is a website we’ve used for a number of years to book trips to not only Europe, but also South America and Asia. A cost-saving engine that provides great deals, you may have even read our thorough review on Tripmasters earlier in the year. However, a recent trip to Italy and Greece with Tripmasters gave us an opportunity to evaluate this cost-savings booking site based on an itinerary we hadn’t done before – Rome and Greece.

If you haven’t read the original article on Tripmasters, Tracy and I urge you to do so if you’re looking for more information on how the site works, Tripmasters’ interface and a little background on the company. What we’re looking at here is, instead of a hypothetical look at how to book on Tripmasters, is a real-world example of how a vacation booked on the site actually turns out.

We began planning our most recent trip a few months ago, and there were a few ideas we had in mind before ultimately settling on a “historical” theme. Normally, we either decide what theme or vibe we want for a trip, then start to look at what areas of the world best fit that idea. With “history” as the main driver, and neither of us having been to Athens or Rome, the decision was easy. We were ready to experience all Athens’ history had to offer, and walk the steps of Dan Brown characters in Rome!

The Erechtheion in Athens, Greece.

Once that decision was made, we started playing with itineraries in Tripmasters. You want to experiment a bit on the site, as the slightest change in flight times or city order on your itinerary can result in savings of hundreds of dollars. Ultimately we found the perfect itinerary – four nights in Rome followed by three each in Santorini and Athens, capped with a 14-hour layover in Amsterdam. Mind you, we could have foregone the layover in Amsterdam, but we love the city so much that we actually wanted the long layover. It even gave us a chance to add on our favorite hotel in Europe – the A-Train Hotel in Centraal Amsterdam.

Once we had the itinerary, thanks to Tripmasters’ flexible booking arrangements, we put 60% down-payment on the trip, with the remaining 40% to be paid in two installments. This was easy, considering the entire cost of the trip was $1,300 per person. Now, I remind you that for $1,300 we each got this:

  1. Direct flight on Alitalia from Miami to Rome
  2. Four nights at the Residenza Ave Roma, which was perfectly located on the River Tiber near Castel Sant’Angelo
  3. Flight from Rome to Santorini, with a layover in Athens on Aegean Airlines
  4. Three nights at the Theoxenia Hotel in Santorini (which turned into an upgrade to a matrimonial suite facing the caldera – more on that in a moment!)
  5. Direct flight from Santorini to Athens on Aegean Airlines
  6. Three nights at the Hotel Plaka in Athens, which was perfectly situated in one of the most popular areas of Athens, at the base of the Acropolis
  7. Flight from Athens to Miami, with a 14-hour layover in Amsterdam. Since the layover was over night, we booked the A-Train independently (only about €85), making our return flight home essentially a direct

What does $1,300 get you anywhere else? Currently it’s the cost of one round-trip flight from Miami to London. That’s it. No hotel. No 2nd city. Nothing else.

So, it’s easy to see the value we get with Tripmasters, from a pure cost perspective. But, how were the hotels? How was the flight? How was the trip?


We’ll be writing more on this, but Alitalia’s direct flight from Miami to Rome was the worst international flight we’ve been on. Ever. In fact, imagine if RyanAir or Spirit Airlines had 10-hour international jaunts. Are you visualizing? Scared yet? Exactly. It was bad.

This beautiful view on Alitalia – one of many photos taken while waiting on water.

Now, we don’t attribute this poor flight to Tripmasters, as we have had short haul flights on Alitalia that were just fine through the website. However, if you have the chance to do the long haul between Miami and Rome – don’t. Why? Tiny seats (even for upgraded economy), bad food, bad service (four+ hours with zero service – no water, no refreshments), and rude staff. Just understand that sometimes you do get what you pay for, and sometimes that isn’t very much.

Residenza Ave Roma

As bad as the flight to Rome was, the hotel made up for it. We’ve written about how we enjoyed the Residenza Ave Roma, as it’s exactly what we like when we travel. Small, cozy, comfortable enough, clean, and very warm staff. The location was perfect, and we will return when we go back to Rome.

Aegean Airlines

We flew Aegean three times, technically, including the laid-over flight from Rome to Santorini and the flight from Santorini to Athens for our final stop. The flights were at decent times (no red eyes), full, safe, well organized, and timely. The only whisper of a delay we had on the trip was a 15-minute delay returning to Athens from Santorini, but that’s practically nothing.

Comfortable flight on Aegean Airlines.

We were pleased at the spaciousness, the kindness of the staff, and generally enjoyed our flights. There was one drawback, which we’ll get to in a moment, but I can’t fault Aegean for having what most other airlines have –  bad food.


Going to Santorini, I went against my better judgment. Failing to prepare prior to our flight from Rome to the layover in Athens, my hunger overcame me and I did the one thing you really shouldn’t do on a plane – eat. Not only did I eat, but it was pasta. With spinach. Now, if you aren’t aware of how most airline food is made, that’s a subject for a different day. However, just know that it isn’t fresh, and that your digestive system all but shuts down at high altitudes, allowing that food to back up, create one nauseated traveler, and often make you sick.

For me, this turned into food poisoning our first night in Santorini. The staff at Theoxenia, who seemed genuinely upset that we were missing out on lovely Santorini because of my illness, upgraded us to a matrimonial suite overlooking the caldera. Our view?

A little something like this…

Santorini view

And this…

Santorini sunset

We enjoyed the Theoxenia prior to my getting ill, but our move into the suite and return to health allowed us to really indulge in a rare Santorini experience in a room that was way above our budget.

So, if you’re wondering what type of hotels Tripmasters makes connections with, it’s the kind that takes care of you. This has been our experience 100% of the time.

Plaka Hotel

The Plaka Hotel was one of the best locations we’ve had in a hotel, as it was next to the Metro line, at the base of the Acropolis, and perfectly between Athens’ hip Monastiraki and Plaka districts. It was absolutely perfect.

Acropolis view from Plaka Hotel
Nighttime view of the Acropolis from the Plaka Hotel in Athens.

The Plaka was one of the bigger hotel rooms we’ve stayed in through Tripmasters (yet, still a boutique), and it had a phenomenal view of the Acropolis from their rooftop at nighttime.  The staff was great, the rooms were incredibly clean, and we loved the location.


Our flight from Amsterdam to Miami made up for the “fail” that was Alitalia. As unattentive as Alitalia was, KLM seemingly came around every 45 minutes to shovel peanuts, water, and booze down your throat to keep you happy. It worked, and I obliged, happily.

The staff was exceptional, and our upgraded economy seats (only €50 bump from standard economy) were well worth the upgrade. At 6’3″, I had the space to stretch out, rest, and have a wonderful flight. The staff were either the nicest people in the world or great actors, as 10+ hours seemed to go by rather smoothly and I left the plane thinking “I can’t wait to fly KLM again!”.


The plan for the trip was to spend enough time in Rome to get the “must see” things down, but also to spend some time in Florence and to see Pompeii. Rome’s proximity allowed us to do this, as we booked day trips for both excursions (which can also be done through Tripmasters). Things slowed down for us a bit in Greece, especially after the inital bout with food poisoning and Tracy’s subsequent battle of her own in Athens, but we got a lot done and many things seen. Overall, we had an amazing time in Athens, and Greece in general.

Tripmasters gives you the layout of your trip in two easily usable ways. First, upon the completion of payment of your trip, they’ll issue you paper vouchers via e-mail. These will be essentially a script of your itinerary, but also include all validation information you need to check into flights and hotels. Some hotels will require you have this voucher to show, while others will only ask for your name.

However, Tripmasters has also moved into the 21st century with their recent release of a Tripmasters App for iPhone and Android. We’ll write more in depth about this, but the app is simply great. Not only does it include all of your itinerary information and vouchers, but also comes with GPS information in the city you’re staying, and a real-time glance at what attractions are nearest to you no matter where you are – including food, drinks, attractions, museums, and shopping. It is far better than what we imagined a “first run” with new technology via a mobile app would be!

The trip was a success, overall, and we were able to knock some major wishes off our bucket list with ease by going with Tripmasters. They continue to provide unparalleled service at a price that we haven’t seen matched by any other multiple-city tour aggregator.

In total, it was a very standard trip for us through the Tripmasters website – in a very good way. There’s no Ritz waiting for you at the end of a long flight, but the bill isn’t $10,000, either. As long as Tripmasters continues providing this type of service with these type of partners (I’ll give them a pass on this Alitalia crew), there’s no question we’ll continue booking with them.

Useful Travel Resources

Google Maps – Plan your trip anywhere with Google Maps. Also great for directions on the go! – Great site for comparing rental car prices – Our favorite place to book cheap airline flights – Book affordable accommodation or bundle flights and hotels
What’s the one travel accessory we never travel without? RFID Protected Travel Money Belt
Suggested Reading: Journeys of a Lifetime: 500 of the World’s Greatest Trips

15 Comments on “Tripmasters Review: Italy and Greece

  1. Tripmaster is really good for arranging vacations …I think you guys really enjoyed holidaying those picturesque places with Tripmaster’s company..

    • It is a great company, and none of our reviews are paid reviews. We just like and trust the company so much that we want our readers to know also 🙂

  2. Travel is living, I love traveling very much. Nice to see places which I did not discover yet, but time to make my ownn memories, i have an idea now.

  3. Stunning photos, Florence and Pompeii i would love to visit, yes one day!.. Will browse your tripmaster app it sounds like a pretty neat tool to have around during travelling. Will come back for more..,

  4. That sounds like a great price no matter what time of year but could you share the month you went in order to get a better understanding of the value. Hotel prices in Santorini, specifically, vary a lot by the season….


  5. Great review. How do you handle the transfers to/from the hotel and airport with Tripmasters? Do you have to add that on as an additional cost? Am looking at the Italy packages on Tripmasters and curious how the transfers to/from the airport/hotel/rail station will work?

    • Good question, Tania – most medium to large cities outside the U.S. have decent public transportation. We use a LOT of trains, and always plan ahead to make sure we have tickets/cash, whatever we need. Depending on the city, cabs are okay. Make sure to run an estimate prior to your trip of how much a cab will cost however, just to make sure you don’t bust your budget!

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