Narrow Road to the Deep North
One of the most famous travelogues ever, the Narrow Road continues to inspire Japanese art and visitors to Tohoku, and each of the places Basho visited continues to revere his poems and observations.
In Basho's day, the land of Oku (奥), literally "Within", was the back of beyond in Japan, where farmers eked out a meager living and bandits and hermits roamed in the mountains. Well aware of the dangers awaiting him, Basho fully expected to never return, selling his house and preparing a will.
When reading Basho's work, it is important to note that he takes more than a few poetic liberties with the exact route chosen and the sights seen. Fortunately, he traveled for most of the way with fellow poet Sora, whose more factual diary has allowed the reconstruction of the route.
Back in 1689 Basho walked the entire distance, starting in late spring and taking over five months (156 days, to be precise) for the entire journey. Even with the assistance of modern transportation and perfect scheduling (public transport is sparse in this neck of the woods), it would take a month for a whirlwind tour of all visited sights.
Due to Basho's predilection for mountain climbing, a faithful copy of the itinerary can only be done in summer, after the heavy snows of the Sea of Japan coast have melted and the mountains are accessible.
 Get in
The starting point of the trip is Tokyo, the capital of Japan. As the first stretch of the trip has been largely absorbed into urban sprawl, many choose to head straight for Sendai (Stage 18) and start their trip there (with a possible detour to Nikko).
Basho's original itinerary is as follows, with modern place names or major nearby cities in parentheses where applicable.
Intriguingly, Basho does not even mention Nikko's largest tourist draw, the extravagant Tokugawa mausoleums. Instead, he climbs Mt. Nikko and visits Futarasan Shrine, dedicated to the mountains' guardian spirits.
Sendai is the largest city in Tohoku, home to few attractions but a pleasant enough place to rest for a few days.
Matsuo's chosen route of boarding a boat here for Matsushima remains very popular today.
The craggy pine tree islands here are considered one of Japan's Top 3 scenic spots.
The island of Kinkazan, while not visited by Basho, makes an interesting detour from here.
Once a capital that rivaled in Kyoto in splendor, today's Hiraizumi has little left except two famous temples — and some famous haiku lamenting the loss penned here by Basho.
At this point Basho abandoned the original plan to head all the way north to Aomori and instead decided to head across the mountains. Naruko is now a popular hot spring resort.
The temple of Ryushakuji is quite literally carved out of the mountainside: hence the common name Yamadera, "Mountain Temple".
The three holy mountains of Dewa Sanzan are the center of worship for the Shinto-Buddhist Shugendo sect and its mountain-climbing yamabushi ascetic monks.
The province of Echigo is now Niigata prefecture. A worthwhile side trip here is Sado Island, once a harsh place of exile known for its gold mines, but now home to a yearly music festival that draws people from around the country.
Near Komatsu, Basho visited Natadera, a famous temple still visited by many Japanese (but few foreign tourists).
 Stay safe
The roaming bands of Ainu bandits that Basho feared (but did not encounter) are long since gone. Now the riskiest parts of the trip are inclement weather and the mountain ascents.
 Get out
The ending point is Ogaki, which is 30 minutes by rail from Nagoya, a Tokaido Shinkansen stop. Nagoya is home to the Chubu Centrair International Airport. Ogaki is also not so far from Kansai, and it is only a few hours back to Tokyo.