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
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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
