How to plan a holiday like a pro – 88 holiday planning tips

How to plan a holiday like a pro - People relaxing on a beautiful beach

Welcome to our ultimate guide on how to plan a holiday, designed to give you all of the information you need to become a pro at booking holidays. As avid travellers, we’ve been booking 10+ trips per year for some time and have picked up lots of handy tips and tricks over the years. From saving money on your holiday to getting the best car hire and choosing a good travel insurance policy, you’ll soon have the knowledge you need to plan a holiday of your own.

Read on for 88 tips on how to plan a holiday like a pro.

Finding the perfect destination

1. Decide first and foremost whether you want a short city break, a traditional beach holiday, an adventure trip or a bit of everything. The type of trip you’re looking for will narrow down booking options and destinations right away. This is always the first step of your holiday planning journey.

2. How long are you allocating for your holiday? Do you have a set amount of time off work? The duration of the holiday will narrow down destination options. You wouldn’t want a long flight for a short trip. Equally, some destinations need more time to explore.

3. Once you’ve chosen the type of holiday you’d like, decide on a budget for the entire trip. How much are you willing to spend? This will narrow down your destination options further.

4. Take into account overall holiday planning costs when choosing a destination. Some destinations may be cheap to fly to and stay in, but eating out and activities might be expensive. On the other hand, flights might be expensive for another destination but super cheap living costs and hotels will more than make up for the high flight prices.

Holiday planning tips - Shows a remote beach in Cuba

5. You won’t be able to fly to all destinations from your local airport. Keep convenience in mind when choosing a destination and opt for flying from an airport that’s easier to get to.

6. Where possible, avoid multiple flights and layovers to get to your destination, especially if you have to change plane 2 or more times. It can cause a lot of headaches.

7. A key consideration for how to plan a holiday is short haul versus long haul. Long haul destinations can sometimes be a better deal than short haul due to low costs in your destination. For example, flights to Thailand are more expensive than flying within Europe. However, once you arrive at your destination, hotels, eating out and attractions are very cheap.

8. Safe choices aren’t bad choices. Love a particular place but feel like you should try somewhere new? There’s no harm in visiting a destination you really enjoyed. We personally love to book holidays to new places, but also visit destinations we’ve been to many times.

Porto river from above - How to plan a holiday

9. On the other hand, try to be open minded about your destination. Thinking of visiting somewhere completely different to your usual holiday spot? Chances are you’ll enjoy it. If not, you explored a new place and can return to your favourite next year.

10. See what’s on in destinations before you book. Festivals, events and other big occasions happen across the globe every month and visiting during one of these events can make your trip even better. For example, April is a great time to visit Seville, Spain for their Easter parade and celebrations. Songkran is an amazing event to experience in Thailand. April-May is the best time to visit Madeira for its world-renown flower festival.

11. Watch Youtube videos of destinations you’re interested in. Watching a video of a place gives you a much better idea of it compared to browsing website photos and reading about it.

Checking entry requirements, passport and visa information

12. Check the UK government travel advice website here for all you need to know about entry requirements for a particular destination. If you’re in the US, this website is the go-to for government travel advice guide.

13. Look out for visa information. Do you get a visa on arrival at your destination or do you need to apply in advance? How long does it take to be approved? Visas also have specific durations. If you’re planning a longer holiday, check that your visa covers the entirety of your trip.

14. Ensure that you have at least 6 months validity on your passport before travelling. Some destinations won’t let you enter the country with a passport that expires soon. We recommend renewing your passport if you have 12-months before it expires.

15. Double check to see if any vaccinations or other safety precautions are needed for your destination. Immunisations are recommended if visiting at-risk areas. Visit the websites we linked to above and speak to your doctor for vaccination advice.

16. Does your destination require you to be vaccinated against Covid? Verify Covid entry requirements if your destination has restrictions. Many countries are dropping restrictions altogether so this will become less apparent as time goes by.

Booking flights and accommodation

17. Book in advance to save money, especially if travelling during peak times. For summer holiday planning, November – December the year before, or January of the same year is a great time to book.

18. Great deals can also be found for last-minute bookings, especially when travelling outside of peak periods. We often find great last minute deals between October and February. It’s easier to find a last-minute deal if you’re flexible on dates and are able to travel within 1-2 weeks of booking.

19. If you’re going on a holiday with one destination and hotel, compare package holidays versus booking flights and accommodation separately to find the best price. Follow our step-by-step guide here to find the best prices.

Shows a boutique hotel from above

20. Consider booking a package holiday for ease and extra cover if anything goes wrong.

21. For extra freedom and the chance to stay in multiple hotels and areas, book your flights and accommodation separately.

22. What facilities are essential for you on holiday? Are you a swimming pool lover? Maybe you like a spa? Are you looking for an all-inclusive experience? Keep this in mind when booking and filter your hotel choices to include must-have facilities. You’ll narrow down your accommodation choice quickly.

23. Not sure about booking Half Board, All-Inclusive or Self Catering? In our experience, you can decide on this when you arrive at the hotel. The hotel sometimes has a special offer for upgrading your package when you check-in.

24. When it comes to any holiday planning, always look at hotel reviews on Tripadvisor or Google Maps before booking. Aim for any hotel with a rating of 4.5 stars+. Anything 3.5 stars or less is more likely to give you a poor holiday experience.

Luxury hotel swimming pool - How to plan a holiday

25. Once you’ve decided on a destination, flights and/or a hotel, compare different dates to find the best prices. We recommend using a comparison website such as Trivago or TripAdvisor to compare hotel prices for different dates. Skyscanner is the go-to search engine for finding the best flight prices. Simply select ‘month view’ instead of an exact date.

26. Are you someone that often likes to speak to a travel agent when researching how to plan your holiday? Book your holiday online instead of visiting a travel agent store. It’s almost always cheaper.

27. Search for promo codes, discounts and offers for your chosen booking site before going through the checkout. Popular airlines, hotel booking sites and package holiday travel agents often have money-off deals listed on promo code websites. Simply Google ‘*insert website name* promo code’ and review the top 5 or so results.

28. Sign up for a rewards credit card such as AMEX British Airways Avios or Amex Platinum to claim travel points and cashback on holiday bookings. Search for ‘travel credit cards’ in your country to find the best offers.

29. Do you want to do a lot of sightseeing or be near the main attractions in your destination? Location is very important, especially for city breaks. Research hotels in central areas and you’ll be able to walk to most attractions. On the other hand, if you prefer a more remote, secluded location, look for the opposite. Location is very important!

30. Travel outside of popular holidays to save money. Valentines, Easter, bank holidays, Thanksgiving and Christmas/New Year are the most expensive times to travel. Other expensive times to travel are the entire months of July and August.

31. Email the hotel in advance if you’re celebrating a special occasion or just fancy your chances at a free upgrade. It’s not uncommon to get upgraded if you’re celebrating an anniversary, birthday, or another special event. At the least, you’ll probably get a free bottle of wine.

TUI aeroplane taking off

32. Consider paying the small extra cost for seat selection or extra leg-room seats on the plane. On the scale of your holiday costs, these are small fees that will help you have a comfortable start to your trip.

33. Some travel booking websites give you an extra discount for downloading and booking using their app. This can be as much as 10% off! This is a how to plan a holiday tip that’s often missed.

34. If possible, book a refundable hotel over non-refundable. If your plans change or you find a better deal, you can cancel the original booking without losing any money.

35. Look out for travel packages and hotels where you can pay later, either on the day or just before travel. This will give you longer to save money for your trip. Some package holiday booking sites offer a low deposit to secure your booking. The rest is then due 1-3 months before travel.

36. Do you prefer to book in-person at a travel agent store? If so, find a good deal online with the same travel company and ask them if they can price match it in-store.

37. Are you planning on a long stay (over 28 days)? Consider booking a long-stay apartment on or Airbnb. It’s a lot cheaper than the hotel option and you’ll have your own facilities to make meals, plus a lot more relaxation space. Many accommodations offer big discounts for long stays.

38. If you’re arriving on an early flight, email the hotel in advance and ask if they can accommodate an early check-in. It never hurts to ask and there’ll be less waiting around on arrival.

Buying travel insurance

39. Always buy travel insurance as soon as you’ve booked your flights and accommodation. You’ll then have cover if anything changes and you need to cancel before your holiday. This is something that’s often missed when thinking of how to plan a holiday.

40. Do you go on a few or more holidays per year? Buying an annual insurance policy can save you money.

41. If visiting the USA or another country with high healthcare costs, be sure to buy a policy with high healthcare coverage value (5 million+).

42. Are you a UK or EU citizen travelling within Europe? Sign up for an International health card for free healthcare abroad.

Pharmacy sign

43. Always be upfront to the insurance company if you have an underlying health condition. If you do and don’t declare it when buying a policy, you probably won’t be covered.

44. Compare the best travel insurance policies for your trip by using a comparison website such as Compare the Market.

45. Planning on doing an adventure activity, winter sports or going on a cruise? Make sure you declare this when buying your travel insurance policy. Check the policy wording to ensure that your activity is covered.

46. Travelling with a partner or your family? Consider a couple or group policy to save money compared to buying separate policies.

47. Is anyone in your group over 65? Be sure to set the correct date of birth when buying your policy. Insurance is usually a little more expensive for older age groups.

Skiing on the Alps - Holiday planning tips

48. Get a policy with the lowest ‘compulsory excess’ charge you can find. Usually it’s only a few £/$ more to reduce the excess to a low amount. This is the amount you’ll pay in the event of a claim.

49. Do you travel long-term for over 30 days at a time? Consider long-term travel insurance or ‘backpacker’ cover. World Nomads is a top-rated provider for this type of insurance.

50. Buy a policy with ‘cancellation cover’ in the event that you might have to cancel your trip.

51. Check that your policy has ‘end supplier failure’ or ‘scheduled airline failure’ cover. This will protect you in the event your travel company goes bust.

Booking car hire

52. Always look at reviews for car hire companies in your destination before booking. Simply Google ‘car hire/rental in *insert destination*’, browsing the top-rated companies on Google Maps and reading reviews. The Tripadvisor travel forum is another great resource for finding reputable car hire.

53. In Europe, it’s often best to choose a local car hire company over a multi-national chain. Chain car hire is franchised and they almost always have poor reviews compare to local companies. In the US and Asia, well known brands (Sixt, Enterprise, etc) can be a good option. Always check the reviews, even if you recognise the brand. Not all locations of a multinational car hire company are up to the same standard.

How to plan a holiday - Susie standing next to a hire car

54. Planning a holiday and want great car hire rates? Book online well in advance of arrival for the best prices, especially if travelling during busy periods.

55. Compare prices online. Look at both the official car hire company website for a quote, but also comparison sites such as Kayak or Holiday Autos. You can sometimes save money by booking through a third party.

56. Look for car hire discounts and promo codes for your chosen car hire company before booking. Simply Google ‘*insert car hire company name* promo code*’ and review the top 5 Google search results.

57. Check that full insurance is included with your car hire package. You always need insurance cover and it would be a bad decision to go without it. You’ll also avoid the hassle of being sold expensive insurance policies at the car pick-up desk.

58. Some car hire companies require an excess payment in the event of an accident, which can be as much as £/$1000. Whilst you can pay more to reduce or remove your excess liability, it’s almost always cheaper to buy a separate excess insurance policy online. Buy this insurance separate to your car hire to remove your excess liability. We recommend buying this through

Getting to and from the airport

59. Make your ‘getting to the airport’ travel plans at least a week before so you feel organised and know what you’re doing.

60. Compare all airport transport options to find the most beneficial way to get there. Buses can be the cheapest, but if it takes hours, it can make your trip that little bit harder. Look at taxis, private transfers, Uber/Lyft, car parking, trains, buses and even seeing if a friend can drop you off.

Shows a classic red car - Holiday planning

61. If you’re planning on parking your car at the airport for the duration of your holiday, compare prices online on a comparison site such as Holiday Extras. They offer convenient on-airport options, but also off-airport cheaper parking. Book as far in advance as possible for the best prices. 2-3 months before you travel is ideal. Booking with the official airport you’re flying from is also a good option. Many airports offer discounts.

62. Unsure how to get to or from the airport in your destination? Rome 2 Rio is a great resource that shows journey times and costs for various methods of transport.

63. If you’re planning a package holiday, opt for the free coach transfer option to save money.

64. Plan to arrive at the airport at least 15-minutes before check in. This is usually 2 hours 15 minutes before your scheduled flight. That extra 15-minutes can help you skip the big queue of passengers that arrive to check in exactly 2 hours before.

How to plan a holiday - Empty airport terminal

65. Consider buying ‘skip-the-queue’ security fast pass / TSA approved tickets if you’re travelling during a busy time and the airport is expected to be busy. It’s often cheaper to buy them online in advance on the official airport website.

66. Buy plane and holiday snacks at the supermarket the day before you travel. Airport food is expensive and this can save you a lot of money. You’ll also have more choice.

67. Travelling during a busy period, have a long wait in the airport or want to indulge a little bit? Consider booking an airport lounge. Booking online in advance (as far in advance as possible) is often cheaper than paying on the day. You can also compare lounges, look at reviews and search for discounts and special offers.

Preparing to travel / packing

68. Pack as light as you can for easy unpacking and stress-free travel. If you don’t think you’ll wear an item, don’t pack it.

69. If you’re travelling with checked-in luggage, buy all toiletries such as sun cream, insect repellent, body lotion, etc, at home before you travel. You can compare prices between supermarkets and look online to find the best prices. Essential toiletries such as sun cream are almost always more expensive in your destination.

Holiday packing tips - Shows a half packed suitcase

70. Don’t pack any electronic or fragile items in your checked-in suitcase. They should always go in your hand luggage.

71. Bring a USB cable and portable power bank with you. Some planes and airports have areas where you can charge your devices. Your handy power bank will keep you charged when charging facilities aren’t available.

72. Buy a set of compact travel luggage scales and weigh all luggage to check that it’s under the allocated weight. This will save you the hassle of re-packing at the airport. We personally use these luggage scales from Amazon.

For more advice on packing for your holiday and what you bring along with you, check out our packing guide here.

Interested in some cool holiday gadgets? Read our Best Holiday Gadgets and Accessories guide.

Planning and booking attractions and tours

73. When planning your holiday, write a list of the top things you want to see in your destination and group them together to form itinerary days. Seeing multiple sites that are close to each other will save you travel time.

74. Some excellent resources to find out the best things to do in your destination include:

  • Tripadvisor’s ‘Top things to do list’, which is ranked based on attraction reviews.
  • Google ‘things to do in *insert destination*’ and read the top travel blogs links. We’re a little biased, but travel blogs are a great way to read about your destination from other travellers.
  • Search Youtube for video guides.
  • Ask friends and family who already been to your destination.

75. In addition to the attractions you want to visit, research the best way to get there. Can you walk there from your hotel? Maybe you need to catch a bus or hire a car? Some attractions can only be seen with a tour guide.

Holiday planning tips - Flamingos at a theme park

76. Take the hassle out of seeing your destination by booking an organised tour. You’ll cover multiple attractions in one day and everything is organised for you.

77. Save an ‘offline’ Google Maps for your destination and add pins/save all of the attractions you’d like to visit. This will give you a good idea of where they are in relation to each other and where you’re staying.

78. Consider booking some attractions online before arrival. Theme parks, water parks, popular museums and other sought-after attractions often have limited spaces. Booking in advance secures your space and you’ll sometimes save money versus paying on the day.

79. Check the reviews for tour operators, attractions and other tourist activities before you go. This will give you a good idea of the best companies to choose and whether an attraction is worth visiting. It’s particularly important when doing a big activity such as scuba diving, rock climbing and paragliding. You want a reputable company that has a good safety record. Checking reviews is as easy as doing a Google search for the company name and viewing their Google Maps reviews.

Budgeting for your holiday

80. When planning your holiday, always have a budget for flights and accommodation, but also for spending money whilst you’re abroad. Although it’s fun to not worry about spending and just enjoy your holiday, ensuring you don’t overspend will put you in a good position financially when you return. Any savings can be spent on another holiday!

81. Consider whether you’d like to use physical local currency or pay for everything on credit card. Sometimes this will depend on your destination; is it a cash-only area that doesn’t really accept card? Do your research before arriving. Some people find it easier to track spending with cash; others prefer card.

82. Sign up for a travel credit card such as the Halifax Clarity. This will give you the best exchange rates and they don’t charge you fees for spending abroad. A credit card also comes in handy when keeping payment on file for your hotel room expenses, or for a car hire deposit.

How to plan a holiday - Shows the canals of Venice

83. Research restaurants and attractions in your destination to find out how much things cost before you arrive. Noting down the costs of key attractions you want to visit and looking at restaurant menus will give you an idea of a daily budget.

84. Similar to the above, researching and noting down a good collection of top-rated, affordable restaurants has two benefits. 1. You’re more likely to have a good meal. 2. You won’t get a surprise bill after visiting an unknowingly expensive restaurant.

85. Plan a rough daily spending budget and try to loosely stick to it. Some days you might spend more, others less. This way, you’ll have an idea of the total holiday cost before you get home.

86. Look for discounts online for attractions you want to visit. Museums, theme parks and other set-admission attractions often have online discounts, promo codes and offers when booking in advance.

87. Research public transport options for your holiday. These are almost always cheaper than taxis and car hire. With the right research, you’ll be able to navigate local metros, buses and trains without knowing the language.

88. Visiting a destination where you phone data plan won’t work or will be too costly to use? Research a good SIM network in your destination. You’ll then know exactly where to get it and what SIM to choose when you arrive in your destination.

That brings us to the end of our guide on how to plan a holiday like a pro. We hope you found our holiday planning tips useful and can now use them to book your own adventure. If you have any questions about the ideas and advice we’ve given or have your own tips you’d like to share, be sure to leave a comment below. 😊


By Ricky

Author bio:

An adventurer at heart that loves anything outdoors. Beaches, mountains and amazing scenery is everything I love about travel! I also enjoy home comforts and need a nice place to relax and re-charge after every trip.


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Comments (1)

My family and I are going on a trip to South Coast next month, so I need to find a holiday house for us to book for our stay. I’m thankful you told us to consider the facilities that are essential for our trip to help us narrow down our accommodation options quickly. I’ll be sure to do as you said once I’ve found holiday accommodations to consider.

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