Laying on the beach is the easy part, but planning travel can be stressful and sometimes, we can be indecisive. Here are some of the tools that can help!


I checked out a bunch of packing apps, but PackPoint is simple and easy to use. It does just what you think: helps you create packing lists so you don’t forget a thing.

Pop in a few details about your trip, including where you’re going, the dates, type of trip and which activities you’ll be doing. The app will assess the weather and will generate a list with everything you might need.


Lots of people told me they like TripIt for travel, but it is geared more towards the business traveler.

Tripsy is more leisure focused, with a fresh app design that makes it easy to organize your travel itinerary and share it with friends and family.

Just forward your confirmation emails to the app and it will do the rest.

I also like how you can store important documents related to your trip – PDFs, images, whatever.

Finding a hotel

When it comes to searching for a hotel, there is no one way that works for everyone.

But here’s my system, and it works most of the time.

First stop: You can type in an address and sort by distance to find the hotels closest to a certain landmark. Say you want to stay near a relative’s house or a convention center. While many hotel sites sort by distance from city center, I like how I can see exactly how far a hotel is from where I primarily want to be.

TripAdvisor is a great resource for helping you figure out which hotel is the best in the city. I’m not talking just 5 star, but you can set your filters to the preferences you want, then sort by “Traveler Ranking” to see the best places to stay in any destination.

Finally, I also like to scour Google Hotels for my travel dates. I’m not necessarily booking my hotel through this site, but I like to use the power of Google data to help my search and find the best deals. Google will mark hotels a “deal” if the price is lower than what’s typical. This could save you a lot of money.

Just beware – sometimes Google’s pricing information is too good to be true or it will lead you to some random travel website you’ve never heard of, so use caution.


Flighty is the go-to app for beautiful flight tracking on iOS.

You’ll get the basics for free, but if you really want to make the most of this app, including up to the second alerts, you’ll want to pay for a Pro subscription.

This app is incredible in its simplicity but also the depth of information it shows about your flights.

The best part: it can automatically sync with your calendar to find all your past and upcoming flights and give you fun insights like how many miles you’ve flown in a year, how many times you’ve landed at a particular airport or lifetime miles.

Flighty also takes advantage of the new live tracking feature in iOS which shows up to date information on your iPhone lock screen.


If you’re on Android, or just want something that doesn’t cost anything, check out FlightAware.

It’s not as slick, but still has excellent free flight alerts from takeoff to landing.

I often use this to track a family member’s flight if they’re coming into town so I can get alerts about the progress of their journey without constantly refreshing a web page.

Out of Office

This is a relatively new app that helps you cut through the clutter of Yelp or Google Maps or the millions of blogs out there with travel tips.

The App helps you find the best restaurants and other places to go, all recommended by your friends or tastemakers who know the area well.

The app also has exclusive access to a few secret experiences and perks in cities throughout the U.S.

I talked about this website on my radio show. It uses the power of AI to generate amazingly detailed travel itineraries for just about any city you can think of. The website is already generating about 100,000 itineraries on a daily basis, and each of them are fully customized based on the parameters you set including destination details (Rome with kids!) and dates.

Cheap Airfare

When it comes to airfare, I’ve got my tried-and-true method of finding the cheapest flights and the cheapest days to fly. It involves Google Flights and their excellent airfare calendars plus filters that make sure you’re not getting restrictive flights that might not even include a carry on. Unless you’re into that sort of thing.

You can see my step-by-step instructions on how I search here.