Best sites and apps to plan your next vacation

Best sites and apps to plan your next vacation

It’s time to go on vacation! Where do you even begin? Vacation planning can be a headache, but it doesn’t have to be if you use some of the site and app recommendations below.

Quick disclaimer: Most of the apps below are designed for urban areas, and work most places in the U.S. But depending upon your vacation destination, they may or may not work extremely well (or at all) in all locations.

Stage 1: Inspiration

Pinterest is built on inspiration. Just go to the Travel boards and explore. Or use Pinterest to pin things you would like to save from other sites. I pin things to my Travel Board just because I like to look at them all at once, side-by-side.

Google Voyager- Travel makes looking around strange cities a breeze. Get a sample of the famous landmarks, look a little closer by using Street View, and save places to My Places so you can find them when you actually get there, using Google Maps.

TripAdvisor is a great all-around resource. You can get destination ideas by entering the kind of vacation you like, find restaurant and attraction suggestions, and see what other people thought of those places. You will come up with a wealth of recommendations just by reading the comments.

tripadvisor lets you choose the type of vacation you want


Stage 2: Planning

Find a vacation package deal:

In the age of the internet, travel agents aren’t doing so hot, so you can find some pretty amazing deals where most of the work has been done for you; you just have to show up.

Groupon always has fabulous vacation packages for not a lot of money. My latest 2-week vacation to 5 capital cities in Europe cost around $4000 for 2 people—and that included airfare, hotels, multiple tours in each city, and flights or trains between cities! A word of warning: before booking, make sure to Google reviews for the agency you are considering. There are plenty with a bad reputation running deals too good to be true.

Hotwire, Expedia, and other discount booking services don’t just do hotels—you can book a package deal including accommodations, car rental, and flights at a package discount. searches a bunch of cruise lines all over the world for the best deals. Maybe you prefer to cruise where it’s sunny and tropical. Maybe you’d rather see the Alaskan coast. Maybe you would like to cruise down a famous river in Europe. Just select your dates, preferred departure port, and destination, and see what kind of deals you can find


Flight deals are mostly the same across the web. The factor that affects flight prices more than the retailer is the travel date, and even the date it is booked. Time is on your side, and you are usually better off if you have more than two months to plan.

Google flights is better than other flight bookers, and here’s why—they will tell you when the price of your desired flight is about to go up, they actively provide tips that will save you money (like tweaking your travel dates a bit), and you can use the “flights” filter in Google maps to see what it costs to fly to several different cities.


One of the biggest expense of travel is the accommodations. This can also determine how much you enjoy yourself: a hotel with free wifi, private bathrooms, and a definition of “clean” that is similar to yours is far preferable to the alternatives.

Hotwire is my personal choice of hotel booker, though I’ve heard that some of the others are becoming more competitive. I like booking the “Hot Rate” hotels—you get some details (general location, comparable chains, amenities, and reviews), but the actual hotel is a mystery, which makes it exciting. This is also how you can stay in a 4-star hotel for a 2-star price.

Airbnb lets you book a single room or an entire house, and if you are traveling with a group, booking a house or condo might a lot more economical than staying in a hotel. Not to mention that staying in a local’s house is more interesting, and you can ask them where to eat or what to see. And safety isn’t an issue.

Stage 3: While you are there


Renting a car can be super convenient if you have a long distance to drive, or you are not in an urban area. Otherwise, it’s a hassle. Who wants to drive in traffic or find parking (that you then might have to pay for)?

Uber makes getting around super fast, easy and cheap. The app is incredibly easy to use, and your payment happens through it. Not to mention that the company tracks your car through Google maps, making sure that the driver is taking the most direct route (unlike some cab drivers who take you all over the city to get an extra $20). And the background checks and strict review system make it hard to be a bad Uber driver.

Lyft is Uber’s direct competitor and may be easier to use in some cities.

Public transport:

While Google Maps works extremely well in some locations, it really doesn’t in others (like Vienna).

Transit authority’s app (if available). Some cities make getting around easy (mostly cities that get a lot of tourists every year) by providing an app. If the app gives you options for multiple modes of travel, great. If it doesn’t (maybe it is owned by one transportation company, and only shows you how to get around using that company), you’re better off finding a third party app that shows everything available.

Google Maps is still my favorite map app, because it is easy and puts navigation, public transport, and saved places in one spot. Very occasionally it isn’t available. Or is extremely inaccurate, depending on the support they have in each city.

Citymapper is a free app which includes options for train, underground, bus, Uber, or bike.

BONUS: Citybike is a bike sharing service in Vienna that I used. The concept is that you rent a bike at a kiosk, ride it to the kiosk closest to your destination, and then turn it in. The whole process is automated, and the first hour was free, with the second hour costing 1 euro, and then rising from there. If you are on a budget and comfortable on a bike in a city (and some cities are better for bikes than others), check out more about bike sharing.

Find food/attractions:

Why do we travel? TO EAT! Or is that just me?

Yelp is my favorite site/app combo to see what customers really think about a restaurant. Reading the comments also can give you ideas about what to order on the menu.

Eat24 is a great app for food delivery. Hey, I didn’t come all the way here just to look at the inside of a hotel room! I know, but also my feet can’t take anymore. If you’re wiped, but also don’t want to eat out of the vending machine (or room service), get something delivered. Different cities support different apps: in Paris, we used Deliveroo to get food delivered to our hotel from a place that didn’t do delivery, for 2 euros extra. Nifty!

Currency exchange:

If you go somewhere they don’t use American dollars, you need to know local exchange rates. Trust me, some vendors will take advantage of your unfamiliarity with their currency.

XE Currency is an excellent app that calculates prices for you using the most current exchange rate.


Sure, a lot of places have a lot of English speakers. But once in a while, you need to know the word for something pronto. And it seems like the best restaurants and stores are always run by little old ladies who don’t know a word of English.

Google Translate is a quick and easy-to-use app, has voice-to-text AND can translate signs using the camera. Watch people smile when the phone asks them where the nearest bathroom is, but beware: Google Translate is improving, but it isn’t perfect. You may experience a misunderstanding or two. Chalk it up to stories to tell when you go home!


Maybe the most important tool to use in a strange city, a digital map has several perks over a paper one, one being that you look less like a tourist if you are looking at your phone rather than a big paper map.

Google Maps lets you can drop pins over places you want to see (along with notes to remind you why you wanted to see it), which lets me save places directly to my Google account and have them available on the app. Directions, public transit, and all of the power of Google is in one place. But beware: not all cities have great support for Google maps (Vienna didn’t).

BONUS: Disney World and Universal Studios have their own convenient apps that track your Fast Pass, dinner reservations, and on-resort hotel details.

Happy vacationing!