If you are anything like me, you need at least one trip planned at all times. Sometimes, you build an itinerary around a timeframe while other times, you build an itinerary to know what your timeline should look like. I will explain both methods in this article so let’s start with the major question…

Where or when are we going?

My husband and I go on a trip for our anniversary every year. Both of our birthdays and anniversary fall into the month of October so we decided in the beginning that we would focus on experiences instead of presents. We do not buy each other “gifts” until Christmas. We plan a trip and do a fancy dinner while there. This year, we are planning around a school schedule. Fall break is a 4-day weekend in October. This timeframe will determine our location which started our planning with the “when are we going?”

Other times will revolve around a location. Two years ago, we decided to go on a cruise for our anniversary trip. This cruise ended up being in November so the “where are we going?”determined our trip for that year

I like to have certain itineraries planned for whenever the time is right to go. The two itineraries that I am referring to, of course, are in Europe. Flights to Europe usually determine when we can go and so I have planned itineraries of our “must do’s” so I know the minimum amount of time needed for those trips. This method has other benefits too. I know exactly how much the trip would cost so we can start saving money and it gives you something to look forward to.

Flights

As mentioned above, flights are the biggest cost when going on a trip. It truly can make or break a trip. One thing I like to keep in mind is that convenience is almost as important as cost. You wouldn’t want to have a 10 hr layover if you are going for four days.

My biggest tip for looking at flights is to use “google flights”. You can enter a destination without dates to find the cheapest flights within six months. You can enter your specific dates of fall break and search for the cheapest destinations.

Must-do’s

The first thing I do when I start planning my itinerary is looking at the most important stuff. For my trip to Portland, I really wanted to visit “Halloweentown”. When you do your research, the weekend has the most activities. So as a rule of thumb, we would spend all of Saturday exploring “Halloweentown” and use the first two days exploring the city.

Always check for events or conflicts when you are looking at activities. For example, you wouldn’t want to spend a Monday exploring the Trevi Fountain because that is when they do the fountain cleaning.

Reservations

I am all for a spontaneous trip and site seeing. However, you wouldn’t plan a trip to Washington DC and expect to take a tour of a federal building without a reservation.

Reservations help to not waste your limited time. An example of this was when I went to Nashville with my best friend. We wanted to go to Puttshack, a bar and adult miniature golf course. We showed up and wanted to get a playing time before dinner. The next available time slot was in two hours. We sat and waited at the bar until then because we had already paid for our parking. Luckily, they had a table available for us to sit and order dinner.

Food

We are foodies. We love trying local restaurants and food spots whenever we are traveling. Our rule of thumb regarding food is that we need to eat somewhere that does not exist back home. I am searching hidden foodie spots on Tik Tok and will plan a day around it as well. To us, this is just as important as a “must do” activity. Some places are nicer and are only open for dinner while others have a good happy hour deal.

Write sh*t down

I am a planner but I understand that other people are not. I may have an itinerary calendar going for our trip, however, I know that I won’t follow it down to a “T”. Creating a calendar itinerary gives you an idea of how much you can fit into a day. Let’s take a look at a before and after look of my Portland trip.

A normal person would think “I’m flying home on Sunday so I don’t have time for anything”. That was my exact thinking too. I put down my timeframe to be at the airport (before my actual departure time) and I can see that I still have all morning to explore some more. So once looking at this, Eric and I decided that we could do one more activity beforehand. Once that was added, you can still see that we have time to go out to eat afterwards.

When the time comes, I will say “we have enough time to go to these places today” and will spend the day actually enjoying these places.