The Travel Game Is A Journey. The Destinations Along The Way Are Just Part Of The Fun, Part 1

I’ve been playing the travel game, collecting miles and points, for well over a decade now.  While it’s gotten harder to find all the perfect flights, there’s still plenty of fun to be had.  I’ve been planning a family trip this summer to Italy and it came together to include some pretty special elements for my family and I.  As the final pieces came into place this weekend I thought I would share the story.  Parts of this are special just for our family or for an airline geek like me, but I hope you’ll come along for the ride and find some things you can enjoy.  I’ll cover as much of the process as possible in case it helps with planning for a trip in your future.

It started about 2 weeks ago when I was trying to figure out a way to burn some United miles prior to the insane gutting they did to their partner award chart took effect on February 1st.  But, where to go?  We already had a trip to Paris scheduled for this year.  We haven’t been to Asia as a family but I’m not brave enough to try those flights with our 3-year old who doesn’t handle flights as well as we’d like him to yet.

 Travel Game

I wanted the destination to be somewhere on a partner of United’s since those awards were going up so much.  That likely meant Europe and likely meant Lufthansa.  I was pretty sure I wouldn’t find 4 business class seats on United to Europe in the summer and those suspicions were proven out pretty quickly.

Should we go somewhere new in Europe or go with an old favorite like Italy?  Italy was our first love and we’ve enjoyed going back.  I did some searching for other destinations but bailed on that line of attack after not a whole lot of effort and started researching Italy.

I had forgotten how much capacity Lufthansa really had.  There are literally dozens of flights every day that connect through Lufthansa’s mega-hub in Frankfurt as well as a bunch more through Munich.  And, for those of you who have spent time trying to book flights on United’s website, the availability was a sea of blue and green!

 Travel Game


We’ve previously visited Rome, Florence, Venice, Catania, Taormina, Messina, Positano & the Amalfi coast as well as Naples, some multiple times.  Each holds its own special place for my wife, but Rome and Venice are high on our list for return trips.

I was thinking of something in the neighborhood of 8-10 days overseas but was having a little bit of trouble putting together exactly what I wanted.  See, when you travel with kids there are extenuating circumstances. I knew we wanted to hit Rome and Venice if we could since my daughter had only faint memories of Rome from a previous trip and Venice was one of our favorites that our kids were sure to enjoy.  But, I wanted to throw a new city in the mix.

While I’m spending a bunch of time plugging in dates and cities, looking for 4 business class seats, I also enlisted the help of some smart folks on Milepoint to evaluate whether I should add Milan to our list.  While there were plenty of good things to say about Milan, the opinion of the group didn’t sway me that it was a city built for kids.  I want to see Milan as well as points West of it, but with Rome and Venice likely locks on this trip, Milan would have to wait.  There were some helpful comments on other cities along our way and I think we’ve settled on Bologna since it’s easy to access via train.

Back to those extenuating circumstances when traveling with young kids.  Flight departure times are pretty key, especially when headed East.  We had 3 basic ranges to choose from for departure times, 3:30-ish in the afternoon, 5-6pm or 10pm.  Our kids go to bed on the early side, usually by 8pm.  10pm has some advantages, as the kids will be up a bit later but likely will sleep the entire flight.  3:30-ish is brutal, as we would be landing right around the time Michelle and I usually go to bed and the kids likely wouldn’t have gotten much sleep either.  Oddly, they rebound more quickly from abbreviated sleep than their parents do, but they get crankier quicker!

The 6pm window seemed the most optimal and also created an opportunity to fly the new Boeing 747-8 Intercontinental, which I’d love to cross off the bucket list.  When I first started searching for award inventory I found a handful of days where the 747-8i was available.  After a couple days of searching there was only one day left where the 6pm flight was available.  I grabbed that one day so I had a placeholder but that stretched out the length of the trip due to available return dates.  I was shooting for 8 or 9 days overseas (not counting travel time) and this was working out at 11.  Not the end of the world but not ideal.

I booked a tentative return from Venice, giving us a routing of IAD-FRA-FCO (Washington Dulles to Frankfurt to Rome) on our outbound.  We’d make our way North through Italy and depart from Venice, back through Frankfurt and on to Dulles (VCE-FRA-IAD).  That left hotels and possible tweaking of dates.  I had a few days before United’s award chart increases to get everything figured out (as it turns out I’d have a bit more wiggle room but didn’t know it at the time).

 Travel Game


 Travel Game

I’ll be summarizing the rest of the planning in part 2 shortly.  I’m hoping to illustrate that while it’s not necessarily simple and quick to book your dream vacation using miles and points, a bit of work can pay off with a great itinerary.  Feel free to ask questions or poke fun at my reasoning!


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  1. Well, I don’t know about Rome, but Venice is one of my favorite places on earth. It should be a fabulous trip for both yourself and your kids! Congrats! Can’t wait to go back. I can’t tell if you’ll be hitting Venice during the Redentore (celebration of the end of the Plague) which is totally amazing–best fireworks display I ever saw, and over the Grand Canal too! Looks like its the 19th/20th of July this year, so its certainly a possibility. I can make a hotel recommendation–the Danielli is crazy expensive but the hotel right next to it, the Campiello is not. And honestly I don’t think the hotel rooms themselves are that important. But getting up each day and eating breakfast with the view of the Grand Canal and doing people watching… that was amazing!

    1. Glenn, we truly love Venice too. I wasn’t familiar with Redentore but now it’s something I need to investigate. Do you happen to know how late the fireworks were in the evening? Trying to figure out if the kids would be able to stay up that late v

  2. Hi Ed,
    We were in Italy last June (with an adult child, much easier to travel with), and we loved staying at the Hilton Molino Stucky in Venice. If you have Gold status with them, you get amazing breakfasts and a high chance of an upgrade to a suite of some sort. They are on Giudeca, but the shuttle boat runs often and gets you away from the hustle and bustle of the city when you need a break.

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