Planning the perfect vacation

Vacation planning is one of my favorite things. I spend hours pouring through websites, reading guidebooks, research hotels and train routes. There’s a lot to consider and you want your trip to be perfect, or as perfect as possible.

A friend of mine is planning a  multi-city trip to Italy and was recently asking me lots of questions about trip planning. All those details that can easily become obsessive. While helping her out it occurred to me how much I’ve learned through this whole travel process and thought I’d share some of these tips. For a single destination trip this much planning is obviously overkill.

For this exercise, let’s assume you already know where you want to go. I’ll use my last trip to Italy as an example: Rome – Sienna – Florence – Cinque Terre (Vernazza) – Venice – Milan (shown below as a driving route via Google Maps that shows the distance covered. While this is a driving map, we used the train).

Italy route

The first thing I do is figure out how much time I want to spend in each location.  I’m not a fan of cramming in a different city each night in order to visit more places. I prefer to spend several days in each location depending on the sites. For this trip we spent 4 nights in Rome, 3 in Sienna, 4 in Florence, 2 in Vernazza, 2 in Venice then one last night in Milan for a total of 16 nights.  It could have been done in 10 by cutting a few days here & there, eliminating Vernazza and Milan.

So, I had a basic plan that was flying into Rome and out of Milan and knew the total number of days needed. I also was aware through the tour books as to which days major sites were open or closed. Another thing I quickly explored was how long the train travel was between cities (more on this further down). It’s a good idea to check this ahead of time as you may use night trains or even eliminate cities that are inconvenient to reach.

All of this helped me determine in which direction I wanted to travel. But a bigger consideration for the actual days/dates and direction of travel were based on airfare. price differences booking airfareAs you can see from the American Airlines booking tool, you can save based on which days you travel.  From here, I settled on which days I was going to travel as well as details about arrival and departure days. What I mean by this is if you have a late arrival, you might not want to continue to travel but stay a night near the airport or if your return flight is super early in the morning, you want to stay close to the airport the night before departure. Check the times for arrival and departure in each travel direction. You might find the times work better in one direction versus the other.

So,  I’ve booked my airfare, identified direction of travel and nights in each city. Now I need hotels and transportation. Since this trip example is starting with several days in the same airport, I just need to figure out how to get to my hotel upon arrival. Tour books fill you in with all the details (for Rome there’s an airport train that runs to the main terminal, then you can walk or cheaply grab a cab or you could splurge on a very long an expensive cab ride directly from the airport, but I’m cheap).

I usually rely upon trains to move between cities although lately I’m enjoying having a rental car and leisurely exploring along they way, but I digress.  While I don’t book my train travel ahead of time, I like to get an idea of how long it’s going to take to get between cities. The biggest challenge is just correlating to your tour book to get the right train station and city spelling (it’s a bit of trial and error).

TrenitaliaThe above is from Trenitalia but I actually prefer using the German Bahn website, which I just find a bit more user-friendly. Be sure to look for either the USA or United Kingdom flag to use the site in English. When looking at schedules you’ll also want to pick the same day of the week as you’ll plan on traveling.  Again, I don’t actually book my ticket at this time, but I’m planning travel times.   In the case above, I would need to be at the main terminal in Rome for a 10:20 departure with an arrival into Siena at 1:38pm (all of Europe uses a 24 hour clock so be prepared!)

I prefer to make my departure around 10 – 11 am which allows me time to enjoy breakfast, pack and reach the train station after the morning commutes. And, keep in mind that while your destination hotel will store your bag, you may not be able to access your room until 3pm or later.

When it comes to purchasing the tickets I tend to rely upon the kiosks at the train station as ticket lines tend to be rather long. If you want to use a ticket line just be sure to allow for extra time and get into the correct line (international v domestic travel – advance v same day). The kiosks are very easy to use, but most won’t accept our US credit cards so you’ll need Euros.  Unlike airports you don’t need to arrive at the train station hours ahead of time. Just enough time to purchase your ticket, find your platform, and work your way to your seat/car.

Upon arrival in Siena, one of the first things I’ll do is go ahead and check the posted train schedules for my next leg. I can then either go ahead and purchase my next ticket there or just make note of the times. Often I’ll wait as then I’ve the flexibility of taking a later train if the tickets are train/time specific.

So, I’ve my transportation squared away now I just need accommodations. My two favorite websites for this are and  I tend to play back and forth between the two using Booking as my main reservation system, but TripAdvisor to read hotel rankings and reviews. One thing I really like about is that your reservations are all listed in one place.  But, just to complicate things I’ll also often contact the hotel directly to see if they offer a better deal since they’re not paying a reservation fee.

The final thing is whether you want to book any tours ahead of time. The only things I really do ahead of time are museum tickets where reservations are necessary or highly advised. Your tour books will detail which ones need reservations and the best way to book (either through the site or your hotel). Other than that, I tend not to book organized tours ahead of time as often I find the tour books provide ample information for me to explore on my own.

Phew! Lots to consider. Lastly is how I keep track of everything. During this process I tend to use a few Excel spreadsheets to create calendars and budget estimates. They basically become my master plan with all confirmation #’s and basic details listed. If necessary I’ll also print out confirmation pages but the overview page is what I rely.

ITALY calendarOver time this calendar has evolved and now includes rough budgets to help me determine how much my trip will cost. It’s just a system that works for me.

Hope you’ve found some of the above helpful. I know it seems like a lot but I find it fun and part of the excitement about the overall journey.  Happy travels!



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One Response to Planning the perfect vacation

  1. Natalie says:

    I love all your info and I have really been enjoying my planning time on the weekends! You’re right – it’s all part of the fun. And I’m already so excited about it & I don’t know how I’m going to stand the wait! Thanks again for everything!

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