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The Best 24 Trip Planning Websites & Apps

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Updated on June 6th, 2023

There are now so many travel planning websites & apps to choose from, it’s hard to decipher which are the most useful. I scour the internet regularly on the lookout for how I can use technology to make my travelling life easier. As a result, I have compiled a list of all the trip planning websites & apps that I cannot leave home without.”


The Best 24 Trip Planning Websites & AppsOn the worldwide web!


I am hoping that Sue Where? Why? What? will develop into the go-to place for women over 40 looking for ideas, inspiration & everything else you need to embark on your first adventure alone. As a result, it felt important to share my favourite ways that the internet & apps can help to make our lives on the road easier. Therefore, I have compiled my list of the 24 best travel planning sites & apps. Many are well known, some less so. Most I use regularly; some I have only discovered recently & will be invaluable on future trips. I hope to help you uncover a few unknown gems too.

A blonde woman in a light blue t-shirt standing in her garden, pointing to a mobile phone smiling, with a white text overlay and red YouTube button

Where to go?

The Best 24 Trip Planning Websites & AppsBefore I start on the technology, I just wanted to acknowledge that I get a lot of inspiration & planning help from talking to actual people! I think after recent events, travel agents have come into a realm of their own & my go-to is Trailfinders. I find their agents are always knowledgeable & friendly. They understand independent travel as well as potentially organising everything on a client’s behalf. I often ask them about the practicalities of a location but feel they are indispensable with stopovers & multi-destination trips. They can also be invaluable at uncovering deals that are impossible to find online. For example, they once uncovered a bargain business class seat all the way to Australia for me. Then, on my recent trip to the USA, car hire was included for cheaper than the flight itself! In addition, I have often used their visa service & always make sure I am covered through their annual multi-trip travel insurance.

Now I’ve got that out of the way…on to the technology…

The Best 24 Trip Planning Websites & AppsThe Best 24 Trip Planning Websites & Apps
Keeping organised

Tripit for me is the ultimate in trip planning websites. It keeps all your planned trips in one place, either online or on the free App. It scans your email to pick up any future bookings, or you can simply forward messages & it automatically adds your activity to the plan. I believe it is an essential tool for those of us who love independent travel, pulling bookings from all sorts of providers together for you.

Tripit keeps everything in order, which makes it easy to see when you have an issue… Please tell me I’m not the only one who sometimes books for the wrong month by mistake?”

When I spent 6 months exploring the Caribbean, I was regularly asked to show evidence of my onward journey on arrival at immigration. Countries often need to know that you are not planning to outstay your welcome. Tripit was always accepted. It allows me to share plans with others, be they travelling companions or friends & family back home. In addition, I recently discovered is that it even adds up your mileage, cities & countries for those of us who like that sort of thing. Currently, my total since starting with Tripit is 50 countries & over 760,000 km…that’s pretty mind-blowing!

Where to stay?

Booking.com is my go-to for all my accommodation needs. It offers a bed for the night at all levels of budget & includes hotels, hostels & homes, as well as flights, car rentals, attractions & handy airport taxis. The website also has a loyalty program (Genius) which gives you a 10% discount just for signing up. After that, all you need to do is book 5 stays within 2 years & you have lifetime access of up to a 15% discount, free breakfasts & room upgrades. The app is really user friendly too!

The Best 24 Trip Planning Websites & Apps

The Best 24 Trip Planning Websites & AppsI have long been a fan of Airbnb for the opportunity to stay more locally, in residential homes instead of big hotels. The range of accommodation on offer is wide, from a single room in a home, to an entire party house for yourself. Costs are lower than hotels & they also offer experiences to enhance your stay. In a similar vein to Airbnb, VRBO collates accommodation in villas, cottages & apartments across the world. Trivago is a useful tool to search for a comparison of which sites have the best deals, particularly if you have a hotel in mind already. It’s surprising how significantly the prices can differ between different websites.The Best 24 Trip Planning Websites & Apps

Or how about free accommodation if you’re a pet lover?

Trusted Housesitters is the perfect way to find free accommodation while living in someone’s house & looking after their much-loved The Best 24 Trip Planning Websites & Appspet. The location & duration of your stay will depend on when you are needed, but in essence for an annual joining fee (£99/year), you can search thousands of destinations & dates to find your perfect fit. For more information, you can read all about my experience with cat sitting in the Cayman Islands.

The Best 24 Trip Planning Websites & AppsWhat about flights?

Skyscanner is an excellent resource for flight information, airlines & routes. It searches for the quickest & cheapest routes which cuts out a lot of site juggling when you are looking for the best deal. Skyscanner also offers hotels & car hire, however, I have only ever used it for flights.

What I especially love is the option to choose to fly “Everywhere”. It gives you a list of destinations & prices that are available from your starting point & can be a great source of inspiration.”

A new discovery for me is Jacks Flight Club. They search the internet constantly for discounts, hidden offers & error fares which could mean saving a lot of money on your flights. Once you sign up you get regular emails with flights they have found & how much you could save through booking now.  For example, recently their searches found London to Tokyo for £261 or Glasgow to Toronto for £142, both return trips.

Getting Around

The Best 24 Trip Planning Websites & AppsRome2rio is another essential trip planning website & app as it helps you to get from A to B pretty much anywhere across the globe. Rome2rio includes searches on over 200,000 train lines, 700,000 bus routes, 12,000 ferries & 50,000 flight paths. It’ll provide numerous alternatives with how long it will take & how much the likely cost will be. This is one I really do find invaluable.

Bookaway is also a new discovery for me as an online ground transportation booking system for bus, train & ferries across the most popular routes around the world. Their activity is mainly focused on travel in Europe, Central & South America & Southeast Asia. If you’re planning on exploring these areas more, then it will be a valuable trip planning website at your fingertips.

Uber is also available in many places across the world. Once you have an account it will automatically charge you in your home The Best 24 Trip Planning Websites & Appscurrency, taking away the need to have foreign banknotes & that embarrassing fumble when you don’t know whether or how much to tip (or is that just a British thing?!).

Meeting people

The Best 24 Trip Planning Websites & AppsWanderful is a network of female travellers who share travel stories, local tips & advice on planning. Once a member you can also meet up with local travel enthusiasts at home or connect to members of the community while travelling.

Wanderful embraces women across the ages (their oldest member is over 90) with all levels of travel experience. It encompasses women from the well-worn nomads among us to those just embarking on their journey.”

They also organise trips (currently on offer is a very tempting one to Antarctica), events (such as the first outdoor travel festival (in 2022), webinars & local groups (chapters) for you to get involved with. Since joining I have found the group an excellent resource. It is welcoming, supportive & inclusive. You can even purchase a membership as a gift card for fellow travel lovers.

The Best 24 Trip Planning Websites & AppsCouchsurfing isn’t something I have tried yet for accommodation but once we start to explore again, I think it could be a fantastic way to meet people. You may not fancy staying in someone else’s home, but it is a great place to connect with other travellers. They organise regular events in 200,000 cities across the world & you can put a message out if you want to meet other travellers or locals & see who comes back to you. Although staying has always been free, they now ask for a small charge to be a member (£1.79 per month, or yearly £12.49). If you use the service even once for a free room, this will probably pay for itself.

Finding your way

The Best 24 Trip Planning Websites & AppsGoogle Maps is probably everyone’s go-to for finding maps, distances & directions. However, downloading the maps is more of a challenge. Picture the scene:

It’s the Dominican Republic & I’m about to set off on a solo road trip. While checking the route, it seems straightforward enough. I get a flash of concern & decide to write down each part of the directions. I leave my hotel & my wifi connection only to discover that I can’t access the route…& that none of the roads has signposts, even highways.

Female intuition had served me well as I went to my notebook for directions & the distances between each stage. With several incidences of doubling back & the occasional need to drive over 40 kilometres before I could tell that I was headed in the right direction, I knew there had to be a better way!”

The Best 24 Trip Planning Websites & AppsThen I discovered Maps.me. This is an app which you can use offline to find your position, get directions & lots more besides. One of my favourite features is the ability to put a pin in all the places you visit. It enables you to look back on your travels visually. The app came into its own when I was among a group of 9 who were tackling the Quilotoa Loop in Ecuador, with notoriously bad signposting. Between all our brains, trying to decipher the directions & Maps.me, we emerged triumphant from a very muddy riverbed!

Planning your activities

The Best 24 Trip Planning Websites & AppsGet Your Guide is my go-to trip-planning website for organising tours & activities. It is a great resource to see what is on offer & available in any destination & gives you the opportunity to book in advance, get organised & start looking forward to a stress-free trip. Tripadvisor is a good starting point for some of the more popular activities in a The Best 24 Trip Planning Websites & Appslocation, but personally, I often find the reviews limited. I have more recently asked Google Maps to find restaurants & more nearby. It gives great reviews & all recommendations have so far been excellent.

Get Your Guide also offers vouchers that you can gift to other travellers, check out all the details and loads more in my 26 Travel Gift Ideas for Travel Lovers.

Staying Safe

The Best 24 Trip Planning Websites & AppsEmpowerful via the Solo Female Travel portal is a recently launched “always-on” female festival of all things safety, wellness & sexual well-being. During a massive solo female travel survey, they identified safety as the number one concern among women who travel alone. As a result, they put together Empowerful as a one-stop-shop of resources for all things female, safety & travel related.

On the site are over 30 sessions, involving 35 experts across 50 hours of content. Therefore, if safety is one of your concerns, signing up will gain you access to all of this resource.”

The Best 24 Trip Planning Websites & AppsURSafe is a personal safety app that for a small monthly fee, has global coverage & many useful safety features. For example, it allows contacts to follow you & know where you are, sets up a fake call anytime you may need it & has an SOS voice-activated emergency button. Use this & it will alert local police or security & start streaming live on your camera, just by saying a safe word that you choose when setting the app up.

What3words has divided the entire planet into 3-metre squares & given each one a unique combination of 3 words. It is now the easiest way to share & identify your exact location. Anywhere in the world.

For example, Machu Picchu sits at referred.grilled.folktales, the Tower of London is swift.blitz.funds & Uhuru Peak on Mount Kilimanjaro, repair.speeds.kilowatts.”

The Best 24 Trip Planning Websites & AppsCommunicating

If you don’t speak the language, then you could try taking lessons or use an app. The one I have been trying to boost my Spanish skills with is Duolingo. If learning an actual language isn’t accessible for you then there is always the genius of the Google Translate app which now even uses your phone’s camera to decipher menus or instructions. I have no idea how it works but it is genius!

Deciphering money

The Best 24 Trip Planning Websites & AppsXE is perfect for quickly getting a calculation on currencies around the world & as such an essential travel planning website. XE has all sorts of tools & resources for tracking & sending currency overseas. However, for me, it is a simple & easy tool to quickly identify correct currency conversions, in an instant.

And finally…

Mark O’Travel is a fun app that tracks the countries, states, regions or even World Heritage Sites that you’ve visited. You can add areas to your wish list, keep an eye on your travel stats, & add photos or notes as you go.

So, there you have my top 24 trip-planning websites. Have I missed any that you feel are invaluable? If so, I would love to hear from you. I’m always on the lookout for anything that will make my travelling life easier. If some of them are new to you then I hope you enjoy making the most of your next trip, with all these tools at your fingertips.

The Best 24 Trip Planning Websites & AppsInterested to read more?

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  1. That’s a really exhaustive list, Sue! I’ve hosted on Couchsurfing but have never been a guest myself. Met some really interesting travellers that way, quite different types than guests that when I host as an Airbnb host.

    I’d like to contribute my go-to airline booking site (well, at least back when travel was normal). I’m the first to admit it has a doubtful name, ‘Cheapoair’, but it’s actually good. Best rates (at least for the places I wanna go to) and if I need to make changes, the processes actually do work – there’s a person that gets back to you!

    1. Thank you! Very interesting re your experience with Couchsurfing & Airbnb. Thanks for sharing. Also, I need to check out Cheapoair – always great to have recommendations. 🙂

  2. I am a bit of a planning nerd. So I was interested to see your list of trip planning websites and apps for something new to add to our arsenal. We use AirBnB but have yet to try VRBO. Something we need to try as we look for alternatives to hotels in busy season. I must admit that Rome2Rio is one of my all time favourites. We use the transportation options and times to help plan the routes and travel times. Good to know that GetYourGuide is a good one for planning things to do. Might cut down on our research time. We put all our travel planning details in MS OneNote and share it. But are looking for options to that right now.

    1. Thank you Linda – I’ve never used OneNote so will look into that too. It’s always good to share resources!

  3. Like you, I love TripIt. But I didn’t know that it is often accepted as proof of onward travel, that’s really helpful. I also use many of these other tools–Booking, Rome2Rio, Uber, etc. There is so much great technology these days that really makes travel easier.

  4. I love your list! I am aware and use some of the apps already but had not known much about What3words! There are so many travel apps and lists these days but your list really does top them all. Thank you for sharing.

    1. Thank you! It’s always good to share these things – whatever makes our travel lives easier!

  5. We use several of these for planning our trips, as well as use during our trips. Maps.me is a game changer for us, especially when we’ve been exploring Europe. We will check out more of these sites too – what a great resource!

  6. This is awesome…a few on here I don’t know about so I’ll check it out. Thanks for all your research and insight. Always valuable.

  7. These websites all look so useful! Id love to be able to travel again – this is making me jealous!!

  8. This is a really helpful list! I often use Skyscanner for my flights, but haven’t tried out many of the other ones that you’ve listed. Thanks for the tips!

  9. Good list, I used a lot of these apps myself. I’ve recently joined wanderful, looking forward to engaging in the community.

  10. I love your list as I’m always looking for great apps to help my Uber planning obsession. I will use this in future and try some new ones.

  11. What an amazing resource Sue! Some of these I’ve used a lot, some I’ve never heard of and am glad I finally did. Excellent!

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