by | Nov 23, 2021 | Blog, Executive Assistant

Creating a travel itinerary for your boss is one of the most important duties you’ll perform as an executive assistant. A well-organized travel itinerary can make an executive’s business trip and save them a great deal of stress and time. It also showcases your attention to detail and time management skills as an EA

Creating a travel itinerary is a lot of responsibility, even for the most experienced executive assistant. But not to worry, we’ll run you through exactly how to put together a successful itinerary for your boss.

Creating a Travel Itinerary for Your Boss

There’s a lot to keep in mind when planning a business trip for your boss. You have to book their flights and make hotel reservations. There’s creating daily agendas and aligning schedules. You will be combing through the small details and little extras. And even after you’ve done all of this, you need to be ready for problems or last-minute changes. There’s a lot to consider.

Discuss Their Travel Preferences

One of the first and most essential steps in creating a travel itinerary for your boss is understanding their personal travel preferences, especially if it’s your first time booking a trip for them. You want to be on the same page from the start.

Flight considerations:

  • Do they have a preferred airline? Or do they collect air miles for a particular airline?
  • What are their seating preferences? Do they expect to fly business class? Window or aisle? Front or back of the plane?
  • What’s their in-flight meal preference? Do they have any food allergies?
  • Are layovers okay, or should you pay more for direct flights?

Transportation preferences:

  • What is their preferred transportation style? Do they like a hire car, private driver, rideshare service, or public transport?
  • Should you book transportation in advance, or would they rather do it when they arrive?

Accommodation preferences:

  • Do they prefer staying in a hotel or a rented apartment or condo?
  • Any particular amenities they like to have? Such as an on-site restaurant, gym, pool, conference rooms, etc.
  • Do they want breakfast included at the hotel, or will they eat out?

Additional things to know:

  • Do they like to explore the city in their free time or do they like going back to their hotel to rest?
  • Will they want you to book any additional activities?
  • What about meals? Should you book business or personal dinners?
  • Do they prefer a digital travel itinerary or a printed paper itinerary?
  • Do they want a bare-bones itinerary or a super detailed itinerary?
  • Does the company have any corporate discounts you can use?

You can find out your boss’s preferences by asking them directly, asking other colleagues, or asking their previous assistant. Keep a document with these details, so you can refer to it when booking future travel.

Know The Purpose Of The Trip

Once you know your boss’s general travel preferences, it’s time to get down to the specifics of their upcoming trip. 

Understand the trip’s purpose:

  • What is the goal of the trip? Are they conducting research, attending a conference or business meeting, or pitching business to a client?
  • If a lot is going on during the trip, what are your boss’s priorities?

The objective of the trip will largely dictate the itinerary and travel plans. For example, if your boss is trying to impress a prospective client, you may want to book a nice hotel close to the client’s office with an on-site bar for post-meeting drinks.

Know The Details

Creating a travel itinerary for your boss requires knowing exactly where they need to be and when. Once you know the key meetings and events, you can plan the rest of the itinerary around them. Be sure to note the time, date, and location of every meeting, appointment, and business dinner or event.

Make Note of Non-Work Related Requests

Even if your boss is going away on a business trip, they may also have other things they want to do in the place they’re visiting. Ask if they have any personal requests and factor these into the itinerary too.

Non-work requests may include:

  • Meeting up with friends or family who live in the city
  • Keeping up with their exercise routine
  • Sightseeing and attractions
  • Eating at certain restaurants
  • Shop recommendations to buy gifts or souvenirs for their children

Creating the Actual Itinerary

Now that you know your boss’s preferences and the specific details of the trip, it’s time to create the travel itinerary.

Book From Door-to-Door

When you start booking, think about your boss’s journey from door to door. You’re not only securing the flight. You also need to reserve transport to and from the airport at each end. Put yourself into their shoes and think clearly about what they need at each stage of the journey.

Timing is Key

The when is just as important as the where and how when travel planning for your boss. Think about the time needed to get from A to B and factor it into the itinerary. Is there enough time for meals, filling in paperwork, or buying tickets on public transport? Make sure your boss doesn’t rush around at the last minute or show up late to important meetings.


  • How long ahead of their flight do they need to arrive at the airport? 
  • How long will it take them to get to the airport, accounting for potential traffic?
  • How long will it take to get from their hotel to the client’s office?
A white woman stands at a desk with a monitor on it and papers in her hands

Be Mindful of Small Details

“The devil is in the details” is a saying which particularly rings true when travel planning. It’s the small details that catch you out and cause the most significant problems. And as an executive assistant, it’s your job to be mindful of these small details when travel planning for your boss.


  • Have you taken time zone differences into account?
  • If your boss arrives before the hotel check-in time, will they store the luggage?
  • Does the hotel have good Wi-Fi in the rooms?
  • Do local buses take credit cards or will your boss need local currency?
  • Is there a ‘Plan B’ if something goes wrong like a hotel cancellation or flight delay?
  • How can you help from the office if your boss experiences a delay?

Think of ‘Little Extras’

Aside from the key travel plans, there are plenty of ‘little extras’ that will improve your boss’s trip and make you stand out as a fantastic executive assistant.

Extras to consider include::

  • Putting together a packing list based on the local weather forecast
  • Ordering extra business cards for the trip
  • Downloading city guide apps or local transport apps onto their phone
  • Compiling a list of restaurant recommendations
  • Researching things to do during downtime
  • Packing healthy snacks for the plane journey

Make Sure Travel Documents Are Updated

Don’t let all of your travel planning go to waste by letting your boss get to the airport with an expired Passport. While you’d like to think they keep these things up-to-date themselves, don’t take this for granted.

Before the trip, double-check:

  • Are your boss’s passport and driver’s license expired?
  • Is their travel insurance up-to-date?
  • Do they need a Visa for traveling out of the country?
  • Do they need any vaccinations for the country they’re visiting?

Stay Organized and Keep Details in One Place

The final travel itinerary you give to your boss should include all relevant travel documents and information in one centralized location. You can create a digital travel pack or a physical wallet. Or both if you want to be extra prepared.

The travel pack should include:

  • A daily schedule with all locations and times
  • Booking details for flights, hotel, and transport
  • Contact numbers for the airline, hotel, and transport companies
  • A list of names and phone numbers of your boss’s overseas contacts and any colleagues they’re traveling with
  • Boarding passes
  • Any necessary visas
  • Insurance policy documents
  • A copy of their passport and driver’s license
  • A packing list based on the weather forecast
  • Any extras, such as a map of the city or local restaurant and attraction recommendations

You could consider using a travel planning tool such as TripIt to help keep all of these details organized in one place.

Hire An Executive Assistant to Plan Your Next Business Trip

A well-planned travel itinerary can make or break a trip. If you’re looking for an assistant to plan your next business trip, LifeSquire can help. We help you find, interview, and train the ideal executive assistant. Contact us for more information.


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