A Guide to Planning a Weekend Trip by A Pair of Passports

Our Comprehensive Guide to Planning a Weekend Trip

As you know, we are the (self-proclaimed) king and queen of weekend trips. Between 9-5 jobs, occasional working weekends, and existing plans, we only have a few weekends when we can actually travel, so we try to make the most of them. But the whole planning a weekend trip thing isn’t always easy with our schedules. Sometimes we book tickets and a hotel, but do not get around to even thinking about what we want to do until the day before we leave. That leaves me scrambling to build an itinerary at the last minute. That may sound weird to you, but, as much as we love to be spontaneous, planning is essential for quick trips. And, to be honest, we actually enjoy the process of planning a weekend trip in depth!

When cramming an entire city into a couple of days, it is important to have an idea of what you want to accomplish. Otherwise, you’ll feel like you did not get to know the city, and will probably shine a more negative light on the city as a result. We thinking planning a weekend trip can be really fun and interesting, and actually look forward to it most of the time.

These are the steps we take for planning our weekend trips, including links to all of our favorite resources.

These steps consistently work for us, so give it a go and let us know if it works for you, too!

1. Pick a Destination

This is by far the best part of planning a weekend trip – or any trip for that matter! Sometimes we pick our destination months in advance (like our weekend in Paris for the Euros); other times, it’s a spur of the moment decision. Either way, you can’t do any useful planning without first knowing where you are going!

A Guide to Planning a Weekend Trip by A Pair of Passports

We always have a running list of places we want to visit, but usually plug our dates into Skyscanner’s “Everywhere” search to see what our other options are as well. We do not pick our destination on price only, but rather a mix of the following:

  • Price: Because we will only have 2-3 days in our location, it is never worth spending more that £150-200 on our flights. We really like when we get flights that are £50 round trip!
  • Time of year: Is it going to be crowded? If it’s the off season, will places be open? What will the weather be like?
  • Desire to go there: If the prices aren’t too different, we would rather pay a bit more to knock something off our list than save a few £ to go somewhere random
  • Travel time: We only have 2-3 days, so we don’t want to spend a full day on planes/trains/buses!
  • Special events: If we are interested in attending a festival or event, that will likely influence our destination decision

2. Book transportation & accommodation

Once you pick your destination, it’s time to solidify the plans. After all, there is no point building out an itinerary only to find out that flights have skyrocketed out of your budget! When planning a weekend trip, we usually book our flights/transportation first, followed by accommodation.

Whenever we book transport & accommodation, we use our Chase Sapphire card, so we are gaining points no matter which airline we book with! These points are transferrable 1:1 with airline & hotel loyalty programmes.

Booking Transportation

A Guide to Planning a Weekend Trip by A Pair of Passports

In our opinion, Skyscanner is the best tool out there when it comes to flights. We search for our destination, filter for the times we prefer (leave London after work on Friday, return late Sunday), untick the airports we refuse to go to, and start to browse! After finding our perfect flights on Skyscanner, I usually check them against booking with the airline directly to ensure we are getting the best deal. MintNotion has a great guide on booking cheap flights which is worth checking out if you are on a budget! Friends of ours have also previously used Hipmunk, Kayak, and Skiplagged for flights, but we have no personal experience.

If we are not flying, the booking process is a bit different. For trains, I always research the best booking method on Seat61 – this site has detailed information for nearly every destination! Of course, if we are staying in the UK, we just book our trains directly through National Rail. For rental cars, we also use Skyscanner, or book directly through Avis.

Finding accommodation

If we are booking far enough in advance, we try to find a private Airbnb in the centre of whatever city we are visiting (check out our guide to having the perfect Airbnb experience). If we cannot find an Airbnb that we are happy with, we turn to Booking.com. We prefer Booking.com to other hotel sites because it has a great mix of boutique hotels, bed & breakfasts, and bigger brand names. When Booking.com does not have a satisfactory selection, I turn to TripAdvisor or Expedia for research and book directly on the hotel’s site.

A Guide to Planning a Weekend Trip by A Pair of Passports

When it comes to accommodation, we factor in the following:

  • Location, location, location!
  • Ease of transport to/from airport or train station
  • Safety of neighborhood
  • Written reviews
  • Price to quality (stars) ratio
  • Design*

*This one is weird, but I am a blogger after all! I love checking out the “style” of hotels, and will actually spend more to stay in one that has a really cool vibe, just to try something different. #Instaworthy

Dog Friendly Travel: When we travel with Giorgio, we have the best luck searching “dog-friendly hotels [city].” I have tried previously to find hotels on Booking.com or TripAdvisor, but their pet friendly category is not always reliable. I much prefer to find a section on the hotels website that confirms they accept pets. I found The Fish Hotel by googling “Dog Friendly Cotswolds” and it worked out perfectly!

〈 RECOMMENDED: If you’re traveling within the UK, we already put together a list of 8 dog friendly UK hotels – it might be a good place to start. 〉

Summary: Our Favorite Resources for Booking Transport & Accommodation

Car Hire
If you are new to Airbnb, sign up here and receive £32 off your first stay!

3. Gather information

Ah, I love the research phase of planning a weekend trip! It is so fun to peruse articles and blog posts, reference guide books, and chat to friends about what they loved about a specific destination. We approach the gathering information stage in two parts: essential information, and fun stuff.

Essential Information

Essential information includes putting together all our reference numbers, directions to our accommodation, and confirmations for any pre-booked activities. I like to make sure I have everything stored in my email Travel folder as well as on my trip information OneNote page (more on this in step 5 below!).

Things to do

This is when Pinterest can be your best friend, as well as Facebook groups such as Girls vs. Globe. I sometimes spend hours collecting blog posts and articles to read about the city we are going to. I tend to lean toward 24-48 hour itineraries and quick lists for a short trip, but sometimes will read an entire city guide if we are really unsure about what we want to do. The New York Times 36 Hours series is a great place to start for initial information about a city – I know a couple of other publications do them, as well.

Sean and I have a priority list of things that we try to do in every city – try local beer or wine, go for a nice meal, and view the city from a high vantage point. It’s great to have a list like this because it gives us a starting point for research. We usually research these items first and then plan around them. That’s how I found out about the Slovak National Collection of Wine in Bratislava, which I don’t think I would’ve found if I hadn’t googled “wine tasting in Bratislava”.

A Guide to Planning a Weekend Trip by A Pair of Passports
Loving our Slovakian wine in Bratislava!

I usually steer clear of TripAdvisor when planning what to do because it is sometimes just too much information. I’ll look for a restaurant or something like that, but not things to do. I much prefer blog posts as they come from real experience and are in a well-written and well-photographed format. Hand Luggage Only is one of my favorite blogs to check for weekend trip information – they have great itineraries and even better photos!

4. Filter information

After we pull together as much information as we can, we sit down and sift through it. I read a ton of articles and blog posts and put all of the options out on the table. Then, Sean and I sit down together and decide what we want to do. This includes deciding what neighborhoods we want to visit, any specific attractions we feel are must sees, and setting objectives for what we really want to get out of the trip.

〈 RECOMMENDED: Neighborhood Guide – Exploring Paris’ Le Marais District 〉

This is the hardest part because it requires us to face the absolute truth of weekend trips – time is limited. We often have to sacrifice things that we really want to do, like seeing the Blue Church in Bratislava. However, I also really like this part because it is when the planning really starts. From picking out restaurants to researching what exhibits are on at museums, it’s fun to see all of the options that we have, and how much even a small city has to offer!

At this stage, budgeting also comes into play. We immediately nix the ideas that are going to take up too much of our budget, and instead look for things that we can do on the cheap. I would much prefer walking around a city all day and seeing all of the sites then going for a fancy meal over spending a large sum on one or two attractions and having to squeeze in a quick dinner! However, we do love organized tours, and at this stage we have to find out if there’s one available that is actually going to be worth it.

5. Organize information

A Guide to Planning a Weekend Trip by A Pair of Passports
A fully organized OneNote page usually has all of our confirmations, as well as an itinerary.

Microsoft OneNote is the best tool for organizing a bunch of information on one page, and I am obsessed with it! I use it to organize all of our travel, all of our wedding planning details, and all of the content that ends up on this blog. OneNote is free to download, available for both Mac and PC, and syncs across all of your devices.

I have a page for each trip we are going on, and I manually order them by date in the side bar. Within the trip’s page, I paste all of our transportation & accommodation information, public transport directions to our accommodation, and information on everything we are planning on doing.

When gathering information, I paste URLs to blog posts, itineraries, tourist center information, etc. into the page. Then, when filtering, I go through each link and just make note of the information we actually need. That’s when I get to the organizing! I take all of the information and build it into an itinerary – sometimes this is an hourly itinerary (like in the photo above), and other times it is a rough list of this we should try to do.

A Guide to Planning a Weekend Trip by A Pair of Passports
Our Japan plans are in the early stages – literally just a bunch of links to go back to later!

Are you ready to start planning a weekend trip?

Weekend trips can be stressful and jam packed, but they are so much fun. We also think they are a great way for couples to start traveling together, or for friends to plan a reunion without breaking the bank.

The key to a great weekend trip is having a plan. I am such a planner and the excitement I feel for each trip we go on starts with the planning stages. If you’re not a planner, I recommend at least giving it a try – travel is completely different when you have an idea of what you are going to do, and it can take the stress away from the limited time you have on the ground.

Once you’re on your trip, don’t forget to be flexible and spontaneous. What? Did I just say that after a post about planning? Yes! Things don’t always go according to plan – don’t let that ruin your trip! Your plan is your guideline, but you don’t need to follow it 100%. Go back to that little bar you saw on the corner, spend an extra time in the museum. Chase that local celebrity down the street if you want to. Above all, enjoy yourself. That’s what travel is all about.


If you liked this post, check out our guide to planning a road trip for more travel planning  tips & tricks!


This post contains some affiliate links. If you click one of these links and make a purchase or booking, we receive a small commission. Each link included in this guide is handpicked by us as a genuine recommendation and we only partner with brands we personally support.

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A comprehensive guide to detailed planning for weekend trips. Includes links to essential resources. Tried and tested by A Pair of Passports.

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