Planning the Perfect Trip | Pennies, Places, and Paws

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Top Vacation Planning Tips

One common thing that stops people from going on vacation to new places is that they do not know how to plan a vacation. Planning the perfect trip can be intimidating. From deciding where and how long you want to go, to the finer details of your day-to-day itinerary, there are several steps to get through all the planning stages. This guide will break these steps down so you know what you will need to do to successfully plan your next vacation. Get excited and get ready to learn how to plan the perfect trip so you can start exploring the country.

Road that fades into the distance. There are mountains in the background

Things To Consider When Planning a Trip

The first step is to consider what your vacation budget is going to be. A vacation in Alaska or Hawaii will cost significantly more than a trip to Arizona or Michigan. This will tie into the second step, which is to figure out what kind of vacation you want to go on. Do you want a vacation to see nature and wildlife or museums and shows? Do you want to relax or see and do as much as physically possible?

If you are traveling on a budget, make sure to check out these Low Budget Travel Tips.

Rolling hills and mountain scenery — (Visit Theodore Roosevelt National Park for nature and wildlife)

Once you realize what you want out of your vacation and what your budget will be, you can start looking at where you want to go. For example, if you want a budget-friendly vacation where you can see plenty of wildlife, the national parks in North and South Dakota would be excellent destinations. If you are looking to relax on beaches, then Florida is a great option that will provide different locations with different price ranges.

several foldable chairs with umbrellas on a beach — (Do you prefer to relax on a beach?)

Another factor to consider in the original planning stages is whether you want to fly or if you will want to plan a road trip. If you plan on making it into a road trip, then you will also need to decide how far away you are willing to drive to get there.

Don’t forget your pets if you have any! Will they be coming with you? Then take a look at Best Tips to Vacation with Your Dog to make sure your vacation is pet-friendly. If you plan on keeping them at home, check out What Your Pet Sitter Needs to Know Post so you can relax and know that they are in safe and knowledgeable hands.

Vacation Planning Resources

Once a destination has been decided on, you will need to start gathering the resources to start planning the details of your vacation. One of the best resources for U.S. travel is the states’ tour guides which you can order or access online. Many of the states offer more specific guides based on your interests or the specific area that you want to go to. These guides will provide a list of places to stay and numerous attractions available in that state.

Display of several tour guides from different states — (These guides are an awesome resource to find out what the state has to offer!)

Pinterest is another popular resource for vacation planning. You can find links to different blogs that will give you details about different places with great suggestions about where to stay, eat, along with different sites to see.

If you are a National Park aficionado, then a National Park Passport would also be a great resource. The passport lists every National Park and Historic Site in the country with a nice little map of each state that shows where they are all located.

National Park Passport; the front cover and a shot of an inside page with Mount Rushmore on it — (It tells you all of the National Parks, etc. and has cool spots for your stamps!!)

If you are interested in visiting weird or unusual places then Atlas Obscura is a good resource. This website will list all sorts of museums and roadside attractions available.

Planning the Itinerary

Once you have your travel resources, start making a list of anything that piques your interest. Once you have your list, then you need to start compiling the basic information about each stop. You will want to find out if the place still exists, what the hours of operation are, an overview of what it is, the price, and how long people typically spend there. As you find this information, some of the places on your list will start being cut from your final itinerary.

Go back over your list and rate the places according to whether you consider it a “must-see”, a “would like to see”, or “not that interested”. This list is what you will need for the next step.

Setting Your Road Trip Schedule

Pull up a website or route planner like MapQuest. This tool is going to be your best friend. Enter every location on your list into this system and let it populate a potential route for your road trip based on the least amount of time in between stops. Decide which stop will be first; this will be based on which stop is closest to your starting point.

(Sample of a Day Itinerary with Tentative Budget and Notes)

This is where the hours of operation and the average amount of time spent at each stop come into play. Use that information, to estimate the times you will arrive and leave each stop. You may have to adjust the route that MapQuest set up to accommodate the stops that you “must-see” to match the times that they are open. You will also decide on where you will be spending the nights during your vacation at this point (hotels, campgrounds, etc.).

As you decide on the times that you want to arrive at your first stop of the day and how full you want your vacation itinerary to be, continue to design your trip schedule. Adjust as necessary as you add, subtract, and reorganize your route accordingly. Do not forget to keep your vacation budget in mind as you decide on your finalized list of stops and places you will stay. Once you have selected the order of your stops, double-check the map to make sure that it visually makes sense. Sometimes the route planner will make a change to your itinerary that you did not catch or did not want. This will help make sure that there are no surprises.

Map of South Carolina — (Sometimes it helps for me to highlight the places I plan to visit on a map so I can visualize where everything is in relation to each other when I make the tentative schedule for a trip)

The route planner will also most likely be able to calculate an estimate of how much gas you would need to accomplish your trip. This is helpful if you are creating a budget and with your financial planning for your trip.

If you are trying to see as much as possible on your vacation, do not forget to make sure you have enough time to eat and set up camp if necessary. You will also want to add some cushion to your itinerary in case you run into traffic or other surprises.

Vacation Planning Tips

A few weeks before your actual trip, I suggest re-confirming your itinerary to make sure all your stops are still open and have the same hours. This way you will have time to make any necessary adjustments.

Make sure your car is road trip ready by following this Road Trip Car Checklist.

Be prepared for the unexpected. Make sure you have a backup plan of sorts in case you must change your plans due to weather or other unforeseen circumstances.

Trees are spaced out in the foreground. There are mountains in the distance. The sun is just starting to rise over the mountain. — (The Black Elk Peak trail in Custer Park was a hike that we squeezed into our itinerary after finding out about it during our trip.)

Know what you are willing to skip. If you find something better or a stop is more time-consuming than you thought it would be, knowing what you can cut out of your schedule will save you a lot of stress and frustration. It will be much easier if you do not have to scramble to make sudden decisions in the middle of your vacation.

Book Your Travel Insurance

Once you have planned your perfect vacation, it is time to take steps to protect it. Consider purchasing travel insurance in the event that something happens that you can’t control that may result in altering or canceling your trip. There are three main types of travel insurance to consider; Comprehensive, Limited/Travel Medical, and Specialty. Comprehensive give you the most coverage for your vacation including trip cancellation. Limited or Travel Medical typically covers illness and injuries that may happen during your trip. Specialty insurance targets a variety of specific circumstances.

Travel Insurance Master: Researching travel insurance options can be overwhelming. Travel Insurance Master's trusted algorithm recommends the best travel insurance for your travel needs to you can spend more time planning your vacation.

Consider using Travel Insurance Master to help you find a travel insurance company and plan to fit your exact needs and budget. There is even an option to help with veterinary care in case your pets get sick or injured while they travel with you OR if they get sick at home and you need to cut your trip short to be with them.

A perfect vacation

Though this process can be tedious and time-consuming, it is time well spent! Following these steps will ensure that your vacation will be filled with activities that you are excited about and that your trip will run as smoothly as possible. This means a relaxing and worry-free vacation so you can spend your energy enjoying your experiences and making memories!