Trip Planning Tips: How I Plan My Travel

After planning dozens of trips all over the world I wanted to compile my trip planning tips and how I plan my travel in one step-by-step guide.

Call me crazy if you want but I love planning my trips almost as much as I love taking them. After planning dozens of trips, visiting 21 countries and territories and 27 U.S. states, I’ve learned lot about the trip planning process from budgeting to researching and beyond.

This is my comprehensive guide to planning a trip from start to finish with my trip planning tips sprinkled in. Also be sure to check out my Trip Planning Tips and Travel Essentials for 2024.

Where do I start?

I hear time and time again that the reason people don’t plan trips is because they don’t know where to start and are overwhelmed by the whole process.

Personally, I do not believe the starting point is or should be the same for every single person. Knowing what your priority is and what your parameters are can greatly help you decide where to start.

The 3 starting points are: the where, the when or the how much?

Where: you may have seen a travel destination on social media or a friend or family member told how much they loved their vacation last summer or you may have had a destination on your bucket list for years. In these cases, and when you do not have restrictions on when you can go and are willing to make your budget work regardless, the “where” will be your starting point.

When: while the “where” may be the most popular starting point, it isn’t the only way to start your trip planning journey.

In a perfect world, you would be able to pick your dream destination and go whenever you want with no worries about budget. However, we know life doesn’t always work out like that.

If you have restrictions on when you can travel, for example, you are a teacher and can only travel during breaks, it’s smart to start with the “when” first. That way you can narrow down your search to destinations that are ideal for the time you will be traveling.

This can help avoid disappointment when you get to your destination. You may have been dreaming of going to Chicago, but you might not enjoy it as much if you have to go during your February break. Whereas, a beautiful beach getaway in Mexico may be more appealing for that time of year.

Likewise, also think about the amount of time you have off. If you know you’ll only get a long weekend off from work, a trip to France (from the U.S.) isn’t going to be your best option this time around. Save that trip for when you know you’ll have more time.

How much?: Yes! It is absolutely possible to travel on a tight budget (more on this later). While setting a budget should always be a step in the trip planning process, if you are on a super tight budget, I recommend making this your starting point. I do not recommend starting with a location or set dates, as this can make things difficult down the line when you discover the cost of flights or that the cost of living in your destination makes food, drinks and activities more expensive than you were expecting.

If budget is your top priority, follow the budget setting steps below and use that as your guide as you begin to research locations and dates that will fit within your budget.

Even if your starting point is the “where” or the “when”, your next step should always be to set a budget. Moving forward I am going to use the “where” as my starting point and use Greece as my destination.

Set Your Budget

If you haven’t done so already, think about how much you can or are willing to spend on your trip, then divvy up that total budget into either categories or a daily budget.

I personally prefer to make a budget for each category like flights, accommodations, ground transportation (car rental, train, ferry, Uber, subway, etc.), excursions and activities, food and drink, shopping and souvenirs and misc. (travel insurance, visa, etc.)

I prefer this method because it is likely that your flights and accommodations will be the biggest expenses and can allot more of my budget to those categories up front. A daily budget may prove difficult if you plan to do a mix of activities and relaxing.

Research Your Destination

Research, research, research! You’ve picked your destination and you’ve set a budget. Now it is time to research your destination so you can get a better idea of when you want to go and how much time you will need to see and do everything you’re interested in. I cannot stress enough how important it is to research your destination before booking anything. Important items to research include:

• Weather: this will help you decide when you want to go. Take note of average temperatures and rainfall, as well as things like hurricane season, if applicable.
• Peak and non peak tourism times: this is may heavily impact how busy a destination is, if businesses are open or closed for the season and the general prices. My favorite time to travel is in the shoulder season, which is at the very beginning or very end of peak. During this time, businesses are still open but there are not as many tourists.
• Holidays and major events: holidays and major events can majorly affect the crowds and the prices of flights and accommodations so always double check for both. For example, you may be looking at a trip to Paris at the end of July and wondering why Paris is so expensive. A quick search would tell you it’s because the summer Olympics are taking place in Paris…something that you would want to avoid at all cost if not going there specifically to watch the Olympics.
• Average prices: I’d recommend doing a general flight and hotel search as well as look at a few activities and restaurant menus in your destination, just to get a general idea of pricing. Some destinations like Switzerland and Iceland are going to have a higher price tag on accommodations, food and even activities vs. destinations like Mexico and Bali. This general search will provide ease of mind that you can travel to your destination during your desired dates and within your set budget.

It may sound like a lot, but you can get a good idea of the categories above with a few quick Google searches. Once I have an answer for each of the categories above, I am able to narrow down on the dates I want to go.

Going back to my Greece example, my husband and I knew we wanted to go to Greece this year and we had set out budget. So I researched the weather, peak travel times, holidays and major events and average prices and landed on going some time in September.

It is considered shoulder season in Greece, where there are less crowds than summer, but still warm weather, warm sea temperatures and most or all businesses should still be open on the islands.

Since our schedule allowed, we kept ourselves open to any time in the last three weeks of September. Having flexible dates is one way you may be able to cut costs with flights and accommodations (more on that soon).

Should I book my flights or accommodations first?

There is no correct order of booking flights and accommodations. However, when I think about the last dozen or so tips where I took a flight, I always seem to follow this formula:

Domestic trips: accommodations first, flights after
International trips: flights first, accommodations after

When it comes to international travel, there are many variables at play and the cost of flights can be drastically different between days, airlines, etc. I like to have peace of mind that we will be able to arrive and depart on our desired days before booking accommodations in those locations. This is especially important if you are planning a multiple city trip.

For example, if I were to book my hotel in Athens from Saturday night to Thursday night first but then find out that flights to Athens on Saturday are twice as expensive as flights that leave on Sunday, I either now have to change my booking (which may not be possible depending on the type of booking) or I’m stuck paying way more on flights than I was anticipating.

With domestic travel, there are usually more flight options and those tend to get posted later than international flights.

Book Your Flights

I recommend using Skyscanner and/or Google flights to search and compare flights. When searching pay attention to the following:

• Prices: does the price include checked bags and seat selection, or will those incur additional fees? Pay close attention to the type of ticket you’re looking at. A $200 ticket from NYC to Athens may sound good, until you realize that ticket class does not allow changes, carry-on luggage and is non-refundable.
• Number of layovers and the length of the layovers: for international layovers, I do not recommend a layover less than 2 1/2 hours as you will need to go through immigration and, depending on the country, collect and recheck your bags. Conversely, some flights can have crazy long layovers that will make your travel day exhaustingly long.
• Layover airport: sometimes if a large city has multiple airports (think NYC or London), airlines will have you land at one airport for your layover and take off from another airport. I never recommend this, no matter how cheap the flight is.
• Departure and arrival times: keep in mind standard check in times for hotels and rentals are between 3 and 4PM. If the flight you’re looking at lands at 9AM, what are you going to do (and what are you going to do with your luggage) until you are able to check in to your accommodation. Also keep in mind with late arrivals that public transportation options to get to your hotel may be limited at that time of day.

Once you’ve selected your flight, I always recommend booking directly on the airline’s website. It is a lot easier to work directly with the airline if travel delays, cancellations or issues arise vs a third party company. I also find that the deals on the third party websites are for the lowest tier ticket (which may not be what you want) or actually have more fees than just booking direct.

For our Greece trip, I used Skyscanner and Google Flights to track a few different flights leaving from any NYC airport with a 3 day flexibility on departure date. Once I choose a flight, I went to the airlines website to book direct.

Once I booked our flight to Athens, I then immediately booked our domestic flight to Milos that is due to depart Athens 2 1/2 hours after we land. This is the last flight of the day to Milos so I wanted to ensure it was booked before booking our hotel in Milos.

Determine Where You Want to Stay

When choosing accommodations, there are few things you should keep in mind:

• Do you want to stay in a hotel or rental: this may depend on where you are going, length of stay, who you are traveling with and if you are planning on spending a fair amount of time on property or are wanting to cook. Please note, rentals through Airbnb are illegal in some cities. Never book an illegal rental!
• What you want to do: if a lot of the activities you’d like to do are in one area, it may make sense to stay in or close to that area to reduce time and money commuting to your activities each day. Bonus points if they are within walking distance!
• Access to transportation: how far away is the accommodation from the airport and modes of public transportation? If you do not plan on renting a car, you may want to consider staying close to public transportation.
• Safety: safety can be a huge deciding factor when it comes to deciding location and type of accommodation. I recommend researching different neighborhoods to get a better sense of not only what they have to offer but whether they are considered safe for travelers.

For our trip to Greece, we opted for hotels for our 4 destinations (Milos, Paros, Naxos and Athens) due to the early hours we’d be getting the majority of these places. It is generally easier to store your bags at a hotel vs a rental. This is very convenient if you are not planning on renting a car and want to explore the day you arrive.

Book Ground Transportation

Now that you have booked your accommodations and have a general idea of some of the things you may want to do, its time to book ground transportation such as:

Rental car: not all destinations require a car, but some places it is a must. A quick Google search can give you a better idea if you need a car if you are unsure. I recommend booking your rental car in advance as prices have increased significantly over the last few years and booking early can help you save. Again, I recommend searching on a site like Expedia where you can compare prices of multiple companies, and then book direct. Also consider supporting locally owned car rental places.
Trains: trains between destinations (i.e. Paris to London) should be booked in advance for better prices and to ensure a seat. Local trains and subways can wait but it’s helpful to start getting familiar with train lines and timetables if you plan on using them.
Ferries: may not be applicable for your trip, but if it is book in advance as you would train tickets. Ferryhopper is a great website to compare ferries.
Transfers: if you are not renting a car, you will want to consider how you are going to get from the airport, train station or port to your accommodation. You may choose to use public transportation, take a cab or ride share or book a transfer with a car/van service. First check to see if your hotel offers free or paid for shuttle services. If not, they may be able to recommend a company.

We are only booking a car while in Milos, and so we booked this shortly after securing lodging on Milos. Since Milos is a small island, we opted for a local rental car company. Since we are island hopping on this trip, our next step was to book our ferries. We waited until the full schedule was released in mid March before searching via Ferryhopper and booking via the ferry company’s direct site.

Plan What You Want to do

Arguably the most exciting part of trip planning: figuring out all the thing you want to do and see. This is where I usually go down a rabbit hole reaching all the possibilities and start to get really excited for my trip during this phase.

Because this part of the trip planning process is so exciting, it can be easy to get carried away and feel like you need to do and see and eat everything. However, it is important to be realistic and realize you can’t do all the things (at least not in one trip), so it’s best to prioritize and not overbook yourself.

I recommend one planned activity per day. This allows you plenty of flexibility for travel time and just plain wandering and enjoying. You can always book additional things to do once there if you’re feeling up for it. I recommend booking popular attractions at least 1-2 months in advance to avoid things selling out. If you do happen to be traveling to your destination during a major event, plan to book even further in advance.

I love using Google maps, Trip Advisor, Youtube and social media to research popular sites and attractions, activities, excursions, restaurants and bars. I love booking excursions through Viator or Get Your Guide.

Consider visiting historical sites, participating in the local culture, trying local cuisine and booking with small businesses, if possible. Immersing yourself in the culture and living like the locals live is a great way to not just visit a destination, but experience it.

Thank you so much for reading about how I book my travel and my trip planning tips. I hope you found these trip planning tips helpful. If you did, please check out my Trip Planning Tips and Travel Essentials for 2024.