Hello, looking for advice on a 2 week trip at the end of May 2019, for mother/daughter pair (I'm the daughter, mother in early 70s). Santorini is a must, but I'm struggling with other options. Mom is not the biggest walker, but she is without health issues, and will work to gear up a bit for the trip. I'm still trying to avoid too strenuous of activities for her, and in Santorini hope to find a place to plunk and enjoy views. I can do some short activities without her. She likes picturesque villages with unique shops, people watching, seeing and relaxing by "turquoise blue waters." I like similar things, especially taking pictures of those types of towns and beautiful landscapes/waters. We aren't big hikers. I do like museums and things that show the culture. I had been considering Santorini/Parthos/Athens only, but Mom saw some pics of Milos that I showed her, and really loved the water/beach pics, so I was considering adding that destination. Finally, I'm trying to do more flying, as I have seasickness concerns (was planning slow ferries for the ferry trips).
Questions: 1) How does the below itinerary sound? Should I cut one of the islands out besides Santorini? Is Milos worth it? 2) Naxos vs Paros: I chose Paros over Naxos as the two main towns in Paros looked more picturesque to me, and possibly easier driving to rent a car. We probably wouldn't do much with interior villages, and won't spend full days at beaches, just a few hours. I also thought Antiparos looked delightful 3) Would it be better to cut an island out and do Nafplio instead? I'm not too excited about taking a bus or renting a car in mainland Greece, so that makes me hesitant for Nafplio. 4) When to book main airfare (out of detroit), hotels, domestic flights, ferries. Looks like many hotels won't even book that far in advance. 5) Ideas on hotels that are more senior friendly (not handicapped, just not tons of stairs everywhere).
Thank you sooooooo much for your help. My mom is the best woman on the planet, and deserves the trip of a lifetime.
Sat May 18th: Leave DTW daytime, layover, on plane overnight.
Sun May 19th: Land in Athens in AM, take flight to Paros. Stay in Paros.
Mon May 20th: Day in Paros, stay in Paros
Tues May 21st: Day in Paros, stay in Paros
Wed May 22nd: Day in Paros, stay in Paros (4 nights total).
Thu May 23rd: Slow Ferry to Santorini 11:45 to 14:50, stay in Santorini. (based on best guess from 2018 Ferry Schedule)
Fri May 24th: Day in Santorini, stay in Santorini.
Sat May 25th: Day in Santorini, stay in Santorini (3 nights total).
Sun May 26th: Slow ferry to Milos, 7 am to 12:25 pm, stay in Milos
May 27th: Day in Milos, stay in Milos.
May 28th: Day in Milos, stay in Milos (3 nights total).
May 29th: Fly Milos to Athens, stay in Athens.
May 30th: Stay in Athens
May 31st: Stay in Athens. (3 nights total).
June 1st: flight home