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Cinque Terre with Mom (4 days)

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My mom and I are traveling to Europe (for her first time) at the end of August. At this point I have all of our flights, trains & lodging arrangements taken care of, and I'm trying to finalize an itinerary that covers the most possible attractions in the least amount of time, with the least amount of strenuous activity for my mom. (I'm aware this is practically an impossible combination, yet, alas...)

Paris (3 days, 2 nights)
Flight to Rome (2 days, 2 nights)
Highspeed train to Florence (1 day)
Regional Train to Cinque Terre (Manarola home base 3 days, 4 nights)

We're ending our trip in Cinque Terre with Manarola as our home base. I assume we will be exhausted by this time (especially mom) and decided it best to end the trip on the beach. While neither of us are necessarily stoked on the idea of hiking in general, I realize hiking is a huge aspect of what the area has to offer and I cannot wait for the incredible views and fresh air. (please no rain!) Should we purchase the hiking pass even if we don't plan to hike every leg of the trip?

I know my mom would love to do a wine tasting/vineyard tour. Any suggestions?

Also, a boat tour/cruise is a must. Suggestions? I've heard of Angelo's Boat Tours http://www.angelosboattours.com/tours/ Any experience?

Must see restaurants? ocean views, of course! Shopping/markets? Best hiking trails and directions for the best pictures?

Also, we are flying our of Milan Airport. I've found three potential options to get there:

Train- cheapest, but longest and most strenuous option
Taxi- fastest, but most expensive option
Carpool, fast & cheap, but reliable?

Any and all suggestions are welcome and appreciated!!

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