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Six week Dream Trip Italy Need help w train or good travel agent

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Hi all-
I really thought I could plan this trip on my own - but finding out specifics about train travel is a big issue - can't book room if I don't know when or how I'll get to city.

Must arrive at Sinalunga train station on Saturday the 8th to begin 3-weeks working at a vineyard - but after days searching through train websites trying to find out how to get to Sinalunga from Rome - or possibly Venice - I'm totally frustrated.

I'll SEND A GREAT BOTTLE OF ITALIAN WINE TO ANYONE WHO CAN WALK ME THROUGH THE SPECIFICS OF TRAIN TRAVEL FROM ROME TO SINALUNA + AN ALTERNATIVE ROUTE THERE FROM VENICE...and Sinaluna to Amalfi..

Would also love some feedback on possible itineraries. Open to different routes, cities, other hotels, B+B, etc, input on need for car, or any other suggestions.

ITINERARY #1
-NY-ROME-SINALUGA (Tuscany:Venice/Flore/Siena) -AMALFI COAST - NY
SEPT 1st :Fly NY to ROME: spend week at Hotell Navona ($1374 for 7-nights...unless you know something I don't). SEPT 8: Take train to Sinaluga for 3 weeks working at vineyard (Spending weekends traveling through TUSCANY by train on for over-nights in Venice, Sienna + Florence ...unless that's to ambitious?). Sept 28th: Take Train to AMALFI COAST (afterthought - never been. Know I have to take train to Naples and then find train to get there (haven't a clue) Spend 1 week in Postano at Palazzo Talama ($1300- looks to0 good to be true)

ITINERARY #2 - (Start from Venice (in north, before it gets too cold)+ Skip Amalfi Coast)
NY-VENICE-SINAGULA(Tuscany: Florence/Siena) - ROME (with day trips) - NY

ITINERARY #3 - NY-VENICE-SINAGULA (Tuscany) - ROME - AMALFI COAST - NY

I can deal with finding out that the order of my itinerary was not the best, and that I could have found better, more practical, better located places to stay - But I have to know the specifics of train travel from Rome or Venice to Singula, and then Singula to Amalfi Coast - because if I'm off my lodging reservation will be messed up, and may have unexpected travel expense that I can't afford.

I've gone to the websites of the 2 train systems, but in the date - but nothing comes up - can't read the timetable and don't understand the how to make connections - or the best way. 50+ woman, lone traveler - will be lugging a suitcase and computer and overnight bag. If a bus is easier - I'm game.

Need to book my air by Monday or my vouchers expire...need to confirm space at B+B or hotel before I book air - so I need to have the specifics of the travel by train down pat.

Can anyone out there guide me through the train portion of the trip?
Input on which itinerary is the most realistic would also be appreciated.

Thanks for your help!
Nicole

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