Finally decided Greece is next

As for Monemvasia lodging, mainland or the rock?

If you are on the mainland you can SEE the impressive rock; especially so at sunset!

Parking is a challenge, to say the least -- https://www.google.com/maps/@36.6865137,23.0543615,3a,75y,270h,83.71t/data=!3m6!1e1!3m4!1sqmFsLCQt7iSf92EO3kAYfQ!2e0!7i13312!8i6656

We flew from Athens to Santorini on Aegean Airlines and would recommend flying. The Aegean plane was new and clean and we preferred a short flight to a very long boat ride. Have fun planning your trip!

We took the RS Greece Tour a couple years ago. We were very pleased with the tour itinerary. We extended our time in Athens prior and 6 nights in Naxos and 4 nights in Santorini afterwards. You can easily see Greece in 3 weeks. We flew back to Athens and stayed at the Sofitel Airport Hotel. In addition to the RS guidebook we found the “The Rough Guide to Greece” an excellent resource.

Enjoy your planning!

We just finished the RS Greece tour a few weeks ago. As for Monemvasia, we stayed off the rock and had a wonderful view if it from our balcony at Hotel Panorama. However, my husband and I both commented that sleeping inside the fortified city would be nice too and we saw people doing just that. Know that the walkways are all cobblestone.....not fun with large, rolling luggage. I would park off the rock and take the shuttle or taxi to the entrance.

I would choose either Mykonos or Santorini and spent the rest of your island time on a less touristed island. I think Santorini is more unique than Mykonos and would choose that and another island such as Paros or Naxos.

We flew to Santorini on the same day we arrived from the U.S. on a separate ticket. We ferried to Naxos and then flew back to Athens and rented a car and drove to Nafplio. We only had two weeks so did not do most of the Peloponnese.

We spent 3 nights in Santorini and four in Naxos. We could have spent another day on Naxos but with seven nights I would divide my time the same way.

If you are following the Rick Steves itinerary, I would skip Hydra in favor of more time somewhere else. I originally was going to go to Santorini and Hydra but substituted Naxos for Hydra and was very glad I did. Naxos has the beautiful sand beaches you associate with Greece while neither Santorini or Hydra do. Ironically, we only spent a few hours at the beach in Naxos because there was so much else to do (hence why we would have liked another day!)

While a ferry ride is an essential part of a Greek trip, distances can be long and each ferry hop easily eats up a half day. Even the one hour ferry trip between Paros and Naxos saw us checked out of our hotel at 10AM and we finally hit the beach in Naxos at 3pm. I guess that was a long winded way to say fly to you first Island. Time is precious so spend in ways that get you to your next Island destination quickly.

We just returned from a September trip where we toured the Peloponnese specifically to see the Mani. We spent our first night in Monemvassia. It is a 14th century medieval walled town with a fortress high up on top of the rock. It is impressive to see. Having said that it is way more impressive to spend the night in Monemvassia. Even our Greek friends love staying in Monemvassia. The hotels are restored period rooms spread out around the town. Each one has been lovingly restored. Our bathroom had a gun port in the wall.

Indeed the who town is paved with cobblestones and virtually every room is up or down stairs. Because of the topography our hotel Byzantino had a man with a wheelbarrow to pick up you luggage and deliver it to the room. There were several porters from other hotels also.

As for parking as you can see from Joe32F link the parking is on the right side going down the causeway. That means no parking going up the causeway road. You virtually have to drive up to the gate (where you can drop off your luggage) and then drive down the hill until you find a parking spot. Actually Joes pictures were taken on a light day with some empty spaces less than 100 meters from the gate. In September with a mid afternoon arrival we had to park close to a kilometer down the hill.

With a choice of the mainland or staying in the walled town. Its walled town every time.
The first page of our Mani/ Peloponnese album is totally devoted to Monemvassia.
Mani https://www.flickr.com/photos/stanbr54/albums/72157711323535897

We also relied on the RS guide in planning our trip. As for Monemvasia, we loved staying on the rock. We did our 3 week trip with just carry on luggage and for this stay we packed a few essentials in our back packs, leaving the roller bag in the car. We parked on the causeway. Staying inside was truly was magical and the hike up to the top the next day was spectacular.

We flew into Santorini and then ferry to Naxos and flew back to Athens. We are planning our next trip for 2020 and my only regret about my last trip was that I planned too many nights in Santorini. It was a beautiful island but just too touristed and crowded. Naxos was far more enjoyable. This time we are visiting Milos, Sifnos and Paros after touring Northern and Central Greece.

Enjoy!