1

Should you rely on an agency or organize everything on your own?

I’ve always preferred doing everything by myself (or with Daniele). DIY trips allow for more flexibility in choosing the itinerary, cheaper budgets and the freedom of changing your mind at the last minute.
This isn’t the right way to organize a trip, yet it’s my way of doing it 😉

2

Where do you start? From the flight, obviously.

If I managed to plan the trip beforehand, it’s because I try booking the flight right away. The closer the departure date, the higher the price. It’s ideal to be able to book the flight 3-4 months in advance.
Normally I rely on Skyscanner to evaluate the best rates, then I go directly to the airline website that this search engine finds and compare prices.
This time, for the outgoing flight (Milan-New York) I chose Alitalia (help, help, fingers crossed), whereas for the return flight (Vancouver-Milan) we booked with KLM. Unfortunately, when landing at different cities the cost increases and I ended up spending € 827.

3

And what about sleeping… should we book everything right away or along the way?

I normally prefer to book the first night, so as not to have any worries once we arrive at destination, and then decide as we go along. It depends a lot on the destination. In Southeast Asia finding a place to stay at a low cost was always easy, in America in August it’s a little bit different.
For now, we booked where to sleep in the larger cities (i.e. Boston, Chicago, Los Angeles, Las Vegas, Vancouver). We booked through Booking.com, Airbnb and other local sites after reading the reviews and browsing on the websites of the hotels chosen so as to establish the best rates. In the past, thanks to my being curious and sometimes a little too meticulous, I managed to get the hotel to repay part of the amount I spent. But that’s another story, and I’il tell you about it when I recount the Marina Bay Sands in Singapore.
As far as the rest of the stops are concerned, I’ll choose, along with Daniele, the place that inspires us the most along the way.

4

What about Internet?

It’s often essential for Daniele and I to have Internet while we travel. This is why we just bought a portable router, a sort of “pocket WiFi”, a godsend to navigate in total freedom, at a high speed, everywhere: it’s a portable device that can be used with various smartphones simultaneously and that allows you to access Internet at all times. Alternatively you can buy a SIM card to use with your mobile phone; yet there’s two of us and we also prefer to keep our Italian mobile numbers active.
After some research we chose TP-Link M7350 Mobile Router Hotspot, which costs €79.99 on Amazon. It works with the 4g LTE network, reaches a speed of 150 Mbps for downloads and 50 Mbps for uploads, is simple to use and has a battery that lasts up to 8 consecutive hours. It has an intuitive display to monitor the data and avoid exceeding the traffic foreseen by the tariff plan and is in Italian.
If you are looking for portable hotspot routers, this article by Salvatore Aranzulla can be interesting to understand what features to take into account when choosing a device of this kind.
If instead you want to know what the best portable Wi-Fi routers for 2018 are, here’s an interesting article to read.

5

Prevention is better than cure.

On a coast to coast trip of the United States and on a trip to Canada health insurance is not only advisable, but necessary, because without coverage you are likely to pay sky-high costs in case something happens.
In the past I used both EuropAssistance and Worldnomads.
Despite both offer great services at good prices, I prefer WorldNomads. WorldNomads is the insurance that Daniel and I had when we were in Southeast Asia and unfortunately we had to rely on them on various occasions. During the 4 months we were away, I had my bag snatched, Daniele injured a rib and I hurt my knee. Worldnomads was efficient and effective; impeccable both in the search for healthcare facilities and with regard to refunds once we returned to Italy. I reccommend it.

6

Adapters, transformers, portable external batteries.

Remember to pack everything required to make the technological equipment you have with you work. I often travel with my computer, cellphone, external laptop battery, smart watch and camera. This is why I normally carry a multiple socket, so that I have only one adaptor to connect almost all the devices.

7

Read, study, inquire, ask for advice. And use Excel.

Before leaving on a trip, I like to get to know the places I am going to visit. This is why, with regard to our trip to America and Canada I got off-line guides and on-line PDFs: Lonely Planet (on Canada, the eastern United States, Vancouver and Route 66), a PDF on the Grand Canyon National Park Trip Planner and a PDF on Route 66 in 13 days.
And I also asked friends and relatives for their opinions; I read reviews and TripAdvisor.

Once the itinerary was chosen, Daniele created a splendid Excel file with all our stops, the relative kilometres to travel and driving hours, the day of arrival, the number of nights and our accommodation stays. This file was shared on DropBox, so we can always have it with us on our coast to coast trip.

8

Documents needed: ESTA and ETA.

ESTA is the electronic system for authorisation to travel in America. It’s mandatory, costs €12.45, can be requested online at least 72 hours before departure and does not warrant the applicant’s right to enter the United States.

ETA is the electronic travel authorization required for those wishing to visit Canada for a period of less than six months. It’s a mandatory visa, it can be done online, it costs €4.68 and the processing is almost immediate.

9

A sour note: the cost.

At the moment, the trip’s budget has increased due to the hotels in the big cities: the hotels located in central areas, normally 3 stars, which cost between € 100 and € 230 per night.
If you want to find cheap deals, I recommend booking well in advance.