How to Create the Perfect Travel Itinerary for a Boss

Four Parts:Planning the TripBooking the TripOrganizing the ItineraryBeing Ready for Problems

Putting together a travel itinerary for a boss does not have to be an exhausting process. With careful planning, both you and your boss will be ready for whatever may befall a planned trip.

Part 1
Planning the Trip

  1. 1
    Meet with your boss to discuss their travel preferences. Is he a smartphone junkie aware of every app from A to Z? Is she a luddite who uses a flip phone and buys maps at the gas station? Before you construct a travel itinerary for your boss, you need to learn how your boss wants to access the itinerary, as well as their likes and dislikes.
    • What do they want to prioritize: their comfort and convenience, or saving company money? (Your boss's preference here will help guide borderline decisions that come with your planning.)
    • Do they prefer digital itineraries or paper itineraries?
    • What kind of seats do they like?
    • How much detail do they want in the itinerary?
    • What corporate discounts would they like to use?
    • How do they want to spend their time before and after meetings?
    • Do they want to invest in a travel agent? [1][2]
    • Such questions can be helpful in charting a path forward so that you and your boss can be on the same page in building a great travel itinerary.
  2. 2
    Get insight from colleagues who know your boss better than you do. Sometimes your colleagues have already had experience with your boss's travel. They may know things your boss finds essential in an itinerary.
  3. 3
    Know the purpose of your boss’s trip. Whether your boss is traveling for business or pleasure, you will want them to be as prepared as they can possibly be. Think about the impression they'll want to make on the people they meet and what they'll need to make that impression.
  4. 4
    Prepare a checklist of items suitable for the trip. A business trip will likely require a mobile office- include in the checklist any and all mobile versions of items the boss typically uses to conduct their work.
    • Consider phone chargers, adapters for foreign countries (if necessary), flash drives, tablets, batteries, and business cards. [3]
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    Make sure your boss has the essentials packed for the trip. Before departure, you may want to contact the boss to double-check that they didn't forget anything.

Part 2
Booking the Trip

  1. 1
    Search for the most cost-effective or the most convenient flight. If the trip requires air travel, it’s best to investigate multiple options for the best flight and/or hotel. Kayak will cross-compare a variety of travel sites to pinpoint not only the best current price, but also if the price is likely to get higher or lower if you were to purchase the ticket or reservation later. [4]
    • If your boss has indicated a preference for convenience, you may end up choosing a slightly pricier flight that suits your boss's needs.
  2. 2
    Assess whether a travel agent would be helpful for your boss’s particular trip. [5]
    • Travel agents can generally contribute more of their know-how if the trip involves indirect flights, international travel, or refundable tickets. [6][7]
    • If your boss has a preferred travel agent, definitely work on establishing a strong relationship with this person. Be kind and grateful and aware of their services. You never know when the agent may be able to get you or your boss out of an unforeseeable travel jam.
  3. 3
    Schedule your boss’s arrival for the night before any meetings. You want to allow as much flexibility as possible in case of delays. Plus, your boss will be able to focus on preparing for meetings rather than on getting to the meetings on time. [8]
  4. 4
    Look for direct flights rather than indirect ones. Whenever you can eliminate possible complications, do it. Indirect flights tend to introduce gate changes and delays.
    • If a layover is inevitable, search for flights with shorter layovers. [9]
  5. 5
    Ensure your search is accounting for alternate airports. If your boss’s meeting is in Washington, D.C., for example, you’ll want the search to account for Reagan (DCA), Dulles (IAD), and Baltimore (BWI).[10]
  6. 6
    Find your boss a comfortable seat. A service like SeatGuru provides detailed analysis on aircraft seats and their legroom, window access, ability to recline, and proximity to lavatories.[11]
  7. 7
    Consider budget air carriers like JetBlue and Southwest that Kayak does not include in its searches.[12] These airlines may provide better deals. Also, if your boss likes to work on the plane, JetBlue has been highly rated for its WiFi connectivity. [13][14]
  8. 8
    Learn if your boss has frequent flyer miles or corporate discounts. Have the information ready for these miles and discounts when you book with the airlines. [15]
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    Consider package deals. If your boss needs a hotel and/or rental car along with a flight, purchase a package deal and save up to 50%. [16]

Part 3
Organizing the Itinerary

  1. 1
    Create a travel packet for your boss. The travel packet should include the following:
    • airport arrival time (at least two hours before the scheduled flight)
    • flight's airline
    • flight's number
    • departure and arrival airports
    • departure and arrival times
    • departure and arrival gates
    • destination hotel with address and check-out time
    • car rental information.
    • The packet should also have phone numbers for the hotel, the airline, and the travel agent (if applicable).
    • Include copies of your boss’s passport and driver’s license.
    • If your boss is traveling to a foreign country, supplement the travel pack with information on exchange rates, customs, and any security concerns for the country they are visiting. [17]
    • You want your boss to be able to find this important information easily. [18]
  2. 2
    Include information on car services in the travel packet. If your boss is not renting a car, they'll need a way to get around.
    • Ride-sharing services like Uber and Lyft have gotten popular and suit cost-sensitive or more casual bosses just fine. That said, some airports do not permit ride-sharing services.
    • For a boss seeking to spend on a more luxurious ride, allows you to reserve a chauffeured limo or car service in cities worldwide. [19]
    • If your boss wants a towncar rather than a limo, research the boss's destination to see what local companies offer towncar service.
  3. 3
    Include daily agendas in the travel packet. A schedule with specific meeting agendas and times should be handily accessible to your boss.
    • Consider scheduling cocktail hour or dinner meetings if your boss does well in more social settings.
    • Helpful additions to the daily agendas are weather predictions, a map of the area around the destination, and relevant driving directions.
  4. 4
    Map out your boss’s free time on the daily agendas in an easily readable font.
    • If you are familiar with your boss’s tastes, include information on nearby restaurants or events that your boss may enjoy during this free time. [20]
  5. 5
    Make sure your boss has a ready way to organize all trip receipts. A simple folder could do the trick. [21]
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Part 4
Being Ready for Problems

  1. 1
    Be calm. Think about all the times you traveled and ran into unexpected weather, delays, and other events beyond your control. Your boss may very well face travel hiccups, but you can work to be prepared if not everything in the itinerary goes to plan.
  2. 2
    Notify your boss’s bank of the travel plans so the bank won’t freeze any of your boss’s credit or debit cards. [22] You want everybody to be on the same page when your boss is out of the office.
  3. 3
    Establish a rapport with your counterparts in the meeting location. Before the boss goes on the trip, briefly introduce yourself over the phone to the destination hotel’s front desk and any relevant staff members involved in meetings your boss is set to attend. This is your chance to get a sense of what your boss is walking into, and perhaps if certain meetings are likely to go long or start on time.
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    Know how your boss wants to communicate when they are away. You’ll want to have a consistent way to get in touch with each other. [23]


  • Use templates. Some who have planned itineraries for bosses or others in the past offer their work for the edification of future planners. These existing documents can help form the basis for a better itinerary for your boss's upcoming road trip, whether it's just for a rough comparison or if there happen to be actual parts of the document that are closely based on the template.
  • It cannot be stressed enough that your boss’s preferences will determine how detailed of an itinerary you should make. Some bosses prefer a bare-bones itinerary; others want specific detail on each and every stage of their trip. Either way, you should maintain for your own knowledge a detailed itinerary for reference.
  • There are many mobile apps that consolidate travel planning. Apps like TripIt and Hotel Tonight have been positively reviewed. [24] Install them (and others) on your phone and experiment with their various features. Gauge whether or not they would be a good fit for your boss.

Sources and Citations

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Categories: Interacting with Bosses