Live booking a multi-family trip to Europe
Group Size: 9 Adults + 1 Lap Infant (10 total)
Origin: Seattle (SEA) & New York (JFK)
Destinations: Germany, Portugal, Italy, and France
Total Cost & Valuation
Points + Cash Breakdown
JFK → FRA → LIS (Parents): 150k Aeroplan points (Amex MR) + $358 CAD
SEA → YVR → FRA (Wife & MIL): 140k Alaska Mileage Plan miles + $99.80 USD
SEA → IST → LIS (Self, Son, Brother): 220k Aeroplan points (Amex MR) + $75 CAD
SEA → IAH → FRA (FIL & BIL): 180k Aeroplan points (Amex MR) + $157.60 CAD
SFO → AMS/MUC → LIS (Brother's GF): 100k Flying Blue miles (Amex MR) + $277 USD
CDG → SEA (Return Leg - 5 Pax): 240k Flying Blue miles (Amex MR w/ 20% transfer bonus) + $1,687 USD
Hyatt Regency Lisbon (3 Rooms): 273k World of Hyatt points (Chase UR transfer)
Grand Hotel Victoria Menaggio (Lake Como): 340k Hilton Honors points + Free Night Certificate (FNC)
Hotel Keppler Paris: 93.75k Citi ThankYou points (375k IPrefer) + 1 paid night & €40/night upgrade
Total Out-of-Pocket Cash: ~$2,654 in long-haul flight taxes/fees + minimal hotel extras
Estimated Retail Cash Value: Over $75,000 across all business class cabins and luxury properties
Goal of This Trip
I have been blessed in my life to be surrounded by such a loving and caring family. Ever since I was born, I feel like I’ve been given the support and tools I needed to succeed. I give my thanks to none other than my parents for that—from traveling all over the state(s) to staying up late or getting up early to help me prepare for tests at school. My parents are nearing retirement and have never traveled much together aside from our family trips to Hawaii and such. Ever since I got into the points world, I always imagined being able to book an amazing trip for my parents to scratch that itch for them to see the world. I felt hesitant sending them off on their own, so I decided to bring myself, my wife, and our kid, too!
I also figured, why not extend the thanks to my in-laws who so gratefully paid for my wife’s and my beautiful wedding and whom I consider family. My in-laws have also never been overseas, and I thought I could give thanks by creating memories in different countries that we can all cherish forever.
Initial Research
We are all based on the West Coast and all fly out of SEA. That limits how we can really get to Europe direct, so I knew connections would most likely be required. I was sitting on over a million points collectively, mainly through Amex MR, some Chase UR, and Alaska miles. I had the tools to track down flights and hotels to build an initial itinerary. I knew:
I wanted to get everyone to Europe and back.
I was okay with splitting itineraries—meaning we travel in pairs.
There were 8 adults and one lap infant (initially).
We wanted to fly business class for long routes (inner-Euro travel I didn’t care as much, but needed to consider luggage).
We wanted to visit at least 3 countries.
Because our priority was having all of us arrive within 1–2 days of each other, I had to sacrifice holding out for standard saver space across a single flight and get creative across airline alliances.
The Planning Journey
Late September 2025: Outbounds & Creative Routing
I started searching for flights in pairs and common routes to Europe from Seattle (or the West Coast). I came across a couple of options from FlightConnections. The ones that seemed most common were:
SEA → FRA
SEA → LHR (yeah, not gonna pay $$$$ in surcharges)
SEA → FCO (less common)
SEA → CDG (less common)
Okay cool. Now I knew that most likely I’d need to have family meet up in Frankfurt, Germany.
Now I thought, let’s make this trip very special for my parents. For one, they haven’t been to New York City. I wanted to make this trip memorable and remembered hearing about a fifth-freedom flight offered by Singapore Airlines: JFK → FRA. How amazing! I looked for availability and found JFK → FRA on Singapore Airlines Business Class through Air Canada Aeroplan (both Star Alliance members). While chasing options to Lisbon, I saw on Air Canada there was JFK → FRA → LIS! One of my favorite things about Air Canada is the 5k stopovers in business class. So I booked this for my parents for a total of 150k Air Canada points (150k Amex MR) + $358 CAD.
Next on the agenda was flights for my wife and her mom. I volunteered to take our to-be 1-year-old on my brother's and my booking. I expanded my search to Vancouver (YVR), a short drive or 45-minute flight from Seattle. I found SEA → YVR → FRA on Condor’s brand-new Airbus A330-900neo for 70k miles per person. This was my mother-in-law’s first business class experience, and I booked it for 140k Alaska miles + $99.80 USD total.
Now I wanted to book my son, my brother, and myself. My son is technically a lap infant. I don’t know why, but I saw a clip of a golf simulator in the Turkish Airlines Business Lounge at IST and was like—I gotta try this. That is basically why I locked in the weirdly routed SEA → IST → LIS on Turkish Airlines' A350-900 with a 15-hour stopover. I called Air Canada over the phone to confirm the lap infant attachment for 220k Air Canada Miles (Amex MR) + ~$75 CAD.
Finally, the last outbound tickets were for my father-in-law and brother-in-law. How awesome of a gift to take not just my MIL to Europe, but her family, too? Back I went to my bookmarked routes and found SEA → IAH → FRA on Air Canada through United/Lufthansa. The cool thing about this itinerary is my FIL and BIL flew on the upper deck business class on Boeing’s 747-400 "Queen of the Skies"! The total cost was 180k Air Canada Miles (Amex MR) + $157.60 CAD.
Late October 2025: Inbounds & First Hotel Locks
Now that I had some breathing room, I mapped out hotels. I was sitting on a stash of Chase UR (Hyatt points) and had Amex Platinum FHR credits. Knowing our core spots were Frankfurt, Lisbon, Rome, and Paris, I started mapping Hyatts. I saw decent availability for the Hyatt Regency Lisbon ranging from 21k–24k points a night. Traveling in groups of three, I booked three rooms under my name for a total of 273k Chase UR.
For return flights, I saw a 20% transfer bonus from Amex to Air France-KLM Flying Blue. We wanted to end in Paris, and I found award availability for 5 people in business class direct from CDG to SEA on their A350-900 for 60k Flying Blue miles (48k Amex MR with the bonus). For 5 people to fly direct in business class on that date, cash retail was $29,677. I booked it for 240k points + $1,687 USD.
February 2026: The Plot Twist & Lake Como Locks
I got a text from my brother asking if we could add his girlfriend to the trip. Normally it’s easy to find two seats per booking, but three on our exact Turkish route wasn't happening. I called Aeroplan, and after two days of missed callback tag, they confirmed zero award space. I set alerts on Roame and Seats.aero and snagged SFO → AMS/MUC → LIS in business class on Air France/KLM for 100k Flying Blue miles (Amex MR) + ~$200 USD, with my brother covering her positioning flight down to SFO.
For hotels, I opened an Amex Hilton Aspire card (and had my parents open one) for the Free Night Certificate and 175k welcome offer. I booked the 2 Michelin Key Grand Hotel Victoria Menaggio on Lake Como for 170k Hilton points + FNC (saving ~$1,300/night retail). By the time my parents hit their welcome bonus, standard award space at Menaggio had vanished, so we booked them across the water at Hilton Lake Como for 100k points/night + FNC. I continuously checked Grand Victoria on points and eventually space opened up, allowing them to also book for 170k + FNC.
I also locked in Hotel Keppler in Paris through Citi points right before the 1:4 to 1:2 IPrefer devaluation (93.75k Citi TYP transferred to 375k IPrefer points + 1 night cash). When I called IPrefer:
Me:“Can I book this on behalf of my parents?”
IPrefer:“That is not allowed.”
Me:“Is that a hotel policy or an IPrefer policy?”
IPrefer:“IPrefer policy…”
Me:“Can we pretend I didn’t say that?”
IPrefer:(laughs)“Sounds good.”
Because European hotels have strict occupancy limits for infants, Keppler noted my room couldn't fit a crib without an upgrade. I coordinated directly with the hotel and upgraded for just €40/night.
May 2026: Inner-Europe Transit & The "Last-Minute" Logistics
At this point, the core long-haul framework was complete, but I still had a puzzle of intra-Europe positioning legs and short stays to lock in.
The Amex FHR Check-In Hack at Steigenberger Icon Frankfurter Hof: For our transit night in Frankfurt, I booked the room using the annual Fine Hotels + Resorts credit on my Amex Platinum card, but put the primary guest name under my wife. An awesome feature with Amex FHR is that as long as the person whose name is on the reservation checks in with an eligible Amex card in their name, the full suite of FHR benefits applies (noon check-in when available, 4:00 PM guaranteed late checkout, daily complimentary breakfast, and the on-property experience credit). She checked in using her Amex Business Gold with zero issues, making our stopover 100% free with top-tier elite perks.
Positioning Flights on Ryanair (LIS → FCO): Intra-Europe award space from Portugal to Italy was pretty limited on Star Alliance/SkyTeam, so I kept it simple and booked cash tickets on Ryanair for about $350 total across 4 adults.
Frecciarossa High-Speed Rail (Roma Termini → Milano Centrale): Trenitalia’s schedule release can be a bit delayed, but as soon as the summer timetable unlocked, I secured Frecciarossa Business Class tickets for about $45 per person. Riding high-speed rail in Italy with wide leather seating and ample luggage storage was significantly less stressful than hauling a family and baby through Italian airport security.
Lake Como Rental Car via Hertz: Once we pulled into Milan Central, we picked up a larger full-size vehicle through Hertz (~$300 total) to drive our group up to Lake Como. I made sure to pay with the Robinhood Gold card to take full advantage of its primary auto rental collision damage waiver (CDW), so we were covered on those notoriously tight lakeside roads without paying extra daily insurance fees.
Positioning to Paris via Milan Linate (LIN → CDG): To get from Italy up to France for our final stretch, I bypassed pricey cash tickets and booked short-haul Air France award space out of Milan Linate for ~12k Flying Blue miles per person.
Trip Execution & In-Flight Reviews
Turkish Airlines A350-900 (SEA → IST → LIS): 9/10. The seat was wide and comfortable, and the in-flight entertainment had Bluey, which was an absolute lifesaver for my lap infant. Service was top tier: the crew proactively moved us to a bassinet seat, offered to hold the baby, and brought out desserts, snacks, and Turkish Sauvignon Blanc when infant duty delayed dinner. We had an operational diversion to APG before landing in Lisbon, but the crew handled everything smoothly.
Condor A330-900neo (YVR → FRA): 8/10. Super modern lie-flat product with an amazing fluffy duvet blanket. The amenity kit was basic and the YVR partner lounge was simple, but tarmac views were great.
Lufthansa 747-400 (IAH → FRA): 8.5/10. An unforgettable bucket-list experience for my FIL and BIL riding upper deck on the Queen of the Skies.
KLM Business Class (SFO → AMS → LIS): 8.5/10. Modern, comfortable seats with great hidden storage. The fresh crab salad wasn't a hit, but the rest of the meal and mid-flight treats were great. Collecting the signature Delft Blue miniature house at the end was an incredible touch.
Air France A350-900 (CDG → SEA): 8/10. The hard product with sliding privacy doors is top-tier. An unexpected plane swap threw off catering and delayed departure by two hours, but the second cabin crew turned things around with stellar French dining (beef and carrots) and wine.
Hotel Stays & The Road Through Europe
Steigenberger Icon Frankfurter Hof (Frankfurt): Historic luxury property fully covered using an annual Amex Platinum Fine Hotels + Resorts credit with zero out-of-pocket room cost.
Hyatt Regency Lisbon: Incredible Category 6 value. The suite had an in-unit washer/dryer and a full kitchen, which made traveling with a one-year-old seamless. Excellent gym, great lobby cafe coffee, and walkable along the water to Belém and Pink Street.
The Rome Airbnb Pivot: We flew budget on Ryanair from Lisbon to Rome (~$350 cash for 4 adults). Right before landing at FCO, I checked our Hyatt Regency Rome reservation only to find it completely gone. I called and they nonchalantly said they weren't taking bookings until December—canceling our multi-room stay with zero phone call or email notice! We took the train into Roma Termini and scrambled to find an Airbnb literally a 2-minute walk from the station, which ended up being a great, spacious rescue for the whole group.
Grand Hotel Victoria Concept & Spa (Menaggio, Lake Como): 2 Michelin Key perfection. Staff memorize your name before you even introduce yourself, escort you across the grounds, and even collapsed my wet umbrella for me in the rain. The massive complimentary hydrotherapy spa circuit (Mediterranean bath, steam rooms) was stunning, and dinner at their Asian fusion restaurant, SHIORI 1827, had incredible sushi.
Transit to Paris & The Milan Linate Scramble: We took Frecciarossa high-speed rail business class from Rome to Milan. From Milan, we rented a larger car through Hertz (~$300 on our Robinhood Gold card to leverage its primary rental auto insurance) to drive up to Como. To get to Paris, we booked cheap Air France award flights out of Milan Linate (LIN) for ~12k Flying Blue miles per person. But right before boarding at LIN, we realized I had completely forgotten to add my lap infant to our flight tickets. I immediately called Air France customer service, and the phone agent told me it was literally IMPOSSIBLE to add an infant this close to departure because their system couldn't process the fee within 3 hours of the flight. We were looking at being stuck at the airport for over 8 hours with a one-year-old, or having to rebook last-minute cash tickets for around $2,300. In pure panic, we ran straight to the physical Air France ticketing counter at the airport and practically begged for help. Thankfully, the in-person agent worked some magic and manually added him to our ticket in minutes.
Hotel Keppler (Paris): Intimate boutique luxury tucked right behind the Champs-Élysées, wrapping up our final nights in pure comfort.
Key Lessons Learned
Airport Ticket Counters Beat Phone Support Every Time: When Air France customer service insisted over the phone that it was impossible to add our lap infant within 3 hours of departure—risking an 8-hour delay and a $2,300 cash rebooking penalty—we ran straight to the physical ticketing desk at Milan Linate (LIN). The airport agents resolved the issue and handed us his boarding pass in minutes.
Avoid Rental Cars in Historic European Cities: We rented twice and only used them for airport/station-to-hotel transit. Navigating narrow streets and paying for parking wasn't worth the hassle—high-speed rail (Frecciarossa) and rideshares are far superior.
Double-Check Bookings Pre-Departure: The sudden Rome cancellation was a massive shock. Always call properties directly 72 hours out to re-verify multi-room group blocks.
Group Travel with a Baby: On the first flight out, it was just my brother, my son, and me—and since my son only wanted me, it was tough to fully enjoy the cabin. On the flight home, having my wife and both sets of grandparents made the long-haul experience infinitely smoother and more relaxing.
Direct Concierge Communication for Small Loyalty Programs: When booking niche programs like IPrefer, handle infant crib logistics, upgrades, and check-in name authorizations directly with on-site hotel managers rather than program phone reps.