Best trip planning pre or post Viking trip Moscow to St. Petersburg August 2021 trip

No worries about Communist countries. We have never had any issues in them and have visited many,

For planning purposes: assuming that you are a US citizen, you will most likely apply for and receive a 3-year multiple entry Russian visa, so the single entry point is moot.

Baltic States will work great as an extension - but I think they deserve a separate trip. I'd start with padding several days on either end of the cruise in Russia proper (Moscow and Spb for sure and, perhaps, an outing elsewhere like Kazan or Sochi) and see where that leaves you with your time allotment. Personally, if I were to extend a Russia River cruise, I'd rather go to places like Armenia or (not AND/or) Azerbaijan - the ones that you'd unlikely dedicate a separate trip to. That said, Finland by way of Allegro from Spb is an easy addition.

Oh, on a separate note, there are not too many Communist countries left out there, and Russia is not one of them.

Since the price for a multiple entry visa to Russia is the same as for a single-entry, why would you even consider a single-entry? I'd be interested to know if Viking's recommended visa-service company charges more to apply for a multiple-entry for you.

Since I have an interest in Kaliningrad, I would go there while I had a valid Russian visa. We have not been to Gdansk, but it would make sense on a Baltic itinerary.

We were on that Viking trip many years ago, but our "Scandinavia" (independent, three countries) was an entirely separate vacation, based on an air sale by Scandinavian Airlines. Many cruise companies charge a small fee for air tickets that are not strictly to and from the embarkation/disembarkation cities. I've had the experience that "free" air tickets are often multiple segments, adding to the travel time. I haven't had the experience of forced overnights, but that possibility is always in a cruise-air "disclosure" statement.

I'm not whining, but our "free" air (or was it "$199") for Viking China was NYC- Minneapolis, Minneapolis-Tokyo, Tokyo-Shanghai. I think the return was probably Beijing-L.A., L.A.-NYC. I remember a few hours wait in the Copenhagen transit lounge for our flight to Moscow. I don't remember the St. Pete departure.

I’m kind of expecting an abysmal routing for a free airfare. I’ll have to check into what they charge for a 3 year visa. All I know is the standard form Viking sends out is a one year visa. And I really doubt we go back. I would never have really thought of Russia as anywhere near the top of my travel list. I let my husband pick the destination and I don’t hate the idea so we are going.

First,
Russia is not a Communist country anymore. After the Soviet Union collapsed, the government under Boris Yeltsin divested itself of the vast majority of its ownership of homes, flats, businesses, etc. It privatized the collective farms (now collective ownership, not the state). The government gave vouchers for people living it their apartments that allowed them to purchase them for a modest amount. The KGB was broken up into a domestic and foreign service.

Elections are held for President and their Parliament (Duma). This doesn't mean that the country's government functions like a liberal democracy in Europe, or even the former Communist satellite states, but it is not communist.

Back to travel issues. We did a three and a half week tour that included Kiev, Ukraine, Russia (including a river cruise) and the three Baltic States. You don't need a visa to visit the Baltic States and I would strongly recommend those three countries. They have all prospered and modernized, even more than Russia. Ukraine is a great place to visit, despite its economic and political problems. We did four nights in Kiev and loved it.

You will need a Russian visa and you probably can't enter and leave the country more than once. I recommend finding a tour for Ukraine, but you can do the Baltics on your own. Not sure about what type of transportation you would use between the countries.

If you are paying a visa service to get the visa anyway, why wouldn't you get the most you could for your money? And if you're trekking to the Consulate/Embassy, it's the same number of trips to drop the passport off and pick it up again.

A river cruise is not quite the same thing, but we recently took a Windstar cruise from Tokyo to Hong Kong. Because of Chinese diplomatic capriciousness (the technical word was "cabotage"), a stop in coastal China was cancelled. But this caused a break in continuous China stops. So people on the ship who had [unwisely] settled for the Single-Entry China visa had considerable extra paperwork. Winstar certainly assisted them, but anyone who might have had an independent visit in the next China city would have forfeited it, I think. They could only go on "official" ship excursions without the multi-entry visa.

My point is not the details of the trip, but on the poor "economy" of going with the flow and imagining that you will never return. It's like the people (I think I'm referring to a high-school assignment novel ... ) who used to think you could hold up an American passport in front of you, and the locals would stop shooting! You're not in Kansas anymore.

I would certainly buy travel insurance for such a long in advance booking.