Prepare for an adventure. Travelling between Azerbaijan, Georgia and Armenia is not precisely smooth, though increasing numbers of people are willing to sign on for the trip. But, by and large, these are backpackers, willing to take the rough with the smooth.
First, Azerbaijan: its capital, Baku, is a good entry point. The city is a curious mix of shiny modernity a la Dubai (but more charming) that circles its Unesco-listed old city. Heritage attractions include the 12th century Maiden’s Tower and the 15th century Palace of the Shirvanshahs; top hangout areas are the Bulvar waterfront and the Fountains Square piazza. The Heydar Aliyev Cultural Centre is an acclaimed piece of modern architecture. Try the well-located Giz Galasi Hotel (from $35; gizgalasi.com). The Guest House Inn and Hostel is also centrally located and even cheaper (from ₹1,700; guesthouseinn.com).
Next, head to Georgia, to its capital Tbilisi. You’ll have to, anyway, since tension between Armenia and Azerbaijan means that the border is closed. This is probably where the adventure aspect of your trip will start—getting there. Flights do exist, but since there are few they also tend to be expensive. You could do your own check on fares, depending on when you choose to travel, but the most affordable options will be overland—either rail or road. An overnight train connects the two cities; travelling by minibus (shared) is also an option (5-6hrs).
Tbilisi is a good base for your Georgia visit. Make a day trip to take in some of the country’s major destinations, from the picturesque foothills of Mount Kazbek, to the famous monastery built into cliffs at David Gareja, to the fortified town of Sighnaghi (see later in this para). But only a couple of days seems inadequate to truly savour what many say is one of the most beautiful countries on the planet—especially if you’ve made the not-particularly-comfortable journey from Baku to Tbilisi. Anyhow, in Tbilisi, do not miss the Narikala Fortress; the Museum of Georgia; the 13th century Metekhi Church; and the sixth century Anchiskhati Basilica. Do also take a ride on the newly-built cable car. As for accommodation, Tbilisi has a growing selection of hotels, which also means that prices are higher here than in Baku. GS Hotel is recommended (approx. $40; no website, use hotel booking engines such as booking.com). The Envoy Hostel offers private rooms as well as dormitory accommodation (from approx. ₹2,000 doubles; envoyhostel.com). A related concern, Envoy Tours (envoytours.com), not only conducts tours in and around Tbilisi but can also help with road travel from Tbilisi to Yerevan, in Armenia (if you’re not taking the train).
Armenia completes the trio of ancient, beautiful and richly rewarding destinations in the South Caucasus. A land of monasteries, capital Yerevan is packed with museums that tell of the country’s tragic past and showcase its treasures: the History Museum, Armenian Genocide Memorial and Museum, Erebuni Historical and Archaeological Museum, the Cafesjian Center for the Arts, and many more. Try the SD Hotel (from ₹2,500; sdhotel.am) or the stylish Caucasus Hotel (from ₹2,400; caucasus.am/en). There’s an Envoy Hostel here too.
When to travel: Summer and autumn are beautiful and the most popular months. Visas: You’ll need to get visas before travelling for all three countries, and you’ll probably also have to make a trip to Delhi for an interview at the embassies. More information on Azerbaijan visas at newdelhi.mfa.gov.az, on Georgia at india.mfa.gov.ge and on Armenia at india.mfa.am/en/visa.
Other resources: seat61.com/caucasus.htm for information on train travel, and azerbaijan.travel, georgia.travel/en and yerevan.am/en/tourism for general information and trip planning.