On your flight back from your trip and ready to plan the next one? Let’s get started.

PLANNING GUIDE

Where to next?

RESEARCH

The following are key elements (listed in order of importance) I take into account while planning for a trip.

• Dates - when can or must you travel?

• Are there any government advisories for the country or in any region within the country? For Canada, https://travel.gc.ca/travelling/advisories, but most western countries have their own.

• Weather - what is the weather during those dates? If you plan to travel around a country, what is the weather like in different regions? Are you happy with these conditions?

• International Flights:

1. What is the cost of the international flights? Flights are a significant cost to any trip. As early as possible, I start to track the cost of the flight to understand what might be a good price or a bad price. I buy as soon as I am satisfied that I am getting a good price. If flights remain expensive, I may choose another destination or try and adjust my dates.

2. What is the best flight? For long haul destinations, a direct flight might not be possible; or you may wish to try and have a stop over on your way to explore another destination without incurring the cost of another flight. These are issues to explore here.

Getting Started

KEY FACTORS

Where to Go?

Usually, there is ONE factor which drives my decision where I want to travel:

• A burning desire to visit a country (let’s say India);• A burning desire to see an attraction in a country (let’s say Petra in Jordan); or• The dates that I must travel (let’s say end of March)

Accordingly, identify that factor.

• How should you divide up your time? Ideally, I try and stay in one place for 3 nights before I move. Based upon the total number of days you have, how many locations could you visit? Ultimately, decide whether you want to visit multiple locations or stay in one place.

• Within the country, identify where you may want to go.

• What accommodation interests you in each location? Cost?

• How should you travel from location to location? Cost?

• What should you do each day? I always outline a rough plan before I finalize anything. This is very important for a couple of reasons. It helps you determine whether:

1. You allotted enough (or too much) time in a location

2. You may need to book tickets or a tour far in advance because demand may be greater than supply

• How should you get from the airport to your accommodation? Cost?

• How should you travel within the location? Cost?

• Where should you eat, have a drink, or people watch? or Where are the closest grocery stores if you plan to cook?

• What night life are you interested in? Shows, clubs, night tours?

BOOKING GUIDE

Once I research and create a plan for where I want to go, for how long, and what I want to do, I then start focusing on booking my trip. What and when I book depends on importance and cost. The following is the order in which I book, the importance of each, and the issues that you need to consider.

The two most important items that I book as early as possible are international flights and accommodation. Minimum 6 months in advance if possible.

Bring the Plan to Life

FLIGHTS1. Every item that you have researched and planned is in jeopardy if you can’t get to your destination, for the price that

you think is reasonable, or on the flight path that you would like.

2. For many trips, this could be the most expensive item for your holiday. I like to find the best deal early and get that expense out of the way.

ACCOMMODATION1. Having the right accommodation is important. I don’t want to settle on a place because that is what is left. I want to

choose a place because it is in an excellent location and has the amenities that I am looking for.

2. Booking early usually means the rooms cost less. As hotel rooms fill up, the cost of rooms normally increase.

3. I try to only book accommodation that I can cancel for two reasons:

A. If my plans change, I can cancel the room without penalty. Since I try to book accommodation early, it is very possible that I might change my mind about my itinerary.

B. If for some reason the cost of the hotel room decreases (normally because the rooms are not booking up), I want to be able to modify my reservation and take advantage of the lower cost (or even cancel if I have found an equally good hotel for a better price). I regularly check on the cost of the hotel leading up to my trip.

TRANSPORTATION WITHIN COUNTRYIf I need to book flights within a country or a rental car, I also try to book these items early.

Flights

How early depends on two factors:

1. How many flights there are, the size of the planes, and the number of seats available.

2. How important that location is for my holiday.

If there is only one flight per week on a small plane and the destination is the main reason that I am going to the country, then I will likely book soon after I book my international flights. However, if there are multiple flights on large planes at reasonable costs, and I am ambivalent as to whether I go to that location, I might wait until a couple months before I book. Again, you do not want to wait too long as the cost of the flights will eventually go up as the planes fill up.

Rental Cars

The cost of rental cars is also a product of demand. If you book early, you will likely get a better rate than booking last minute. However, rates can decrease if there is less demand at the car rental agency than anticipated. Accordingly, like hotel rooms, if your rental car reservation is cancellable, you can modify or cancel your reservation if you find a better deal. I like to lock in a rental car early and then, continue to check back on the cost leading up to my trip.

Private Car and Driver

Usually you are required to pay in advance for a private car and driver. Accordingly, I am cautious about booking this too early unless I am absolutely certain of my travel plans. However, if my research has shown that there is limited number of services offering this or that there is a risk of the cost increasing if I wait too long (because the less expensive services will usually be booked first), then I will book this soon after International flights, accommodation and other internal transportation has been finalized.

DAILY ACTIVITIESI like to have a plan for each day of our trip. Even if it is a “sleep in, hang by pool, and shop”, I like to take a look at the overall plan for the trip to see if we will be doing too much, too little, or too much of the same thing. I also want to give us time to rest if it was a long travel day the day before, or a late night. Once I confirm the schedule, then I start booking tours or purchasing tickets.

When I book varies. Most, if not all, tours and activities require immediate payment without a refund. Accordingly, I may wait a month before I start to book or even a couple of weeks, it really depends on how important one particular experience is and whether I think that the tour or activity could sell out. There might be something so important to me to see or do that I book right after I buy my plane tickets. However, that is unusual. Normally, daily tours and activities fall into two categories - 1. I really want to do “that”. So I book a month or more before we arrive; or 2. “I’d really love to do that, but if there isn’t room, I’d be happy to do something else”. So I book that a couple of weeks before we arrive.

If it is high season, you need to be more alert. Some things could sell out months in advance.

EVERYTHING ELSE

• How should you get from the airport to your accommodation?

• How should you travel within the location?

• Where should you eat, have a drink, or people watch? or Where are the closest grocery stores if you plan to cook?

• What night life are you interested in?

Whether these areas need advanced booking or if they can be booked once you are on your trip is complex. For example,

• If your research indicates that the best way to get from the airport to your accommodation is with Uber or Lyft, then you book once you arrive. However, if you are a family of 6 and you want to book a private van and driver, then you should likely do that a couple of weeks to a month before you arrive. If you are relying on a rental car, then you should book as early as possible for the reasons stated earlier.

• The same goes for travel within the location. If you are relying on public transportation or ride sharing, then nothing more needs to be done. If you need to book something more formal, like a private driver and car, then I would do this at least a month in advance. If you are relying on a rental car, then you should book as early as possible for the reasons that I stated earlier.

• If you are keen to try certain restaurants, then you may want to make a reservation a couple of weeks (or earlier if it is a popular restaurant) in advance of arriving.

• If you want to see a show or something else that requires tickets, then you will need to book depending on the popularity of that show and how important it is for you to see it. Accordingly, that could mean as soon as you book your international flights, or only a few days before.

RESEARCH

FLIGHTS1. Every item that you have researched and planned is in jeopardy if you can’t get to your destination, for the price that

you think is reasonable, or on the flight path that you would like.

2. For many trips, this could be the most expensive item for your holiday. I like to find the best deal early and get that expense out of the way.

ACCOMMODATION1. Having the right accommodation is important. I don’t want to settle on a place because that is what is left. I want to

choose a place because it is in an excellent location and has the amenities that I am looking for.

2. Booking early usually means the rooms cost less. As hotel rooms fill up, the cost of rooms normally increase.

3. I try to only book accommodation that I can cancel for two reasons:

A. If my plans change, I can cancel the room without penalty. Since I try to book accommodation early, it is very possible that I might change my mind about my itinerary.

B. If for some reason the cost of the hotel room decreases (normally because the rooms are not booking up), I want to be able to modify my reservation and take advantage of the lower cost (or even cancel if I have found an equally good hotel for a better price). I regularly check on the cost of the hotel leading up to my trip.

TRANSPORTATION WITHIN COUNTRYIf I need to book flights within a country or a rental car, I also try to book these items early.

Flights

How early depends on two factors:

1. How many flights there are, the size of the planes, and the number of seats available.

2. How important that location is for my holiday.

If there is only one flight per week on a small plane and the destination is the main reason that I am going to the country, then I will likely book soon after I book my international flights. However, if there are multiple flights on large planes at reasonable costs, and I am ambivalent as to whether I go to that location, I might wait until a couple months before I book. Again, you do not want to wait too long as the cost of the flights will eventually go up as the planes fill up.

Rental Cars

The cost of rental cars is also a product of demand. If you book early, you will likely get a better rate than booking last minute. However, rates can decrease if there is less demand at the car rental agency than anticipated. Accordingly, like hotel rooms, if your rental car reservation is cancellable, you can modify or cancel your reservation if you find a better deal. I like to lock in a rental car early and then, continue to check back on the cost leading up to my trip.

Private Car and Driver

Usually you are required to pay in advance for a private car and driver. Accordingly, I am cautious about booking this too early unless I am absolutely certain of my travel plans. However, if my research has shown that there is limited number of services offering this or that there is a risk of the cost increasing if I wait too long (because the less expensive services will usually be booked first), then I will book this soon after International flights, accommodation and other internal transportation has been finalized.

DAILY ACTIVITIESI like to have a plan for each day of our trip. Even if it is a “sleep in, hang by pool, and shop”, I like to take a look at the overall plan for the trip to see if we will be doing too much, too little, or too much of the same thing. I also want to give us time to rest if it was a long travel day the day before, or a late night. Once I confirm the schedule, then I start booking tours or purchasing tickets.

When I book varies. Most, if not all, tours and activities require immediate payment without a refund. Accordingly, I may wait a month before I start to book or even a couple of weeks, it really depends on how important one particular experience is and whether I think that the tour or activity could sell out. There might be something so important to me to see or do that I book right after I buy my plane tickets. However, that is unusual. Normally, daily tours and activities fall into two categories - 1. I really want to do “that”. So I book a month or more before we arrive; or 2. “I’d really love to do that, but if there isn’t room, I’d be happy to do something else”. So I book that a couple of weeks before we arrive.

If it is high season, you need to be more alert. Some things could sell out months in advance.

EVERYTHING ELSE

• How should you get from the airport to your accommodation?

• How should you travel within the location?

• Where should you eat, have a drink, or people watch? or Where are the closest grocery stores if you plan to cook?

• What night life are you interested in?

Whether these areas need advanced booking or if they can be booked once you are on your trip is complex. For example,

• If your research indicates that the best way to get from the airport to your accommodation is with Uber or Lyft, then you book once you arrive. However, if you are a family of 6 and you want to book a private van and driver, then you should likely do that a couple of weeks to a month before you arrive. If you are relying on a rental car, then you should book as early as possible for the reasons stated earlier.

• The same goes for travel within the location. If you are relying on public transportation or ride sharing, then nothing more needs to be done. If you need to book something more formal, like a private driver and car, then I would do this at least a month in advance. If you are relying on a rental car, then you should book as early as possible for the reasons that I stated earlier.

• If you are keen to try certain restaurants, then you may want to make a reservation a couple of weeks (or earlier if it is a popular restaurant) in advance of arriving.

• If you want to see a show or something else that requires tickets, then you will need to book depending on the popularity of that show and how important it is for you to see it. Accordingly, that could mean as soon as you book your international flights, or only a few days before.

BOOKING GUIDE

FLIGHTS1. Every item that you have researched and planned is in jeopardy if you can’t get to your destination, for the price that

you think is reasonable, or on the flight path that you would like.

2. For many trips, this could be the most expensive item for your holiday. I like to find the best deal early and get that expense out of the way.

ACCOMMODATION1. Having the right accommodation is important. I don’t want to settle on a place because that is what is left. I want to

choose a place because it is in an excellent location and has the amenities that I am looking for.

2. Booking early usually means the rooms cost less. As hotel rooms fill up, the cost of rooms normally increase.

3. I try to only book accommodation that I can cancel for two reasons:

A. If my plans change, I can cancel the room without penalty. Since I try to book accommodation early, it is very possible that I might change my mind about my itinerary.

B. If for some reason the cost of the hotel room decreases (normally because the rooms are not booking up), I want to be able to modify my reservation and take advantage of the lower cost (or even cancel if I have found an equally good hotel for a better price). I regularly check on the cost of the hotel leading up to my trip.

TRANSPORTATION WITHIN COUNTRYIf I need to book flights within a country or a rental car, I also try to book these items early.

Flights

How early depends on two factors:

1. How many flights there are, the size of the planes, and the number of seats available.

2. How important that location is for my holiday.

If there is only one flight per week on a small plane and the destination is the main reason that I am going to the country, then I will likely book soon after I book my international flights. However, if there are multiple flights on large planes at reasonable costs, and I am ambivalent as to whether I go to that location, I might wait until a couple months before I book. Again, you do not want to wait too long as the cost of the flights will eventually go up as the planes fill up.

Rental Cars

The cost of rental cars is also a product of demand. If you book early, you will likely get a better rate than booking last minute. However, rates can decrease if there is less demand at the car rental agency than anticipated. Accordingly, like hotel rooms, if your rental car reservation is cancellable, you can modify or cancel your reservation if you find a better deal. I like to lock in a rental car early and then, continue to check back on the cost leading up to my trip.

Private Car and Driver

Usually you are required to pay in advance for a private car and driver. Accordingly, I am cautious about booking this too early unless I am absolutely certain of my travel plans. However, if my research has shown that there is limited number of services offering this or that there is a risk of the cost increasing if I wait too long (because the less expensive services will usually be booked first), then I will book this soon after International flights, accommodation and other internal transportation has been finalized.

DAILY ACTIVITIESI like to have a plan for each day of our trip. Even if it is a “sleep in, hang by pool, and shop”, I like to take a look at the overall plan for the trip to see if we will be doing too much, too little, or too much of the same thing. I also want to give us time to rest if it was a long travel day the day before, or a late night. Once I confirm the schedule, then I start booking tours or purchasing tickets.

When I book varies. Most, if not all, tours and activities require immediate payment without a refund. Accordingly, I may wait a month before I start to book or even a couple of weeks, it really depends on how important one particular experience is and whether I think that the tour or activity could sell out. There might be something so important to me to see or do that I book right after I buy my plane tickets. However, that is unusual. Normally, daily tours and activities fall into two categories - 1. I really want to do “that”. So I book a month or more before we arrive; or 2. “I’d really love to do that, but if there isn’t room, I’d be happy to do something else”. So I book that a couple of weeks before we arrive.

If it is high season, you need to be more alert. Some things could sell out months in advance.

EVERYTHING ELSE

• How should you get from the airport to your accommodation?

• How should you travel within the location?

• Where should you eat, have a drink, or people watch? or Where are the closest grocery stores if you plan to cook?

• What night life are you interested in?

Whether these areas need advanced booking or if they can be booked once you are on your trip is complex. For example,

• If your research indicates that the best way to get from the airport to your accommodation is with Uber or Lyft, then you book once you arrive. However, if you are a family of 6 and you want to book a private van and driver, then you should likely do that a couple of weeks to a month before you arrive. If you are relying on a rental car, then you should book as early as possible for the reasons stated earlier.

• The same goes for travel within the location. If you are relying on public transportation or ride sharing, then nothing more needs to be done. If you need to book something more formal, like a private driver and car, then I would do this at least a month in advance. If you are relying on a rental car, then you should book as early as possible for the reasons that I stated earlier.

• If you are keen to try certain restaurants, then you may want to make a reservation a couple of weeks (or earlier if it is a popular restaurant) in advance of arriving.

• If you want to see a show or something else that requires tickets, then you will need to book depending on the popularity of that show and how important it is for you to see it. Accordingly, that could mean as soon as you book your international flights, or only a few days before.

BOOKING GUIDE