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A few people have asked me where I'm finding the information used to plan this trip, so I thought I'd just ago ahead and post it here for everybody:

Accommodation:

• Trip Advisor
• Venere
• Dubrovnik

Location

• Rough Guides
• Find Croatia
• Korcula
• Lonely Planet
• Travelblog
• Florence, Italy
• Siena, Italy
• Dubrovnik, Croatia
• Dalmatian Coast, Croatia
• Split, Croatia
  

Travel

• Argus Rentals (auto)
• Eurrail (rail)
• Traghetti Online (ferry)
  

Spontaneous Planning (The Itinerary)

I know I originally said that the itinerary for this trip would be "completely spontaneous", but I guess I'm becoming responsible in my old age, because I went and made some plans.

Here is our tentative (we reserve the right to be spontaneous if the mood strikes us) Itinerary:

Great Britain (30 May - 31 May)

• 30 May - Arrive: London, Accommodation: Generator Hostel
• 31 May - Depart: London, Destination: Paris, France
  

France (31 May - 31 May)

• 31 May - Arrive: Paris, Depart: Paris, Destination: Rome, Italy
  

Italy (1 June - 11 June)

• 1 June - Arrive: Rome , Depart: Rome, Destination: Florence
• 1 June - Arrive: Florence, Accommodation: Hotel Cestelli
• 5 June - Depart: Florence, Destination: Siena
• 5 June - Arrive: Siena, Accommodation: Borgo Grondaie
• 8 June - Depart: Siena, Destination: Piedimonte Matese
• 9 June - Arrive: Piedimonte Matese, Accommodation: Villa DePertis
• 11 June - Depart: Piedimonte Matese, Destination: Bari
• 11 June - Depart: Bari, Destination: Dubrovnik, Croatia

Croatia (12 June - 22 June)

• 12 June - Arrive Dubrovnik, Accommodation: TBD
• 16 June - Depart: Dubrovnik, Destination: Korcula
• 16 June - Arrive: Korcula, Accommodation: TBD
• 19 June - Depart: Korcula, Destination: Split
• 19 June - Arrive: Split, Accommodation: TBD
• 22 June - Depart: Split, Destination: Ancona, Italy

Italy (23 June - 23 June)

• 23 June - Arrive: Ancona, Depart: Anconca, Destination: Rome
• 23 June - Depart: Rome, Destination: Paris, France
  

France (24 June - 25 June)

• 24 June - Arrive: Paris, Accommodation: TBD
• 25 June - Depart: Paris, Arrive: Londond, Great Britain
  

Great Britain (25 June - 25 June)

• 25 June - Depart: London, Destination: Chicago, USA