How to plan a trip, luggage and airplane

Plan A Trip Like A Professional Using Our Step-By-Step Planning Guide

Step by step planning guide on how to plan a trip

“Our step-by-step travel guide will walk you through how to simply plan a trip and relieve the stress of wondering if you have forgotten and important detail.”

Planning a trip can be exciting and stressful at the same time. Whether you want to travel locally or to a lush tropical destination overseas, it can seem overwhelming when you start to plan a trip. We’ll show you how to take the stress out of planning. Using our “step-by-step guide for travel planning,” you can feel confident you haven’t forgotten any details.

When you are in the process of planning a trip, there are so many things to think about; destination, budget, accommodations, transportation, adventures, packing, and safety, to name a few. It can be stressful. We get it. We have been there!

There are so many details that you have to take care of. At times, it’s hard to remember if you have them all covered or are overlooked something. I used to panic as we got closer to the date for our trips. I was so sure I had forgotten something important. After much trial and error, planning a trip now is almost as exciting as the trip itself.

I love scouring the web for travel deals and searching through Pinterest and Instagram for destinations and things to do. We are by no means professionals at planning a trip, but hey, that would be a great job! There is excitement knowing that you have all the details taken care of and can enjoy the trip from the time you leave for the airport or pack your car.

I wish I could say that nothing will go wrong because you did your homework and planning, but we all know better. If we plan right, when those little things don’t go the way we want them to, you will be prepared for that, also.

If you don’t like planning a trip or are new to planning, this step-by-step guide was written for you. Gary and I (Michelle) travel as a couple, and what we share is focused on traveling as a couple, but it can easily be adapted for single or family travel.

Steps to plan a successful trip

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1 ~ Set your budget

Travel money in a jar

The first step when planning a trip is to know your budget. For some of us, vacations come once or twice a year, and for others, only every couple of years. In between those trips, we are saving for our next adventure.

You need to be thinking about your travel budget long before you plan a trip. Even if you plan on putting it all on your credit card, knowing a budget helps keep those surprises at a distance. Not only should you know your budget, but you should also know how much of a cushion you can handle. We also plan for unexpected adventures that might present themselves along the way.

How to set your budget ~ If you have been saving and planning for a trip, you will have a ballpark number of what you can spend.

Your budget is your guidelines, it will determine many things. With the right planning, you can have an unforgettable trip on almost any budget.

If your budget is tight, you may want to plan a trip closer to home. We have found some amazing places not far from home that we didn’t know existed until we started looking. If you have wiggle room in your budget, you might be able to go on a more elaborate trip.

Break your budget into the number of days you will be traveling. Example ~ If you have a travel budget of 3000 and you are planning to vacation for 10 days. Subtract the cost of the airlines and then divide the remaining by 10.

Budget 3000
Airfare -1000
Remaining budget for 10 days is $2000 or $200 a day for accommodations + transportation + activities + food.

Breaking it down like this is helpful when it comes time to figure out the rest of your details. It will help when you start making the decisions of hotel vs Airbnb, rental car vs uber, etc.

Your budget will help you with all the next steps. It will determine your destination, length of stay, and type of transportation. It will also play a key role when looking for accommodations and the kind of activities that will have your attention.

2 ~ Choose your destination

Travel map with tacks

This is exciting!! Researching and planning get the adrenaline going. At this point in the planning, anything is possible. You can go anywhere. We have even pulled out the paper map and just chose a place to visit. Unless you are really adventurous, you may want to save this option for someday.

With any place a possibility, it’s time to narrow things down a bit. Once you know your budget, sit down together and get a feel for the direction of your tip. Is it going to be that dream destination that both of you have longed to visit? Are you going to visit someplace adventurous, or are you looking for relaxation and romance?

Maybe it’s a romantic getaway (our favorites), a honeymoon (CONGRATS), a road trip, or something as simple as a weekend getaway,

Knowing what you are looking to gain from your trip will help you decide on a destination. A road trip is great, just because you have a day off and are looking for adventure, a weekend getaway because romance is on your mind, or a two-week trip to Bora Bora for relaxation, adventure, and romance.

Gary and I met later in life, and we have both traveled to many places. He has been to places I have not, and I have been to places he has not been. Then there are places that we have both been to but not together.

When we plan a trip, we have the unique element of deciding if we will be going someplace new for both of us, if I take him someplace that excited me when I visited, or do we go someplace that he wants to show me.

On some of our trips, I get to feel like the tour guide, and other times it’s like I have my own personal tour guide with me.

Tips to use when picking your destination

Look for inspiration ~ Deciding where you will be traveling to is the most important part of planning a trip. When it comes time to plan a trip to someplace that is new to both of you, start by looking for inspiration. The best way to get inspired is from other travelers. Start with Instagram, Pinterest, and Travel Blogs

Build your own bucket list ~ Create your own Pinterest boards with categories for the type of travel and places to visit that you both wish to do as a couple someday. These dream boards or travel bucket lists can be your inspiration when you start planning.

I even use the note section on my iPhone and jot down destinations and why I’m adding them to my list. These might be destinations that I read about in the magazine while waiting at the doctor’s office or from a conversation I overheard in the coffee shop. We have gotten some great ideas that way.

Do some preliminary searches for airfare and accommodation rates. When you plan a trip and have things narrowed down to a couple of destinations, do a quick search of flights and hotels on Skyscanner. Skyscanner will show you the cost of flying anywhere in the world from your closest airport on different dates. We have found some places that we might not have even considered otherwise.

When you are choosing your destination, there are many things to take into consideration.

What will the weather be ~ if it’s the middle of winter at home and you are headed someplace warmer, fantastic, but if it warm at home and you are headed to that same destination, you might be headed someplace where the temperatures are unbearable.

When are the local holidays ~ If you are traveling to another country, be sure to know their holidays. Depending on what you plan to see and do, you don’t want to visit when things are closed because of a local holiday or customs.

Is it Spring Break ~ If you are traveling anyplace near the spring break dates, make sure you are traveling is not a hot spot for spring break travelers unless you don’t mind sharing your romantic moments with thousands of travelers on spring break.

When is the peak tourism season ~ Know when the peak tourism season is for the area, you are traveling to. It could be hard to get a hotel room during peak season, and attractions might be very crowded. Likewise, during the off-season, you may find some of the places you wish to visit are closed.

Find out your passport or visa requirements

passport and travel documents

When deciding on your destination, be sure to check into the requirements. If you are traveling out of the country, you need a passport and maybe a visa. Depending on how soon you are traveling, you will need to make sure there is time to get the needed documents for your travels. During busy travel times it can take longer for your passport.

If you don’t have a US passport, I would ask why not. It opens up the whole world! Check out the US website to get the ball rolling you ~

US Passport

If you don’t know if a Visa is required for the country you will be visiting. You can check out your countries visa website ~

USA Travelers
Canadian Travelers
UK Travelers

Looking for more…Check out a few of our other posts…
Tips for Traveling as a Couple
Unique Gifts for Travelers

3 ~ Determine the length of your trip

Calendar with trip dates

One week? Two Weeks? A 4 day weekend? Just overnight?

When it comes to time to plan a trip, there is no right or wrong answer. Every trip will be different. If you are lucky, you will have a combination of trips of different lengths throughout the year.

For each trip we take, these are the things we consider

Finances ~ Knowing your budget when you start to plan a trip is key. The longer a trip, the more you are going to spend.

Time available ~ You need to look at how much vacation time you have available and can afford to take. Some employers only give you a week or two off from work a year. You will want to use this time wisely.

Location of your destination ~ The location of your destination will play a key role in determining the length of your trip. If you are traveling overseas and will be changing planes with possible layovers, this could take up to a couple of days out of your vacation. Add that to both ends of your trip. It could cut your vacation really short.

Don’t forget the time change. Most travelers lose the first day or two of their trip due to jet lag. When my daughter flew from the states to Japan, her first week in Japan, she was miserable. Had she only vacationed for a week, it would have sucked. Good thing for her she had planned for several weeks of vacation.

The time needed to enjoy and relax ~ When it comes time to decide on the length of your trip, consider the activities you hope to do while on vacation. Make sure you are planning enough time to really enjoy them. Keep in mind that you don’t want to plan every minute of your schedule. Give yourself some downtime and some free unexpected adventure that may present themselves. We like to have one day fit into our schedule where we have nothing planned.

4 ~ Create a ‘tentative’ itinerary

activity brochures to use when planning a trip

Once you have decided on your destination and how long your vacation will be. Now the fun really starts.

If you are traveling as a couple, each partner should make their list of potential sights and activities that interest them. It’s okay if everything on your list does not match your partners. Even though you are traveling as a couple, it does not mean you have to spend every minute with each other. After all, we may be a couple, but we each have our own likes and dislikes.

If for a part of one day you each explore something different, later that afternoon, when you both meet up for a couple’s massage, it’s even more exciting to be back together.

Do your research and find those fun and interesting things to do. Again use Instagram, Pinterest, and Travel Bloggers to get you started. We also like to use Trip Advisor and Airbnb to find amazing places.

The visitor center in the city where you are going to vacation can also be of some help. Keep in mind that visitor centers work for the city, and it’s their job to sell you on something. We have gotten great leads this way, but we have also been steered wrong. Also, double-check for reviews on places.

What you do for activities really should be what you enjoy. I have heard some say to skip all of those popular tourist destinations, and others say those are the things you must do.

Let’s be real, there really is no must-see or must-avoid attraction or city.

If you enjoy popular tourist destination, then by all means, put them on your vacation list. After all, they became popular for a reason. And if you are set on avoiding those attractions, then keep them off your list. It’s your vacation you plan your trip your way!

Remember, no matter how much time you have, you can’t see or do everything. How many of us have things in our hometowns that we have not even done yet?

Decide on the things that you must do, the things that you can’t not see or do. Trust me, you will have so much fun doing those things that you won’t even give a second thought to the things you missed.

5 ~ It’s time to book your flight

inside of a airplane

You have started to plan your trip, and much of the fun part is done. You have set your budget, determined your destination, and made a tentative ternary. Now it’s time to book your flight.

You have done your research on everything and have a tentative plan for your trip. We do recommend booking your flight before anything else. If a flight is full, you and you have to choose a different day. It could mess with your schedule. Before you book your hotel, car rental, or adventures, get your flights confirmed.

We use Skyscanner for the majority of our searching for flights and either book with them or, in a few cases, directly through the airlines’ website. By filling out the form below, you can do some fun searching for possible vacations.

When searching for flights, be open to flights that are not direct. We have been able to save money by playing around with which airports we fly into. Sometimes we have even had layovers and were able to explore the city.

If time permits, sign up for price alerts and receive email notices when fares drop. When you finally do decide to book your flights, clear the cache on your computer before you book.

6 ~ Book your accommodations, rentals, and activities

Book vacation accommindations

Accommodations ~ There are a couple of things we always consider when we are booking our accommodations.

Location ~ We like to have prime real estate when vacationing. Yes, sometimes you can save a few dollars by being a distance from the activities. But nothing beats being able to walk down to the beach at night or to the local pub for a nightcap.

Amenities ~ We always consider if there are any amenities included that we would want to use and would cost us extra out of our budget. If the amenities are something I would not use anyway, it does not influence me. Staying with VRBO and having our own pool and kitchen for the cost of a hotel room is a win-win. Or staying with a local hotel chain that includes breakfast and transportation to the activities we want to do might make us choose a hotel.

Most of the time, we book a place to stay using VRBO (Vacation Rentals By Owners). We enjoy the added charm of staying in something that is not your boxy typical hotel room. We have found some amazing places and great deals that way. Not to mention many times, the homes have amazing views, great locations, and wonderful perks.

When we are not staying with VRBO I searching for hotel rooms on This is a great tool to use when shopping around. It allows me to see reviews and pictures.

I have even gotten better deals through than I would have gotten going directly through the hotel. By using the form below, you can check some possible hotels.


Car Rentals ~You have your flight and your accommodations booked, now is the time to decide how you will be traveling between the various sites during your trip.

Your hotel may provide airport transportation and transportation to some of the various sites, yet if you are considering any day trips to nearby cities, you may want a rental car.

If you do plan on renting a car, we recommend reserving it ahead of time. Don’t wait until the last minute or until you get to the airport. Skyscanner can help you find rental car deals.

Activities and Tickets ~ Now is the fun part sit down and get out that ‘tentative’ itinerary of things to do and make a master list of the things you “must” do. Add these must-do activities onto your itinerary and get any tickets possible ahead of time so as to not be disappointed if something sells out.

This is a great time to be checking for any amazing restaurants that might be near any of the activities you may have planned, and make sure to jot them down.

Keep in mind your itinerary should not be booked minute to minute. Leave plenty of room for spontaneity. Everyone has their own way of doing things. Suppose you prefer to make your plans at the last minute, that is fine. Even if you are not purchasing your tickets to something ahead of time, still do your research. It will even help you decide on those last-minute additions to your itinerary.

7 ~ Get travel insurance

Travel insurance

Travel insurance is not something many of us think about. It really is something we would not travel without. Being away from home and having the possibility of something going wrong is a very real possibility.

One of the most popular travel insurance companies is World Nomads. They are very easy to use and will cover you worldwide. Fill out the information below to get an instant quote.

For more ideas on how to stay safe and protect yourself while traveling, be sure to read our Staying Safe and Healthy While Traveling.

8 ~ Pack for your trip

suitcases packing for a trip

Packing for your trip can feel daunting, but it shouldn’t things are really exciting now! While traveling, we want to be prepared and worry that we will forget something. Yet, at the same time don’t want to overpack. Remember you have to carry it.

I have been on both ends of this ~ I have over-packed and came home with most of our things, having been lugged around and never used them. We have also gone to the other extreme and packed very minimal and ended up going shopping for the things we needed.

One tip I use is to take a week and look at what we used. I lay it all out on the bed and do a trial run at packing. From there, I usually take away a bunch of stuff. I make sure what we pack are mix and match. Toiletries are where I usually stumbled, I would pack everything and anything just in case. I was so sure If I didn’t pack it, I would need it. Guess what nine times out of ten, I never touched it.

Everyone’s situation is different, and what you need to travel with is different. Over time we have put together a packing list and use it as a starting point when we plan a trip.

9 ~ Recheck last-minute details

Map, luggage and sunglasses

It’s time to take care of all of those last-minute details. That could be double-checking with the dog sitter or the gal next door that will water your plants. But these are a few of the last-minute things that I always do.

  • Confirm all my reservations and verify the addresses
  • Make copies of our travel documents ~ I have a photocopy on my phone, and I leave one at home
  • Make an itinerary, one for myself and one to be left at home
  • Notify your bank and credit card of your travel plans ~ I forgot on one trip, and the bank shut my card off
  • Make sure you have cash for tips and incidentals where they may not take cards
  • Have a plan for currency ~ If you are traveling to a foreign country, know the exchange rate and check to see if you are better off ordering currency from your local bank instead of doing an exchange at your destination
  • Download some helpful apps such as Google maps and movies, and double-check your hotspot.

10 ~ Enjoy your vacation

Enjoy your trip from the moment you start to plan a tip. Gary and Michelle

There you have it, that is the step-by-step guide we use when we plan a trip. We find by using these tips it takes much of the stress out of travel planning.

You have put in all of the work. You have done your research and planned your itinerary. Your efforts have paid off! Your vacation is going to be a blast, it’s going to be romantic, and you get to spend it together.

Enjoy your vacation ~ relax, eat till your heart’s content, soak up all the sights, and make some great memories!

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We would love to hear for you. Are there any tips we forgot that might make planning a trip easier? If you have any further questions about planning a trip, we would be glad to help.

Gary and Michelle Signature

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