How to Plan for a Trip

Trip planning and prepping is something that I really love to do.  The excitement of thinking about what we will be doing and where we will be going always gets my heart pumping.  But I also know that planning isn’t for everyone.  A few times recently, friends and family have commented on how our trips are so well planned out and how we don’t miss a beat (thanks guys!).  So while my advice might seem obvious to some, these are the steps that I take when planning an upcoming trip.

1.  Choose your destination / timeline.

  • How much time do you have off from work?  Is this just a weekend getaway or a Summer holiday?
  • Budget: Do you want to keep this on the cheap, or are you wanting to splurge?
  • Has a certain city / destination been on your mind for awhile?

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2.  Book Airfare & Hotel.

If you are flying somewhere, and you know you only have for example, 4 days, then go ahead and book your airfare right away.  When my time is limited I always try to get on the earliest flight out and the latest flight home.  I love to maximize my time during vacation.  If you are driving somewhere, then you have more flexibility and you won’t need to worry so much about departure times.

If you know how long you are going to be gone and where, then go ahead and book your hotel right away also.  Typically the sooner you can book your airfare and hotel, the cheaper the rate is.  I  personally love to do my hotel research on TripAdvisor.  I think that it is great to get other travelers opinions and pictures.  If budget willing, I always try to stay in a hotel that is in the “top 10” for the city that we are traveling to.  However, in some cities, where there are a lot more hotels, like New York City, I often shoot for the top 30.  I always check the rates through different travel websites, and through the hotel itself.  I have found that it often pays to join a hotel’s free rewards program; they will typically give you a discount just for being a member.  And if you are a part of  AAA, don’t forget to check for your discount.

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2. Start Researching.

Once I have chosen my destination and have a general idea about how much time I will have, I start researching what things I wouldn’t want to miss – the must do’s.  Typically I start my research here with TripAdvisor.  I will search for the city that I will be visiting, and go through the list of “Things To Do.”  I make notes of all of the top sites that I want to visit while traveling.  Then I move on to the travel forum for that city and look through the posts / search for advice.

For example:  search for “3 days in San Francisco.”  This will pull up itineraries that other people have used for their trips, and destination specialists suggestions for those itineraries.  This is where I find a lot of great ideas.  Reading someone else’s itinerary helps you to understand how much time to allot for different activities and often gives you a better perspective.

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3. Start a Word Document.

While up to this point I will have been taking notes about all of my ideas, it normally looks like a big mess.  This is when I start my word document, my travel itinerary.  I start with the basics.  I type out all the days I am planning on being gone, and if I will be in different cities, I try to mark where I will be each day.  (Although, the itinerary can still be flexible at this point.)  Then I start to plug in all of the attractions/activities that I want to accomplish while away.

It is a good idea to try and allot how much time you are thinking that you will need for each activity as well.  For example, you might only want to spend an hour at a museum that others may want to spend their entire day at.  It’s good to know what your interests are, and where you want to spend your time.  Also, I always account for travel time in my itinerary as well, whether just a quick train ride, or a several hour car ride.  I feel that it helps to better plan out your time.

4.  Time Check.

Once I have my basic itinerary planned out, I double check my timeline.  I go to the actual websites for the museums, restaurants, etc… and double check the times that the attractions are open.  After making adjustments to my itinerary,  I then often post my itinerary on TripAdvisor, just to see if my timeline looks good to others.

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5.  Book Hotels.

If you didn’t book your hotel at the start of your planning, then get on it now!

6. Bars & Restaurants.

Now that most of the grunt work is done, it is time to move on to the fun stuff, food and drink.  For this part, I use a lot of different platforms for research.  I am the kind of person who loves to keep notes about restaurants that I heard about on TV shows, or I might rip something out from a travel magazine and keep it.  So while I do look through my personal notes, I also do online research.  Here I do use TripAdvisor, but I also use Yelp and just simple Google searches, “Best Restaurant with a view Paris.”  If you have a favorite Chef, look to see if they have a restaurant where you will be traveling to, or even look at Anthony Bourdain’s travel guides.

If you find a restaurant that you really want to try, but it’s out of your price range, check to see if they have a happy hour, or dine there for lunch.  I always aim for a mix of restaurants – local haunts, famous places, street food, etc…  After picking out places to eat, I try to plug them into my itinerary based off of location.  This helps to cut down on the amount of time you might spend going back and forth.  Often the restaurant you want to try is very close to a major attraction that you will be going to.  And don’t forget to check opening times here too.  A lot of restaurants are closed on Mondays, or only serve lunch a few days a week.

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7.  Pack Light & Have Fun.

Travel time is here!  I always aim to pack as light as possible, and bring things that I can re-wear or easily launder on the go.  I make sure that I have my itinerary with me, along with printed copies of hotel /airline reservations (sometimes the internet service is lousy and it is helpful to be able to have your reservation number on paper).

While I have spent time working to put together my itinerary, I still check in with hotel concierge to see if I have missed any must do’s for the city I am visiting, or if they might have any inside knowledge on a special tour, etc…  But since all of the work is done, you can just completely enjoy your time.  No need to worry about when the shop is opening, or when the museum is closing, or where you will get lunch – it’s all done!  The only thing that I do try to do, is make notes of change on my itinerary, or likes/dislikes.  This way, if I ever go back to that destination, I have an even better idea of what to do.

Bon voyage!