (Rainbow Tower), Round Table Pizza, Jenny's vs. Big Wave shrimp trucks, Paia Fish Market Waikiki, Haleiwa Beach + Caged Shark Diving, Matsumoto Shaved Ice, Polynesian Cultural Center, Halona Blowhole, Pearl Harbor, Electric Beach, Tropical Farms Macadamia Nut Farm
- KAUAI: Grand Hyatt Kauai, Hanalei Bay snorkeling, Tunnels Beach snorkeling, Poipu Beach sleeping turtles, Capt. Andy's Na Pali Coast Tour, Waikomo Shave Ice
- MAUI: Hyatt Regency Maui, whale watching, Maui wildfireTrip Tales is a travel podcast sharing real vacation stories and trip itineraries for family travel, couples getaways, cruises, and all-inclusive resorts. Popular episodes feature destinations like Marco Island Florida, Costa Rica with kids, Disney Cruise Line, Disney Aulani in Hawaii, Beaches Turks & Caicos, Park City ski trips, Aruba, Italy, Ireland, Portugal’s Azores, New York City, Alaska cruises, and U.S. National Parks. Listeners get real travel tips, itineraries, hotel reviews, restaurant recommendations, and inspiration for planning their next vacation.

Trip Tales is a travel podcast sharing real vacation stories and trip itineraries for family travel, couples getaways, cruises, and all-inclusive resorts. Popular episodes feature destinations like Marco Island Florida, Costa Rica with kids, Disney Cruise Line, Disney Aulani in Hawaii, Beaches Turks & Caicos, Park City ski trips, Aruba, Italy, Ireland, Portugal’s Azores, New York City, Alaska cruises, and National Parks like Grand Canyon, Yellowstone, Grand Tetons and Yosemite. Listeners get real travel tips, itinerary recommendations, hotel reviews, restaurant recommendations, and inspiration for planning their next vacation, especially when traveling with kids.

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 drinks. Tune in to hear the full itinerary, travel tips, and the hilarious mistake Kelsey made buying her souvenir t-shirt!Our Arizona Trip Itinerary: https://kelsey-graves.kit.com/14eacab1acIf you’d like to share about your trip on the podcast, email me at: [email protected] Me A Coffee: https://buymeacoffee.com/kelseygravesFollow me on Instagram: https://www.instagram.com/kelsey_gravesFollow me on TikTok: https://www.tiktok.com/@mskelseygravesJoin us in the Trip Tales Podcast Community Facebook Group: https://www.facebook.com/groups/1323687329158879Inflatable Travel Bed: https://amzlink.to/az0wCGVzlVgpSAir Vent Phone Car Mount: https://amzlink.to/az0yKJBd0JcJyMentioned in this episode:
- 4th Grade National Park Pass
- Bearizona
- Holiday Inn Express Grand Canyon (IHG)
- Grand Canyon: Arizona Steakhouse, Prickly Pear Margarita, Mather Point, Kolb Studio, Lookout Studio, El Tovar, General Store
- Navajo Nation, Navajo Bridge, Cliff Dwellers, Vermillion Cliffs
- Hyatt Place Page / Lake Powell
- Page: Horseshoe Bend, Lower Antelope Canyon, Ken's Lower Antelope Canyon Tours, Lake Powell Italian Deli, Grand Canyon Brewery
- Flagstaff: Urban Pine, Sweet Shoppe Candy Store
- Scottsdale, Arizona: Grand Hyatt ScottsdaleTrip Tales is a travel podcast sharing real vacation stories and trip itineraries for family travel, couples getaways, cruises, and all-inclusive resorts. Popular episodes feature destinations like Marco Island Florida, Costa Rica with kids, Disney Cruise Line, Disney Aulani in Hawaii, Beaches Turks & Caicos, Park City ski trips, Aruba, Italy, Ireland, Portugal’s Azores, New York City, Alaska cruises, and U.S. National Parks. Listeners get real travel tips, itineraries, hotel reviews, restaurant recommendations, and inspiration for planning their next vacation.

Trip Tales is a travel podcast sharing real vacation stories and trip itineraries for family travel, couples getaways, cruises, and all-inclusive resorts. Popular episodes feature destinations like Marco Island Florida, Costa Rica with kids, Disney Cruise Line, Disney Aulani in Hawaii, Beaches Turks & Caicos, Park City ski trips, Aruba, Italy, Ireland, Portugal’s Azores, New York City, Alaska cruises, and National Parks like Grand Canyon, Yellowstone, Grand Tetons and Yosemite. Listeners get real travel tips, itinerary recommendations, hotel reviews, restaurant recommendations, and inspiration for planning their next vacation, especially when traveling with kids.