Aside from a May summit with Kazakh President Nursultan Nazarbaev, this will be the newly elected Medvedev's first meeting with fellow CIS leaders. In a series of informal meetings, Medvedev will seek to reassure them that his foreign policy remains the same: Russia wants to remain on friendly terms with each and every one of them.
But in the cases of Ukraine and Georgia, Medvedev faces a tough task. With both countries pursuing NATO membership and closer ties with the European Union, they have come into direct confrontation with the Kremlin, which regards the former Soviet republics as being within its sphere of influence. Relations have also deteriorated since revolutions in both Georgia and Ukraine saw the overthrow of their pro-Russian leaders in favor of westward-leaning governments.
In this respect, Medvedev's meetings with Ukraine's Viktor Yushchenko and Georgia's Mikhail Saakashvili aren't likely to change the situation significantly, according to Fyodor Lukyanov, editor of the "Russia In Global Affairs" journal.
"In the Ukrainian and Georgian cases, there are very profound differences in approaches. I don't see any serious place for compromise," Lukyanov says. "This meeting is an informal one, and any official significant decisions or breakthroughs are not planned."
Medvedev -- a close ally of former President Vladimir Putin who came to power with the full backing of the Kremlin -- has indicated he does not intend to change Russia's position regarding Georgia and Ukraine. Though his soft-spoken style contrasts with Putin's often aggressive tactics, his message remains the same.
Medvedev's "approach might be softer, his wording will be softer, certainly. But as for the substance, I don't see any bigger space for maneuvering and for softening," Lukyanov says.
Yevgeny Volk, the Moscow director of the Washington-based Heritage Foundation, agrees that little is likely to change in relations between the countries. "I personally think [Medvedev's] efforts will not be very successful, because actually, both the Georgian and Ukraine leadership have already made their choice, and in fact they are pursuing their goals to join NATO and the European Union quite persistently," he says.
At the same time, Russia and Georgia appear once again to be on the brink of conflict over the Georgian breakaway region of Abkhazia. In recent weeks, Georgia has accused Russia of amassing troops and shooting down unmanned aircraft in the territory, while the Kremlin says Georgia is preparing for a new war.
In a separate meeting with Turkmenistan's president, Gurbanguly Berdymukhammedov, Medvedev is expected to seek to cultivate friendly relations, in order to secure lucrative transit fees for oil and gas exports.
"For Russia, it's very important that all the energy resources which are produced in this area -- either oil or gas -- should be transported to Europe and other parts of the world through Russian territory, rather than circumventing Russia through some kind of southern, trans-Caspian route," Volk said.
Russia has been angered by the construction of the multibillion-dollar Baku-Tbilisi-Ceyhan pipeline, which transports Caspian Sea oil from Azerbaijan to Turkey via Georgia, bypassing routes through Russian territory.
But Lukyanov of the "Russia In Global Affairs" journal expects Medvedev's meeting with Berdymukhammedov also to be a difficult one. "Turkmenistan again -- as in the good old days of Turkmenbashi [former President Saparmurat Niyazov] -- is trying to play a very sophisticated game with all possible partners simultaneously," he says.
Although Putin, now Russia's prime minister, is not expected to attend the talks, observers say there is little doubt that his presence will be felt.
"Mr. Medvedev is not a very independent figure; he represents the interests of the group which brought him to power, which actually supports him, and thus his window of opportunity for any kind of maneuvering is very narrow," Volk says.
Medvedev is expected in St. Petersburg on June 5.