How to plan a long weekend trip

Aimless Walking > Traveling > How to plan a long weekend trip
Closeup of aircraft

Most of my trips are long weekend trips, no more than three to five nights. Consequently it is something I have become an expert on planning. The following is a few tips and methods I use when I plan a long weekend trip. I’ll say a few words on insurance, a lot more on finding the right destination and flight and also of course a few words on finding out where to live and other practical stuff.

Most – if not all – of the tips and thoughts below can be used for trips of almost any length. Though there might be a need for some adaptions.


It is always a good idea to be insured will traveling. What if you are robbed? Get sick or injured? Anything can happen and it is always good to be prepared. Insurance is an important way for that.

Start by checking out which insurances you have to now and if they cover international travels and the possible problems that might happen. I do know that here in Sweden your home insurance may cover many incidents that may happen. But regardless it might be a good idea to sign up for a traveling insurance.

Travel insurance: simple & flexible

You can buy and claim online, even after you’ve left home. Travel insurance from is available to people from over 130 countries. It’s designed for adventurous travelers with cover for overseas medical, evacuation, baggage and a range of adventure sports and activities.

You can also read more information about travel insurance from World Nomads on my page dedicated to them.

Find your destination and flight

When I plan my weekend trips finding my destination and flights have a symbiotic relationship. I very seldom has a clear idea of where I want to travel. Instead I have a few days leave on Thursday and Friday or Monday and Tuesday to give me a long weekend. So I have fixed dates and are need to find my perfect weekend.

I use one of my favorite three sites for searching for cheap flights, they are described more closely below. Enter the airport you will travel from, Copenhagen for me, and the dates you want to travel. You will then get a list or a visual representation of all possible destination these dates and the cost for those flights. Next step is going through the different destinations to see if it is interesting enough and if the time of the flights are ok for you. Remember that the most early or late flight might be the cheapest, but also not the most attractive. On some sites it is also possible to filter out flights with the right take of times for you. Not everyone want to take of at 11:35 PM as I have seen a few times. Especially not for trips that are shorter than a week.

If you have a little more flexible work schedule you can move the flights a day ahead or back, or even looking another weekend might give very different costs. Do not be afraid to experiment. Cheaper flights will give you more money over for fun activities at the destination!

This is also an efficient method to find new interesting destinations that you have never consider before. This is how I ended up in Nantes in France and loved it!


Before booking the flight make sure to check extra cost for eventual luggage for the different airlines that fly those lines. A cheaper flight might become more expensive than others due to extra cost for checked in luggage. There might also be other extra costs that you have to be aware of before you make a final decision.

When you are thinking about luggage, also check the size of your luggage! Many airlines – especially budget airlines – has unique and different max size for luggage. And that is both for checked in and carry on luggage. Double and triple check the airlines max size and the size of your luggage. If you are unlucky and your luggage are slightly to large you might get charged several hundred euros to get your luggage on the plane. I have myself seen and heard travelers being charged up to 500 € for oversized luggage. Not worth the cost!


I find mainly three different sites useful when looking for interesting destinations and cheap flights.

Skyscanner is one of the better known websites for this purpose. Easy to use search functionality and you get a list of countries sorted by cost. Clicking on one of the countries pops up all the destinations for that countries with costs. You will also have easy links to hotels with costs and local guides. Easy and fast, but not the most functionality.

Momondo is another good example that are easy to use. Basic functionality are the same as Skyscanner, but instead you get a visual representation of your destinations and you can filter the list for price and type of destination. If you choose a destination you can also see how the price varies from day to day, a good way to find the cheapest weekend for your trip. On Momondo you can also look for rental cars, hotels and package trips.

Google Flight is the third and final website, and one that do not seem to know about. Basic functionality as above but with many more variables you can use as filters to find the perfect weekend trip. Just as Momondo it is possible to see the cost per day of you choose a specific destination. Google Flight is the only one where you can use the time of take of as a filter.

All of the three sites has very different feels. Try them out and see which one you like the most. Maybe the clean and ease of use interface of Skyscanner, maybe the more visual and broader Momondo or the more in depth and complex Google Flight.


Have you booked the flight yet? No? Good! Never do that until you have checked the prize of accommodations. Maybe you found an extraordinarily cheap flight to your dream destination, but after booking the flights and are checking for some place to live you find out that the only acceptable places are far to expensive. Because of that never book your flight until you checked that the lodgings are affordable. I have been very close to make this mistake myself, but stopped myself in time to check for cheap hotels and couldn’t find any in my price range.

There are several possible ways to search for your accommodations. Go through the different sites and use the one that fits your needs best. No site are able to list all possibilities, so if you do not find what you need on one check the next one. Also remember that some hotels and hostels are not on any aggregating site, or maybe only on a local on. Some google searches might give you more options and also check out local blogs and sites for recommendations.

Websites is one of the larger websites with lots of choices and good filters. They also have a reward program for returning customers. With several hundred thousand possible accommodations they are a large player.

Booking is a second choice with lots choices and filters Returning customers can be part of their Genius Program for perks and discounts. has over 22 millions booking-alternatives.

TripAdvisor is my third recommendation. With lots of reviews and choices and a large variety of accommodations and activates it can be a good choice too.


While looking for the perfect place to stay do not forget to look it up on a map to get a feeling of its location in relation to the city center, public transport and your planned activities. A badly located place might not be worth the lower cost. It is also important to look up the safety of the general area before you book. Do searches on your favorite search engine with the name of the area and/or city + “safety” for some advice. Finding out your hotel is located in the worst area of your destination will make the trip so much less perfect.


After a few minutes – or if you are like me a few hours – of research you have found you destination, your flight and a place to live, will you now be ready for the next step? Remember you have not booked anything yet, I hope.

Before you book it might be a good idea to also look up if your planned or favorite activities really are possible during this time. Maybe that nice museum are closed that weekend, the opera theater are closed during their vacation, the only tour guide have a few days of, the nature reserve are closed due the the birds breeding season or anything like that.

I try to always have everything ready before I make my final booking. Or at least enough stuff to ensure a great stay! But minimally always research how and when to travel, where to travel and where to live before you book anything.

I will get back to you about more practical tips, on how to pack and find your preferred activities in future post.

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