How To Plan An Itinerary For Your Trip: A Beginners Guide

Ever wondered 22how to plan an itinerary without feeling overwhelmed? I’ve got you covered! I know it can be daunting if it’s your first time, especially if it’s a big trip like a backpacking adventure or an offbeat road trip.

One of the biggest challenges of travel is knowing how to plan an itinerary that balances adventure and relaxation, and taking the first steps to do it solo can seem overwhelming. With this in mind, I wanted to share my knowledge to help you get started.

For those of you who know me, you’ll know I love planning trips. Sometimes, I don’t even take the trips; I just plan them for the fun of it in hopes that I might one day go on this amazing adventure!

In this post, I’m sharing how to plan a trip for beginners. I’ll go through my 8-step itinerary planning process and share all the tidbits you’ll need to know to have a fantastic holiday.

I’m Going On An Adventure contains affiliate links and is a member of the Amazon Services LLC Associates Program. I will earn a small commission if you purchase through any qualifying links at no extra cost to you.

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How To Plan An Itinerary For Your Trip: Summary

I used to struggle with how to plan a trip itinerary—I’d either plan too much or not enough. But over time, I found a system that works! If you’re unsure how to plan an itinerary, follow these simple steps to make your trip stress-free.

• Step 1—Choosing a destination: Choose where you want to take your trip. Consider your budget, the type of holiday you want, and which destinations fit that brief.
• Step 2—Determine the length of your trip: Consider how much time you can travel, remember to factor in travel days, and allow some flexibility for the unexpected. 
• Step 3—Begin researching flights and dates: Consider when you want to travel and set up price alerts to find the best flight deals.
• Step 4—Decide on your budget: Start building a budget based on flights, accommodation, transport, and activities.
• Step 5—Start building your itinerary: Begin creating the itinerary by breaking down each day into things to do/see and a logistical travel route.
• Step 6—Arrival plan: Research and plan how you’ll get from the airport to your hotel. 
• Step 7—Time to book: Ensure you’re happy with your itinerary and then start booking flights, accommodation, and any activities that require advance booking. 
• Step 8—Final preparations and travel tips: Make a packing list, arrange for travel documents (passports, visas), and download useful apps. 

Learning how to plan a trip itinerary takes practice, but with this approach, you’ll be able to design a perfect travel plan.

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How To Plan An Itinerary: Step-by-Step Guide

I remember the first time I went on a big trip. It was my gap year in Australia, and I used a company to help with the initial planning. This is a great way if you’re feeling less confident and want some direction. However, over the years, I’ve really honed my itinerary planning skills, and I’m sitting here writing this as a confident trip planner.

It’s the little things that can make or break a trip, like not leaving yourself enough time at each destination, trying to pack in loads of activities, and forgetting about travel time between destinations. 

I also think one of the most important things to remember is to stay flexible. I like to research and plan as much as possible, but I always travel with a flexible schedule.

For example, if I don’t fancy an activity or want to spend longer in a certain city, I will. I’ll adjust my itinerary according to how I feel, and I won’t feel bad about it or like I’m missing out. This is your holiday, after all.

I recommend keeping this in mind when planning your trip, too. Here are my 8 steps on how to plan an itinerary that works for you:

Step 1: Where do you want to go?

The first thing to do when planning your itinerary is to choose a destination. It might seem trivial, but a lot of factors can impact this decision.

For example, budget and timeframe. If you have a budget of £1,000 and ten days, there’s really no point in considering a destination in Western Europe since it’s a pretty expensive place. 

On the other hand, a trip to Bali or Thailand will be much more affordable, depending on where you’re based. Flights can take up a huge chunk of money. 

When learning how to plan a trip for beginners, start by choosing a destination that matches your budget and interests.

If money is a factor, try to think of destinations with a lower cost of living compared to your own country and places where your money will go further. If not, the world really is your oyster.

Additionally, what type of holiday do you want?

I like both city escapes and natural getaways. Sometimes, I prefer one over the other. However, if I want a cityscape, there’s no way I’m going to be choosing a trip to the Cotswolds (one of my favourite countryside areas in England) as it’s just not going to give me what I want.

Choosing where to go can be a really fun part of the travel planning stage. Look up popular countries and determine if they’re for you. I’m continuously making a list of possibilities, which is now pretty huge – a bucket list of my dream destinations.

Afterwards, see which one makes your heart sing the most. You might find there are more than one. If this is the case, maybe consider a backpacking trip.  

This leads me nicely to my next point…

Decide on the type of trip

You might have already decided this, but by researching your chosen destination in a little more detail, you’re going to figure out what kind of trip to take. I’m quite fond of backpacking and budget trips, as opposed to luxury escapes. 

However, some places are catered towards luxury getaways, for example, a weekend in Paris, rather than a budget holiday. That’s not to say Paris can’t be visited on a budget; it sure can, but I’d suggest splurging a little more for popular big cities. 

Once you’ve decided on the type of trip and destination (or destinations), you’re ready to move on to step 2.

Step 2: Figure out how long your trip will be

How long will your entire holiday be, and how many nights will you spend in each place? One of the most important parts of travel planning is knowing how to plan a trip itinerary that fits your schedule and interests.

As a rule of thumb, I suggest a minimum of two nights in each place, with at least three in major cities. If there’s a place I think I’ll enjoy more, I tend to plan three or four nights, but attractions and activities also play a role in figuring out how many nights I’ll stay in a city.

🌟 Pro tip >> Try to avoid one-night stays, as this can be stressful. You have to check in and out of hotels and travel too frequently, often not allowing yourself time to rest.

Activities & Attractions

If you’re unsure how to plan a trip itinerary, start by listing your must-see attractions, then organise them by location to save time.

Start browsing things to do in your chosen location to grasp an understanding of how long to spend there. This step kind of blends into Step 5 but you can start researching early on. I’m guessing you’ve already got a handful of activities in mind, which is a great starting point to work out how long you’ll need. 

Major attractions can easily take up a full day – whether you’re exploring cities or visiting famous landmarks. It’s important to factor in enough time for these experiences when planning your itinerary. 

I always ensure I’ve got rest days and never pack too much into one day. Sometimes, visiting one attraction is enough; this also leaves me open to spontaneous excursions. When figuring out how to plan a trip itinerary, consider mixing popular sights with hidden gems for a more balanced experience.

Once I’ve listed all the attractions I’m keen to explore and decide on how long it’s going to take, I’ll also jump onto Get Your Guide. or Viator to see what kind of tours are available. I’m a fan of foodie tours, and there’s usually some sort of food tour on there I can add to my itinerary. 

🌟 Pro tip >> These tour companies are a great place to find additional activities and popular attractions as well. You don’t need to book them if you prefer travelling independently, but they do provide ideas that might have otherwise been missed.

Step 3: Begin researching flights and dates

It’s now time to begin researching flights and possible dates. For me, choosing when to travel is a fun part of the itinerary planning stage, as it opens up tons of possibilities. Depending on the time of year, different activities become available, which is exciting stuff. 

Decide whether your trip is best suited during the summer months, which are generally peak seasons, or during the off-season. Peak season brings optimal weather conditions, but it is usually more expensive and crowded, while off-season has lower prices and fewer crowds. 

Think about the type of holiday you’re after and your travel preferences.

• Flights are more expensive during peak season, weekends and bank holidays. Certain days during the week also offer price fluctuations. For example, booking a flight during mid-week tends to be cheaper than on a Friday.

• Another thing I want to make you aware of is the shoulder months. You might have come across this term, which refers to the period of time on either side of the peak season. This is usually my favourite time to travel; prices often remain low, crowds are fewer, and the weather is generally still decent.

• I get asked a lot if there is a sweet spot for booking flights, and the truth is, it’s hard to say. Generally, I look to book long-haul flights two to three months in advance. For shorter trips, I’m kind of a last-minute booker. It really depends. Sometimes, great deals can be found, and sometimes, leaving it last minute can be more expensive.

• Just remember, when you’re figuring out how to plan a trip for beginners, start by researching the best time to visit your destination to avoid bad weather or peak crowds.

That said, finding flight deals by tracking flights is a useful tool.

Track flights

I absolutely love the flight tracking tool on Skyscanner and tend to track flights to destinations I love, even if I’m not planning a trip. It’s very easy to set this up. On Skyscanner, it’s the “Get Price Alerts” button, usually shown on the left-hand of the sidebar after searching.

I also use Skyscanner’s flexible date search, which searches by month and provides an overview of the cheapest months to fly. This is another great tool if I know what month I want to travel, but I am flexible with the dates.

🌟 Pro tip >> There are also companies out there that can help track cheap flights. Going (formerly Scott’s Cheap Flights) and Jack’s Flight Club are two of them. I’ve used Jack’s in the past, and they are good at sending flight deals through on the free version; I’ve not personally used the premium service. 

However, I find tracking flights myself on Skyscanner just as useful and a bit more helpful as I can specify the exact destinations I’m interested in rather than a selection of random destinations. Then again, if you’re struggling to decide on a destination, receiving such flight deals could help you get started.

Find the best flight deals

If you already have some dates in mind, Skyscanner’s search tool can help you begin pricing flights.

Step 4: Decide on your budget

An essential step in how to plan a trip for beginners is setting a realistic budget—this helps determine where you can go and what you can do.

Figuring out how much to budget for a trip can be done before or after the initial planning. How you plan your itinerary depends on whether the cost of your trip is a deciding factor.

Think of it like this: if you only have a set amount of money to spend on a trip, then I suggest planning a holiday around the budget, choosing where to go, the type of accommodation, and activities that fit within your budget. However, if your budget isn’t as important, plan the trip first and then work out the budget.

How I do it…

There’s also a third way, which is what I tend to do. I like to create my itinerary first and then work out the budget. I usually have a budget in mind, although it’s generally a little flexible. I’ll work backwards to accommodate it.

This means I’ll choose the destination, accommodation, and activities, plan my itinerary, and then remove activities and stops and maybe alter accommodations to suit the budget I have in mind. 

By doing it this way, I feel like I’m not restricting myself to what I can and can’t do, which can take the fun out of planning. As I fill up my itinerary, specific places and attractions naturally become more important to me, and it becomes easier to choose what to do and where to go, or what not to do and where not to go.

I’ve created a budget planner, which I love and use regularly. I find it super helpful. You can access it by subscribing to my newsletters.

Step 5: Start building your itinerary

Travel tip >> When you’re figuring out how to plan an itinerary, consider local opening hours, transportation schedules, and meal breaks to create a realistic daily plan.

My favourite part of the planning process, well actually, it’s all pretty fun to me. But for most people, this is when the real excitement kicks in – when we can start dreaming and imagining the possibilities.

There are loads of ways to start this, and we all have our quirks. I’m pretty organised and love using notebooks and spreadsheets; Google Maps is by far my favourite tool. If you’re unsure how to plan an itinerary, use Google Maps and travel apps to estimate travel times between locations.

Blogs, Books and Socials

I always start by researching for my destination online. I love reading travel blogs and firmly believe they’re the best source for discovering things to do, the best routes, must-see attractions, and valuable insider tips.

I have a few favourites:

• Two Wandering Soles
• Nomadic Matt
• Goats On The Road. 

There are also socials, such as YouTube, Pinterest and Instagram, to help get inspiration. Create mood boards, discover must-visit sites and get a feel for the country through visuals! 

I also love having a hard copy, and I’ll always purchase a Lonely Planet guidebook specific to the country or region I’m travelling to. Lonely Planet aside, there are tons of useful travel books out there. Pop into your local bookshop and have a browse, or check Amazon online.

No matter how you prefer to do your research, spend some time diving into the destination.

Save locations on Google Maps

This step usually coincides with my reading about destinations. I’ll often save locations I read about on my Google Maps; these days, it’s filled with green flags of places I want to visit, red little hearts of places I love, and so on. When I want to get extra fancy, I create a new list so I can easily identify places of interest.

🌟 Pro tip >> You can do this all on the Google Maps App, which I highly recommend downloading if you haven’t already. Then, use the “Save” button to start saving places of interest.

The time between destinations & route plan

When I want to get into the details, I’ll use Google Maps to plan the route. You can do this, too; it’s super helpful in planning backpacking trips and the travelling part of any itinerary. 

For example, if I want to work out how long it takes to travel from Strasbourg to Obernai (this was part of my Alsace trip in France), I add the places to the directional map to get the journey details. I’ll do this for each location, creating a spreadsheet of travel times and distances. 

If I’m visiting more than one place, I’ll start by adding the destinations to my map, which will create a map full of pins. By doing this, I can determine which spots are closest to each other and begin planning a logical route.

Eventually, this will help me form the best route for my itinerary.

Travel tip >> While you’re learning how to plan an itinerary, always group nearby sights together to minimise travel time and avoid unnecessary backtracking.

Spreadsheet & Notes

I love spreadsheets. It stems from my old job as a Quantity Surveyor, in which my life revolved around creating spreadsheets; you’d think I’d hate them but it’s a great tool. I also love jotting down details in my notebook, your phone’s notes is another good place.

This is where I visually plan out my route. I’ll add details like destinations, activities, attractions, places to eat, trending spots and any other useful tidbits. At this stage, my itinerary really begins to take shape.

I also estimate how many days I’ll need in each location and factor in travel time between stops. It all comes together, and this is how I plan the perfect trip itinerary.

Itinerary Inspiration

I create itineraries from my trips and share them on my blog, but I also create custom itineraries that are personal to you. If you’re interested in having me research and plan your trip, get in touch here.

Below are some pre-made itineraries to some of my favourite destinations to give you some inspiration.

• 2 Day: 2 Days in Marrakech: The Perfect Itinerary
• 4 Day: Cartagena 4-Day Itinerary
• 5 Day: 5 Days In Bali: The Ultimate Budget Itinerary 
• 5 Day: 5 days in Singapore For Free: Itinerary For Budget Travellers
• 5 Day: 5-Days In Mauritania Budget Itinerary For First Timers
• 14 Day: 2 Weeks Island Hopping The Andaman Sea, Thailand
• 14 Day: Alsace 14-Day Wine Route Itinerary
• 2 Month: Ultimate Northern Italy Road Trip Itinerary: An Epic 8 Weeks

Step 6: Arrival plan

Quite important, really. There’s nothing worse than arriving in a foreign destination and not knowing what to do next. 

I’ll always have an arrival plan, which generally entails how I’m going to reach my hotel. Once at the hotel, things are easy.

• Think about arrival time, hotel check in and transportation: how you’re going to get to your hotel from the airport.

• Booking the cheapest flights sometimes comes with early morning arrival times, which are not ideal. It’s better to pay a little extra to ensure you arrive at a reasonable hour. Also, consider the journey time from the airport to the hotel.

• Most accommodations have an early afternoon check-in, although it’s certainly possible to arrive earlier, drop bags, and explore the local area before checking in. Consider departure times as well, since morning check-outs are common. If I know my flight times don’t align with hotel check-in/check-out, I’ll often email the hotel to arrange early/late check-out. This sometimes comes with an additional fee. 

Getting to the hotel from the airport is one step that I always pay attention to. After a long flight, navigating local transport can be a headache, and these days, I tend to jump in an Uber or a similar alternative straight from the airport to the hotel. I budget for this, and it’s usually one of the luxuries I give myself. 

However, if I am on a tight budget then local transport is the way to go. You’ll need to research the best way to reach your accommodation but there is always a bus or train going into a city from the airport. From the city centre, it’s a choice of walking to the hotel or jumping in a taxi or catching a local bus.  

Data on the go

However you choose to get to your hotel, you’re going to need data. 

I always buy a local sim card when travelling for long periods of time. I’ll either buy one at the airport, which is usually more expensive but easier, or once I’m in the city.

🌟 Pro tip >> Recently, I’ve been using Airalo’s e-SIM for my initial arrival, which is great, but I don’t recommend it for long-term use as it’s expensive. 

However, to save buying a SIM at the airport is a useful resource for having data when I land. You will need to download the e-SIM prior to departure and have it ready on your phone to activate when you arrive.

Alternatively, I’ve also managed to get my network provider to add on a Europe data pack when I was road-tripping in Europe for not much more than my monthly contract. I’d recommend giving yours a call and see if there’s any deal to use your existing contract overseas. This is usually possible for destinations within Europe.

Step 7: Time to book!

Once I’ve finished all my research and my itinerary is set, I like to sit with it for a few days at least before booking anything. This gives me time to think about any last-minute changes and make sure the plan feels right before finalising it.

Flights

The first thing I book is the flights. It’s important to do this early, as flight prices can fluctuate significantly, even within a few days. If you’ve already booked accommodation and activities, you’re locked into specific dates, which could limit your options. 

Flight costs can sometimes swing by hundreds of pounds from one day to the next, so booking flights first can save you money.

I use Skyscanner because it compares hundreds of airlines and flight routes. Google Flights is also a great option. Once I find a flight, I sometimes book directly with the airline. While prices are usually similar, booking directly can make resolving any issues, like cancellations, much easier. If you experience a cancellation, AirHelp is a fantastic service that can help you claim compensation.

I also occasionally call the airline to book over the phone. They can sometimes offer a better rate, especially for long-haul flights.

Accommodation

My go-to booking site is Booking.com. I use it all the time and love how easy the website is to navigate. Plus, they offer discount deals to returning customers through the Genius programme. After Booking, I usually check Agoda, as I find it helpful to compare hotel deals between the two. Sometimes, Agoda has better rates.

If I’m looking for hostels, Hostelworld is another good option, though I find their choices can be a bit limited.

For shorter trips, especially city breaks, I often use Airbnb. It’s fantastic for finding unique stays in great locations. A similar platform is Vrbo, although it’s much smaller and has fewer choices. I’ll sometimes find better deals.

Whenever I book accommodation, there are a few key things I always check

• Location is important. Choosing somewhere close to the city centre, major sights, good food, and nightlife can save you heaps of time and stress.
• Look for character and a unique charm. Although not essential, I always like quirky hostels, boutique hotels, family-owned guesthouses, and beautifully decorated Airbnbs.
• If I can find a place with a great view, it’s a massive bonus.

Activities

Booking attractions can be a little bit of a minefield, and it depends on the type of trip I’m taking. I don’t tend to book activities too far ahead of time, a few days to a week at maximum, but this is a personal preference since I like to keep my itinerary loose. 

If you like to have your whole trip planned and booked, then at this stage, this is the next big thing to book. 

Travel tip >> A simple trick for how to plan an itinerary is to plan your must-see activities in the morning when you have the most energy and leave flexible time in the afternoon for spontaneous adventures

However, if like me, you prefer to stay flexible, booking your activities can be done nearer the time of travel or even while you’re on holiday. For backpacking trips it will be impossible to pre-book everything. That said, for major attractions booking ahead might be a necessity. 

But, not booking has risks…

I got caught out in Florence and missed walking up the dome of Florence’s Duomo (Cathedral of Santa Maria del Fiore) because I left it too late and tickets were sold out. Instead, I climbed the Bell Tower, which was still pretty amazing; so I don’t feel like I missed out. However, it would have been nice to see the stunning frescoes.

I’ll still include plans in my itinerary for visiting attractions and doing activities on specific dates, but in my experience, sticking to a rigid schedule can take away from the enjoyment of the trip.

By not booking activities straightaway, I remain open to changes and can do the activity in the following days if something else comes up, which is often the case when backpacking.

So just keep this in mind when booking. 

Where to book tours?

For the most part, I use Get Your Guide. Again, I love the site and its usability, which makes finding tours super simple. Viator is another of my go-to companies. I’ll usually compare prices between the two, but there’s not typically too much difference; be sure to check the terms and conditions and what is included.

For lesser-known spots, Viator seems to offer more options. They’ve been around for a long time and are a more established company. If using any other third-party company to book excursions, I recommend researching the company before booking. I do this by checking Google Reviews or Trustpilot.

Transportation

A key part of how to plan a trip for beginners is researching transportation options—should you fly, take a train, or rent a car?

Although I do the research, actually booking transportation is another part of the itinerary I tend to leave until later. For holidays, you might need a car for the whole trip, in which case book ahead of time. I like to use Discover Cars for overseas rentals. 

However, for backpacking trips, I won’t book transportation until a few days before I want to move on to the next destination. For the same reasons I mentioned above, I like to remain flexible. 

There are some great transport booking platforms out there. 12Go is fantastic for travel in Asia, and BookAway is excellent for booking a wide network of buses, trains, and ferries. However, if you’re booking ferries within Europe, I suggest Direct Ferries.

For Europe, Trainline offers discounted train tickets, and Busbud is great for finding cheap long-haul coaches. If you’re looking for private drivers, Viator is a helpful resource, especially for things like airport pick-ups.

Ride-sharing apps like Uber are available worldwide but only in some places. In Southeast Asia, Grab and Gojek are the popular alternatives. These apps don’t require pre-booking, but you’ll need to download them and have data to use on the go.

Check out how much a car rental is going to cost you:

Step 8: Final preparations & travel tips

The final stages of itinerary planning involve the less exciting but essential tasks that ensure a smooth trip. Gathering the right documentation, arranging insurance, getting vaccinations, sorting out money, and creating a packing list might seem tedious, but I always make sure they’re done.

Documentation & Visas

Most countries will ask for at least six months on your passport, so to avoid any issues, make sure you check it before booking anything. 

Other documents, like visas, need to be applied for before booking since they can take a while to arrive. Sometimes, they’re instantaneous, but I wouldn’t bank on them.

Jabs

These days, I’m not too concerned about jabs. I’ve had most of them, but I will do a quick check on the NHS Fit For Travel website, which has a list of recommended vaccinations for each country. 

If this is your first time travelling, you might need a few, and in many instances, they’re not free. Just keep in mind that this is an additional cost that can quickly add up. 

Certain vaccinations are super important, including Rabies. Typhoid and Hepatitis A and B are also important. Make sure you’re up to date with these. 

Travel Insurance

Travel medical insurance is important for health emergencies, trip cancellations, theft, and accidents. I use two companies depending on the type of trip I’m planning. For my Europe road trip, I used SafetyWing. 

⭐ Here’s a guide to why I think SafetyWing is one of the best travel medical insurers available.

Get local currency

What’s the best way to get local currency? Personally, I’m a little rubbish when it comes to arranging local cash before travel. I tend just to use my Wise Card to pay since most destinations accept card payments.

I highly recommend Wise. It’s a multi-currency debit card that lets me send, receive, and manage money across different currencies with low fees and real exchange rates. I use it all the time and love it.

That said, it’s always a good idea to arrive with some local cash, and there are ATMs at almost all airports. I tend to just grab some when I arrive from my Wise account. 

If I’m going off the beaten track, I ensure I have cash, typically dollars (USD), which can be easily exchanged on the streets. 

If you prefer to arrange local currency before you leave, the Post Office is a good option, or I’ll sometimes exchange money at the airport or at a currency exchange bureau on the high street.

Inform Your Bank

Remember to let your bank know when you’re going to be travelling. If you start making numerous transactions overseas, it will likely flag up, and the banks tend to put a blockage on your account. It’s happened to me, and it required a phone call to unblock, which was the last thing I wanted to do on holiday.

Brush up on local customs

Every country is different and have their own tradtions, with this in mind, it’s important to be respectful of other cultures. Some of the things we find normal at home might be considered rude in another country. To ensure I have a comfortable and enjoyable trip, I’ll always have a quick check online at local customs. 

Google Translate

Technology is superb and has made travelling so much easier. I enjoy interacting with people, but if there’s a language barrier, it can be challenging. There’s a lot to say for hand gestures and friendly smiles, but if I really need some help, like asking for directions or information, nothing beats Google Translate. 

It’s such a useful travel tool that I use regularly while abroad. I recommend downloading it and keeping it handy for your trip, too.

Ultimately, don’t stress too much about getting it perfect—learning how to plan a trip for beginners is all about trial and error.

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Final Thoughts On Itinerary Planning For Your Trip

When I first started travelling, I had no clue how to plan an itinerary efficiently. But after years on the road, I’ve learned a few tricks! It might feel overwhelming, especially if you’re venturing out on your own for the first time, but try not to worry. By following my steps, it can become a fun and rewarding process!

I’ve shared my 8-step process to help you get started, drawing on my own experiences and what I’ve learned over the years. It’s all about finding a balance between thorough planning and leaving room for spontaneity.

Remember, the key is to break it down into manageable steps. From selecting your destination and deciding on your trip length to researching flights and creating a flexible schedule.