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  • Writer's pictureAmy Leggett

How to Plan Your Best Vacation Yet!

Updated: Jul 23, 2022

I love traveling! That's why I decided to start this travel blog. But I also love PLANNING my trips. I truly enjoy scouring the internet to figure out where to go and then really digging in to make the most of my time in the location I choose to visit. Time spent researching and planning your trip before you go generally makes for a more enjoyable relaxing vacation. This is not to say you shouldn't be flexible and leave time and space in your schedule for unplanned exploring and relaxation. But having a general framework for your getaway from the outset ensures that you have time to fit in all you want to see and do so you can just relax and enjoy!

Here are the steps that I generally take when I decide it is time to plan my next trip:


Sometimes this is the hardest part! If you are like me, you have a Travel Bucket List a mile long that gets longer every time you see friends' pictures from their latest adventure, Instagram Travel Accounts or Pinterest posts. My mind flits from one place to the next with anticipation and honestly I can get overwhelmed. To narrow it down, I consider the following:

  • Time of Year. What is the best time to visit some of your top spots? When you are planning to visit correspond to the activities you want to enjoy? Avoid the rainy or hurricane seasons in the warm weather locales. You don't want to spend the whole time hunkered down in your hotel room. Also, if you can, avoid peak tourist season and try to hit the "shoulder season" which is right before and right after the peak season. Not only will it be less crowded, but you may be able to find better deals. Finally, make sure you aren't going to be visiting a location during the slow season or during an important local holiday as places may be closed or have severely restricted hours/services.

  • How Much Time Do You Have? If you only have a few days, choose a smaller location or somewhere close by. You don't want to spend a big chunk of the limited time you have traveling back and forth. If you plan to take a longer vacation, you can travel a further distance and should choose a location that may take longer to fully explore.

  • Who Are You Traveling With? Whether you are going on a solo trip, a family vacation, a girl's getaway or a romantic rendezvous will greatly influence where you decide to go and what things you want to do when you get there.

  • What Is Your Budget? Have you saved for that dream vacation you finally get to take or are you looking for a budget friendly getaway? As noted above, if you can hit the "shoulder season" of a location you are considering you may be able to find some deals.

  • Do You Need a Passport or Visa? Make sure you know what documentation you need to visit a specific location. Some countries require a visa in addition to your passport. Even if a visa is not required, certain documentation may be required for entry. Check out to determine the requirements for places you are considering. If you need a passport and already have one, check the expiration date to make sure that your passport will remain valid for the entire length of your planned trip. If you need to get a new passport or a visa make sure you can secure those documents prior to your departure date. Check the State Department's website at to check out the latest passport processing time estimates. As of June 2022, the State Department estimates that expedited applications (which cost a bit more) are taking 5-6 weeks and routine processing is taking 8-11 weeks (which does not include mailing time which may vary by region). The time required to secure a Visa may vary depending on the Embassy you need to work with to get visa approval.

  • Special Events. One thing I like to do when narrowing down my travel choices, is to see if there is any kind of special event I may enjoy during my trip. Often I will attend a concert or a sporting event in addition to my "touristy" activities. Review the tour schedules of your favorite bands or the game schedules for your favorite sports team. If they line up with one of your possible destinations, that can help make your decision. I went to see Zac Brown Band at Bridgestone Arena in Nashville, Tennessee during one of my trips and was able to secure Pit tickets at a very reasonable price! They were some of the best seats I have ever had at a concert and made the whole trip especially memorable


  • Book your flight.

  • Reserve accommodations. Consider whether you want to stay in a hotel or an Airbnb. This decision will be based on price, location and space needs. While initially an Airbnb may seem cheaper, make sure to look at the total cost for your stay as additional cleaning and booking fees are added at the end of booking which may erase any potential price disparities. Even if the Airbnb is more expensive, you may save money in the long run by having access to a kitchen to make some of your own meals. I especially like having access to a refrigerator and kitchen for breakfasts and snacks. In Venice, Italy we stayed at a beautiful Airbnb with a nice kitchen and made our own home cooked Italian meal with fresh ingredients from the local food store around the corner. It is a special memory and one that stands out from an incredibly memorable trip. Check out the scene below. Regardless of whether you stay in a hotel or Airbnb, I highly recommend skimming the reviews to confirm that the location is good, what amenities are available, and notice if there are any consistent complaints (about cleanliness, noise, service, etc.).

  • Do you need a rental car? Consider whether there is adequate public transportation that you can utilize to get around and do all the things you plan to do. Can you join tour groups to do those things that are further away? Are you within walking distance of most sights? I often utilize the 48 hour ticket most hop on/hop off sightseeing bus tours offer to get back to certain spots I want to revisit after I take the initial tour. Many places also have access to taxis, Ubers or Lyfts that can provide needed transportation. Even if you decide you need to rent a car for certain things you want to do, can you just rent for a day or two as opposed for the entire trip? There is nothing worse then paying for a rental car that sits in the parking garage most days.


This is the fun part! The internet is the best tool to learn all you can about your chosen destination. I generally start with the Tourism website for the location. This gives you a general overview of the area and highlights the most obvious hotspots that the tourism board is proud of. Then I use Google search to find articles or travel blogs (like this one!) that provide useful insights and travel tips for the area I am traveling to. I will look at several different sites and notice what things consistently appear on the "Must See" lists. I take notes on any tips they provide about how to time tours, what things require prior reservations, and other helpful tips for making the most of the area. This research is also where I look for those lesser known spots that are charming or quaint and will provide a less "touristy" experience. Of course I want to see the Eiffel Tower when I am in Paris, but where are the places the locals frequent off the beaten path?


From the research, make a list of the activities and sites that interest you. Research the things the want to see and do so you are aware of best times to visit and whether you need to make reservations or buy tickets way ahead of time. (For example, if you want to tour the Pearl Harbor Memorial in Oahu, there are limited advance tickets and even fewer next day tickets that become available every day at 7 am. If you don't plan ahead, it is likely you will not be able to visit this well-known historic attraction.)

After I get the details for the things I have decided I want to do and see during my trip, I create a day-by-day agenda for each full or partial day I will be on vacation. When organizing this agenda, I consider the amount of time each activity will take, travel time to and from, will I need recovery or clean up time after a certain activity, are there sights/activities that should be grouped together because of location, does a tour or activity have to be done on a certain day or at a certain time because of availability, etc. I always cushion time frames in the schedule so I am not rushing from thing to thing and can relax and be present in the moment. I also make sure to leave open time so that I have space to include things that I discover while I am there. It is also important when creating your schedule to know yourself (and any fellow travelers) and anticipate if you will want or need afternoon refresher naps, early bedtimes, later start times, etc. Also, make sure you allow time for meals in your schedule. Nothing worse then being a hangry traveller!


If there is a tour or activity that you KNOW you want to do and it is a popular tourist attraction, consider booking your tour or buying entry tickets ahead of time. Once you have completed your itinerary, you will know the day and time for the tour/ticket. Hopefully your research indicated if a particular tour sells out early or needs to be done on a certain day or time so you will not be unpleasantly surprised and need to rearrange your carefully crafted schedule. I also recommend checking out for packages that group together tickets to popular attractions at a discounted price. Usually these tour packages include "skip the line" access to the attraction so you don't have to waste precious vacation time standing in entry lines. I DON'T buy tickets ahead of time if I am not concerned about it booking up or selling out so that I can maintain some flexibility in the schedule if I need to switch things around due to unplanned weather, new discoveries, or unanticipated delays. Make copies of all tickets and purchase confirmations so you have easy access to confirmation numbers, pick-up information (if transportation from your hotel is provided), address for attraction (if you have to get there yourself), meet-up time and other details. If I am going on a long trip with lots of planned activities, I will keep all this documentation organized in a folder that I bring in my personal item carry-on.


When it gets closer to your departure time, make sure you have done everything you need to do to take care of your home base while you are gone. Things to consider:

  • Stop mail or arrange for someone to bring your mail in so it does not accumulate in your mailbox alerting people that you are not home. Also consider whether you need to arrange for someone to take your trash out or care for indoor or outdoor plants while you are away.

  • Arrange for care of your pets. In-home visits by a neighbor (this is great job for a younger child in the neighborhood to earn some extra cash and learn responsibility!) or an in-home pet care company allow your pet to stay comfortable at home while you are wandering the world. My daughter has used a pet care company and they send daily pictures of her cat from each visit to reassure her that he is doing okay. An alternative is to take your pet to a traditional boarding kennel or cattery.

  • Call your credit card company to alert them that you will be traveling. Failure to do this may result in your credit card from being declined putting a big damper on your vacation!

  • Consider where you are traveling and whether an international cell plan needs to be considered. You can choose to rely on wifi to check messages or use FaceTime to keep in touch with loved ones, but wifi can be spotty in areas and leave you stranded or having to use costly international data.


Check out my separate blog on how to pack (and also how NOT to pack) here. Beginning to pack is exciting because it means your well-planned trip is getting close!


Your trip is here! All of your work to research and plan your great vacation will pay off. Relax and know that everything is in place for you to have an incredible, memorable getaway.

Bon voyage!

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