TravelStories Episode 85: A Multi-Generational Round the World Trip – 2026 Edition

Trevor and Tom recap a multi-country, multi-generational family trip built around Trevor’s youngest nephew’s “once in a lifetime” journey. The episode covers Japan, Thailand, Italy and a quick stop in Toronto, with a strong mix of award travel, food, and cultural sightseeing. We talk through some of the challenges of coordinating such a trip, how we called a few audibles, and pushed ourselves to see things that we hadn’t experienced before. This one is less a polished travel guide than a real trip log with practical lessons, standout hotels, a few booking wins, and some honest misses. If you care about premium cabin value, family award travel, and what actually works on a fast-moving round-the-world itinerary, there’s a lot here. **Key Points From This Episode:** 03:01 - How the Japan itinerary came together after the older nephew’s trip 04:16 - Four-seat award booking chaos and ticketing fixes 05:40 - Japan Airlines Chicago to Narita on the older 787 product 08:34 - Family food wins and trying new things on board 09:53 - Narrow seats, mini-cabin privacy, and arrival timing fatigue 12:07 - Hyatt Regency Tokyo’s updated feel and gold-heavy lobby 13:14 - A huge sushi tasting menu and the sea urchin disaster 15:22 - Rope-dropping the Pokemon and Nintendo floors in Shibuya 18:10 - Shibuya crossing and the city’s crowd-control rhythm 19:36 - Apple Maps, station exits, and train-car precision in Tokyo 23:21 - Lounge food hits, especially the katsu pork sandwich 25:09 - Akihabara card shops and deep childhood nostalgia 28:13 - Omi beef tasting menu and the most polished meal of the trip 34:13 - Flying south to Hiroshima and checking into Hilton Hiroshima 35:29 - Hiroshima Peace Memorial and the emotional weight of the visit 39:11 - Hiroshima okonomiyaki, wandering pedestrian streets, and lunch plans 47:23 - Miyajima, the floating torii gate, and the ferry experience 53:09 - Himeji Castle’s original structure and careful preservation 58:52 - Osaka Castle as a more museum-like castle experience 63:56 - Osaka to Bangkok on a short overnight and KIX’s scale 67:07 - Bangkok arrival logistics and the Grand Hyatt Erawan reset 69:47 - Why Bangkok remains one of the best value luxury hotel cities 71:01 - Massage, reflexology, and a repeat spa visit 71:44 - Din Tai Fung twice and why the family kept going back 73:49 - Grand Palace, Wat Arun, and the elephant pants tourist uniform 76:46 - Condor award value on paper and the Bangkok to Frankfurt routing 77:29 - Bangkok’s new satellite terminal and lounge hopping 81:54 - Condor business class in practice: seat, food, and service misses 88:28 - Lufthansa lounge access ending for Amex cards and Trevor’s timing luck 95:40 - The Tribune in Rome, stairs, and hotel comfort versus accessibility 98:18 - Vatican tour highlights, the Sistine Chapel, and St. Peter’s Basilica 102:13 - The hop on hop off bus that did not work well in Rome 113:43 - Rome to Milan on Frecciarossa and why the station scale stood out 116:30 - Milan gelato, the Last Supper tour, and the climate-controlled viewing room 126:00 - Leaving Europe via Frankfurt, EES, and the Brussels connection plan 129:31 - Wheelchair logistics in Brussels and making the United connection 131:39 - United Polaris to Washington and losing Trevor’s Google Pixel 135:44 - Final reflections on Japan, family, nostalgia, and wanting to go back —---------------- Key Topics for Episode Discussion Post:  - In this episode: Trevor explains how the trip came together as a three-generation family journey, with his brother, father, and nephew all joining at different points. - In this episode: Booking four award seats to Japan turned into a major planning exercise, including seat changes, typo fixes, and a long multi-reservation refund process. - In this episode: Japan was the emotional center of the trip, with Tokyo food, Pokemon and Nintendo stops, Shibuya, Akihabara, and a strong nostalgia thread around gaming and collectibles. - In this episode: The Japan Airlines flight from Chicago to Narita was solid but dated, with a narrow staggered business class seat, good service, and widely appreciated Häagen-Dazs. - In this episode: Tokyo highlights included the Hyatt Regency Tokyo, a major sushi tasting menu, a memorable Omi beef omakase-style dinner, and a strong lounge experience with katsu pork sandwich praise. - In this episode: Hiroshima was framed as the most solemn stop, especially the Peace Memorial, followed by okonomiyaki, a lounge crowd-control scene, and a ferry day to Miyajima’s floating torii gate. - In this episode: Himeji Castle and Osaka Castle showed two very different sides of Japanese heritage, with Himeji’s original wooden structure and Osaka’s museum-like reconstruction. - In this episode: Bangkok served as a reset and recharge stop, centered on the Grand Hyatt Erawan, massage treatments, Din Tai Fung, the Grand Palace, and some easy access to the city. - In this episode: Condor from Bangkok to Frankfurt was the clear low point, with poor seat design, weak food, uncomfortable bedding, and a cabin experience Trevor would not repeat. - In this episode: Rome and Milan finished the trip with heavy sightseeing and food, including the Vatican, the Last Supper, Rome’s major landmarks, and a strong use case for discounted dining via TheFork. - In this episode: The trip closed with a Europe-to-US routing through Brussels and Washington, including a near-miss at the airport, a lost Google Pixel, and a very positive United Polaris return. - In this episode: The family thread mattered throughout, especially Trevor’s father using mobility assistance when needed, the nephew discovering Japan through his own interests, and the whole group sharing food and nostalgia. **Keywords** Travel, Family Travel, Japan, Tokyo, Bangkok, Thailand, Rome, Italy, Milan, Condor, Japan Airlines, Multi-generational travel