My Italy and Greece trip itinerary – What to do in Venice, Florence, Rome, Mykonos, Santorini, Athens

Yesterday I outlined how to do this 2.5 week trip using miles and points.  Today, I’m going to give you a rough outline of what my wife and I did while we were there.  Before my trip, I wished there was a web site where I could type in “Tell me what I should do in Venice if I had X days.”  It could then list out the attractions, tickets to the attractions (hello referral revenue,) transportation info, etc.  That would have made things so much easier.   Maybe one of my techie entrepreneurial readers can come up with that site.  I’ll even consult for free!  Without further ado, here’s the rough agenda that I wrote in 2013 (I’ll add new comments in blue.)


  • 12:20PM – 1:40PM – Frankfurt to Venice LH326
  • 2:150PM – Land bus to Piazza d Roma
  • 3:00PM – Vaporetto to Palanca bus stop (line 4.1) We decided to walk because I was too cheap to buy the ticket
    • Take direct bus to Piazzale Roma and then board the water bus line 2 to Zattere. From here you can take the hotel shuttle boat, or take line 4.1 to Palanca and walk 5 minutes to the hotel.
  • 4:00PM – Check into Hilton
  • 5:00PM – 7:00PM – Happy hour at Hilton
  • 7:00PM – Dinner in Venice Al Vaporetto (rsvp please) – I vaguely remember this dinner.  Clearly it wasn’t memorable.  



I realize some people may think, “Holy crap!  That’s all the time they spent in Venice?”  Let me tell you that my wife and I are the traveling type that like to see as much as we can versus the type that likes to “soak”in the local culture.  Do what floats your boat.



I had considered spending the night in Cinque Terre since most people do that, but a) it would have broken up my Westin 5 nights deal and b) most people recommend renting a car to drive up there, but I hear driving around Florence is a nightmare due to streets that you can’t drive down and they’ll mail you a ticket months later.  So we just decided to a do a 1 day trip using a tour company.  I thought it was sufficient for us. 


My wife and I enjoy wine, so of course we needed to do a wine tour.  I’m not sure if we got a discount by booking 2 tours.  I’m guessing we did.  Regardless, we thought this tour was also great.  Wine in the morning and some city walking in the afternoon.


  • 9:00AM – Shopping day I would say this was for my wife, but in all honesty, it was for me.  We bought bus tickets to the shopping outlets at the bus station.  I believe it was Barberino.  It had all the big Italian brands – Prada, Gucci, Dolce & Gabbana, etc.
  • Dinner (hh style) – All’Antico Vinaio ( probabl dont need rsvp – I don’t think we ate here.  We just walked around and found a random packed restaurant.


  • 9:00AM – Check out of Westin Florence
  • 10:00AM – Train from Florence to Rome pre-ordered I think
  • 2:00PM – Check into Radison Blu Rome we walked from train station (10-15 minutes)
  • 4:00PM – Sightsee We walked from the Radisson to the Coliseum (that was a long walk.)  We actually walked all day until the cab ride back at night.
    • Coliseum
    • Forum
    • Spanish Steps
    • Pantheon
    • Trevi Fountain
    • Campo Fiori
  • Dinner: La Fata Ignorante ( make rsvp No idea.



  • 12:00PM – Chek out of Radisson Blu Rome
  • 1:00PM – Check into Hilton airport
  • 2:00PM _ Take shuttle into Rome
  • Dinner: Osteria Barberini ( make rsvp No idea
  • 9:00PM – Bus to Hilton Rome
    • Our complimentary shuttle leaves from the hotel every two hours from 8:00 am to 10:00 pm.  The return is in the odd hours from 9:00 am to 11:00 pm. Drop off and pick up are in Via del Teatro Marcello close to Piazza Venezia.


  • 5:30AM – Check out of Hilton Rome
  • 6:35AM – 9:35AM – Flight to Mykonos (Easyjet)
  • 12:00PM – Check into AirBNB This was when the retractable handle on my brand new Samsonite luggage broke, and I had to drag it from the handle.  It’ll be my last time buying a Samsonite bag.
  • 2:00PM – Sightsee


If you’ve heard of Mykonos, then you know it’s the party city of Greece.  My wife and I are EDM fans, and so we went to a club the 1st night at around midnight (we paid for a shuttle bus to get there.)  It was a bad mistake because it turned out to be pretty dead.  You know – one of those clubs in your city that you no longer go to, but yet the tourists go there because they don’t know any better.  On the 2nd day, we went to Paradise beach at around 4PM, which was close to sunset.  The music was better and the vibe was even better.  It also had a 7-11 convenience type store right on the beach, so you could buy a bottle of wine at 7-11 prices and drink it on the beach.  The DJ wore a hilarious banana-hammock.  Oh good times indeed.  

  • Sightsee
  • Paradise Beach


  • 2:30PM – Ferry to Santorini (Sea Jets2) Apparently there are 2 ports in Mykonos, which I didn’t realize it until after the shuttle bus dropped us off at the wrong dock.  I went to the ticket booth, showed him my prepaid ticket, and he said it was at the other dock.  We ran back to the shuttle bus and hopped on, and it would have been cutting it close.  Turns out the shuttle bus was going to the airport first.  There was no way we could make it back in time.  I definitely didn’t want to spend another night in Mykonos, especially after paying for the hotel in Santorini.  Then my wife calmly said, “Just buy tickets for this boat.”  So we did that.  On the boat, I tried to borrow a cell phone to call our hotel (which was going to pick us up at an earlier time), but no one would let me.  🙁  Luckily when we landed, another couple was going to the Mystique, and so we hopped on the shuttle.  Worst case, we would have had to pay for a 30 minute cab ride to the Mystique.  I was just so relived we were in Santorini and not back in Mykonos.
  • 5:50PM – Arrive in Santorini
  • 6:300PM – Check in to Mystique
  • 07:00PM Dinner: Nimeli ( make rsvp No clue.



  • 12:00PM -Check out of Mystique
  • 8:25PM – Fly to Athens.  Aegean A3359
  • 10:00PM – Check in to Grande Bretagne We took the subway (pretty easy.)  The stop was like a block away from the hotel.
    • Either by cab or by subway. The train [subway] terminal is a five minutes walk from the arrival hall, just follow the signs. Take line 3 and get off at Evangelismos. When you exit the subway terminal you’ll be in a small park. Follow the path for approx. 3 min. towards a big street. As soon as you leave the park, you see the Hilton on the other side of the street. Don’t forget, it’s Greece, so always be prepared for a strike!
    • Airport Express Bus X95 is operating 24×7 and the bus stop to the airport is right outside of the hotel. No need to take a taxi to the airport at anytime.


If you do go to Athens, I suggest you take a day trip up to Delphi.  The ruins there are pretty nice, and they have a nice museum.  We did NOT do the city tour because c’mon, who wants to see graffiti everywhere?  


  • Http://
  • Acropolis (Akropolis)
  • The Acropolis Museum
  • 8:00PM – Dinner at Funky Gourmet (1 Michelin star) – RSVP done  NEED TO CONFIRM RESERVATION ONCE WE GET THERE; They will contact hotel at 6:00PM to confirm us as well. My wife and I are foodies.  This was one of the most memorable prix fixed meals of my life.  I forgot how much it was; maybe 200E per person with wine pairing.  You know it’s fancy when the first course is brought out on a wood branch and they spray a woodsy scent at your table to you know, get your sense of smell to match the taste of the food.  


If you have any questions, feel free to leave a comment or shoot me an email

  • Michelle B.


    I really like this itnerary but wanted to know if there was a way to do Italy and Greece in 15 days max? We want to celebrate out 10th anniversary next year (2018) around August (our anniversary is Aug 8th) We’ve been to other parts of Europe (Spain, France, Netherlands) but never Italy or Greece. For those trips we planned it all ourselves and it turned out great. We’re flying in from the US (Miami) and it seems it’s cheaper to fly roundtrip to Rome than doing multi city or flying roundtrip to Athens. Any suggestions would be truly appreciated. I’ll still use this itinerary as a guide to focus on what places we should see and what to do, Thanks again!

    • Miles per Day

      Oh yeah that shouldn’t be a problem. If you take out Mykonos, you’ll be at 15 days if you follow the itinerary. It also depends on what type of travelers you guys are. If you are laid back and want to immerse yourself in the culture, then maybe take out another city. My wife and I like to move around a lot so that’s why our itin looks a bit jam-packed. If you’re going to use a United award, I would reco you fly into Rome and then back from Athens to save you money as well as a half day of traveling as well. Let me know if you have more questions.

      • Michelle B.

        I tried to return from Athens but it’s more expensive that way, I’ll try to use points but I don’t know how much we’ll have by then. From what I’ve read on your itinerary, our “travel style” is similar to yours, we like to see the important sites but at the same time we don’t need to “immerse ourselves”. I still have about a year to plan so hopefully I’ll still be able to get a decent price on tickets, and determine how many days our trip will be depending on the days we can get off from work. Thanks for your replay and I’ll take your suggestions into consideration 🙂

  • Judy Ip

    Hi there, this is super helpful! But do you mind to give me more ideas and advice? My husband and I are not a super fan for museums, we won’t mind to visit one or two but not like a few for each city if you know what I mean. Santorini and Milan are the places I wanted to go for my honeymoon so I was wondering which other places should I go as well. I saw your mentioned Florence also have a shopping outlet and I have heard of its beauty. Is cinque Terre worth to visit? I have been to Rome when I was really young so I doubt if I should go back again. Do you think I should still go to Rome and Florence? Or which one would you suggest out of the three? We are planning to go in early June for about 13 days. Hope to hear from you soon! Thanks so much.

    • Miles per Day

      Aw man, I typed up a super long reply before Disqus crapped out on me. Let me recap.

      For 13 days, I’d do 3 Santorini, 3 Rome, 4 Florence, 2 Milan. Santorini – you’ll be bored after 3 days. After 2 days even. Rome – I visited twice as an adult. I was fine going back cuz my wife hadn’t seen it yet. I was okay seeing the Colisseum and Vatican again. I mostly enjoyed the pizza. I’ve been to Florence twice and wouldn’t mind going back a 3rd time. I love that city. Very walkable; lots of sights. Cinque Terre day trip IS A MUST! It’s a long trip, but well worth it when you’re there. Another day, go to the shopping outlet that’s not too far away (gucci, prada, d&g.) Third day in Florence, visit the museums and such.

      Milan I’ve been to once and wouldn’t ever go back. Just nothing to do there except for the Duomo unless you like paying full price for clothes. I did go on a bus trip to a shopping outlet in Switzerland and bought a lot of things at the D&G store there. I don’t remember the Swiss one that much; I just remember buying more stuff from there (maybe bec it was pegged to USD price when I went and the euro was like 1.45). Lmk if you have more questions.

      • Judy Ip

        So you mean I should skip Milan? And what about Venice? If I really don’t have enough time for Rome Venice and Florence? Which one do you think I should skip?!! I am more like a drinking person, prefer to chill and sightsee instead of museums. Which one would you recommend me to skip? Ah yea and I forgot to ask about Mykonos. I didn’t think of going there before but only Santorini. So would you recommend me to spend a night there or I can skip it? And one important question, should I take train or book a flight or ferry for going to all these places? I am abit lost in transporting to all these places . Thanks so much for your help

        • Miles per Day

          Definitely. Venice >>>> Milan. If you only do 2 places and you’ve seen Rome, then I would do Florence and Venice. I think you have time for 3 though. Venice can be done in 2 days.

          Mykonos does have a beach, so if you love beach, then go there. You’re tight on time though so I’d prob skip it.

          I’m assuming you have flights TO europe already. You should fly trom Santorini to Italy. Then train around there.

          • Judy Ip

            That’s the problem I’m having because I am not so goood at planning. I will be flying from Asia, so you mean I should first fly to Santorini? People told me there is no direct flight so I have to fly from somewhere and then I should fly from there to ? Would be great if you can give me a suggested itin. And when I should takentrain ?

          • Miles per Day

            Judy, there are no major direct flights to Santorini. You can wikipedia the airport code to see which cities fly there. We flew there from Athens. So you’ll most likely connect in Athens to Santorini. Then maybe take EasyJet or whoever from Santorini to Venice. Then train from Venice to Florence and then maybe Rome too. Then fly directly home from Florence/Rome. A detailed itinerary will take more time than just comments on a blog, so you may have to do the legwork here unless you want to pay someone to do it for you, which I may know some people.

  • Jennifer Fenton

    This is super helpful!! We’re currently planning a honeymoon trip to ALL of these places, with the addition of the Amalfi Coast so I love seeing your itinerary. It’s a bit overwhelming right now.

    • Miles per Day

      Glad you found it helpful Jennifer. Let me know if you have any questions. I may not remember, but I’ll try my best.

  • jthacker

    Wow — great info. I’ve booked a Central European trip for next summer — any chance you have similar info for Budapest, Bratislava, Vienna, Brno, or Prague?

    • Miles per Day

      I did a bus tour of most of those places over 10 years ago. The tour scheduled everything, and so we didn’t have to think about anything.

  • nick

    Have you tried Tripit?
    Its pretty good for local destinations, haven’t tried it for international yet, not having data will suck for it.
    My wife hit Greece last month, she loved Santorini and hated Athens and recommends more time in Santorini.
    I didn’t like Venice at all, bring rain boots as there are frequent floods. The city is flooded every morning. The view was nice but I had a much better time in Florence, food was way better too. Rome is a tourist trap, hit the sightseeing stuff and get out as fast as you can.

    • Miles per Day

      Nick, I have tried Tripit, but not for those features. I agree with you about Santorini, Florence, and Rome. You must have went during the wrong season, but when I went in September, Venice wasn’t flooded nor did it rain, so we enjoyed it (but not for too long since there’s not much to do and eat there). We loved Florence the most.

  • Fanfoot

    If I was going back to Florence the one thing I’d want to see again would be the

    Galleria Borghese where we saw the most amazing sculptures I’ve ever seen. The Rape of Persephone was awe inspiring. But you and your racing around…

    No sunset in Santorini? Head up to Oia and park your butt in one of the many restaurants on the cliff face and watch the sun go down and drink.

    Good times…

    • Miles per Day

      Hmmm I hadn’t even heard of Gallerai Borghese until you mentioned it. I don’t know if we’ll go back to Italy ever again. There’s just too much to see in this world.

      The Mystique is in Oia and so all of our dinners were on the cliff. Like you said, it’s gorgeous.

      • resonance940

        I loved the Galleria Borghese as well. Absolutely stunning sculptures in a beautiful building and gardens. Prearranging tickets is essential, I saw many people turned away at the ticket office. And the Borghese is located in Rome.

  • Points For Later

    I was at Da il Latini 12 or 13 years ago. It was awesome. The owner comes around at the end of the meal (at least back then) to talk to each table, and depending on his interaction will give you a discount (he liked us, apparently). After that we just sat around on the steps of the Duomo for an hour or so digesting…

    • Miles per Day

      Yeah, I don’t know who would NOT like Da il Latini. I swear it was rated as a top 10 place on Tripadvisor when we went, but now it’s something like #600. I wonder if quality has gone down in the past 2 years, or if the haters are intentionally sabotaging the restaurant.