Finding and booking a trip
I employ two disparate strategies to book flights on the cheap. The first is to keep an open mind and buy tickets to wherever is inexpensive (and appealing — we’re old friends, Rochester, but I don’t want to vacation with you). The second is to pick a destination and wait until a good deal rolls around to book it.
Skyscanner is a top tool for either strategy. Pick your home airport and where you’d like to go, and Skyscanner will pull up a calendar that lists departure and return prices for each day (Google Flights offers similar functionality). Alternatively, pick a departure airport and list “Everywhere” as your destination and Skyscanner will create a list of the cheapest places you can fly to.
If you’re more of a wait-and-see type, or if you don’t want to scour those sites for cheap flights every day, there are a handful of email newsletters that surface good deals and send them directly to you. I’m signed up for Scott’s Cheap Flights, Matt’s Flights and FareDrop, and have booked some astoundingly good flights from them. Scott’s and Matt’s are free but offer robust paid versions. FareDrop
costs $50 a year but is more customizable than its competitors.
All of them can save you a load of dough. As an example, I’ve snagged flights from Miami to Paris for less than $300 and to Rome for less than $400. Both cost double that on a regular day.
And since you’re saving a couple hundo on plane tickets, consider reinvesting some of that dough back into the planet. I recently started using Cool Effect, which has been recommended by The New York Times, to offset my carbon emissions. Cool Effect distributes the money you donate to environmental organizations that replant trees, distribute fuel-efficient stoves to parts of the world that need them, and pay for protections for endangered areas. You can also just use their carbon calculator to decide how much to donate to your
environmental charity of choice.
You can take as many vacations as you can afford, but there’s only one Earth.
Planning a trip like a digital pro
Once you’ve got a flight booked, it’s time to dig into what you’ll actually do there. This, my friends, is the best part.
Any good trip is a balance between rigorous planning and allowing serendipity to hand you your next favorite travel memory. I like to start with a list of all the things that I’m interested in (more on how I actually do that in a minute).
It typically includes the Big Sites — the Eiffel Tower, the Colosseum, three separate statues of small beings relieving themselves — and a few in-the-know stops from friends and family. Then I prioritize that list and assign one or two things to each day of the trip. This involves a lot of resisting temptation to pack the itinerary and a lot of self-persuasion about how it’s OK to let the rest fall off. That, my friends, is the worst part.
From there, I gather information about anywhere that seems interesting. A few regular sources:
- Atlas Obscura, a site that catalogs interesting places around the world, offers a map that includes all of its beautiful and bizarre locations.
- The Washington Post’s By The Way guides to cities around the world are indispensable. If you’re interested, I wrote about how it’s different from other travel sites.
- Instagram is a goldmine. Search hashtags for #[yourdestination]travel or #[yourdestination]food for awe-inspiring and mouth-watering photos (just be prepared for those places to be overrun with other tourists).
- Airbnb isn’t just for lodging. The site also offers a “things to do” section that allows you to book, erm, things to do. Even if you don’t use Airbnb to book lodgings, it’s a good way to see what’s out there. Viator offers similar features.
- La Liste is an app with a restaurant list curated by some of the world’s best chefs (in addition to the crowdsourced lists you’d find on other apps). If you’re looking for truly local restaurants, look for those in which the online reviews seem to be mostly written in that country’s native language, or try searching for the city’s name and terms like “hidden gem,” “local favorite” or “locals only.”
- It’s not for people with little patience, but YouTube travel vloggers often surface miraculously weird and wonderful things to do in the places they visit. Think about it: They’re trying their hardest to stand out, so the impetus to find new classics is high. I like Kara and Nate (the creators of FareDrop) and The Endless Adventure.
- Oh, and ‘tis the season to see fall foliage in the U.S., so here are the best places for that.
This is where the tech stuff comes in.
TripIt and App in the Air are both adept tools for keeping track of your flights and reservations. Both offer the ability to scan your inbox for information and automatically adding it to your itinerary, but I’d caution against that if you use that email account for anything sensitive (and even if you think you don’t, you probably do). Instead, I typically just forward my emails to them as they come in.
Both tools combine all of your bookings into one itinerary, both can automatically add that information to your calendar of choice, both automatically update that information if flights change or plans get canceled, and both offer quick and easy-to-parse interfaces for when you panic about your departure gate in the middle of the airport.
Both also offer paid versions. App in the Air Premium is cheaper than TripIt Pro and offers more features — automatic check-ins, airline reviews, seating advice, expected wait times for security, fun badges for mileage and more.
Neither can effectively keep track of your non-ticketed plans, though, and that’s where Google Docs and Google Maps come in.
My friends think it’s extra (and it is), but I create a fresh Google Doc for every trip. I start with dates, destinations and travelers. The itinerary starts taking shape with flights, then I fill it in with reservations. There’s a section where we drop ideas about things to do on a list. Once we decide which of those are must-do’s, they find a place on the itinerary. There are sections to list the average weather, to track whether we have access to clothes washing machines throughout the trip, to compile costs, to sort out who will watch our pets and a to-do list as we approach the date of travel.
All locations with an address make it to a Google Maps “my map” (here’s a sample map from a recent trip my friends and I took to Nashville). When someone gets hangry, we can consult the map for a quick, vetted restaurant recommendation. If we decide to chill in a neighborhood, we can see what’s interesting around us. Or we can just ignore it and let our feet and eyes decide for us. The map functions as training wheels — there if you need them, easy to remove and ignore if you don’t.
Addio for now, miei amici,
Ren LaForme
P.S. This edition of the newsletter won’t be concurrently posted to the Poynter website like usual. If you’d like to share it with someone, please forward it directly to them or otherwise hold your horses until next week, when I’ll post both parts together on the site. Grazie!
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