The City of Calcutta stretches about 15 kilometers from north to the south along the east bank of the river Hooghly. Flanked by the river that has traditionally been the lifeline for Calcutta's maritime interests (a reason why not too many bridges have been built across the river over the centuries) to the west and swamps to the bayous of New Orleans to the east, Calcutta does not stretch a lot in the east-west directions. Calcutta has a very large suburban area stretching almost 100 kilometers  in all directions except the east. Most of the tourist attractions are located in the city itself, or in suburban towns that are all very well connected by public transport from the city.

Calcutta's most famous district is the Chowringhee area. The name comes from the road that once led to the Kalighat temple in the south, one of the most important centers of Kali worship in medieval India. Apparently, the road was home to a permanent fair revolving around the pilgrim traffic, and was regarded as very colorful. Chowringhee literally translates to "four-colored" and was probably a reference to a "multi-colored road". Modern day Chowringhee Road came into existence after the British, after they had been assured that Calcutta was secure from invasion, moved out of the narrow confines of Fort William and built lovely mansions along the eastern fringe of the Maidan. In due course, the land facing the Maidan, along the Chowringhee Road, that is was filled up, first by private homes, many of which gave way to public edifices, and people moved along a road that used to lead to nowhere more interesting than the English cemetery, and was therefore known as the English Burial Road. When the then Justice of the Supreme Court built his "garden house" on this street sometime towards the end of the 18th century, this street suddenly became a fashionable address, and promptly changed its name to Park Street, a fashionable address to this day. Chowringhee Road runs roughly north to south while Park Street shoots off from Chowringhee roughly southeast. Somewhere south of Park Street a theater was built, perhaps in the early 19th century and a road was built, going east from Chowringhee Road. This soon came to be known as Theatre Road (this road was renamed Shakespeare Sarani to honor the bard in the 1960s, and today both street names are equally used). The specific theater has since disappeared from the face of Calcutta and the road now goes all the way to meet Park Street. This area is home to some of Calcutta's most famous institutions, the Grand Hotel, Indian Museum, Asiatic Society, the 120-year old "New Market" and Calcutta's most fashionable shopping and dining district.

The Maidan is a vast tract of open green space that stretches from the river to Chowringhee Road and includes Fort William. This expanse was cleared so that Fort William's guns could be fired to their maximum range should there be another invasion on Calcutta (in 1756, the old Fort William's guns could not be fired simply because the town had been built close to the walls of the fort itself). It is another matter that no guns have been fired from the new Fort William in its 270 years of existence, except to greet dignitaries, but the Maidan is largely a blessing to the city and home to most of its sporting and recreational activities. The most visible landmark on the Maidan is also Calcutta's most famous sight - the massive marble Victoria Memorial, built between 1903 and 1921, some say to rival the Taj Mahal in Agra. Other sights include Fort William, Birla Planetarium (the second oldest in the world), Ochterlony Monument (built to commemorate British victory in the 1817 war with Nepal but used far more for political rallies during the Independence Movement, and since renamed Shahid Minar or Martyrs' Tower), St. Paul's Cathedral (Calcutta's Anglican cathedral), Nehru Children's Museum, the Nandan/Rabindra Sadan complex (modern-day center of Calcutta's vibrant cinema and performing arts activity), the Academy of Fine Arts (Calcutta's premier destination for art) and the Eden Gardens & Stadium (one of the most celebrated cricket pitches in the world). The Maidan is also home to the local football (soccer) clubs - Mohanbagan, East Bengal and Mohammedan Sporting, whose games are as animated as European soccer matches.