Our Anniversary to Italy: Part 1 – Planning and Introduction

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Emily Jablon:  Daraius and I went to Europe in September to celebrate our 2nd anniversary for ~2 weeks.  It was my first time in Italy so I was very excited!  In Italy, we visited Varenna on Lake Como, Milan, Venice, and Rome.

Since we were in Europe, we visited a friend in Strasbourg, France and also spent a night in Zurich.  We started our trip with a one day layover in Chicago to see friends!

Miles And Points To Italy

Daraius and Emily Celebrating Their 2nd Anniversary in Italy

Our Anniversary to Italy – Trip Report Index:


We got a lot of wonderful tips from the Rick Steve’s books on Europe.  In particular, we used (our Amazon links):

Keep in mind that the chart below covers only the cost for trains (these were expensive!), hotels and airfare, and not for dining, activities and other travel expenses.  The table also includes a very expensive last minute train ticket from London to Strasbourg, France to visit Emily’s pen-pal.

I wrote to the hotel in advance letting them know that it was our anniversary, and we got great upgrades at the Park Hyatts, though I’m sure that our top-tier Hyatt Diamond status also helped.

And at the Hilton in Venice, we got upgraded to the Tower Suite which sells for ~$3,466 a night!  Again, I’m sure our top-tier Hilton Diamond status helped!

 Retail CostOur Cash CostMiles And Points UsedSources of Miles & Points
Two one-way tickets from Austin to Chicago~$175 a person ($350 total)$2.50 per person ($5 total)9,000 Avios (18,000 Avios Total) - Transfer from American Express Membership Rewards Points

- British Airways Credit Card
1 Night in the Park Hyatt in Chicago (Lake View Room)~$540 a night ($540 total)None22,000 Hyatt Points Total - Transfers from Chase Ultimate Rewards Points
Two round-trip tickets from Chicago to London in Upper Class on Virgin Atlantic~$4,000 a person ($8,000 total)~$298 per person ($596 total)100,000 Hawaiian Air Miles (200,000 Miles Total) - Hawaiian Air Credit Cards

- Transfers from American Express Membership Rewards Points
Two train tickets from London to Strasbourg~$300 a person ($600 in total)~$300 a person ($600 in total)NoneNone
3 nights at the Hotel Cathedral in Strasbourg~125 a night ($375 total)~$250None - 1 Night Credit From Hotels.com
1 night at the Park Hyatt in Zurich (Park Delux Room)~$1,051 a night ($1,051)None22,000 Hyatt Points - Transfers from Chase Ultimate Rewards Points
2 nights at Hotel Eremo Gaudio$300 a night ($600 total)$300 a night ($600 total)NoneNone
2 nights at the Park Hyatt in Milan~$880 a night ($1,760 total)None22,000 Hyatt Points (44,000 Hyatt Points Total) - Transfers from Chase Ultimate Rewards Points
2 nights in a Tower Suite at the Hilton Molino Stucky in Venice~$3,466 a night ($6,932)None - 1 Weekend Night Certificate
- 50,000 Hilton Points
- 1 Free Weekend Night from the Citi Hilton Reserve
- Hilton Credit Cards
4 nights in at the Rome Cavalieri (Rome View)~$516 a night ($1,032)None - 145,000 Hilton Points - Hilton Credit Cards
- Hawaiian Air Credit Cards
- Virgin Atlantic Credit Cards
Two train tickets from Strasbourg to Zurich~$68 per person ($136 total)~$68 per person ($136 total)NoneNone
Two train tickets from Zurich to Varenna~$110 per person ($220 total)~$110 per person ($220 total)NoneNone
Two train tickets from Varenna to Milan~$14 per person ($28)~$14 per person ($28)NoneNone
Two train tickets from Milan to Venice~$55 per person ($110 total)~$55 per person ($110 total)NoneNone
Two train tickets from Venice to Rome~$55 per person ($110 total)~$55 per person ($110 total)None
Total$21,944$2,50518,000 Avios Points, 88,000 Hyatt Points, 200,000 Hawaiian Air Miles, 195,000 Hilton Points, 1 Hilton Weekend Night Certificate

You’ll see that we could have saved ~$850 if we hadn’t visited our friends in Strasbourg.  But we had a great time visiting Emily’s pen-pal and his brother in France!

Austin to Chicago

We spent 9,000 British Airways Avios points per person for a one-way award from Austin to Chicago on American Airlines.  Our Virgin Atlantic flight was leaving from Chicago, so we decided to stay in Chicago at the Park Hyatt and visit friends!


We stayed at the Park Hyatt in Chicago for 22,000 Hyatt points for the night.  We got upgraded to a Lake View room!

Miles And Points To Italy

The View From Our Room at the Park Hyatt Chicago

Virgin Atlantic

We flew on Virgin Atlantic Upper Class to London.  Upper Class costs 90,000 Virgin Atlantic miles and $1,100 in taxes and fees per person!

But we paid 100,000 Hawaiian Air miles and ~$298 in fees and taxes.  That’s because you can redeem Hawaiian Air miles on Virgin Atlantic.  We earned the Hawaiian Air miles from the Hawaiian Air credit cards when they were issued by Bank of America.

Unfortunately, this redemption costs more now.  It is now 125,000 Hawaiian Air miles for a round-trip from the US East Coast to London!

Miles And Points To Italy

Emily and Daraius Enjoying a Meal in Virgin Atlantic Upper Class

The flight was nice, but it didn’t live up to the Virgin Atlantic hype.  We’re fairly thin, but still found the seats cramped compared to business class on other airlines.

If you’re new to miles and points, there are easier ways to go to Europe (with American Airlines, United Air & Chase Ultimate Rewards) than with Hawaiian Air miles.  We had a lot of Hawaiian air miles which we wanted to use up.


We took the ~ 1 hour underground train from London’s Heathrow airport to King Cross station.  And then took the Eurostar train from London to Strasbourg, France.  It took only ~2.5 hours from London to Paris!

We stopped at the Gare du Nord station in Paris and then had to walk ~15 minutes to the Gare de L’Est station to catch the train to Strasbourg.

Miles And Points To Italy

Emily and Daraius on the Train to Strasbourg

We booked the train journey from loco2 which lets folks in the US pay the best price for train tickets.  We booked the trip to Strasbourg at the last minute, so the train tickets cost us more than it usually would have.

See this post from The Man in Seat 61 for the best tips on booking train tickets!

If you use Google to search for train tickets, you will likely be directed to the raileurope website, which doesn’t show folks in the US the cheapest tickets!

We stayed at the Hotel Cathedrale in Strasbourg.  This is a small hotel which is right across from the Cathedral in Strasbourg.  We booked the hotel using 1 free night from our Hotels.com account and paid cash for 2 nights.  In all, we paid ~$250 for 3 nights.

Miles And Points To Italy

We Spent a Night at the Hotel Cathedrale

I’ll write more about Hotels.com later, but it is one of the best ways to get rebates for hotel stays in non-chain hotels or if you don’t travel frequently enough to take advantage of hotel loyalty programs.

We walked around Strasbourg, met our friends, and ate lots of good Alsatian food!

Miles And Points To Italy

Emily and Daraius Having Fun in Strasbourg


We spent 1 night in Zurich.  Switzerland is very beautiful, but is also home to the $12 Big Mac!  We stayed at the Park Hyatt in Zurich for 22,000 Hyatt hotel points.

Miles And Points To Italy

Big Macs Costs $12 in Zurich – Ouch!


We took a train from Zurich to Milan and then a 1 hour train to my (Daraius’) favorite town in this trip – Varenna!

Miles And Points To Italy

Emily in her Favorite City – Varenna

Varenna is a beautiful small town with a population of less than 1,000.  We had a great view of the city from our hotel!

Miles And Points To Italy

View of Beautiful Varenna From our Hotel

We stayed at the Hotel Eremo Gaudio which Rick Steve’s describes as “for monks with champagne tastes.”  The Terrace Bar overlooks the lake and offers wonderful views of Lake Como and Varenna.  The hotel is a former monastery.

Miles And Points To Italy

Hotel Eremo Gaudio Terrace Bar Overlooking Lake Como

Hotels in Varenna fill up quickly, so the cheaper rooms were not available when I booked.  So I splurged 230 euro or ~$300 a night for the Teodolinda suite, which had the BEST view of any suite which I’ve been in.  I justified the splurge because it was our anniversary.

The furnishings weren’t so great and included a plastic chair, but it was a delightful place to spend 2 days!


We only had two days in Varenna before we stayed at the Park Hyatt in Milan.

We used 22,000 Hyatt hotel points for each night and transferred them to Hyatt from our Chase Ultimate Rewards points.

Miles And Points To Italy

Our Room at the Park Hyatt Milan

The Park Hyatt in Milan is perfectly located in Milan and it was only a 2 minute walk to the Duomo!

Miles And Points To Italy

Emily Outside the Duomo


Our next stop was Venice, which is really crowded in the day!

We stayed at the Molino Stucky Hilton for 2 nights – 1 night with a free weekend night certificate from the Citi Hilton Reserve card.  And the second night with 50,000 Hilton points.

The hotel had a rooftop pool with a great view.

Miles And Points To Italy

Molino Stucky Hilton Rooftop

The Hilton is not on the main island of Venice, but on the island of Giudecca, which is a more residential part of Venice.  It was only a 15 minute boat ride to the Hilton on the free shuttle boats.  I actually liked being away from the hordes on Venice!

Miles And Points To Italy

We Were Away From the Crowds in Venice!

Oh, and we got upgraded to the Tower Suite which had a separate dining and living room and views of the canal!


Our last stop was in Rome.  We took the Frecciargento (high speed train) from Venice to Rome.

Miles And Points To Italy

We could see the entire city from our hotel – the Waldorf-Astoria Rome Cavaliere.  Daraius booked 4 nights at the hotel using an AXON award for 145,000 Hilton points, before the Hilton devaluation.  It now costs 70,000 Hilton points for 1 night at the hotel.

We got upgraded to a room with a Rome view, which beats facing the back of other buildings!

The hotel is located away from the center of Rome, and we found it a pain to get to and from the city.  The hotel does run free buses, but they get filled up quickly, unless you stand in line early for the buses.

The hotel does have nice views of the city, but we’d skip staying there again.  On our last night, I paid extra to check-out the top-level Imperial floors and the Imperial lounge.  We actually preferred our non-Imperial floor room!

Miles And Points To Italy

View of Rome From our Hotel – Rome Cavaliere

On the other hand, Emily had the best meal of her life at La Pergola, the 3 star Michelin restaurant on the top floor of the hotel.   We ate at quite a few McDonalds to save up for that splurge!

We visited the Colosseum and all the other places which folks visit in Rome!

Miles And Points To Italy

Emily Overlooking the Colosseum

Bottom Line

Miles & Points have helped me ask Emily to marry me, go on our 1st honeymoon in Paris & on our 2nd honeymoon in Bora Bora.  And now we’re on our 1st anniversary!

That’s why I obsess over miles and points!

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72 responses to “Our Anniversary to Italy: Part 1 – Planning and Introduction

  1. Nice post. It’s always great to see how a pro does it:)

  2. Congratulations!

  3. You guys look amazing! Congrats on the anniversary. We’re going to Milan on the Wideroe mistake fare in a few weeks and I can’t wait to stay at the Park Hyatt Milan. Glad you guys had fun in Italy,

  4. Thanks for sharing! I have always dreamed of going to Europe and have never been able to save up the money for the “dream trip” and after having my son, I figured I would never be able to go. I came across “churning” randomly and was so excited to see all the amazing ways that you can earn miles and go on the trip of your dream. Of course, budgeting is required for the extras, but I am thrilled to be sooooo close to booking that dream trip. Just waiting for all the points to post.

    BTW – how did you find Italy to be for English only speakers? I was wondering how hard it would be to get around, especially with a toddler in tow. Thanks!

  5. Congrats! Stunning trip to some of my fave spots in the world. A nagging question, though – what is that fave restaurant in Chicago? I am always on the lookout for good spots there. Thanks.

  6. Congrats on your anniversary… Looks like a fabulous trip. Going to Milan in mid-feb with Wideroe mistake too but with 2 kids so staying in an apartment.
    @Lively- would love to hear about your trip and any tips you have

  7. Hi Dariaus, great post looks like you guys had fun! Can I ask how you currently hold top tier status at both hyatt and hilton? Did you spend $40k on the hilton reserve card or were these gifted to you? I dont see you paying for a lot of hotel stays typically so im curious. Thanks!

  8. Congratulations on the anniversary, Emily and Dariaus! Italy is a fun place to visit, especially on a wedding anniversary.

  9. Nice! I’m looking forward to seeing what you think of the Park Hyatt Zurich. We are going to Switzerland in May and spending our two free nights there. Also I’ll have to check out the train ticket tips. I had a feeling raileurope was holding out on us!

  10. Great trip, congrats on your anniversary. Those train costs hurt your outlay of cash for this trip but overall stayed at places the average Joe would not stay at. Going on my 2nd honeymoon(thailand) trip since being married in August (first was Bora bora), and I used points for 9 nights splurging on another hotel for cash for 3. If I had no points We would not be going at all to asia and Bora bora would have never happened. Its just crazy how much hotels can cost and some great cities.

  11. Your travel posts are always impressive. Impresarios of points and miles who have fun.

  12. Looks like an incredible trip. We’re planning a trip to the Hilton Molino Stucky Venice on HHonors points. How did you get that amazing room upgrade? Do you have Diamond status or just Gold (we have Gold) and did you mention it was your anniversary (we’re going for our honeymoon)? Thanks

  13. Glad you all liked the first report! We made a lot of great memories in Italy!

    @ Chrissy Cutting- It was very easy to get around–English is spoken very widely. You may have more trouble in the very small towns, but even in Varenna we could communicate with everyone very easily. It always helps to know the basics in Italian like hello/please/thank you.

    @ David S.- The restaurant is called Siam Splendour and it’s in Evanston. Be sure to order the Tom Kha Kai. It’s the best we’ve ever had!

    • @Christer @IPG @Miles @John- Thanks! We had a great time in Italy and Emily loved the food!

      @Lively – I liked Milan better than I thought I would and the Park Hyatt is very well located. Order your tickets to visit the Last Supper (if that was on your list of things to do) in advance online or by calling because they sell out quickly.

      @Chrissy Cutting – Thanks for reading. We didn’t have much of an issue with language and most folks in the heavily visited sites speak a little of many languages (including English).

      @David S. – It is Siam Splendor in Evanston (where we stayed for 2 years). We like the Tom Kha soup a lot, but the other dishes can be hit-or-miss.

      @Kadence – An apartment would be much better with kids. Safe travels!

      @Troy – I had a lot of business and personal travel which helped with Hyatt status. I spent $40,000 on the Hilton Reserve card for the Hilton Diamond status.

      @Ryan – The hotel is excellent and is well located since you can walk to most places (a longish walk, but very beautiful).

      @michael – Congratulations on the 2nd honeymoon. The hotel prices in Zurich were a bit over the top!

      @Matt – I wasn’t expecting that upgrade, because when I wrote to them in advance to let them know about kurt trip and anniversary, they mentioned that they were full and wouldn’t be able to do anything. We have Hilton Diamond status from spending on the Hilton Reserve card, which I’m sure helped!

  14. Great summary and thanks for sharing how you use the points.

    Years ago, I almost worked in the kitchen of la pergola. Share some of the photos from the meal or the menu if you can.

    What is the restaurant in Chicago that you visited?

    Happy anniversary!! My 5 year is this May and I haven’t planned anything yet :/

  15. Wow, are you still on the trip? You’ve already covered a lot of territory, but you wrote that this was the first report, and the itinerary doesn’t yet show a return flight. …Congratulations, and thank you showing how you allocated your miles and points to create a vacation.

  16. Congratulations on your anniversary and thanks for this wonderful trip report. Italy is one of my absolute favorite places (I’m half Italian in my heritage), but you have yet to visit one of my favorite cities – Florence. We spent 3 days the first time, but returned for 6 so we had time to relish all the wonderful art. I do hope you got up to the roof of the Duomo in Milan – spectacular!

    And thanks for the tip about loco2. I need to book Thalys tickets soon and was going to book directly with them, since I knew RailEurope would cost more. Now I will have a site to compare prices with.

    Looking forward to the next report.

  17. Congratulations on your anniversary and thank you for such a lovely and detailed travel report! I really enjoying reading it and beautiful pictures made me to like Europe even more.
    I am a newbie to this thing and I am planning for a trip to Europe. Can you please tell me what is the best way to start for me to go to Europe from San Fransisco, CA? Like what credit cards should I apply for to collect the best miles to go to Europe from NorCal. FYI I only have Chase Freedom and SW Premier and Plus cards now. Just a short answer like Citi Thank You Premier, Hawaiian Airlines Card , etc. will suffice and appreciated.

    I am also wondering, is Chase Ink Business Card churnable? for example: I apply Ink Plus this month and meet the spending limit within 3 months, then after 3 months I apply for Ink Bold and meet the spending limit within 3 months, then 3 months again I applied for Ink Classic, then 3 months again I applied for Ink Cash. After I got all the cards then without closing the first Ink card (Ink Plus), then I apply for another Ink Plus again and go on….then cancel each of cards before the second year annual fee’s hits.
    Is this doable and I would still get all the bonus sign up points?
    Thank you so much in advance.

  18. Happy Anniversary to a wonderful couple!!! My husband & I enjoyed a Perillo Italy tour 8 years ago. Your pictures brought back great memories. So glad you enjoyed Italy too. Happy New Year to you both.

  19. Happy Anniversary! I am looking forward to reading more about your trip to Milan since My mom and I are going there in March due to the Wideroe fare.

  20. I can’t believe it’s been 2 years already! Congratulations! We’re stopping over in Rome and Florence on our way back from Japan in April (US 90k award) and I can’t wait.

  21. I’ve been to each of the cities you visited and, although I might quibble with your allocation of days to each city, it sounds like an absolutely smash-bang trip. If you revisit Varenna I can recommend the Villa Cipressi — it’s the yellow building in the foreground of the view of Varenna from your hotel. As I recall, about Eu 120 for a single in June two summers ago. Definitely looking forward to your Como section of the trip report.

  22. I will also be in Milan in February. Varenna looks surprisingly warm and green for winter.

  23. @DavidG

    Chase is usually one lifetime bonus per card, so no sense canceling. But you could get Sapphire Preferred and Freedom to add to your stash. Amex cards are churnable if you follow the t&c of the subsequent offers. Citi cards are highly churnable – see FlyerTalk.

    @MMS – wouldn’t it have been much cheaper to rent a car?

    • @Ore – We’ll have a review of La Pergola with pictures later on. We visited Siam Splendour in Evanston for Thai food. Emily loves the restaurant. Happy Anniversary to you too!

      @ DWG @gussomer – We went on this trip in September for 2 weeks, but am only just getting to the trip report.

      @ Marilyn B – Thanks! I’ve visited Florence about 10 years ago, but Emily hasn’t. But that’s another reason to go back! I’d suggest reading the The Man in Seat 61 for the best tips on booking trains in Europe.

      @ David G – Thanks! I’d collect United and American Airline miles for flights to Europe. There are 50,000 mile offers on the United and American Airlines credit cards. You can also transfer Chase Ultimate Rewards points from the Sapphire Preferred, Ink Bold/Plus to United. You should be able to get the bonus on each version of the Ink cards.

      @ Elena @Krystyna – Thanks and Happy New Year!

      @Lisa – 2 years has flown by!

      @LarryInNYC – It was a wonderful trip! Villa Cipressi was my first pick, but it was full. We did walk in their beautiful gardens, though.

      @Corky – It was more convenient with the train and we didn’t want to mess with parking in busy cities. Also, half our train cost was from London to Strasbourg. The other train rides, weren’t that expensive (compared to flying).

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  25. How did you get back from Chicago when you returned home? is that flight missing?

  26. Thank you Daraius & Emily!
    I have another serious question that I hope you can help:
    1. What do you think is the best Hyatt card offer out there now? I know about cards Hilton are Reserve and Surpass, but I don’t know anything about Hyatt card yet…if you could please elaborate on this I would really appreciate it and if you have a referral link I would like to use it as my way of saying thank you too.

    2. What is the transfer ratio from Chase UR points to United? please let me know if you have the link to your blog that explain the transfer ratio of Chase UR to hotel/airlines.
    And is that true that you will lose your UR points if you don’t use it by the end of the year, because I have Chase Freedom and accumulated some UR points and I got the email from Chase that I have to use my points before it get expired on December 2013. They even sent me a email reminder few weeks before December 31 to use my points! this scared me of losing my UR points and finally I redeemed it for statement credit 🙁

  27. Also, I would really appreciate if you can direct me to the United 50,000 mile offers link! I would like to get started!

  28. What a great trip!! Look forward to reading more. No doubt diamond status helped. We have gold and stayed in Oct at the Stucky in Venice, no upgrade despite advance notice of our anniversary. In fact it wasn’t acknowledged at all. Beautiful hotel with an impressive breakfast, still pleased with our choice.

  29. James, they must have just stayed – who would leave Europe if you didn’t have to? 🙂 Darn 90 day visa limit!

    • @james – I used a ticket bought with United bump vouchers. I’ll add the return journey to the post.

      @David G – The best Hyatt card is the Chase Hyatt which offers 2 free nights in any Hyatt hotel. Here’s a link to the ways to get Hyatt points. The transfer ratio from Chase Ultimate Rewards to United is 1:1. Here’s a post on the United card. Ultimate Rewards points don’t expire unless you cancel the card and haven’t transferred the points out.

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  31. Thanks for the link to United card, however, when I want to apply using your referral link…..the United Explorer card only offer 30,000 sign up bonus miles instead of 50,000…….. any good working referral link that can direct me to 50,000 sign up bonus miles for United? thanks again!

  32. Pingback: Virgin Atlantic Upper Class | Million Mile Secrets

  33. I’m sure that Austin to Chicago is 15000 BA miles for round trip per person.

  34. 100,000 Hawaiian Air Miles for a R/T, US to UK in Upper Class on Virgin Atlantic, that was history. The current chart for Upper Class:
    United Kingdom – North America East Coast: 125,000
    United Kingdom – North America West Coast: 160,000.

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  36. Emily and Daraius, congrats on your anniversary and many many more to come! It’s been great reading your blog, and big welcome for making Austin your new home, hope you’d enjoy it here:)

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  39. How did you book from Austin to Chicago using Avios? Did you have to call? There website doesn’t seem to like it.

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  41. So happy for you and Emily on your anniversary and welcome to Texas! How do you earn top-tier elite status with airlines and hotels if you always pay with miles and points from credit card sign-up?

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  44. Congratulations, Emily and Daraius, on your 2nd anniversary! Can’t believe how time flies. It is always wonderful to see you happy, smiling faces!

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  56. I love the chart that breaks everything down. Curious though…how did you get home from Chicago on your return? Another one way award ticket? OR did you add the return flight to your roundtrip to London ticket?

    • @Tara – Thanks! I have lifetime gold from American Airlines and Hyatt Diamond status. Besides that, I don’t have any hotel top tier status.

      @ Jimmy – Hope you’re doing well!

      @Kate @KKMLT’s travel journal – Thanks!

      @Laura R – We booked a cash ticket from Chicago to Austin and back for the Chicago seminars and used the 1st portion of the ticket to fly from Chicago to Austin.

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