This was a pre-cruise trip in November 2017. We flew from London’s Stansted Airport on Ryan Air($61pp/one way) to Bergamo Airport. A friend joined us for the trip, and we split the costs 3-ways. Per person cost for the rental car + lodgings was about $390. Plus we bought about $120 gas. Meals were about $20pp on the average including lots of wine.
Day 1: Rented a car from Europcar for a week(Euro 192, automatic compact) at Bergamo & drove 2 hours to Stresa on Lake Maggiore. Airbnb 2-bedroom house for 2 nights($89/night).
Day 2: Drove around Lake Maggiore visiting some towns on the lake.
Day 3: Drove to Varenna via Bellagio. Ferry from Bellagio to Varenna(20 minutes, Euro10.90 for the car, Euro4.60 per person). Walked around the town and visited the castle. Airbnb studio for 2 nights($100/night).
Day 4: Day trip by train to Tirano(2 hours, under Euro5 pp) & transfer to the Bernina Express train to St. Moritz(2 hours, Euro32pp each way).
Day 5: Drove 1.5 hours to Milan & explored the city. Airbnb 1 bedroom($100) in an up and coming area east of the center – street parking was possible.
Day 6: Drove 4 hours to Florence. Walked around the city. Airbnb 2 bedroom($125) near Ponte Vecchio.
Day 7: Drove 3.5 hours to a Rome suburb. Airbnb 2 bedroom($85) farmhouse.
Day 8: Drove to Civitavecchia & returned the car. Got on Royal Caribbean Jewel of the Seas for a trans Atlantic cruise.

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