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Organizing Life Travel

A Few Things to Consider When Planning a Trip

Planning a Fun Vacation

If you love traveling as much as I do, you get excited about your upcoming trip months before it happens.  I start imaging the places I am going to visit while I am there, learning more about the culture and people who live there, and the amazing food that I can’t have where I live. Planning for a trip is important even if it’s a weekend trip so you want to make sure that you take time to do that so you reduce forgetting things and spacing tasks out so you aren’t rushing and getting stressed right before your trip. Since I was 14, I have been the planner for our family.  The first time I did was going to Toronto.  I remember I headed to the library (this is before the Internet as we know it today) and researching all the places we should go to.  Also, looking at the map for the best route to get there because it was a car trip, and all the sightseeing we could do.  In another life, I would have been a planner of some sort.  This is how I plan trips for my family and me.

I first think about who I am traveling with and the activities they like to participate in.  My extended family is pretty close-minded about a lot of things.  Therefore, I tend to keep it “touristy” when I am with them.  However, when it’s just the kids and me, we tend to want to go to areas that usually locals attend and it’s not something that an average person would want to go to. I tailor my trip accordingly. We are heading to Toronto for my son’s 18th birthday (Side note: I can’t believe he will be 18! I’m still in shock).  Half the people like to explore while the other half doesn’t.  Therefore, I am working on finding a good compromise where everyone is happy.  This can be hard.  I always make sure to set expectations with everyone so they know what to expect and what they need to be willing to do a thing or two they are not usually into so that.  This will ensure that when we do arrive, they are not shocked or disappointed. 

If we have never been somewhere before, I make sure we make time to visit (at least) the key landmarks.  The food that area is known for is another part of this.  Food brings people together.  I always joke that the way to have world peace is by having people come together and share food.  When I am creating a trip’s itinerary, I always make sure to carve out time to check out the area’s landmarks and food.

I also make sure to check out the tours being offered in that area especially if I am with people who are not the types to go “off the beaten path.” When I went to New Orleans, I went on a great tour of the cemetery (I found out later that this is now the only way to go to the cemeteries in New Orleans)  I also downloaded a great app that had a walking tour that you followed, as well as a ghost one. Food tours are also a great type of tour to check out.

Communication is key.  This is especially true if it’s a big group.  If I am doing a trip with my family from Panama, we use What’s App.  If it’s just my family in the US, we use iMessage (we all seem to have iPhones.  If not, we would use WhatsApp).  It’s important to create a group chat so that everyone is aware of what’s going on, and you can keep track of one another.  When we went on the cruise, we created a group iMessage that all of us were a part of.  We tried using the Royal Caribbean app group chat, but they need to do some enhancements before it’s useful. I try not to overload everyone, so I just let them know the high-level that is basically to make sure that they pay on time (if money is involved) or when they need to be at a certain point so they don’t delay an excursion.

I keep the itinerary organized by using services like TripIt and TripAdvisor.  More and more, I have been using TripAdvisor. They have a great feature that lets you create a Trip and add all the places (e.g. landmarks, restaurants, tours, etc.) that you plan to visit and group it by day.  You can also share with your group and/or make it public so that others can use it for when they visit.  When I was younger, I used to overload the itinerary and it was very astringent.  It wasn’t until my partner told me after our 5th trip that I need to chill out a bit.  I now make sure there is wiggle room, and I don’t get too married to a schedule that can’t be changed if something more interesting comes along. 

Some of the ways that I find places to visit are Pinterest, YouTube, Reddit, and just searching.  The great thing is that someone has already been to where you are going and wants to share it with you.  I also make sure to use Google Calendar to keep track of things that I need to do before the trip (like finding a pet hotel for the dogs) and the main things we are doing during the trip. 

What are some ways that you plan for a trip? Please share them with me. You might teach me something new!

Planning a fun trip

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