Despite of the fact that Plovdiv is a relatively small city compared to a large multi-million population mega-polis it offers surprisingly many things to do.

• The Hills - For starters enjoying the sunset from all the different hills is a must. Walk all the way to the top in the late afternoon, pick something to drink and stay there for the sunset. Go down to enjoy the nightlife once it's dark.
• Old Town - Another must is the old town of Plovdiv which is full of art, free of cars and very enjoyable. Go take a walk try it at day, try it at night it's amazing. Try some of the bars there are life performances sometimes there. You might be even lucky enough to catch an opera performance in the old roman theater.
• Center - Enjoying the central park during the day, especially if it's a very, very hot day. Once the weather settles hit the main street and the bars/discos.

The old center of Plovdiv is compact and walkable, with the main downtown road blocked to car traffic. There is a good collection of Bulgarian revival buildings in use as museums, hotels, and restaurants etc. and is worth a visit if you have chance. The nearby Roman Amphitheater, discovered in the 1970's during a construction project, is part of the pedestrian zone, and typically has merchants selling art and other items nearby. Wander the cobblestone streets near the downtown to find the centuries old St. Marina church with a unique wooden tower, a mosque from the Ottoman Empire, and on the nearby hill the old town center. The old town center was walled, and has a famous gateway entrance. Nearby Puldin Restaurant has subterranean rooms where the old wall and historic artifacts can be seen. Continuing up the hill several older houses are now museums and the Roman amphitheater with an overlook of the town below is partially restored and still used for concerts and other occasions.

To the south of the city there is the Bachkovo Monastery, still in use. Farther into the Rhodope mountains one can find ski resorts and other natural attractions, such as the impressively narrow gorge and caves leading to Trigrad, not far from the mountainous Greek border.

Plovdiv has a small airport, but is most accessible by bus from Sofia.

By train

There are many daily trains to and from Sofia. Duration is about two and a half hours. There is also one daily train from Istanbul in Turkey which takes about 11 hours.

By car

The A1 expressway connects Plovdiv westward to Sofia. It also extends a short distance to the east. This is one of two true expressways in the country (the other was built north from Sofia to communist leader Todor Zhivkov's birthplace). Other destinations require two-lane roads, such as the most direct route to Pleven, which is the somewhat adventurous Troyan pass road.

By bus

Buses run approximately hourly from Sofia.

By boat

There is no boat transportation to Plovdiv.

Taxis and buses are prevalent. Downtown has a large pedestrian zone. Taxis are (Summer 2007) as cheap if not cheaper than bus rides when split between 3-4 people in general. A 5-7km of traveled distance was charged at around 2lv. The taxi arrives in about 3-5min. Remember to order the Taxi from the companies that offer the best deals and wait for it. Generally taking the taxi that is already waiting will cost you more (sometimes upto 5-times more) avoid them or ask for flat price that fits you! Learn who offers best prices from the locals who often use taxis.

Taxiservice: [2]

Generally speaking eating in Plovdiv should be cheap for the westerner's pocket. Fast food is available and of high quality (in general).

Budget

Cheapest fast food could cost as little 0.50-1.00lv to 2-3lv and can be found along the main street. There are plenty of such places offering pizza, traditional food, and duners

Mid-range

There are some low-end restaurants that will be fairly affordable pay attention to the menu and think about 10-15lv for a full meal (salad, main course, dessert, drink(s)).

Splurge

Paying more will probably get you a slightly better food than the options above but most of the cost will definitely go towards the overall experience. The priciest places are located in the old town, on top of the hill. Expect to pay a bit more say 20-30lv and above. There are also a few restaurants outside the center.