171 episodes
TravelStories Episode 85: A Multi-Generational Round the World Trip – 2026 Edition
05/10/2026 | 2h 19 mins.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- Stick around at the end for an extra clip from a patreon show!
0:20 Citi announces JAL as 1:1 Transfer Partner for Strate Premier and Elite
The rumor has come true
1:1 on their higher end cards
30% transfer bonus between now and October 24 to celebrate
Discuss what we think of this
Will this put pressure on Capital one to match 1:1
Plenty of places to earn JAL miles now.
Aligns with JAL’s guidance that they want to double the number of miles they issue by 2030 (source, in Japanese)
10:32 Citi Strata Elite Retention Offers
This card seems to have been populated with retention offers now (wasn’t before)
12,500 TYP -or- $100 statement credit for $2k spend per month for 3 months
Limiting to one Strata welcome bonus lifetime (across their entire Strata product family)?
14:20 Chase Sapphire Reserve Personal 10 Year Anniversary
Direct Link
Chase celebrates 10 years of this card with strange collection of perks, each leaving me slightly concerned they’ll not work as I hope..
DoorDash
NEW: $15 monthly promo on any qualifying DoorDash order (starts Oct 1, 2026)
Two $10 promos each month for groceries, daily essentials and more (is normal takeout included?)
Offers (require activation)
Cardmembers who activate the following Chase Offers®, then complete payment on the partner’s website by Dec. 14, 2026 will get:
$250 back on $1,000 Miraval/Alila (would this work in person?)
$200 back on $200 JSX semi-private jet (what if the jet is fully private?)
$125 back on $500 Sixt premium car rental (would this work for a standard car rental?)
$350 back on $1,500 Wander exceptional vacation home (what if it’s just a regular vacation home?)
$125 back on $500 IHG (US only, expires earlier than the rest, Oct 16)
18:52 Chase Sapphire Reserve *Business* Increasing The Edit Credits to 4x $250
Starting Jan 1, 2027 (visible in T&Cs online)
Still requires 2-night minimum stay
Still requires paying cash (rather than points) for minimum of $250 of each stay
For some reason I thought this was broken up into 6-month increments, but I think you can use these all at once, so you could conceivable book an 8-night stay by stringing together four 2-night stays
But $250 off 2-night stays at expensive The Edit hotels doesn’t seem like a very good discount 🙁
23:36 Chase 70% Transfer Bonus to Marriott
Have seen utility in this for both Marriott bookings (in ideal situations) and for transfers to airlines for miles
With JAL news at the top end of the show might not be worth doing vs. using TYP
25:36 Amex 175k Personal Platinum NLL (̶l̶i̶n̶k̶ ̶now dead)
These come and go and seem to appear when Amex needs new cardholders
This lasted just 3-4 days before being pulled
Does indeed bypass lifetime language and can auto approve and include a sign up bonus even if you have had the card in the past.
Shutdown risk? Are these legitimate?
Patreon Show Exerpt:
28:10 SF Trip Report, or: How Sonesta is taking over our worlds
Sam: Family trip
Talked about this quick getaway and how the hotel was a sticking point
Ended up seeing some hotel collection options with 3rd night free. This helped eliminate the issue of overshoot on a 2 night stay combined with not wanting to string multiple stays together.
Settled on The Clift hotel which just so happens to be a Sonesta property.
Was in Union Square and my wife was not happy about hearing that.
Booked with a Schwab platinum that had ~700 in FHR credits. Hotel was about $710 plus $120 in incidental tax and fees when we check in.
Robert: Booked via work, stayed at the Sonesta Silicon Valley 5 nights.
33:02 Sam Outbound: AA booked with 4,500 Alaska miles.
Interesting wrinkle, this flight earned 500 Alaska status points which I wasn’t expecting. Apparently award travel earns this.
Booked and selected more space seats because of my wife’s AA status.
Never split the record locator to try to get an upgrade. Decided it wasn’t worth it.
55 minute flight, left at 10pm, arrived 11:20pm
Flight about 60% full. 9pm went out full but a regional jet.
Uber pickup was better this time because I assumed a longer wait than the app showed, and I knew how long the walk was.
Still not on the Waymo Airport pickup list :(
37:15 Robert Outbound: JetBlue EvenMore Room
Mosaic 1 can now select EvenMore Room seats 36 hours prior to departure
This can strike at odd times of day and sneak up on you, and often creates dilemma of whether you want middle seat up front, a window/aisle with nobody currently showing next to you etc
Ended up getting a window seat on a packed flight
Pushed back on time, sat on tarmac for an hour, returned to gate for mechanical, ended up departing 2.5 hours late
8.5 hours in Economy is unpleasant, but they wanted a lot more for Mint than I was willing to pay
45:06 The Clift, a Royal Sonesta Hotel
This is a brand I know NOTHING about. In fact I had no idea there are 20+ of these around the country, including one in Kauai.
Prior to the stay I did the same Hilton Diamond status match as Robert. In about 3 days I was matched to Platinum with Sonesta.
At checkin my status was recognized by………a broken link between the hotel and TravelPass.
The hotel is nice, I think it is absolutely better than the two hilton options in the area, and it sits a little further north and west than those hotels.
I’d compare it to a Westin Brand.
325 or so rooms, renovated down to the studs in 2020-2021. Retained a lot of charm from the original hotel built over 100 years ago, including the lobby bar.
Amex Hotel Collection $100 credit recognized and stacked with some $10 daily credit.
Be careful, the lobby bar is closed Sunday and Monday
Everyone was impressed with Union square. Higher end shopping than we remember and plenty of foot traffic with visitors walking the streets even as late as midnight. Felt very safe to be out and about.
Even the hotel is minimizing the Sonesta wording:
47:37 Robert Hotel: Sonesta Silicon Valley
A week after stay, I still haven’t received credit for the stay. What a joke of a program.
Was mildly entertained by the notion of flexing my Sonesta Travel Pass Platinum status on this work trip
Used to be an independent hotel, remodeled then rebranded as a Sonesta in 2018
It’s not a particularly nice hotel, slightly worse than the not-so-nice Sheraton nearby
Interacting with Sonesta’s loyalty program relative to this stay left me appreciating what Marriott/Hilton/Hyatt do. Sonesta felt downright amateurish to me.
Stay was booked by corporate travel
I logged into my Sonesta travel pass to see if I could confirm the dates, but my reservation didn’t show up
I tried to add my confirmation number to my Sonesta Travel Pass account online. You can’t do that. Their site doesn’t support it. Says to fill out a form to contact them:
I fill out the form and immediately get an email back telling me to visit their website or call 1-800-REDLION (ha!)
Figured I’d call the hotel directly rather than mousing around with some flimsy corporate phone tree. Guy answered right up, confirmed my dates of travel, and while I had him on the phone had him add my loyalty number.
Upon arrival, after briskly checking in I asked if my loyalty number was on file. Desk agent said it was not, but then added it. - Summary
Tom Kim and Trevor Mountcastle compare two very different cruise experiences, one on Norwegian in the Caribbean and one on Princess in Europe. The episode is useful if you care about cruise line differences, private islands, food quality, port logistics, and how loyalty status and onboard programs can change the experience.
We discuss why one trip was relaxing but disappointing on food, while the other delivered stronger dining, better port stops, and a more polished overall experience. Trevor also shares several practical travel notes from hotels, airports, lounges, and transfers along the way.
Key Points From This Episode:
00:00 - Cruise update intro and why they have not talked cruises in a while
02:29 - Norwegian Getaway weekend itinerary out of Miami
03:49 - Club Suite booking and what the cabin actually included
05:04 - Relaxing family trip, but the food was a major problem
07:05 - Great Stirrup Key’s docked arrival versus tendering
08:25 - Why Great Stirrup Key exceeded expectations
10:02 - Island layout, pool area, bars, and food walk to the beach
12:27 - Main criticism of Norwegian food quality
13:27 - Great Stirrup Key expansion and the private island arms race
14:30 - Cruise pricing, early booking, and supply and demand
17:18 - Caribbean cruise competition across major ports
19:07 - European cruise setup: Lyon, EasyJet, and Athens
21:14 - EasyJet delay, airport breakfast, and free onboard purchases
24:41 - Grand Hyatt Athens and elite status value
27:57 - Transfer to Piraeus and boarding the Sun Princess
29:14 - Princess Sphere Class and why the line feels more premium
30:28 - Dining on Princess, including the Crown Grill
31:47 - Princess casino policy and how it differs from Norwegian
33:07 - Princess points, free drinks, and better comp opportunities
34:48 - Santorini excursion and the risk of tendering there
36:27 - Bar Montenegro and why Kotor is the more interesting stop
39:33 - Corfu, old town, and Prince Philip connection
41:41 - Messina, the clock tower show, and arancini
43:50 - Cannoli in Sicily and why fresh-to-order matters
46:09 - Sicily, Catania, and why the island deserves more time
48:30 - Barcelona departure, airport lounges, and Priority Pass meals
50:44 - Emirates Gold, Priority Pass, and keeping card benefits alive
52:44 - Air France return, mobility assistance, and smooth immigration
54:46 - Charles de Gaulle heat and Europe’s air conditioning problem
56:24 - Final thoughts on Princess, medallion tech, and Alaska plans
—----------------
Key Topics for Episode Discussion Post:
Trevor’s quick weekend Norwegian cruise out of Miami on the Norwegian Getaway, with Nassau and Great Stirrup Key as the two stops
Why the Norwegian booking was unusual: paid cash, weekend timing, and a Club Suite that was cheaper than an ocean view cabin
The biggest downside of the Norwegian trip: consistently poor food, with meals ranging from mediocre to borderline inedible
Great Stirrup Key as a major bright spot, especially after the switch from tendering to docking
How Great Stirrup Key compares with CocoCay in layout, walking distance, pool design, bars, and food access
The broader cruise market discussion about pricing, booking early versus waiting, and why Caribbean cruises feel like an arms race
Trevor’s Mediterranean cruise on Princess out of Athens, with stops in Santorini, Bar Montenegro, Corfu, Messina, and Barcelona
Travel logistics before the Princess cruise, including Lyon, EasyJet, Athens, the Grand Hyatt Athens, and port transfers
Why Princess felt stronger on food, casino perks, and onboard technology than Norwegian
The value of Princess’s medallion system, including cabin-door unlocking and shipmate location features
Keywords
Travel, Princess Cruises, Norwegian Cruise Lines, Travel Tips, Cruising, Caribbean, European Cruising. - Note: Video of this episode can be found on Youtube and Spotify.
Summary
Join us as we explore the fascinating world of international travel, airline management, and unique travel experiences with John Ryan. Discover insights into Asia trips, airline operations, and travel tips that will inspire your next adventure. Follow along an extensive journey through China and Mongolia, sharing travel tips, airline insights, and cultural experiences. Our guest, an avid traveler and miles enthusiast, provides valuable advice for navigating Chinese cities, using local apps, and maximizing travel rewards.
Key Points From This Episode:
00:00 Introduction to John Ryan and Travel Background
00:10 John's Involvement with FTU and Travel Communities
41:19 Flight from Chengdu to Guangzhou and delays
42:25 Weather and airspace considerations in China
43:19 Main hubs of Chinese airlines and fleet details
44:01 City hopping in China: Guangzhou, Nanjing, and Qingdao
48:02 Staying at the Park Hyatt in Nanjing and hotel experiences
50:03 Traveling in Ulan Batar and city logistics
01:06:29 Highlights in Beijing: The Great Wall and historical sites
01:10:50 Cultural influences and local food in Mongolia
01:13:09 Flying on MIAT and airline fleet insights
01:17:18 Traveling between cities: flights and high-speed rail
01:20:15 How to connect with the guest and final thoughts
Reference:
Lunch at the 747 Cafe https://www.youtube.com/watch?v=oPVnP6UOUnM
—----------------
Key Topics for Episode Discussion Post:
Asia travel experiences including China, Mongolia, and Singapore
Insights into airline operations and management, including airline partnerships and secondary airports
Travel hacks and tips for navigating airports and airlines
Personal stories of travel adventures and unique experiences
The impact of geopolitical issues on travel routes and airline choices Chinese airline industry and fleet details
Traveling in Chinese secondary cities
Using local apps like Alipay and WeChat
High-speed rail travel in China
Hotel experiences in China and Mongolia
Cultural insights and local food experiences
Traveling with limited Mandarin skills
Maximizing travel rewards and points
Navigating traffic and city logistics in Ulan Batar
Unique experiences like the Gobi Desert tour
Keywords
Travel, Airlines, Asia, Travel Tips, Airline Management, Travel Experiences, Frequent Flyer, Airport Lounges, Travel Hacks China travel, Mongolia trip, airline tips, Chinese apps, travel hacking, city hopping, high-speed rail, hotel reviews, travel tips - Join Trevor and Tom as Tom shares his ‘forced adventures,’ hotel and restaurant experiences as he tries to avoid the dreaded expiration of hotel certificates, all while exploring Chicago and New York City. Discover how to turn last-minute travel plans into memorable adventures.
Key Points From This Episode:
00:00 Introduction to Travel Stories and Hotel Certs
02:03 Using Hotel Certificates Before They Expire
03:59 Trip to Chicago: Saint Regis and Lowe's Hotel
08:54 Exploring Chicago Neighborhoods and Hotel Views
15:04 Crossing Chicago's Lower and Upper Wacker
20:01 Travel Mishaps: Shoe Print and Suitcase Repair
25:16 NYC Hotel Stay at The Standard Highline
35:01 Dining Experiences in New York: French Restaurants and Bagels
45:03 Nightlife and Sports Events in NYC
55:00 Reflections on Travel and Hotel Loyalty
Reference:
The Standard Highline, New York - https://www.standardhotels.com/new-york
Gallagher's Steakhouse, NYC - https://www.gallaghersnysteakhouse.com
Apollo Bagels, NYC - https://www.apollobagels.com
Lowe's Hotel, Chicago - https://www.theloweshotel.com
Saint Regis Chicago - https://www.marriott.com/en-us/hotels/chist-the-st-regis-chicago/
Delmonico's, NYC - https://www.delmonicos.com
—----------------
Key Topics for Episode Discussion Post:
Hotel certificate strategies and expiration management
Chicago hotel experience at Saint Regis and Lowe's Hotel
New York City hotel stay at The Standard Highline
Travel planning and last-minute booking tips
Experiences with hotel amenities and service quality
Keywords
travel stories, hotel certificates, Chicago, New York, travel tips, hotel reviews, travel hacks
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