How to Plan a Travel Itinerary

Here are a few tips on easily planning an itinerary. This, of course, if you do not prefer to do it together with an experienced expert.

Destination countries

Choose the destination countries that interest you and your family or buddies the most. The closer these are one to each other the less expensive the tour will be (valid also for destination cities).

Check the travel advisories from your government and from the governments of the countries of destination for updated recommendations and information related to the desired destinations:

• health requirements,
• entry requirements,
• safety,
• local laws,
• security,
• local customs.

Period of the year

Decide the period for your holiday and number of travelers. Make sure you include children and keep an eye on their age at the time of traveling as this might impact some of your travel services. Remember that the sooner you start planning and booking (9-12 months in advance) the more choices you have exactly as you wish. The later you start this process the more flexible you have to be.

Choose the destination cities and sightseeing you are interested in each desired country. Here is where Google Things to Do comes in hands if you do not like the idea of scouring the travel blogs. It will show you the top sights of each country or city you type in, and give you:

• a description,
• the rating and
• the number of reviews per each.

Desired activities

Choose the desired activities possible at the chosen destination cities, using Viator which offers multiple selection criteria, ratings, durations, costs and online booking.

Add all your destination cities in a Google map, inclusively your home city as the first and last one. This will show you step by step directions, estimated mileage and timing. Plus you can use it later while driving. Plus you can easily change the stops order to optimize the route and avoiding back and forth costly transfers. You can add only the cities or each point of interest (hotel, restaurant, sightseeing).

If you added only the cities, consider a plus 10% mileage when calculating the gas costs as you might wish to take detours nearby chosen sightseeing or need to have multiple local transfers, for example if the restaurants are not nearby your hotel / sightseeing and you did not add them to your Google Map. You can use ViaMichelin to calculate the estimated costs for gas and road fees. Keep in mind that the routes proposed by Google Maps and ViaMichelin are not always the same. (Tip: add intermediary stops until the system gets your point.)

Daily scenario

Based on the route map information, and details about the sightseeing and activities, now you can start drawing up the itinerary scenario per days, with informative timings and estimated costs. This will also depend on how accommodated and comfortable you are with spending long hours in the car. Most of the people consider that spending more than 3 hours in the car makes it not feeling as holiday anymore.

If the distance between two stops is too long choose a middle stop looking on the map route, where you can have lunch or visit one of their top sights. This might involve detours.

Check the website presentations for opening timings, entry fees, duration and visiting conditions for each desired sightseeing and activity and add the most important details to your itinerary as well as the website links for later references. Consider about 2 hours for each activity (lunch, dinner, sightseeing… ) if not longer duration is specified on their presentation website. And take into consideration that sometimes there are access queues, traffic delays etc. so it is better to have extra time than to rush or be disappointed.

Generally speaking, if one day you have no transfers at all, you could add up to 3 sights visiting and activities of about 2 hours each. You can add the less interesting ones as optional, just in case you spent less time than estimated. This is because lots of spare moments contribute to the holiday feeling:

• admiring the pigeons in a square,
• enjoying an ice cream,
• forgetting about time while looking at the sunset…

And still, you do not wish to get late to that opera show or river cruise !

Hotels & Restaurants

Add the hotels or your preferred type of accommodation for each night. For upscale and luxury boutique style suggestions (less options) you can use Relais&Chateaux. For (affordable) luxury and more options you can use Michelin Guide. Wherever it is possible you might prefer to have the accommodation unit close to the sightseeing and restaurants, for time saving, unless this affects the quality of accommodation services.

Add the restaurants (at least the ones that mean a real experience) on your itinerary scenario. Michelin Guide is very helpful in this sense, especially if you are looking for Michelin star restaurants !

Check your estimated budget. And if no further adjustments of the itinerary are needed in order to best fit your preferences and interests, you can start make the bookings, day by day. It is recommended to organize your confirmation emails for easy retrieving. There are also applications especially designed for those who prefer to organize their holidays by themselves.

If all these seems too much time consuming, you can always request proposals from several travel advisors that design custom made tours. And then choose the one that best fit your preferences.

Sample tour day

And this is how a sample itinerary day might look at the end:

TUESDAY, MAY 9 ~ BOLOGNA

• 09:00 – 10:30 Drive to Pisa ~ 84 km ~ 1.5 h
• 11:00 – 12:00 Leaning Tower of Pisa ~ Ornate 14th-century tower with a tilt
  • • https://www.towerofpisa.org/tickets/
  • From 27 Euro ~ 29 $ * 4 pax = 116 $ / 4 guests
  • Skip the line ticket ~ Month of May not listed
    • https://www.florence-tickets.com/pisa/tower-of-pisa/tower-of-pisa-tickets?tcode=5247de9a-6e08-421a-9d30-e00bd58d776b
  • Last entrance: 17:30
  • 30 minutes
• 12:00 – 14:00 Optional Tuscan cuisine dinner
  • Osteria dei Cavalieri $$
    • https://guide.michelin.com/en/toscana/pisa/restaurant/osteria-dei-cavalieri
• 15:00 – 17:30 Drive to Bologna ~ 169 km ~ 2.5 h
• 20:00 Optional traditional cuisine lunch in Bologna
  • Vicolo Colombina Restaurant $$
    • https://guide.michelin.com/en/emilia-romagna/bologna/restaurant/vicolo-colombina
• 23:00 Overnight in Bologna
  • I Portici Hotel Bologna 4*
  • From 584 Euro ~ 634 $ / night / 2 double rooms with breakfast and fees / 4* hotel
  • Free cancelation: By May 6
    • https://guide.michelin.com/en/hotels-stays/bologna?arr=2023-05-09&dep=2023-05-10&nA=4&nC=0&nR=2&showMap=false