To start, take the 4, 5, 6, L, N, Q or R train to Union Square. The first store is about a 3 minute walk from the subway, walking along Broadway towards 13th Street.
While starting here will involve a little bit of backtracking later, this is the bookstore you would go to if you only had enough to time to visit one. From Monday to Saturday, the Strand is open 9:30am-10:30pm, Sundays 9:15am-6:15pm. The prices are good and the selection is massive, selling not only books but merchandise for book lovers as well. I spent one hour here but you could easily spend more. You can learn more at the official website, or read my earlier blogpost.
After leaving the Strand, turn left and walk for 6 minutes.
The NYU Bookstore, 726 Broadway
While I didn't initially plan to go to this shop, after seeing it I couldn't resist going in. While selling NYU textbooks and merchandise, the store also sells 'normal' books. However, with all the bookstores I went to, this one was more for fun and less about purchasing anything. It's open Monday to Friday from 10-9 and 11-6 on the weekend. You can read more about the shop here.
After leaving the store, turn left and walk for a minute or two.
Shakespeare & Co. Booksellers, 716 Broadway
This store has no relation to the Paris bookshop of the same name, but it's a cool shop none the less. Be sure to check out the basement which is full of play books. The store is open Monday to Saturday from 10-9:30 and Sundays from 11-8. You find find more information here.
After leaving the store, turn right. Walk past the Strand again and keep walking. It will take about 7 minutes.
Forbidden Planet, 840 Broadway
Perfect for fans of comics, manga and graphic novels. The store also has merchandise, such as t-shirts, action figures and posters. It's open Sunday to Tuesday 10-10, Wednesday 9-12 and Thursday to Saturday 10-12. You can read more here.
Leaving the store, turn right and walk towards 14th street. Turn right onto Union Square East, and left onto E 17th Street. This will take about 5 minutes.
Barnes & Noble, 33 East 17th Street
This is embarrassing, but I actually managed to miss the main location and go to a Barnes & Noble nearby that sells mainly textbooks. The main one claims to be the biggest bookstore in the world and is open every day from 10-10. It looks very impressive. You can read more here.
Leaving the store, walk along E 17th Street towards Union Square West. Turn right on Broadway, left onto E 18th Street, which will become W 18th Street. It will take approximately 5 minutes to reach the next store.
Books of Wonder, 18 West 18th Street
Books of Wonder is a children's bookstore, and was actually the shop that inspired the bookstore in You've Got Mail. There is a little teashop attached to the shop and the store specializes in Wizard of Oz books. Even if you don't read junior fiction or YA, this could be the perfect store to get a gift for someone else. The store sells new books as well as used and rare, and has a great selection of signed books. It is open Monday to Saturday 10am to 7pm, and Sundays 11am to 6pm. You can read more here.
Leaving the shop, turn left and walk for about 15 minutes before turning right onto 10th Avenue. Walk for another 4 minutes until you reach 21st Street.
192 Books, 192 Tenth Avenue at 21st Street
This store is small but still manages to carry a wide range of books. The shop often presents art exhibitions and carries rare and out of print books. It is open everyday from 11am to 7pm. You can find more information here.
To get to the nearest subway, leave the store and walk towards W 22nd Street. Turn right onto W 23rd. The entrance is near the intersection of W 23rd and 8th Avenue, and you can take the C or E trains there.