Holiday Itinerary Planning

How I Plan My Holiday Itinerary

Author: Lauren Coleman

Oh holiday planning. Surely it’s time for holiday planning? Well last night I had a pedicure. When I booked in a month or so ago I imagined I would be driving home in my open sandals with my newly buffed feet drying in the spring air. Errr, no. I had my winter boots on replacing the wellies I’d worn for much of the weekend.

While I’d quite happily just settle for some general March-like weather rather than all these minus temperatures, all this cold weather does start to make me think about summer holidays and warmer climes.

When it comes to holiday planning I like an itinerary. I’m not one of those people who can step off the plane and go where the mood takes them. My down-time is very precious to me and I’m only likely to visit a place once so I like to make sure I soak in as much of the sights and scenes as possible.

I’m sure everyone is quite capable of planning their own holiday but I remember telling one of my friends about one of our upcoming holidays with several stop-offs and I remember her exclaiming – ‘how do you know how to do that without a travel agent?!’ So here we go…

Ask For Recommendations

Once we’ve decided on a rough location I usually put out a request for recommendations maybe through my personal Facebook but more likely through Instagram. (Though last year I took full advantage of the RMS community and opened it up to you lovely ladies). There’s nothing more irritating than someone telling you about an amazing festival that you’ve missed out on by a week. On the flip side it all pays to avoid key events like that too as it often makes the trip cheaper. I’ll check the weather to see what we can expect at the time of year we’d like to visit.


Then comes the research; the instagram hashtags, the pinterest perusing, trip advisor checking and the general web research. I don’t scrimp on this part and can literally spend hours bookmarking and saving articles, especially from previous travellers who have spent a similar amount of time in the location. As with our food shopping, James and I often have a shared google doc to make a note of all the suggestions, and it means it’s accessible anywhere.
I also jot down recommendations for restaurants and activities that it’s advised to pre-book so we can get them booked from the UK. When we went to Turkey a boat trip was recommended over and over again. When I went down to the port to book it for the next day it turned out I was about six weeks too late.
I’ll also check out Amazon for a top rated guide book and add any post-it notes to any points of interest. These books are generally good for maps, transport info, a bit of lingo, customs and highly reported crimes.

Plot The Points

With last year’s Sardinian Road Trip I got so many recommendations across the whole island it was difficult to work out where to go. In the end I plotted every single recommendation on a google map to see how closely together the suggested spots were and from there on a natural itinerary formed.

Booking The Trip

It’s not until I have a general view on the itinerary that I book flights and accommodation. In the case of our Sardinia trip it made sense to fly into one airport and out of another so we could cover more ground.
Wth flights we always try to be flexible with dates to get the best pricing, however I’m never fooled by a flight that’s £30 cheaper to fly home later in the evening – you’ll just spend that on food hanging about waiting to come home. Well maybe you won’t but I often weigh up the cost of the cheaper flights and what that will mean in relation to any additional expenses.
When it comes to booking the trip I generally use and Airbnb for accommodation taking advantage of all the reviews and flexible cancellation policies.
At this point too I’ll check out all the transport options and if we’re not booking a car then I’ll be checking out the trains, trams and taxi prices to get from a to b dependent on the time of day we’re landing.
I’ll email everything to both my email address and James’ so we can access anytime we like. Generally I’m used to folks asking for recommendations when we’ve been somewhere so this makes it easy to share after too.

Before We Leave

I’ll screenshot the accommodation details; the address and the map so if there’s any internet access issues I know exactly where we need to head to. I also download a Google Map of the area to use offline so it doesn’t use up valuable data.

When We’re There

Saying that these days free wifi is available in so many places and in Europe we get to use our phone’s standard data plan so it’s easy to adapt your route when you’re on the move. No-one likes organised fun so we try not to be too rigid. It might be that we have a dinner reservation in mind but have lunch wherever takes our fancy. When we were in South Africa we ended up having four meals in one day as there were so many recommended restaurants. No wonder I came home about a stone heavier.

So that’s how I plan my trips, how do you plan yours? Where are you off to this year and how have you decided what you’ll see and do when you’re there?

Lauren likes Paris, Prosecco and Paint Charts
Follow Lauren on instagram @mrslaurencoleman
This post may include affiliate links.
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36 thoughts on “How I Plan My Holiday Itinerary

  1. I love that your so organised, major travel goals as far as I’m concerned.
    I do like to plan a trip too however, I’m off to London this weekend for a very last minute girls weekend/reunion and other than flights and hotel we have NOTHING planned. I’ve already been frantically texting my friends trying to organise a pre trip planning night – any excuse to crack open some wine.
    Any suggestions would we welcomed, especially for places to eat.

    1. I can certainly help you with London suggestions, Leona! Let me know how many people, what kind of places you like and where you are staying

  2. Brilliant post!

    I start with trailfinders or more usually a specialist or high end providers trip like Abercrombie and Kent as ideas for an itinerary because the distances are usually pretty good. Then I get trailfinders to open up a booking (they have a brilliant online portal) and hold flights. Then I basically do a day at a time and work through hotels – hashtags, trip advisor, and airbnb. I generally find airbnb only works where you’re staying more than one night and I also look for the name of the place and then try and book via the hotel so (a) you don’t pay yet and (b) more importantly, you don’t pay airbnb’s fees on top. Trip advisor forums are very good for internal flight options. When we went to South Africa I was told we couldn’t fly direct to George on the garden route from Kruger NP, only Port Elizabeth. Trip Advisor pointed me in the direction of low cost airlines places like trailfinders couldn’t book.

    What I like about TF (big fan) is that you can book nights 1-5 with them, 6-7 off, 8th night with them etc. They’re totally flexible. And you often get cheaper deals than booking direct. We usually get at least 2-3 nights free a fortnight through their deals.

    Holiday research is the best type of research for sure. We had to put NZ, Canada and another Namibia Safari on hold when we had the kids but I still have my spreadsheets of rough itinerary. Sometimes I look at them wistfully as we load the car for Scotland again.

    1. I’m a big fan of trailfinders too. We had our wedding gift lift with them and they didn’t push us to spend all the funds as they acknowledged their excursions were more expensive then booking direct. They held the remainder of our funds and we used them to book flights to New York for our fifth wedding anniversary.
      Will be so good to revisit your NZ, Canada and Namibia itinerary when your littles are a bit older.

      1. Ooh that’s so good that Trailfinders held the money for you, Lauren! I might have to look into that myself…

  3. I do exactly the same! The idea of not planning some kind of itinerary makes me panic… What if you go all that way and miss something amazing? I think this comes from the fact that at 21, I went to Rome completely unprepared and unresearched, managed to miss the Sistine Chapel entirely and only had mediocre pasta the whole time. Never again.

    My not-so-secret planning weapon is the guide book (both rough guide and lonely planet). I buy both once I have decided on the country, and go through them like a hawk before I decide on a route. Once that’s sorted, I go through them again nearer the time for accommodation and food recommendations, and cross reference these with trip advisor/online articles/ friend recommendations. I also make sure to always have at least one book in my bag once we are there in case we happen to be wandering and want a great coffee/breakfast/lunch spot.

    I enjoy holiday planning almost as much as the holiday itself!

    And on that note, any recommendations for a September Sicily honeymoon would be most appreciated 😊

    1. Gem, exactly the same thing happened to us in Rome! So poorly researched that we ended up with terrible meals. My first time in Italy and I missed the whole red and white pizza thing. Was so disappointed when my first italian pizza arrived with no tomatoes!
      Are you off to any of the Aeolian Islands on your honeymoon? We loved Lipari when we stayed several years ago, especially watching the view onto Stromboli and the active volcano. Sicily is a gorgeous place. You’ll love it x

      1. I am so glad someone else has done this! Usually when I say to people that I didn’t particularly like Rome, and that the food was average, they look horrified. But I really think I did it wrong – I’d love to go back one day, armed with my trusty guide books!

        We heard that the Aeolian Islands start closing down a bit late Sept/early Oct, so we are going to Taormina, Syracuse and Modica. I’m so excited! I have already started my spreadsheet, and am using my commute time to search for amazing places to visit. It all looks so beautiful x

  4. I always remember a weekend away in Berlin (so much to see and do!) whilst I had things in mind I wanted to see, I hadn’t spent any time or effort into pre-planning the trip! Never again! We spent half of the first day wandering around aimlessly! I think planning is definitely necessary when you are in a new place and want to make the most of time there, especially with restaurant/bar recommendations, it can make all the difference to your holiday! Thanks for the tips! X

    1. Totally agree Sarah. It’s a big effort to go away what with sorting out work beforehand, packing, getting to the airport. You want to make sure it’s worth your while when you get there! x

  5. I like to be fairly spontaneous when it comes to holidays, but my hubby would happily have a laminated minute by minute guide! Slight digression, but Us by David Nicholls has characters just like this and it is a cracking holiday read!

    Before settling on a destination I do have a google and look up the sights etc – and I pick a few things I would like to do. I am then relaxed about wandering around and just taking the location in – as long as I can have the occasional wine/pastry break I’m happy. That’s when hubby comes into his element and looks up the best routes to and from attractions and rainy day options etc. I did have a very smug moment in Stockholm when the metro map completely bamboozled him, despite his research, and I figured it out straight away.

    1. Sounds as though you have the perfect partnership Claire.
      James is usually really good at maps but when we went to Reykjavik he got it completely wrong and we walked for about an hour in the wrong direction. We’d just got engaged so I was on cloud nine and luckily for him I didn’t end up murdering him.

  6. I’m exactly the same!! I LOVE spending time really getting in to the details of what we all want to do and then ticking things off geographically as I plan!

    I know it’s a bit old school but you can’t beat getting a sheet of A3, folding it to accommodate the days we’re away and breaking down in to a more visual itinerary. I also leave a box of activities that might be weather dependent or a range of restaurants we could choose from on the day.

    Would love to see some weekend Europe itineraries 🙂
    I love the 36 hours in USA book! But it’s easier to get to Europe or a UK city!!

  7. OOOH I love holiday planning. We are in that happy stage of being DINKYs and are therefore cramming in as many mini breaks as possible. In the last 10 months we have had two long weekends in Wales, a night in a posh beach hut at the Cary Arms in Devon (dreamy), 5 days in York (a mix of glamping with our bikes and a city centre posh hotel), 5 days in Lisbon and Porto, a weekend in London for a wedding, a night at the Bedruthan Hotel in Cornwall, a weekend in Portsmouth to do the historic dockyard……

    Our next adventures are a night in Exeter for a wedding, a night in Christchurch, a bank holiday weekend in Edinburgh (recheduled due to the snow) and last week we booked 8 days in Andalucia with a VW T6 campervan! We are now about to deep dive into the planning for this road trip – I really want to see Granada, Cordoba and Jaen. Any tips welcome! I like the idea of plotting out the points on a map to make an itinerary.

    When I went to NYC everyone laughed at my spreadsheet but it helped us group activities into areas so we didn’t spend the whole time criss-crossing the city on the underground and I’ve sent it to lots of friends since!

      1. DINKY = Double Income No Kids Yet!

        Packing in as much as we can before a wedding, a family house and kids sucks up all our income!

    1. OOOH I did an Andalucian roadtrip in May. We stayed in Granada, Cordoba, Sevilla, Jerez and Ronda (in that order), and I loved them all. However, I’ve got to say – we stopped for lunch in Jaen and I didn’t rate it at all. Maybe I didn’t see the best bits though, as we were only there for a couple of hours.

      Granada was a really really fun city – lots of free food, fun bars, and of course the Alhambra. We stayed in a fab airbnb in the Albayzin, and I’d highly recommend the area. It’s absolutely beautiful.

      Have you been to Seville before? I’d be really tempted to swap Jaen for that, it’s one of the most beautiful cities I’ve ever seen xx

      1. Ooh thank you Gem, did you instagram any of it? We definitely haven’t decided on anything yet and I would dearly like to see Seville but we need to work out what distances are sensible. We’re flying in and out of Malaga so need a circular route form there and we only have 8 nights. We stayed in amazing air bnbs in Lisbon and Porto, having a little balcony to have pre dinner beers and crisps was one of the best bits of the trip!

        1. You’re welcome! I did put a couple of snaps on instagram, although not loads. They’re under @gemmalem if you’d like to see. We flew in and out of Malaga too, and found it really easy to get to Granada from there.

          We flew into Malaga too and headed straight to Granada for 3x nights. The drive was super easy! Our airbnb was called Casa de las Granada, and had a parking spot nearby, and a gorgeous roof terrace. The host couldn’t have been more helpful.

          While we were in Granada we spent one evening at what is basically a bakery/olive oil shop called La Oliva. They are a shop by day, but a couple of evenings a week they do the most amazing tasting menu. You have to book in advance as they only put nights on when there is enough demand, but it’s really worth the forward planning. It’s SO cheap for the amount of food you get!

          From Granada, we then travelled to Cordoba (stopping at Jaen for lunch) and spent 2x nights in there in the Mayflowers Hostel. Again, I would highly recommend – it’s more like a boutique hotel than a hostel, and is really well located.

          From there, we drove to Seville and spent 3x nights there at a beautiful airbnb called Casa de Ines. Again, super well located, and close to an amazing tapas restaurant! So it can all be done in 8 nights easily, if you’re willing to sacrifice Jaen.

          Hope this helps 🙂 We LOVED our trip and had the most amazing time x

  8. I have to say, I’m as regimented as this when it comes to the pre-plan of the holiday. So much of the fun is the researching! But whilst I might have a loose itinerary and a sight/restaurant/beauty spot hit list, I also make sure to leave huge swathes of time free for serendipitous wandering around. We’ve certainly found some absolute gems that way and they feel a little more special for being happened upon.

    I’m starting to feel the itch for sun too. We’ve not planned much holiday budget this year though, so any recommendations for cheap sunny breaks (that aren’t of the package holiday/agadoo variety) are welcome!

    1. We’re in the same boat too Naomi – unforeseen expenditure means I think we’ll be staying at home this summer. I think I’ll be living vicariously through everyone else’s trips instead!

  9. I’m craving a bit of sun too, but with moving house in the imminent future any holiday seems a long way off. I’m trying to convince my hubby that we need some autumn/winter sun though. I will not be moving from by a pool though. No need to laminate that itinerary!!!

  10. Great post! Loving all the organisation. I am just beginning the planning for a trip to estonia next year for my big birthday (where my grandad was from) so if anyone has any recommendations they would be much welcome!! 😁xx

  11. Love this post – I was only introduced to proper itinerary planning for a going away last year – did a girls long weekend away to Venice – and one of our number is ex-military and extremely organised – she did this AMAZING itinerary – and we fitted SO much in to our 3 days thanks to pre-planning, booking and knowing where we wanted to go. I replicated this for long weekend in NYC this year for my birthday – and again it made so much sense – plus the app Visit A City is brilliant for planning and can really help you structure your list so you are not criss-crossing yourself back and forth. I am now a huge fan of planning – and it adds so much to the build up of going away!

    1. I haven’t heard of Visit a City Janey – this sounds really helpful for a hen do I’m helping plan where the current itinerary is very criss crossy! Thanks for that x

  12. I’m a PA and Office Manager so it’s my job to be super organised. I love a spreadsheet and use them for my life admin. When planning a trip I have a document with all our travel details including train times to the airport and key numbers for the travel insurance and the bank along with our bookings printed out for the flights, transport and hotel in order we’ll use them. I obviously have copies kept in a separate place from the originals. I can’t relax until I get to the hotel when everything I’ve booked has gone smoothly. But then once we’re there I let go and for once I’m not all about the planning. I do like to look at the top rated restaurants on Tripadvisor or know of some places we want to go to but we’ve never booked before we’ve gone. We might say, this day we’ll go to the beach and have a rough plan but that’s about it. Holidays are my one place to not have to be fully planned. We love city breaks and find the best way to experience a new city is to just walk it. We walk miles and miles every day and that’s how you find the hidden gems.

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