How to get a Wonderful Trip Itinerary

Wonder how I go from your initial travel survey to a wonderful trip itinerary?

Getting from our initial contact to your completed travel itinerary takes a lot of work!  (The majority of the task is my job to make your complex travel planning easy.)  After you submit your trip planning survey, we’ll take these steps to work together on your dream trip itinerary:

  1. Trip planning kick-off call
  2. Initial trip proposal(s)
  3. Multiple email iterations
  4. Calls as needed
  5. Final itinerary ready

Let’s look at an actual travel planning survey that was submitted early in 2015 for a 20th Anniversary dream trip itinerary through Italy this August.

What is the objective of your trip? Any special celebrations or milestones?

Italiano: Collage di varie foto riguardanti la...

Italiano: Collage di varie foto riguardanti la cultura dell’Italia. (Photo credit: Wikipedia)

Pleasure, celebrating 20th wedding anniversary

Do you have a specific destination(s) in mind? Why?

Rome, Florence (Tuscany – wine country) and Italian coast/rivieria

Do you have specific dates? or a flexible window to travel?

Mid/Late August – somewhat flexible (our anniversary is in August which is the reason for the timing/date….as an option we could consider July but I suspect pricing/availability will be about the same given peak travel months).

This section provides a glimpse into your lifestyle and past “travel personality” so we can collaborate on a memorable experience. Where have you previously vacationed? What did you like or not like? WHY? I want to hear whatever you’ll share.

  • Personal trip through Western Europe out of college.
  • Vienna/Budapest with my wife
  • Australia – Sydney/Adelaide
  • Multiple trips to Hawaii, Mexico and around US.

And, what types of trips have you taken?

  • All-Inclusive Resort
  • Hotel
  • Theme Park
  • Escorted Tour
  • Independent Tour (Multi-city)
  • What will YOUR trip feel like? What do you envision yourself doing? Exciting with lots of activities? Group tours? Time to explore on your own? relaxing on the beach?

Interest in this trip is both site seeing as well as taking in Italian culture (food, wine, etc)….plus relaxation for part of the trip (e.g. beach town on Italian coast/rivieria). As far as site seeing, I am open to both group tours as well as exploring on our own.

Do you have a preferred hotel/resort/cruise line/air line? Loyalty program member? Any “must haves” such as ocean view or balcony room?

No must haves. Would like to stay in moderate to nice accommodations (nice, but does not need to be 5 star).


That was the beginning of the trip planning process or “trip genesis.”

What happens next in planning your trip itinerary?

So after we discussed the trip survey, I went to work designing the “trip flow.”  When I  design a custom trip itinerary, I work out the “trip flow” first which includes:

  • number of cities visited
  • number of nights in each city,
  • order of cities visited
  • required pre/post nights due to air schedules to begin or end the in-country portion of the trip itinerary

We review the trip flow prior to getting into the hotel and tours, etc.  By focusing on the trip flow, my clients clients and I stay focused on designing the optimal trip WITHOUT getting distracted by how nice a hotel looks, or which tours are “must do’s” as this fun stuff will come next.  NOTE: the tours can be the most memorable part of the trip.

Montalcino, Toscana, Italia

Montalcino, Toscana, Italia (Photo credit: Wikipedia)

For this particular trip, staying in Tuscany was mandatory as touring wineries in the Montalcino area was KEY!  Visiting a beach town in  Cinque Terra was also highly desired for relaxation after heavy sightseeing.   There were stays in Florence and Rome to take in the “must do” sightseeing.

We started getting some traction and agreed on the number of nights in each city.  To make the whole trip itinerary work, there needed to be one longer travel day from Cinque Terra down to a Rome (FCO) airport hotel to finish up the trip.  It was also decided to visit Venice as a day trip from Florence.

Now it was time to make this happen by selecting hotels, train, tours, and transfers.  My client had already booked airline tickets to coordinate with the start/stop dates of the trip itinerary.



So, want to see the final trip? Click on the itinerary calendar below to get the whole trip (Zoom in and scroll around if you want to really take in the details.).  Be sure to see some pictures of my travel guests enjoying their trip in Italy below the trip itinerary calendar. Want a custom planned trip for yourself?  Don’t hesitate to contact me today.

Sample Italy trip Itinerary (click for enlarged view)

Sample Italy trip Itinerary (click for enlarged view)

Cinque Terre

View from Hotel Pasquale Monterosso al Mare on Cinque Terre coastline

Cinque Terre

Cinque Terre

Cinque Terre Hiking

Cinque Terre Hiking