How we plan our trips – trip planning advice

This article is quite long! We’ll put into words the process of planning our trips overseas. Trip planning is a huge part of the fun when traveling and therefore we try to share as much of it as we can. Longer trips and long-distance travels are our favorite experiences but they need more planning and more work in general.

We’ll try to summarize what we do when we plan our travels. This plan can apply to short trips to close places as well, but it may be a little of overengineering for a weekend in a European capital with low-cost flight. The process below will perfectly apply to longer trips to more distant places. For example, our two-month trip to Central America. We even asked some other savvy travelers for their best trip planning tricks and tips.

Disclaimer: This is our knowledge and experience with self-organized travels. Feel free to learn from it but keep in mind that it might need some adjustments depending on where, how and for how long you go and other conditions like your nationality or country specifics.

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Travel planning made easy

Hunting for flight deals and travel inspiration

We believe there are not many people who need “inspiration” to travel, but here’s a hint: read books! They could be fiction or travel guides, stories of lost love, or long-time classics. Any book could be a travel inspiration and the trip itself! Here’s a list of some of our favorite travel books, so get started!

There are some websites that gave us enormous amounts of inspiration and ideas on where to go. Those websites are called “Holiday pirates” or the respective on the language and market it serves. We are “deal pirates” who are constantly getting good deals and ideas about flights, hotels, and vacations. You can subscribe and receive alerts on the new deals but be careful – it’s addictive! We had more than a few trips that were just planned because we spotted a nice deal. Not that one needs a bigger reason to travel, anyway.

Here’s the English website: HolidayPirates and the Dutch version VakantiePiraten we tend to use more often as flights usually take off from Brussels and Amsterdam.

Finding flights and buying tickets

Here’s what Georgie from Journey with Georgie recommends:

I have found that Skyscanner is the best tool for finding cheap flight deals. I love that you can search multiple airports in a city at once (no more entering them all individually to compare prices), and also the ability to choose the destination “everywhere” means you can quickly get an idea of what countries are cheapest to fly to. It’s perfect for when you know you want to go somewhere, but you don’t have an exact destination in mind. Finally, you can easily scroll through their calendar to find the best days to fly.

Although I’ve been loyal to Skyscanner for a few years, Google Flights is also an up-and-comer for me! Google recently purchased the software used by most travel agents, so you can use the same tools as the pros. I love the visual map you get of where you can fly to from different places – it worked great recently trying to work out the best place to fly to Cuba from. Personally, I’ve found it works best for flights in North and South America at the moment, but I’m sure it will expand!

Georgie in Mexico, near Maya ruins; how to plan a trip
Flights (deals or not) can take you to amazing places, like the Maya pyramids in Mexico.

We would add – recently we’ve been using it a lot, especially as it gives options for connections at nearby airports. We love the way we can combine low-cost carriers like magic! You can choose the “anywhere” option to find a good deal to anywhere for a given time period. If you book with and our website, this helps us keep this website running at no extra cost for you.


Whatever we find with any of the above platforms or another, we always check the price at the carrier website (if it’s just one carrier or at least offered by one airline company). We compare the fare and whatever website gives the better fare, we book through it.

Here’s a great resource on finding cheap flights with 10 of the best websites for that.

Checking visa requirements

No need to write an essay about checking if there are visa requirements for your nationality traveling to your destination. But never presume you don’t need a visa, always check – it could be pretty uncomfortable and embarrassing to arrive somewhere where you didn’t know you had to pay some fee for the visa when entering.

We partner with a very cool website where you can check visa requirements for your nationality in all countries, find out how to apply for a visa with the respective authority, or even get a visa online. How cool is that!

We are blessed to be EU-passport holders so we’re ok to travel visa-free to many places. For other countries, we check their websites online for visa requirements or check the Bulgarian Ministry of Foreign Affairs website (Gods be with us). Sometimes we research in forums and groups, or ask friends – just to have an estimate of how complicated procedures might be. For the most complicated ones, we even write how-to posts.

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Travel Insurance

We’ve always booked travel insurance by local Bulgarian providers – usually at the very last minute, and they all give similar conditions so we usually choose if we know a friend who does insurance or if there’s an office nearby. So far we have had no problems with claims – assuming you give them a call from the country you’re having the medical issue. We were reimbursed for our medication after our “sick leave” day in Ubud, Bali. We decided to cover the treatment fee ourselves in Argentina, as the phone call usually costs about 20 euros and would have been more expensive than the medicine itself.

When it comes to real-deal world travel insurance, here’s some advice from Ben from Horizon Unknown:

Planning travel can be very intimidating, and it’s hard to know what is worthwhile and what’s a waste of time. One part of planning a trip that, in my opinion, is a must, is getting the right travel insurance. I’ve talked to quite a few travelers who, for many different reasons don’t buy travel insurance. “I’m not going for long”, or, “I think it’s not worth the price” are two reasons I’ve heard multiple times. But in my mind, if you can’t afford travel insurance, you can’t afford to travel! The cost of hospitals can be incredibly expensive, and if the unthinkable happens, your body can be transported back to your home country without your family members having to foot the possible tens of thousands of dollars!

Since I began to travel back in 2013, I’ve used many companies to purchase my travel insurance, but use only one now, World Nomads. Very competitively priced, great flexibility in their coverage, and any questions or claims are dealt with quickly! Travel insurance is something I never leave home without. It’s a massive weight off your shoulders knowing if something goes wrong, you’re not alone in dealing with the consequences.

We are dancing on the beach in San Pedro, Belize
Trip planning for us is as easy and joyful as dancing on the beach in Belize.

Creating the itinerary

The big document

For every trip, longer than a weekend, we use a shared document to keep our ducks in order. We have a table of accommodations, transportation, tours, and activities. If we find something nice for inspiration – we put it in the doc. We add reservation numbers, flight numbers, and totals of what we pay everywhere. It’s easy to keep track of everything and not miss an important aspect. E.g. once we saw we booked the same night in two different places but we had time to cancel one of the reservations.

The map

For trips we have a lot of movement or going to different places every (other) day, we create Google maps with all the places in the itinerary. It’s very helpful to plan how much transportation time you need if you need to book a bus/car/train. Every pin on the map is a milestone and sometimes we add notes to pins to mark our most important milestones. Also, it’s so easy to just send a link when someone asks us what was our itinerary. 🙂

The supporting excel

Here’s a trick from Leah from Leah Little Travel & Fashion.

When my friends and family ask me for travel advice or for help planning their vacations, one of the main struggles they encounter is feeling overwhelmed by the options of resorts and hotels. How to choose which one to pick?! With all the options, it can become very overwhelming. I would recommend narrowing your search to 1-2 destinations, then identifying 4-7 items you want most in your resort. For example, if I live in the Midwest (which I do), and I have a Spirit Airlines Credit Card to offer me ultra-budget airfare (which I have), I may decide to look into the Dominican Republic and Cancun as affordable Caribbean destinations. Then, let’s say the items I want most are 1) a pretty beach, 2) close to the airport, and 3) an ocean view. If you know at least a range of your total budget (either by price per night, or total cost) that will also help.

Then, I make an excel spreadsheet with rows for each resort, and I can then compare with columns for price, each of my preferred items, and additional notes. Each time I have used this method, I have come out with a clear winner, even among all the options. For this research, I use, and TripAdvisor (be sure to read the reviews and look through travelers’ photos), and I like to book through because I earn a free night after booking 10 nights through Overwhelming made easy! The example is below:

Resort namePretty Beach? Y/NHow far from the airport?Ocean view? Y/N NotesPrice
Resort #1Y20 minutesNReviews say the service is slow$$
Resort #2N50 minutesYThe room décor is nice in photos$$$

Finding accommodation 

We have been using for ages and we’re super happy with the reservation experience, as well as with issue resolution (in the very few cases we had issues to resolve). Recently we see more and more homestays, guesthouses, and locally-owned accommodation options, which fits our travel style even better. We’ve found some super unusual and off-beat places to stay there too. So we’re happy to use the platform. Here you can use it too. If you make a reservation through our website, we get a small commission at no extra cost to you. Thanks!

We love the Airbnb platform too, for offering some of the most authentic experiences and accommodations. We haven’t been using it a lot lately, as there were some hidden fees that appeared after we searched and liked places. We felt like it was not fair to put such enormous “cleaning fees” or whatever.

If you’re a hostel fan, go try – we have mixed feelings when it comes to that platform and still, some hostels over there can’t be booked otherwise.

Double-check when you compare prices

A tip from Eloise is to always double-check.

Double-check what’s included (or not!) in the cheapest option when you compare prices. When planning a trip, the budget is often a major influencer to make decisions. And my travel experiences made me realize that what appears as the cheapest option doesn’t necessarily mean it’s the best budget decision. Always make sure you read the details about what’s included. For example, a hotel located within walking distance from all activities with breakfast included in the room price can look more expensive than just a room in a more remote area. But which option is cheaper once you add up the food and the transport? The idea is similar for tours as they may include pick-up, food, equipment, and extra activities.

Flight costs can vary with your departure time. But if you have to add one night near the airport with dinner and breakfast costs to save $100 on a flight, is it really worth it?

Vanuatu - Tanna Island (c)MyFavouriteEscapes; planning a trip, how to plan a trip
Walking for a few kilometers near Tanna volcano in Vanuatu as we hadn’t budgeted well the very expensive costs of transport when we planned our trip and picked a cheap (and remote) accommodation.

Arranging transportation 

For transportation between countries, inside a country or inside a city, we usually find the respective websites and compare the alternatives. We tend to buy what’s the cheapest and most comfortable option. For example, for bus rides within European countries, we check FlixBus a lot (trains can be quite pricey in Europe). We booked the Japan RailPass as we knew it was a great deal for a certain period with lots of train travel (and trains in Japan are amazing!).

We love road trips. Whenever we can, we do them in our car. Wherever it’s not appropriate, we rent a car. We have used various sites to find the best deal for a given place, time of the year, etc. Recently we’ve been using a lot and we’re quite happy with the results. If you rent a car through the link here, we’ll get a small commission at no extra cost for you.


While we always aim to arrange activities once we reach the place, sometimes you can’t afford that luxury. Some activities in some popular destinations can be booked out weeks ahead, so you need to plan and reserve earlier. We usually find local sites to support small businesses, but recently we’ve been using a lot. We actually found out that some tours are cheaper with this website than with local resellers. So it can be a great way to save money on tours and activities.

Here’s some nice advice from Clare from Epic Road Rides.

Like many people, before I travel somewhere new, I seek tips from people that have been there before. Recently, one of the best ways I’ve found to do this is by joining a relevant Facebook group and asking other members for their advice. I’ve been amazed by how many Facebook groups there are and how happy people are to share their ideas and experiences.

By way of example, before I went on a cycling trip to the Pyrenees earlier this year, I asked members of the “Cycling in France” Facebook group for their tips on lesser-known cycle rides around the place we were staying. Within a few hours, I’d received input from four or five different people, all offering their insights. As a result, we made a few changes to our itinerary and loved the off-the-beaten-track places we explored. So, before you go on your next adventure, why not try getting other people’s input via a Facebook group?

Epic Road Rides - a cycle trip in French Pyrenees; how to plan a trip
How can you not enjoy riding along with these buddies? 🙂

We usually read lots of blogs, forums, and opinions to find what we can do and experience in a place. We book in advance top activities that require a guide, special permission, etc. If you want to go to Patagonia in summer, book your glacier walk. If you want to sail in Milford Sound in New Zealand during the high season, please book well in advance. We learned this the hard way.

Any activities that can be done independently, we usually plan and do ourselves. Sometimes there’s an option with a tour and an option to do it yourself. DIY adds some more charm to the experience and builds you as a better traveler and person. And it’s so nice to follow your own whims and pace, to be honest. Like we did when hiking volcano Santa Ana in El Salvador.

How to plan a trip, trip planning tips and tricks
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So these are our best tricks and tips for planning a trip. We will expand the article as new ideas, tricks and tools appear. We’re so thankful to our travel fellows who also shared their trip planning magic! So now it’s your turn – happy travel planning and don’t forget this is an essential part of the whole enjoyment and love for traveling!

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