The Grumpy Retiree has a great dream trip illustration here! This page highlights a trip to Italy and Greece I planned for Spring 2023. I started planning this trip in November 2022 and was mostly booked before the end of 2022. Some sightseeing tickets were not purchased until later due to availability or further research.

This is an actual trip plan I did for Italy and Greece. This is a complicated trip, but you can start slow and work your way up. It isn’t hard!

The Grumpy Retiree

Define Your Trip Goal

My primary goal for this trip was to see someplace warm enough for sightseeing outside during a shoulder season. A second objective was to be back in the US before our trip to Maine in May.

As mentioned before, once you fly someplace stay as long as possible. I started with a 23 day trip and after adding sites and researching connecting travel, I felt I had to eliminate someplace or add more time. I added more time making the trip 27 days!

The weather in Sicily is warm enough by our standards for sightseeing. We have wanted to see Greece, so while already in Europe I looked into adding Greece. This way I am flying overseas one time, but seeing 2 destinations. The weather looks good in Greece in Spring so that isn’t an issue. I’ll check if the logistics make sense to add Greece.

Thanks to Rick Steves he has an Itinerary for Sicily I use for ideas. It shows 11 days (10 nights) in Sicily for around $600 a night for a couple plus airfare. This is not a bad price for a well established company but I can do better. After some research I liked his itinerary so much I am following it closely for 11 nights. Maybe I’ll bump into Rick and thank him.

The Amalfi coast is an area in Italy we have not explored and is reasonably close by train from Sicily. I include the Amalfi area, Naples and Pompeii. Now I needed to find a central location to make all 3 areas easily accessible. After research I decide to take a chance and base myself in less touristy Salerno, right on the train line, for 5 nights. At this point I am at 16 nights.

Itinerary – Add and Adjust as Needed!

If I want to go to Athens I have to figure out how to get there! Flying is the only logical option but I don’t want to waste time going to Italy’s major hub in Rome. Naples has good direct flights to Athens saving valuable time. This worked out perfect as I now can stay 1 night in Naples, see the city and be close to the airport to fly to Athens. No time to waste! I modify the schedule to 4 nights in Salerno and 1 night in Naples.

In Athens I just want to see the highlights and finish on a Greek island to drink wine and relax. Santorini and Mykonos are the 2 most popular islands, so for me that was easy. I eliminated them. Giggly tourists taking selfies = Grumpy! I chose the island of Crete. Total time in Greece; Athens 3 nights, Crete 5 nights.

The itinerary is exceedingly important! Take time using travel sites, blogs, tours and travel guides to define the length of your trip and stay in each area. This is a complicated trip spanning 10 cities and 2 countries requiring more research to do correctly. For example, my research on Athens suggested 3 nights was enough to see the highlights at my pace. Consider your personal interests & pace when planning! Rushing is not fun, but being bored for 2 weeks when 3 days is plenty is not good either. You will still make some mistakes and fall in love with a place wishing you stayed longer. With proper research you can reduce these issues.

The Grumpy Retiree’s Budget

Researching my Italy & Greece trip, hotels are most expensive in Greece and least expensive in Sicily. I can easily find B&Bs, which include breakfast, in the $100-200 range in Sicily. Well located hotels in Athens are $200 and up per night. Luxury hotels will quickly go up to $500 per night, but my eyes are closed 8 of the 10-11 hours I spend in a hotel, so I am sicking to clean well located hotels with great reviews at a moderate price.

Below is my budget, your budget may be higher or lower, but the general fact remains the same. Figure out your daily food & hotel budget and multiply that by the days in your trip. Add on airfare, sightseeing and miscellaneous transportation.

With 2 days round trip flights from the US, my trip is 27 days including 1 day in New York City on the way home. Typically my budget would be about $13,000-15,000 for this trip based on $300 average per day room & food, $2500 round trip airfare to Europe, $2500 sightseeing and miscellaneous transportation and a $1000 cushion. That may seem almost as expensive as a tour, but remember tours usually do not include airfare nor some meals. Also, my trip includes 4 diverse locations, Sicily, Italy mainland, Crete & Athens, requiring additional airfare. I would expect to do this same trip via a tour company would approach $20,000 in the end. I am hoping for at least 25-30% savings over a tour.

NOTE: Based on 2023 prices, $300 average per day room & food is doable. You can easily go above that figure as the sky is the limit, but I don’t budget much under that amount. A room usually averages $150-200/day depending on location leaving $100-150 for food per day. Frequently my room and food is under $300 a day, especially if I have free breakfast or am staying in a less expensive location. Other days I may go over that amount, it averages out, and I rather over budget than under budget. Determine your daily hotel & food budget based on your style of travel and multiply by the number of days.

Check the Must See Sights

This may sound simple, but make sure sights you want to see are open during your visit. Also, check ticket availability, especially for popular places. If you want to see the Last Supper painting in Milan start booking NOW!

Not all attractions are open every day or have the same daily hours. The Vatican Museum is free on the last Sunday of the month but closes early at 2pm with last entry at 12:30pm. Don’t be disappointed! Check websites for operating hours.

Skip the line tickets are a good option when available. These tickets are purchased online and allow you to get into a site quickly. However, many times “skip the line” simply means you will skip the ticket line, which is great as that line can be very long! I do purchase tickets online when possible to ensure entry & avoid a long ticket line. Some attractions (not all) do offer a fast lane entry in addition to skipping the ticket line, which is well worth the price at busy attractions. Also, tour companies will display big “Skip The Line” in their tour descriptions. Frequently they are just buying the skip the ticket line in bulk online, same as you can do individually. Understand what they are offering and decide if you want to go on their tour, if not I just buy the ticket online myself.

For my trip all the major sightseeing, Valle dei Templi, Pompeii, and Athens Archeological Sites were available, however actual tickets purchases were not open as most of these sites only book a few month in advance. I would come back to book these tickets later.

NOTE: Many tickets now have timed entry. The disadvantage booking ahead is you are locked into a specific time which is hard to plan weeks or months in advance. Some tickets have flexibility with the entrance time on your ticket, other don’t. Read the disclaimers carefully. The disadvantage of not booking ahead, especially popular attractions, is you may not get a ticket without advance booking. Booking ahead means you have to work around that timed event.

By this time I had a budget and defined the rough daily itinerary on my calendar. Time to move to the booking process!

Let’s Book It!

Using Kayak and Google Flights I searched direct flights from JFK to Palermo Sicily and also only from JFK to Rome where I would then catch a local flight to Palermo. My return flight is fixed from Athens, Greece. I found round trip airfare (only to Rome outbound) from $600 for Basic Economy up to $1300 for Plus Seating. Add $100-$200 for outbound flights from JFK – Palermo. I wanted to use miles if possible for the airfare, but I still start searching for paid flights. A flight for $600 is likely less airline miles than a flight for $1000, so this is helpful information if you want to use miles to book. Also, if I find a fantastic deal on paid flights, I sometimes opt to buy the ticket and save the miles for a more expensive trip.

Normally I would book Regular Economy or crack open the wallet for Plus seating and been done with it but I saw some reasonably priced flights to Rome returning from Athens on Delta Airlines starting 3 days before my original date. If a 3 day change to my trip leads to savings it may be worth the adjustment! I have a lot of Delta Miles, so I went to their site to check free tickets deals. I would need to book a flight separately to Palermo, but it may still be worth it!

Search for Airline Deals

The earlier dates provided a great deal! I got 2 free flights on Delta in Comfort Plus seating for 69,000 miles round trip per person saving me roughly $2500! I adjust my timeline, booked the tickets and now have my “goalposts”, or start end dates set.

Things progress quickly after initial flights are settled. Next I verify if connecting transportation leaves enough time in each city. I burn the candle at both ends on a trip so my wife frequently hears “we have to be up at 3:30 – 4AM to catch a flight”. Needless to say, we had some very early days. That is our way of traveling and it isn’t for everyone. If we didn’t rise early on this trip I needed to add 2-3 more days. If you don’t want to get up early, plan adding days.

I added flights from Rome to Palermo (one way), Naples to Athens (one way) and Athens to Crete (round trip). Now I have a lot of fixed points to work around with takeoff and landing times defined.

Let’s Add a Car

In Sicily I want to rent a car (one way rental) and in Crete (round trip rental). Cars usually are plentiful if booked early. Also, I want to pick up the car at the airport in Palmero and return it to Messina to catch the train to Salerno. It is worth the extra one way drop off fee eliminating the need to return to Palmero (from Taormina, Sicily). I booked the Sicily car rental since it was a one way rental and critical for the itinerary.

NOTE: Check rental car terms and verify if unlimited miles are included and the cost of one way drop off. Credit cards for US rentals usually include car rental insurance, but verify coverage overseas. I found full coverage in Sicily and Crete to be very cheap and added the insurance.

Next I researched trains from Sicily to Salerno using a combination of the Trenitalia App and Webpage to quickly see Italian train schedules. In Italy trains between major cities are plentiful and there were several options from Sicily to Salerno. I booked this train ticket online for several reasons. It was critical for my timeline, it was around the Easter Holiday and lastly train tickets can go up in price closer to departure. While it isn’t necessary to book trains ahead, I usually book time critical tickets for peace of mind.

Recap so far. I have the following booked (in order of travel not booking).

• Flights from US to Rome
• Flights from Rome to Palermo Sicily
• One Way car rental in Sicily
• Train from Sicily to Salerno
• One Way Flights from Naples to Athens
• Round trip Flights from Athens to Crete
• Flights from Athens the US

Back-fill with Hotels

I already knew hotels were plentiful at all my locations. I quickly get hotels down to 2-3 choices in my desired locations and get my wife’s opinion on hotels. A second set of eyes helps and may see something I missed. A flight is just a flight, but a hotel is a bit more personal. I book all the hotels within a few days after our selections.

Frequently hotels and B&Bs offer a reduced price if you select Non-Refundable rooms. For the extra few dollars I usually book a refundable room, especially if booking well in advance as things can happen.

Tie up the Loose Ends

At this point the trip was essentially fully booked. All that was left was the car in Crete and some sightseeing to book. I booked the car in Crete soon afterwards but still had to wait for tickets to attractions to become available.

NOTE: The Athens Archeological Sites could not be booked until April 1st which was after I left for this trip. Make sure you put reminders on your phone/calendar to book time sensitive tickets. Most hotels and B&Bs have a way to print tickets on the road and many times you can get an electronic ticket.

We really enjoy cooking classes in other countries. It is a great way to learn about the local food, meet people from around the world, have a great meal and have a lot of fun. There were several options for cooking classes which needed to be researched and booked. I prefer to do a cooking class early in the trip to get an introduction to the local cuisine. For my money I prefer cooking classes over food tours.

Over the next few months I book a cooking class in Palermo and the other sightseeing tickets that were available. A few tickets were purchased on site while in Italy and Greece for some minor places. Not everything needs to be booked ahead which also leaves flexibility.

The Final Itinerary

Below are the stops we made in Italy and Greece. This is an ambitious trip for a first time plan, but with some time it can be done by anyone.

• Delta Airfare $2500 FREE
• Airfare to Palermo $200 FREE
• Palermo Sicily $375 for 3 nights
• Marsala Sicily $200 for 2 nights
• Agrigento Sicily $130 for 1 night FREE
• Syracusa Sicily $250 for 2 nights
• Taomina Sicily $315 for 3 nights
• Salerno Italy $400 for 4 nights
• Naples Italy $115 for 1 nights
• Airfare to Greece $450
• Round trip Airfare Crete $300 FREE
• Athens Greece $630 for 3 nights FREE
• Chania Crete $1250 for 5 nights FREE
• Hotel in NYC on return $250 FREE
• Car Rentals $450
• Amtrak Tickets $150

Final Thoughts!

The basic cost of this trip is just under $8000 before sightseeing and meals. I was able to reduce this to under $3000 using points on credit cards and loyalty programs! Savings $5000!!! There are still several trains in Italy and meals & sightseeing throughout the trip. I estimated those expenses at $4000 to $5000 for 27 days.

Admittedly, not everyone has that many points to reduce travel expenses. But that isn’t the point of this article. Even without loyalty points this trip estimate falls just under my original $13,000-15,000 budget coming in at $12,800. Also, a commercial tour for 27 days spanning Sicily, Naples, Athens and Crete for 2 people including all meals and other transportation I estimate at $20,000+. The difference is who does the legwork. Some people value the professional service and planning a tour operator provides.

Well? How did it go?

So how did the trip go? Italy and Greece were fantastic! We had a wonderful time. Did we have any issues? Yes! We had 2 weather related issues out of our control. Bad weather cannot be avoided unfortunately.

There was one logistical problem. Upon landing in Palermo the car rental agent told us the drop off location in Messina was closed! I was able to drop off at another location but now I had to take a train to Messina. I would have expected this to be communicated before arrival in the US, but in Italy … it all worked out. Working with the car rental agent at the pickup location we figured out an alternative. Can anyone say “we have to be up at 4AM”?

In the end food was less expensive as we found great family run restaurants and some good street food. We broke $100 for a nice meal 2 times but a few days we only spent about $50 the whole day eating. There was some gasoline, tolls, gifts and lots of gelato and a canollo or two!

The final cost of the trip was actually well below my original budget. Besides the loyalty point savings, and in addition to food below budget, B&Bs were very inexpensive in Sicily and very clean, comfortable and well located. Overall the raw cost was about $12,000 or about $7,000 after points. By my estimate we saved 40% over a similar organized tour before point savings and 65% savings after using points! I will take that any day!!!