Plan

Climate

Optimizing the climate is crucial. Bad weather can wreck your trip. (“High season” is not always the best weather.) Click below to check odds of good weather using the historical climate by month:

The GIF below was generated from a remarkable interactive map showing optimal times to visit for each of 52 weeks.

Group and Independent Tours

Iraqi Kurdistan, 2013
You can DIY, but you’ll often find advantages taking small group and independent tours. For my suggestions, click here:
If you only want a city tour or short excursion, Viator has extensive options from local tour companies. I've used these often and so far all have been good.

Airline Flights

Scanned card of St. Martin's beach
flight path. Jet exhaust had tossed
me in the water and ruined my camera.
To find the best flights, I rely most on 
For difficult routings, I am sometimes surprised to find connections I don't see Google or Kayak at:

Want to explore destination opportunities from a specific airport? You can always just go to Google Flights and leave the destination option empty!
(Then filter for nonstop or one-stop flights.)
Sometimes I also find it helpful to use:
Boarding a flight from Haiti in 2008

For your many hours on board, be sure to reserve the best possible seat:

Exploit a long layover and take a city tour, sometimes free!

Trains

Don't forget about trains!

Americans especially forget trains are a great option for travel around Europe. And trains can be great adventures elsewhere as well. An amazing site for trains around the world is
Also, another cool site that let's you compare trains, planes, buses, and even ferries between two points

Hotels

For picking hotels, I’m hooked on:

For booking hotels, the best way to save a lot of money is often to gamble and take the prepaid rate.

I’ve saved thousands of dollars by taking that risk, and reckon I’m now way ahead even if I miss a future stay.

I’ve not yet found an aggregator site (even Kayak, Expedia, or TripAdvisor) that has a definitive list of best prices every time. 

Things to See & Do

TripAdvisor has a valuable "Things To Do” sections that let you skim numerous traveler verdicts about the merits of sights and activities. Sadly, the site is increasingly cluttered with its Viator sales efforts, but the key info is still there. 

But I recommend supplementing it with other site like Foders and always doing a web search for "top things to see and do in [wherever]" which will often reveal outstanding blogs and sites with brilliant local tips.

Also, consider investing in a travel guidebook ― to have a convenient summary of information about the sights on your route. As a HuffPost piece points out, such guidebooks do not require wi-fi or batteries, allow quick flipping around, include good maps, and are not theft magnets like tablets.

Destination Safety

To check security in your destination countries, I recommend the clear, concise, and practical travel advice offered by the British Foreign Office. Sad to say but the U.S. State Department's (CYA) travel advisories are usually verbose, rambling, vague, and embarrassingly timorous.

Packing

Packing light is important ― only carry-on if possible. Here are two helpful sites for constructing your minimal checklist:

Currency

When your jet-lagged brain refuses to do math, Oanda’s currency “cheat sheets” are indispensible. Go here (and click on the tab for "Traveler's Cheatsheet") so you can a copy for each destination country:
If you need a converter now, here it is:


Destination Inspiration


Brainstorming about where to go next?
Click here to look over some of the big handsome books filled with creative travel ideas from National Geographic and others.