Highlight Map Florence Italy

Where and How: 5 Simple Steps for Planning the Perfect Travel Itinerary


Flying in to Jackson Hole Planning a trip
Flying in to Jackson Hole

There are certainly things that I get overwhelmed about, but planning a trip is not one of them! 

When I have an idea to go somewhere, I just dive in to all of the planning and research and lose track of time. I’m all about making the most of any where we go, in case we don’t get to go back there again! That’s mainly because there are so many places on our travel bucket list, and we usually want to go somewhere new and exciting. 

Flying to Amsterdam Backpacking through Europe
On our way to Amsterdam

Don’t get me wrong, there are places that we have been to numerous times, like NYC and the Hill country.  I know, sound like two complete opposites, don’t they? They are! And we love both. We always enjoy new and/or favorite things to do at each.  Same with a couple of other places we frequent. Sometimes you just have to make a point to plan (that’s probably a four letter word to all of you free spirits out there!) new experiences, so you keep the trip fresh and interesting. 

Albert Dance Hall around Fredericksburg Texas
Albert Dance Hall around Fredericksburg Texas

This leads me to the point of the post. How to plan and schedule your itinerary. I want to share with you FIVE SIMPLE STEPS for planning your next totally enjoyable get away. 


Pick Dates. You need a date 1st in case you need to coordinate it with other people, and also to be able to research and schedule. Other people that you may need to confirm the date with could be your boss or co workers for time off, spouse or other travel companions, clients, kids, etc. You also may need to make sure people are also available on your selected dates such as babysitters, pet sitters,  housesitters, and any others you may depend on in your absence. Once you have a date you need a place!


Pick a place. I know in some instances you would want to pick a date secondly because you already have a dream destiination in mind and you want to plan to go at the perfect time of year. But if you want to plan a trip now and have your dates set, then you can narrow down places based on where are you would like to go in that particular season. So, somewhat based on the weather,  your budget, time frame, who you are traveling with, and what you want to do or see, you should now have the perfect vacay spot in mind. And now that you have a place and dates, the research begins.

View at Mama's Fish house at lunch during our Cruise of the Hawaiian Islands
View at Mama’s Fish house at lunch during our Cruise of the Hawaiian Islands


Google Flights, Skyscanner and Kayak are good places to to compare a variety of flights and prices. I also keep seeing Momondo, but I haven’t tried it. Let me know if you have and how you like it. A lot of times I will research here and then book through the airlines. By research I mean reading lots of reviews, not just comparing prices of who does and doesn’t charge for luggage. I gain so much insight into what has worked and hasn’t worked for travelers in the past, just by reading reviews. I pour over reviews from various sites on everything from airlines, hotels, sight seeing tours, restaurants, and museums, to locations in general. Just Google something like best places to stay Grand Canyon, or tours Vatican City or really anything.     

Laundromat Florence Italy
Laundromat Florence Italy

You may even need to google where to do laundry. 

I also Google Map locations of transportation (airports, train stations, subways, etc), hotels and activities so I can book the most convenient location in relation to where we are arriving and leaving from. I also take the location of the activities into consideration, if the city is walkable, and how early our flight out might be.

Backpacking through Europe Zurich Switzerland
Backpacking through Europe in Zurich Switzerland
Hotel Guerrini Venice
Hotel Guerrini Where we stayed in Venice

Expedia, Priceline, Trip Advisor, etc are good places to find hotels, rental cars and even flights and vacation packages. Again, sometimes I’ll book directly with a hotel after researching these or sometimes book multiple things on one of these sites. It’s all about the price and reward points for me. You will want to know how long it’s gonna take you to get to your destination and when you’re going to leave to start heading home. These dates are important because you don’t want to not have a place to stay one night or book too many nights! Also, these dates are your bookends and now it’s time to feel in the middle!    

ON a luggage cart at hotel
Playing around at the hotel


So the itinerary- the fun part! Whether you are staying in one location the whole time or you are moving to different stops towards your final destination, you will need to book accommodations and plan activities for each day. Even if you are going to be in one location all week you still want to space out your fun over your stay, and not realize on the last day that you are going home tomorrow and you haven’t done this, this and this. Before you skip on thinking I’m just going to stay on the beach and read the whole time haha, you still might consider what books to take, what restaurants to try or what meals to cook in your condo, etc.     

Restaurant Florence Italy
Love sidewalk seating like this Restaurant in Florence Italy

If you are going to be on the move tho, then obviously a plan ( there’s that four letter word again!) is going to be pretty important. You will want to consider how long it will take you to travel in between destinations and how long you will be at each location for sightseeing, trying  the local food/restaurants and any activities. Some of the restaurants may need reservations and some of the activities you might need to schedule in advance so that they are not booked when you arrive. It would be so disappointing miss out on something that was actually the point of being there in the 1st place.   

Vatican Tour Rome
Vatican Tour Rome

Knowing how much time you are spending at each stop will help you decide on what your priorities are there and which ones you won’t make it to this go around. Again, the reviews you read will help at this step.  I generally have a pretty hefty “must do“ list when traveling and I know that it takes time to get to (and sometimes find) the items on my list so I take that into consideration. List your activities by priority in case you have to skip something and then map them out considerably how much time each will take. Hopefully you have an exciting list of things to do, places to see and where you want to eat after reading comments from others. Now that you have it all planned out, it’s time to book it! 


This is where the research pays off for me. By this point I’ve read lots of reviews to decide on which hotels I book in each city, what activities I do as a tour, which actual tours to book, and rental cars or other modes of transportation I need to use.    

Mopeds Florence Italy
Many, many Mopeds!

Obviously, the hotels need to be booked in advance, but depending on popularity and what other travelers have recommended, I’ll go ahead and purchase tours, transportation and anything else I feel would be best to reserve ahead of time. Of course, I try to book with ‘free cancellations’, or ‘no change fees’ whenever I’m able to. 

View of Eiffel Tower from bike tour
View of Eiffel Tower from bike tour

Woohoo!! So if you followed these simple steps, you should be booked and ready to start packing for your trip! Notice I did not say quick steps. It will take you investing some time in planning your anticipated getaway, but It will be worth it when you arrive and you can enjoy your vacation without stopping continuously to try to figure things out. This is a good place for one note of caution though. Be flexible. It’s great to have a plan, but things don’t always go as planned. I have to remind myself of that constantly!

I’ve just followed  these steps once again and have booked a road trip for me, my hubby and our 16 year old Jack Russell-who has never traveled with us before. We are starting in East Texas, then NM, AZ and back to Texas. I’m really anxious to see how this goes!! If you are too, please follow us on all of our social media to keep up with our itinerary, experiences and no doubt, some twists and turns! Links below!

Hubby and I and dog by truck
Hubby, Trit, and I by our truck

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YouTube UC7ufPc1ugDAie-qfPcJzYOw

Blog https://travelandtell.com

Well I’m ready to start packing and I’ve purchased some things for not only this trip, but some of our travels in general. Maybe some of these things would be useful to you also. You can click on pictures for prices and links. Happy travels everyone!

This post may contain affiliate links and we may earn compensation when you click on the links at no additional cost to you. As an Amazon Associate we earn from qualifying purchases.

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66 thoughts on “Where and How: 5 Simple Steps for Planning the Perfect Travel Itinerary”

  1. I’ve used Momondo to search for flights after it was recommended to me and I think it’s worth checking though I usually take a peek at Kayak too. I’ll add Skyscanner to my resources for flights.

  2. We have a very similar style in how we approach vacation planning! Great article (and photos!).

  3. Great travel tips and I couldn’t agree more! Being flexible with your itinerary is very important when travelling.

  4. Planning is half the fun I agree! Great suggestions and guidelines for planning our next!

  5. Thanks for the travel planning tips! I feel like it’s been forever since I was able to travel, so I’ll need these once I can get out again!

  6. Planning to me is almost as much fun as going on the trip itself. The amount of time I spend planning trips drives my husband crazy, but he loves the results.

  7. Great tips to having a smooth trip! I’m big on research and when I buy things or go places I skis do my homework, I find research is key to getting things right! Thanks for sharing your guide!

  8. My husband is the one that plans our trips. They are always around sporting events for teams that he is working for, so we haven’t been able to go anywhere lately. I’ll have to keep this information handy.

  9. I miss traveling! ::cries:: Thanks for sharing the planning process. Definitely helpful if you haven’t planned a big trip before.

  10. Planning and researching is *almost* as good as going! The anticipation is so enjoyable. Thanks for the info!

  11. These are great suggestions. Very helpful for planning. Thanks for the reminders – always helpful to have a list to go through. And it looks like you are having a great time.

  12. Organization pays off (most times at least!). I can’t say I’m always as organized as I’d like to be about trips, though…some have gone better than others.

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