Germany 10 day 2 week trip

I suggest Franconia... great places to visit, nice old world towns... Bamberg, Bayreuth, Nuremberg, Würzburg. Ochsenfurt, Iphofen and more. Check local TI offices for tour options.

https://images.mygermancity.com/maps/franconia.png

https://www.frankentourismus.com/

Lots of wine there...

https://www.der-weinmakler.de/media/wysiwyg/Landigpages/Franken/Franken.jpeg

second vote for Franconia

Fränkische Schweiz (Franconian Switzerland) cute little Villages ,Castles ,Rocks and Caves

Go for Gössweinstein and Pottenstein and the Teufelshöhle (Devils Cave) for a daytrip

Area with the highest density of Breweries in Germany

Area in triangle Bamberg (45 min northwest) Bayreuth( 30 min northeast) Nuremberg (1 hr south)

Check the local Tourist Offices for Local Guides

How much time do you plan to spend in/around Dresden? There is a lot to see there.
A visit of the National Park Saxon Switzerland is a must (bizarre sandstone formations, canyons, flat-top mountains, all sorts of outdoor activities.)
A paddle steamer trip is another must.
Picturesque towns are Pirna, Meißen (porcelain manufacture!) e.g.
Then there is Bautzen with the Sorbian culture, a slavic minority.
What about narrow-gauge steam railways? There are two in close vicinity of Dresden (Radebeul - Moritzburg and Freital - Kipsdorf).
The historic mining sites in the nearby Erzgebirge (Ore mountains) are on the UNESCO world heritage list.
It's also a wine region - vineyards in Dresden itself and in neighbouring Radebeul and Meißen.

It's a little unclear whether the desire for tours means "with transportation", which could get expensive. And whether it's your travel style, or a practical decision for two couples needing a firm hand about daily schedules. We travel independently, so I can't give any guide advice. We found a car useful for the trip below. I understand about train problems, although this includes a single train ride. It can't be overstated how rich a literary and artistic destination some of these cities are. Better German wineries require reservations, but a good hotel might be able to make some for you.

This 2010 trip was VERY hot weather, and despite big modern hotels, the air conditioning could not keep up. I don't know if that's because this is the former East.

With the understanding that different people have different preferences, I’m sharing our 2010 itinerary (similar time span) that included Dresden:
02 Jul 10 Fri 9:25AM Arrive Frankfurt, Germany,Terminal 1
02 Jul 10 Fri 13:05 Depart FRA LH 1104
02 Jul 10 Fri 2:00PM Arrive LEJ Leipzig, Germany

Airport Express train at :24,:54 (3.6Euro)
02 Jul 10 Fri to 05 Jul 10 Mon Leipzig Marriott Hotel Am Hallischen Tor 1,
Bach, Wagner, Mendelssohn, Mahler, Mazur
03 Jul 10 Sat 3:00PM Organ Concert Thomaskirche
04 Jul 10 Sun 10:00AM AVIS Listbogen, Lud. Erhard Str 53
Dessau-Worlitz UNSECO WHS Gartenreich,
Quedlinburg by car Sunday, park at Hotel)
(BMW Plant by Zaha Hadid)
05 Jul 10 Mon to 07 Jul Wed Dorint Am Goethepark Weimar
(Modern, business, chose for easy daily parking)
(Eisenach, Jena, Qudelinburg)
Erfurt, egapark, Mauthausen X-MON)
07 Jul 10 Wed 5:00PM AVIS RD7 Friedrich Str 24, Dresden 01067
Return Car/Closes at 6PM
07 Jul 10 Wed to 10 Jul Sat Hilton Dresden Hotel An der Frauenkirche 5
(Meissen, Green Vaults, Steamship to Saxon Switzerland)
10 Jul 10 Sat 11:04AM DB Train EC176 Track 17 Dresden Hbf
10 Jul 10 Sat 1:20PM Arrive Berlin Hbf Wag. 253, Pl. 13/15
10 Jul 10 Sat to 13 Jul Tue Kempinski Hotel Bristol Berlin
Kurf'd'm 27, Berlin 10719
13 Jul 10 Tue 9:35AM Depart TXL Berlin CO 97 (757-200)

Hi.
I am a big Dresden fan (lived there for 10 years).
Plan three days there if you can:
- Lots to do and see in the town of DRESDEN (architecture, art, museums, boat trips) and ...
- ... its surroundings (hiking in "Saxon Switzerland", biking along the river Elbe). Join the locals on a warm day at the picturesque riverbanks of the river Elbe, just right downtown.
- Wine region and medieval town of MEISSEN just a stone's throw away from Dresden.
Make sure you don't miss Schloss Wackerbarth winery (near MEISSEN). You can take a guided walking tour and sip a crisp white wine in their breathtaking garden: https://www.schloss-wackerbarth.de/en/highlights/weinsommer

I must not be keeping up with the news. Why are you wary of German train systems? What should I know?

There have been multiple reports here about significant punctuality issues on German trains in recent years, some caused by delayed maintenance.

Franken Wein and Spargel sounds good. Great season. You should probably have a car and also explore into the Steigerwald and Bamberg. June in the Alps is one of my favorites. Wildflowers, still some snow in the higher elevations, Things are vibrantly alive. A good time. Franken Schweitz is nice too. Bookings for canoe and kayak on the Weisent fill fast.