Travel

The Definitive Trip Planning Guide

I have never been a fan of tourist agencies and buying into premade trip plans. Every person has different interests while traveling and no agency can make every passenger in the group happy. This is why I always plan the trip myself not only to get the best experience but also the best value for money.

Planning a trip yourself is no small task. Sure, you can book a flight and just go – but I like having the trip planned day-by-day. This way I can experience as much as possible.

In the process of planning dozens of trips in the last few years, my planning skills and toolkit improved. I figured out how to make the process as efficient and fast as it can get. This process may not work for you in full as we might have different interests – but the tooling I use will surely be helpful in your endeavors.

 

 

The Destination


If you are reading this guide you probably haven’t visited every single dream destination you have on your bucket list. If you currently don’t have anything in mind or budget on your list there are several ways to discover new places.

Use Instagram Hashtags

Instagram is the perfect way to discover new places that match your interests. People post over 50 million posts per day and tag them with hashtags. Hashtags allow you to search Instagram with things that interest you and visually experience them. When you find something you like – check the location information and have fun exploring deeper.

Small note: Instagram is a place where the moments shared are highly edited and curated. Keep in mind that a dozen beautiful images don’t mean this place is something you will like.

Pleasure & Utility

Have a business trip coming up? Need to buy a new computer much cheaper in another country? Want to do a medical procedure costing you a fortune at home?

Combining your vacation with something of utility is a nice way to explore someplace new. If you save a couple thousand dollars getting a dental procedure abroad – why not do it and get a beautiful vacation while you are at it.

NomadList

Nomad List is a site that allows people without a permanent residence find their next city. However, it is super useful for finding new destinations because of its powerful filter. Define anything you expect in your dream destination: temperature, cost, LGBT-friendliness or the number of beautiful women. Whatever floats your boat – Nomad List probably has a filter for it.

Apart from the great filtering, you can find plenty of information that can help you decide if this is a place you want to visit.

Flight That Doesn’t Cost A Kidney


We live in a time where all types of transportation are becoming incredibly affordable as an effect of globalization and worldwide competition. With emerging low-cost air companies and regular airlines trying to compete we get a very healthy market for our wallets.

Tip

As a general rule, you should book your flight 6-8 weeks before the trip as this is the time the flights are usually the cheapest. The best days to book arrival and departure flights are Tuesdays, Wednesdays, and Thursdays. This way you don’t compete with business travelers leaving on Monday and returning on Friday, and get away from weekend travelers. There are exceptions as with any rule so be sure to use the tools below to aid your search.

Skyscanner

Skyscanner is by far the best airfare aggregator out there in my experience. It searches over 380 airlines at the time of writing and allows you several amazing search options.

Nearby Airports

The first such amazing option is adding nearby airports. It allows you to save literal thousands for the inconvenience of taking an additional bus ride to your final destination. This is sometimes a completely viable alternative. Keep the boxes checked unless you are tight on time. This feature saved me over a $1000 for a trip to San Francisco for which I paid only $300. I only needed to book a $40 2-hour bus ride to Venice.

Month Explorer

The other even more amazing feature is searching for all fares during a month. Just select a month in which you want to travel and you will be presented with a grid showing the prices for each departure day. Once you find one that corresponds to the desired timeframe and budget the arrival flight information will be once again presented in a grid with prices.

Finding the best fares this way is as easy as it can get. Just pick the best days combined with the lowest flight prices. Keep in mind that the shown prices are checked in the last 15 days,  and therefore might differ when you actually click “Show Flights” as the fares might change in the meantime. Be sure to try out different options to make sure you are looking at the cheapest one.

After clicking “Show Flights” Skyscanner will search all airlines for fares matching your filter and will show you up to date fares which you can book right away. It sorts the flights by the best ratio of travel time and price, but if you want to find cheaper alternatives you can sort them by price.

The cheapest flights will probably have more layovers, longer layovers or be longer in the total trip length. What I like to do here is find a cheap flight with a really long layover (12-48 hours) on either the arrival and departure trips and explore the city in which I am waiting for my flight. Some airlines will even hook you up with a free hotel for long layovers so be sure to check that out before booking.

Hopper

Hopper provides a very similar service to Skyscanner, however, they only offer a mobile app to do the booking. Fear not! This mobile app comes with a feature that can not be ignored. Hopper analyses the prices over long periods of time and tells you if you should wait with the purchase as prices will drop, or is this the best deal you will get.

Hopper will also allow you to save trips and get live notifications when fares change so you don’t have to continually keep checking them online.

P.S. Hopper once saved me 60% of my airfare as I waited too long to book and the actual airline that operated the flight doubled the prices.

Hitlist

Hitlist is an app that allows you to keep a list of destinations you want to visit and notifies you of exceptional deals that come up for the destination. This is a perfect solution where you have the flexibility to book a trip whenever you want. That flexibility will save you a great deal of money.

Rome2Rio

Doing a short trip where it seems that flying might not be the best option? Going to a destination that is far away from an international airport?

Rome2Rio helps you compare different modes of transportation. Compare the prices and times of going by car, train, bus, ferry, air or any combination of thereof.

Accommodation / Lodging


The second essential part of planning a trip is booking a nice clean place to sleep. For longer trips, this might even be a rental property which you can enjoy on its own.

There are several good platforms for booking accommodation wherever you go.

Booking.com

Booking.com is one of the world’s leading platforms for booking Hotels, Hostels, Apartments or any other kind of accommodation. It features a great filtering system which helps you find exactly what you need and offers free cancellations on most properties for a certain period. This means if you find a better place or your friend decides to join you on your trip – you can cancel the booking and book somewhere else.

The most useful feature of this site is the really good review system which helps you answer all important questions you might have directly from independent travelers.

Tip

Booking.com takes a 15% cut of each reservation via their site. If you want to save some money and/or get a nice upgrade – contact the hotel directly. Both of you will be happy you went that route.

Airbnb

Airbnb is a platform very similar to Booking.com that was initially only used by independent rental properties. Nowadays, many larger Hotels and Hostels started using Airbnb to market their services but Airbnb still remains one of the largest directories of small rental properties.

Airbnb was also considered a cheaper alternative to traditional Hotels but that changed for the most part. You will probably find Airbnb properties more expensive in some countries than their Booking.com counterparts. However, Airbnb’s selection of amazing authentic private houses and flats will amaze you. If you want to book something more then just a place to sleep. Airbnb is the place to go if you are tired of uniform looking hotels.

Tip

If you are traveling in a larger group, renting a house for yourselves will not only give you the amazing experience but may also be cheaper then getting hotel rooms.

Planning Your Day


The important stuff is now all taken care of. You will get there, you will have a place to sleep at night.

There is so much to see, and you are there only for X days. How do you pack as much stuff you want to see in as little time as possible?

Google Trips

Google Trips is (unfortunately) mobile-only app for planning your daily sightseeing. When you first launch the app you will have to log in to your Google account. Why? Here is the fun part – all the booking you just did for your flight and accommodation will be pulled from your Gmail account (if you have one). This means that all of the important information will be ready for you in the app.

Now you can explore your destination and save every single location you are interested in seeing. When you compile a decently sized list, you can start planning your days. When you are creating a plan you will be shown a map of all the locations you selected. This way you can create the plan in such a way to minimize the time on public transportation any given day. (unless you are visiting to explore the public transportation system itself) Google Trips will help you create plans such that each day you will explore one part of the city so you don’t jump around various locations.

One thing I love about Google Trips is that it will optimize the route to match the working hours of the places you want to visit. Nobody likes coming up to a museum only to see a closed door on a Sunday.

Yelp / Foursquare City Guide

Yelp and Foursquare don’t have exactly the same purpose but I put them under the same roof since they will serve the same purpose in this context. They allow us to search for new interesting places on the spot. Let’s say you are in NYC following your sightseeing route and want to grab something to eat. Fire up any of the two apps and you will find a place just to your liking and within in your budget in minutes. This is where they come in handy and why you should have them on your phone before you get on the plane.

 

General Information


Now that we sorted out all of the amazing places to visit, let’s sort out the little but very important things. Things like how does the public transit work, is there a tourist ticket for transit, what kind of plug adapters do I need, how to get to the city from the airport?

There are several apps I use for this. The two most useful one I already mentioned – but I will go in detail here about the specific features.

Google Trips

Google Trips will not only allow you to get sightseeing routes on point. In its “Getting Around” and “Need to Know” menus you can find out everything from how tipping works, which taxies to ride, all the ways to get to the city from the airport and any other essential information.

The beauty of these options is that it does not only give “the best” alternative but lists all so you can decide which one is the most convenient for you. A fast but expensive taxi ride from the airport might be perfect for one person, whereas another person would love a cheap alternative that takes a bit more getting around.

Nomad List

Nomad List maintains a “Nomad Guide” for each of the destinations listed on their site. The guide will tell you what kind of plug adapters do you need, if the water is safe to drink, and many other important information points that will help you make decisions.

 


Got any tips that will improve the guide? Leave a comment below to let me know!

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