Located in SF Bay Area and have traveled to:
1) Greece: Super long travel day from SFO....basically SFO to Atlanta, Atlanta to Athens, Athens to Santorini...something like 15 hours I think?
- Santorini: Oia (amazing views/sunsets - romantic. Went there for honeymoon) and Fira (loved the place we stayed at there, quiet, private and infinity pool overlooking the sea and Caldera).
- Crete: Chania (old port type town, totally cool and a solid vibe). From there we found
http://en.wikipedia.org/wiki/Elafonisi which is still one of the best beaches we've been to inclusive of Hawaii.
-Athens: We stayed in Athens for a couple nights on the return from Santorini and Crete. Great for history but aside from that I'd never go back.
2) Italy: SFO to Copenhagen, Copenhagen to Rome
- Rome / Vatican City: Similar thought as Athens for me, have to do it for historical reasons but wouldn't build a trip around it. Trains worked well and we did do Taxis without getting ripped off. Uber was coming up in stealth mode out there when we were there. Stayed in Vatican City area via Air BnB
- Florence: Without a doubt this place is just amazing. From the history, food, people and vibe, can't go wrong. We stayed in a super old Apt via Air BnB and it was our favorite place on our entire trip. Drove a rental ($$ for automatic, too) car from Rome to Florence stopping in Siena which is probably our favorite "low key" stayover.
- Lucca: Underrated, my family originates from there so had a lot of personal context for me.
- Cinque Terre: Amazingly beautiful. Did the hike between the towns 3 and 4 I think? Either way, we beat the rain and it was worth doing. Took a train between the others.
- Lake Como: I can't remember where exactly we stayed, but it wasn't the super popular town..it was the 2nd most which was fine...definitely can tell there's money out that way. Worth seeing.
3) Switzerland: Train from Milan to Lucerne I think... Once I remember more I will update. Did Air BnB here too...but man, Switzerland is clean, beautiful but mad expensive.
4) Costa Rica: Manuel Anotnio area. Loved it, would go back.