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How much advance planning does a trip to Scotland require?
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My advice would be to book in advance for places that you definitely want to stay in to avoid being disappointed when you arrive, however if you are willing to be flexible, you should be able to find accommodation as you go along. You mentioned going to Skye and Edinburgh, which are both extremely busy places in summer, so depending when you are planning to visit, I would definitely say book accommodation there in advance (as soon as you can!).
You can take a look at the suggested itineraries that we have put together to give you some inspiration and help you to plan your route.
Does anyone else have any tips or advice from past experience of travelling without making reservations in advance?
As I'm sure you've heard, our weather is quite unpredictable, but generally May should be a good month - Spring will be in full swing and you will hopefully enjoy some dry, bright weather. There is more information about Scotland's climate here.
Make sure you advance book a car if travelling by ferry as a car passenger to the isles. I lost count of how many people I saw scrambling this summer because they did not have their car booked on. Book your ferry tickets on the CalMac website about a month in advance.
As @VisitScotlandKim alluded to, Skye is especially busy the whole summer with relatively fewer B&Bs and hotels. Apart from that, calling a week ahead of arrival should be fine.
You might find yourself trying to book accommodation at short notice due to unforeseen circumstances. In those cases try the impressively clean network of Scottish Youth Hostels or Airbnb for a short stay.
Hope your dream vacation in Scotland surpasses all your expectations
Best of Scotland in 1 week itinerary (fully by public transport)
My Scotland travels (includes Edinburgh, Skye, Harris, Mull, Arran, Orkney, Loch Lomond, Islay, Oban, Dunoon, Speyside)
If you are leaving from Glasgow, you will have plenty of choices for car rental. Have a look at our advice page on driving around Scotland where you can find links and listings to popular car rental firms. With regards to planning ahead on the ferries, the CalMac website has some great advice in the FAQ section.
Enjoy your trip and also the planning.