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 w