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Roadtrip. Tivoli to Lake Como.

My wife and I are planning a road trip to Italy and we will be focusing on smaller cities and villages. We have been multiple times to Italy in the past and spent a lot of time in the major cities and cites. Last spring we did a road trip in the Loire Valley, stopping at different Chateau every night and loved it. We love to check out different hotels. So we are looking to do the same thing again, but this time Italy and going from Tivoli to Lake Como, over 11 nights, early April. I'm wondering if you have any tips, suggestions or foreseeable issues. Here's the itinerary:

Day 1: Tivoli, Villa d'Este, Hadrian's Villa, Villa Gregoriana, Temple of Sybil
Night 1: Castello di San Michele, or Albergo diffuso Castello Costaguti

Day 2: Caprarola, Villa Farnese, Viterbo, Bolsena
Night 2: Hotel di Charme il VesConte

Day 3: Pienza, Abbazia di San Galgano
Night 3: Certosa di Pontignano, or Hotel Relais Palazzo del Capitano

Day 4: San Gimignano
Night4: Castello Di Montegufoni or Medici Villa of Lilliano Wine Estate

Day 5: Hills overlooking Florence, Officina Profumo - Farmaceutica di Santa Maria Novella, Gucci Garden
Night 5: Hotel Torre di Bellosguardo

Day 6: Montecatini, Terme Tettuccio, Terme Excelsior
Night 6: Hotel Villa Sermolli or Villa Petriolo

Day 7: Villa Torrigiani
Night 7: Fabbrica Di San Martino or Villa di Corliano

Day 8: La Cervara, Portofino
Night 8: Villa Gelsomino Exclusive House

Day 9: Santa Margherita Ligure, Villa Durazzo, Varenna, Villa Monastero
Night 9: Not Sure, somewhere in Varenna

Day 10: Villa Carlotta, Villa Balbianello, Bellagio
Night 10: Not Sure, somewhere in Varenna

And my last question, should we remove Lake Como from the itinerary and spend more time somewhere else?

Thanks.

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