How To Plan The BIG Trip – Part 2

Part 2 - The Flights

Everyone has their own favourite method for booking a vacation.

Whether you are heading south to an all-inclusive resort or to spend a week in Las Vegas, there are online booking sites and in-person travel enters that are always willing and able to assist.

What if you are looking at a multi-city getaway? Or even a multi-country or multi-continent vacation?

There are many travel experts out there to assist with your bookings. I have arranged many similar travel plans with agents and on my own and I have developed my own foolproof system.

I am currently finalizing a trip to South Africa. It is a company sponsored trip, but we always like to add on a minimum of 1 week to every overseas adventure to allow ourselves time to explore on our own.

This is Part 2 of a 3-part series - Starting with the flight bookings and ending in restaurant bookings to create a seamless vacation package.

Hotel calendar

Using my calendar again as a visual guide, I make a written list of hotel nights needed in each city throughout the trip.

If I plan to include an overnight stay outside of the destination city, I make note of this as well so I don’t double-book any hotel nights unnecessarily.

If I have not visited the city before, I will first look at which area or neighbourhood I want to stay in during my visit.

To avoid having to spend too much money on taxis or car rentals, in major cities, I prefer a downtown location so we can walk everywhere. In more rural locales, I will look for a hotel that isn’t too far from the airport or is easy to find if we are driving on our own.

I begin my research at 2-3 of my favourite hotel booking sites and look for hotels that meet my minimum criteria (star ratings, great guest reviews, price, cancellation policy, neighbourhood). I choose 1 or 2 hotels that are the best value and then look at price and cancellation policy as deciding factors.

The listed price is sometimes based on if you pre-pay for a set number of nights (discounted for a multi-night visit) or if you pay for your entire stay in advance. The price shown on the screen may also be for a basic room with twin beds or shared common areas.

If we aren’t familiar with the city or the hotel’s surroundings, we usually prefer to wait and pay when we arrive so we have the flexibility of changing hotels upon arrival.

We may have booked 3 nights at one hotel, but if, upon arrival, we aren’t happy with the hotel’s location or the hotel itself, we can immediately find a replacement hotel for nights 2 and 3 without any cancellation fee.

Some hotels ask for a deposit in advance and others allow free cancellation up to 24 hours prior to the booking date.

I usually side with the hotel with the most flexibility. Saving $50 per night when I am locked into a contract with an expensive cancellation fee isn’t really savings at all.

Just as I added the flight information to my calendar, I also enter all of the hotel details into my calendar after each booking and note the location details, confirmation number and whether we have prepaid for the stay.

An online calendar will automatically link to a map of the exact location and telephone numbers entered into the notes area will be available for a one-click dial if we get lost en route.

Now that the flights and accommodations are booked, I can start to look at restaurant reservations.

Come back next week for Part 3 - Restaurant Reservations.

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