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Wondering how to plan a trip? Whether planning a vacation, a weekend away, a long-term sabbatical, a ski break, a road trip, a couple, family, group, or solo adventure, our guide details the stages of planning from inspiration to saving, planning to survive on the road.
So let’s get you moving from armchair to airport with our eight practical steps.
Trip Planner: How to Plan the Best Trip Ever
1. Travel Inspiration
Firstly, where should you go and what type of trip should you take?
Inspiration includes movies, books, podcasts, word of mouth, discounts, YouTube, social media, Pinterest, and blogs.
You can check out all the destinations I’ve written about here.
From Cuba to Canada, Northern Ireland to Nicaragua!
When I see fun or exciting destinations, I save it to an inspiration board on Pinterest, a Collection on Instagram, or as a note on my phone.
How to Save to Collections on Instagram
I absolutely adore this feature on Instagram and have many folders covering everything from photo spots to holiday nail art.
When you see an image you like on Instagram…
- Tap the ribbon type symbol at the bottom right-hand side of the app.
- The option to ‘Save to Collection’ then appears to the left. Select this.
- If you then hit the big plus sign to the right, you can create a new Collection, such as the name of the destination you want to visit.
I first discovered the hot air balloon rides in Cappadocia, Turkey, on Instagram and booked a balloon ride the following year.
Visual platforms such as Pinterest, Instagram, and other social media channels are the culprits for many credit card bills!
2. Budget Your Trip
So, now we are talking about cash and credit cards; we need to discuss how to save money for a trip.
There’s no point having destinations in mind if you don’t have the budget.
I have six tips to help you at this stage of planning.
How to Save For a Trip
Tip 1: Location, Location, Location!
Choose destinations that meet your bank balance and/or go in low season.
Avoid big events and festivals unless this is the main reason you want to visit the destination.
For example, take the film, interactive media, and music festival South By Southwest in Austin, Texas.
Thousands of business people and visitors move into the city each March, while many locals move out because they can charge three times the amount on their properties.
Be wary that the time of year can and will impact the weather.
While many popular destinations in Europe, such as Paris, enjoy four seasons in the year, countries such as Thailand experience monsoon season, and different parts of the country get it at other times.
A cheap trip to a city might not work out cheaply if you have to spend money on indoor activities to stay comfortable.
Don’t be put off by winter; I especially love cities and towns at Christmas time.
Do you love winter travel, too?
You can check out our festive guides to:
Here are some roundup posts on the most magical places to spend the winter period in Europe, popular winter destinations in the Americas, Europe’s best Christmas markets, and what to pack for a ski trip.
Finally, don’t miss our guide to fun New Year’s Eve parties worldwide!
If you can, avoid school and public holidays.
This will help keep the flight and accommodation costs down.
We’ll talk about this more below.
Budget airlines don’t always end up being cheap if you land far away from the intended destination.
Check the distance, mode of transport to get between the two, and how long it takes.
If it adds another three hours by bus, it might be worth paying the additional money to fly closer.
Overnight flights can rob your sleep. Factor this into your planning.
If you are keeping costs down, here are the best places to travel on a budget, from our experience:
- Eastern Europe/ Balkans – Budapest (Hungary), Sarajevo (BiH), Bucharest (Romania).
- Southeast Asia – Vietnam and Cambodia, avoid Singapore, Thailand is affordable but increasing.
- USA: Texas road trip for cheap gas, large food portions, and Big Bend National Park camping.
Tip 2: Canada or Crap?
Canada or crap was our philosophy while we were saving for our 18-month career break to travel the Americas and Europe.
It wasn’t being bought if it couldn’t fit in a backpack.
If you are considering taking a sabbatical, here’s how I applied for mine.
Tip 3: Three Bank Accounts For Saving
Open three bank accounts.
Have your income enter one.
Work out how much you spend, and identify your needs (housing, bills, food) and wants (clothes, huge TV packages, nail art).
Create a livable wage and put the majority of the rest of your pay into another savings account.
Do not touch these savings.
But why three?
In the third account, move some money over.
You can take money out of this account if you are struggling.
Maybe you need to buy a gift, the washing machine goes, etc.
Saving shouldn’t be stressful when it is for the end of the goal of the dream trip.
Read our 5s of savings strategy, which saved us £20K for travel.
Tip 4: Cards With Extras
Many credit and debit cards on the market offer a bonus if you shop with them.
For example, you can accrue airline points while you shop or enjoy free cash withdrawals abroad.
Some monthly accounts offer free phone insurance or, even better, travel insurance for short trips.
→ Note: Usually, you will find that the airline points are for one airline only, and you can often get cheaper flights with a budget airline. It depends if you are loyal to one airline carrier to make points cards work. The industry has cracked down on people abusing the system.
Tip 5: The Travel Essentials
There are some items you must fork out for.
Firstly, travel insurance.
While some bank accounts may offer insurance for short-term travel trips, you will need more coverage if going away on an extended trip to a certain location it does not cover or if you plan to do an activity it doesn’t include, like high-altitude hiking or winter skiing.
We use True Traveller, which is a company for Europeans.
I claimed through True Traveller when I was sick in Canada with no issues. You can read about my experience and our comparison guide here.
Secondly, injections and medicine.
There may be vaccinations you have to get to stay safe during your trip and to keep your travel insurance working.
Some companies don’t have to pay out if you do not have the correct vaccinations, and they won’t.
Check with your healthcare provider to see which vaccinations you need for your destination.
Finally, gear. Buy cheap, buy twice! There are some items you need to invest in depending on the seasons, if you are moving around with luggage, or taking a long travel trip.
Tip 6: Travel Gear Essentials
- Waterproof outerwear – We wear Mountain Equipment US / UK and Marmot Precip US / UK.
- Gore-Tex hiking boots or shoes – Salomon Ellipse trek shoes or boots US / UK for me.
- Durable luggage – carry-on-sized bags or rolling cases?
Read next: Every item we travel with and the ones we dropped.
3. Planning Your Trip
OK, now we’ve progressed onto the fun part: destination trip planning!
Open up a spreadsheet or the free online Excel Sheets.
Title tab one, PRICING. Add a new tab and call it ITINERARY.
On tab one, column one, write the step-by-step way to get the destination from your doorstep.
Add each leg to a new line.
For example, ‘bus or taxi to airport’, then on line two, ‘flight one’. Line three might be ‘flight two’ depending on how far you are going or ‘private hire to hotel’.
You get the point.
In column two, write out how much that portion of the trip costs.
Use Google Maps and Skyscanner to help price the journey.
In column three, add the dates, and in column four, return the dates.
The final column, five, should be the total.
Total up each section individually, then total everything together.
Use the code =SUM( then highlight the amount in the row ) for easy addition.
Open up tab two, ‘Itinerary’ and add your intended dates along the top giving each day one row.
Add a rough note of what you think you will do each day.
Use your notes from Instagram Collections and the posts you saved on Pinterest.
This will change, so don’t worry about it.
Go to a tour website like GetYourGuide.
Add the destination to the search bar.
→ WARNING: This may take you back to the inspiration stage!
Pull up the tours and fast passes that grab your attention.
Go back to your planning spreadsheet.
On tab one, ‘Pricing.’
Create a new section underneath transport for tours and activities.
Add each tour/activity you plan to do to its line.
Type in the price in column two.
Alternatively, just use the one I made earlier!
Access it here; you will have to save it to be able to edit it.
Google Maps Trip Planning
I love planning trips, and one of the best tools to use is free, as long as you have a Gmail account.
Go to My Maps by Google.
Select create a new map.
In the search bar, type in one of the areas you want to visit, such as the Duomo in Milan.
Hit search, and a pin will appear.
- Select ‘add to the map,’ edit the icon, and add a note if you have any. For example, the Louvre is closed on Tuesdays.
- You can change the map’s name on the left-hand side of the map.
- Also, edit the name of the ‘layer’ to activities or similar.
- Go through the same process with all the other things you want to do.
- Keep to the icon key and save them to the same layer. This will help you visually plan what you can do in one day and how to group activities.
I also use Google Maps to work out the timings between places.
To add multiple stops to Maps, make sure you are using the walking option.
To save the map, select the three dots, and choose to copy the link and save it in your spreadsheet.
I tend to have a map for each day and use it to help get around during the trip.
Go back to the planning spreadsheet, select tab two ‘Itinerary’ and adjust activities in line with new mapping information.
Here are our recommended apps for staying in contact, too.
Your budget very much dictates the type of accommodation you book.
I tend only to rent apartments if I know that the city doesn’t suffer from ‘buy to rent’ issues, which are out-pricing locals, for example, in Venice or Lisbon.
Sometimes, having an apartment is necessary if I need to work or require a kitchen.
Go to your preferred hotel booking platform, such as Booking.com (usually popular with European readers) or Expedia, and type the destination into the search bar along with the dates.
The most popular properties tend to appear at the top.
You can filter to read ‘hotel only’ and your price point. You can also request details such as hotels with parking, etc.
Browse through the hotels, look at the reviews, double-check how much the room you require costs, and then add it to ‘My List’ by hitting the heart.
Go back to My Maps.
Select the left-hand table and choose ‘add layer.’
Name it ‘accommodation’.
Copy and paste the addresses of the hotels you like into the search bar.
Choose an icon.
Ensure only the accommodation layer is ticked, or the hotel pin will be saved to every layer.
If you add to the wrong layer, select the name of the left-hand side table and then edit on the pin.
You’ll find the delete symbol there.
Once you have added the accommodation layer, tick the boxes for activities and accommodation and check which hotel is best for your itinerary.
Go back to the hotel search website and book your chosen accommodation.
It is worth noting that Booking.com will allow you to cancel within a set period.
Also, it can pay to be loyal; the more you book with some platforms, the cheaper the prices get as you unlock points.
Add the hotel fees to the planning spreadsheet. Do you need to lose a tour? Can you budget another night or a better transport option?
Keep Accommodation Costs Down
Learn from my mistakes; here are some ways to enjoy low-cost travel when it comes to booking accommodation:
- Check that airport hotels are at the airport and have a 24/7 shuttle service, including the price.
- Book hotels near transport lines if in big cities.
- Avoid hotel breakfast unless it seems worth it, and you will be up/in for them.
- Book hotels near an activity if you are into photography/avoiding crowds. We did this in Japan for sunrise shots.
- Pay extra to stay in experiential hotels, like Sultan Cave Suites in Cappadocia, for the views.
We use our feet to get around during long weekend trips, but sometimes areas are too big, the weather is torrential, or we run late.
Check out the bus and train systems and weigh whether Uber is cheaper than national taxi services. In some cases, it will be, in others won’t.
You might find that taxi drivers straddle badges and take hires through taxi apps and at taxi ranks.
Work out if buying a city transport pass is cheaper than doing it trip by trip.
Rent bikes or electric scooters.
If taking a multi-destination trip, consider whether budget airlines that save time are worth the money. If you have time, take the train or bus for a different, cheaper, and often more environmentally friendly experience.
Research car share schemes in bigger cities to make day trips.
Car rental abroad isn’t as scary as you think and is often more affordable. Read our guide weighing up the pros and cons here.
4. Keep Costs Down On the Road
While you are on vacation, there are several ways to keep costs down.
- Walk everywhere.
- Attend tip-based ‘free’ tours.
- Pack a filter water bottle and fill it up.
- Have a big lunch instead of dinner.
- Bring collapsible Tupperware and take a doggy bag home from meals.
- Search for deals, coupons, and 2-4-1, but look for added taxes.
- Get out into nature; hiking is free.
5. Examples of Trip Budgets
We keep a record of what we spend during our trips as it helps us to inform our future plans.
Why not add a tab to your planning spreadsheet and do so too?
Here’s an overview of some of our trips. We’ve not included flights since the price differs depending on long you are going for and where you are departing from.
The below travel budgets are for two people unless otherwise stated.
How Much Does Vienna Cost?
- Hotel: £377 (three nights in November)
- Taxi: £22.71
- Transfers: £48 (from airport to city)
- Food: £100 (food tour included in activities; we pretty much ate from stalls)
- Drinks: £141.92 (£4-6 glass of wine/we went to bars every night)
- City Cards: £30 (discount to top attractions)
- Activities: £334
How Much Does An Iceland Road Trip Cost?
- Accommodation: £484 (four nights in September)
- Car rental: £270 (includes airport pick up/drop off)
- Petrol/Gas: £244 (ouch!)
- Food: £116 (eating out and food shops)
- Drinks: £85.50 (a few drinks, not cheap/not a drinking holiday)
- Activities: £50 (one spa/lots of free stuff)
Our Iceland Guides
How Much Does the Scottish Highlands Cost?
- B&Bs: £400 (5 nights in July)
- Food: £250
- Petrol: £143 (used own car)
- Activities: £5 (1 x Smoo Cave)
Our Scotland Guides
How Much Does One Week in Japan Cost?
- Accommodation: £434 (six nights in September)
- Food: £391 (drinks mixed with some meals)
- Drink: £133
- Trains: £456 (JR pass)
- Transport: £45 (metro/buses)
- Taxi: £49 (avoid taxis if you can)
- Activities: £153
6. Packing For a Trip
Hands up, who is an over-packer?!
What to pack for a trip depends on the length of time, climate, and intended activities and tours.
First, you need to think about the luggage.
How much weight and what size of bag are you permitted to take?
Check individual airline regulations for carry-on sizes.
Cabin-only baggage also restricts the amount of liquid you can take to one small plastic bag with a limit of 100ml per product.
Read our review of the best hand luggage backpacks/cases here.
To wheel or not to wheel?
That is the question.
If you are taking a vacation that involves moving luggage from a bus to a resort, then the quality of the wheels shouldn’t be too much of an issue.
If you plan a multi-location trip, you must invest in a sturdy wheelbase.I recommend something by Eagle Creek, like the Expanse US / UK, which I now use for weekend trips.
Eagle Creek has a lifetime guarantee, but you won’t need it because their cases are built for off-road situations, so no cobbled street or sandy road can beat it.
Unlike the super affordable IT case!
I’ve burnt through two cases now.
Eagle Creek is not cheap, but you get what you pay for.
Remember, buy cheap, buy twice. You can check out the latest wheeled bags review here.
If you are backpacking, you might want to consider a backpack instead of a suitcase.
They are easier to maneuver around places with, give you hands-free walking, and are pretty much the done thing when backpacking.
The downside is you have to carry the weight in your bag.
Some people can’t believe this, but Craig uses an 80L backpack, and he fills it to the brim.
If you can pack lighter, go for a smaller 60L or 40L.
When carrying your backpack on your back, put your day bag on your front.
It looks silly, but it does help balance the weight.
There are two main types of backpacks: top-loading and front-loading.
Top-loading bags tend to have a drawstring at the top and some side and bottom access if designed well.
Front-loading opens up like a suitcase, so you have easy access.
I much prefer this version and used it during our big backpacking trip.
How to Pack
There are two ways to pack a case or bag.
Firstly, the rolling method. This involves rolling items up and placing them in the bag.
This method also avoids the lines that you can get from folding.
Secondly, the folding method, which you will be familiar with.
Whichever way you go you will want packing cubes or large zip-lock bags to separate items.
Avoid bags that make a noise, especially if booking in communal rooms.
You might like our guide on tips for staying on hostels.
I stuff shoes into the sides of the bag/case and pack walking boots in a bag to avoid things getting dirty.
I then close the luggage, pull it by the top handle, and shoogle it.
This then creates more space at the top for a waterproof toiletries bag. If you are road-tripping and/or using communal showers, you will want a hanging toiletry bag.
Check out our road trip packing list for more essential items.
I tend to pack electronics in my day bag, using makeup bags and packing cubes.
Our large tripod has to go in the hold, it wouldn’t get passed security in carry-on luggage.
Read more: Our packing list, item by item.
7. Meet New Friends
Are you going solo, or are you fed up with your travel partner? It is relatively easy to make friends when on a trip. Here are a few ideas:
- Volunteer with the likes of Workaway or HelpX.
- Get friendly on tours; free walking tours are a great way to meet like-minded people.
- Book into social accommodations like hostels. Private rooms and dorms are mostly available.
- Do a bar hop, pub crawl, or craft beer/gin/wine tour.
- Attend festivals or workshops.
- Find communities using the Facebook search function.
- Ask family and friends to connect you with others.
- Learn the language! Here’s how to learn Spanish without leaving your home.
Instagram Collections is also fantastic for helping you remember people you meet on the road.
Ask for their Instagram and save an image you will remember from their profile to the destination/event collection board.
8. Staying Safe On The Road
Whether you go solo or in a group, staying safe is paramount.
Be cautious of cheap accommodation, and double-check that the area is right for you.
Can you walk around in the dark? Are there certain streets you should stick to? Is a hotel with a reception desk better than a self-service apartment?
If it doesn’t feel right, get out.
I left a sketchy hostel in San Francisco and didn’t regret it.
Take a photo of car plates and let the driver see you do this if you are on your own.
Use legit apps that inform you when the driver is on the way and what car they are driving.
They also have bags, but I find them too bulky.
Share your itinerary with family, but don’t broadcast it live on social media.
Give yourself a day or two delay.
Switch on a phone tracking device like Find My Phone.
Avoid large crowds like at street performers in cities, there is a chance thieves are operating.
Take photos of your ID, passport, and medical records if applicable.
Keep a note of your bank lost card contact number.
Check your bank statements often and report anything that seems dodgy.
Most banks will call you on a landline if you DM them on Twitter.
Drink booze and have fun, but know your limits.
Stick to the group, especially in areas you do not know well.
Use a filtered water bottle to avoid getting sick.
If you get sick, don’t be stubborn about seeking help from healthcare professionals.
You have travel insurance for a reason!
Speak to people about the local scams.
You might think some are laughable, but they all happened to us and the people we met.
Cuba is safe by the way, there’s just a lot of economical scams that happen to trusting tourists.
Do as Paris from Gilmore Girls and Kevin from Home Alone do: talk to your invisible friends if you have to answer the door alone.
Planning a long-term trip?
This guide tells you everything you need to know.
I hope this has helped you during your research on planning an overseas trip.
Please share your planning tips in the comments below or leave any questions.