Possible Itinerary - 16 days Lithuania, Latvia, Estonia and Russia

Looks very good and doable. I haven't done the Russian part but did almost the same itinerary in reverse order. I also think you can easily do Trakai without a guide.

Inyourpocket has a separate guide to Trakai that you print/download.

Seems reasonable, but if you have more time, I would add at least one day each to St. Petersburg and Moscow. Enjoy the borstch! Vilnius is a wonderful gem. With the daytrip included, 3 nights is sufficient.

Thanks Tom!

I played around with train schedules and found the express trains that now run between St.Petersburg and Moscow (~4.5 hrs) so we don't have to do the night train. So...could add the 2 nights to each and still be within our time-frame.

Any advice on explaining to the boyfriend why spending 8 nights in Russia makes sense? I think he think's just the 6 nights might be pushing it (I'm the planner/researched generally of the 2 of us).

Ali, would your boyfriend think that 6 nights is enough for somebody coming to the USA for the first time? Well, Russia is bigger.

Ali, we did almost the exact same route last September, only in reverse. You have a great trip ahead!!! Let me know if you would like some ideas for hotels.
Ash

We've been to Vilnius a couple of times--agreeing with Arnold that you don't need a tour to visit Trakai, bus works fine; we recommend the Domus Maria Guest House in a former monastery in old town.

Ash - I would love hotel recommendations for all the cities if you wouldn't mind sharing them. Also, can you include your travel mode between cities? Did you get your Russian Visa yourself or did you use a company? Thanks!

Galen - Thanks for that recommendation for the hotel in Vilnius!

Also, decided if we don't end up doing Russia this trip we'd hit Sweden and Norway instead.

I was born and raised in Vilnius. Vilnius is beatiful, Trakai would make an interesting trip as well (I wouldn't spent there more than half a day). Sunday's market in the old town part of Vilnius is a great place to shop for handmade gifts and souvenirs. If you have time, visit Kaunas, the second largest city in Lithuania. Walk on the Laisves Aleja (pedestrian zone), sit down and do some people watching at any of the outdoor cafes.

Our hotel in Vilnius gave us the name of a restaurant where we had a magnificent meal, after which we could just barely fit into the taxi back to the hotel. The restaurant is "Lietuva" and while I don't have an address no doubt your hotel can direct you there. Take a good appetite with you.

I would love to get any hotel recommendations for the St Petersburg and Moscow portions - did you like where you stayed?

Thanks!

I stayed at the Comfort Hotel in STPB and The National in Moscow. I wouldn't recommend the Comfort Hotel personally. I've never been fussy with accommodations before but our room reeked of smoke, the rug and sofa was filthy, bedspreads as well, there was mold in multiple places in the bathroom...the breads at breakfast were stale...the price was not low either (superior twin) but I would splurge for a nicer hotel if I went back (+location was great). Hotel National in Moscow was the nicest place I may have ever stayed in (I got a great deal that weekend) - it's across from Red Square and Kremlin, breakfast is to die for - you just can't get hung up on the personalities of everyone working there - it's part of the charm.