Santorini
Santorini was more of a relaxed island. When you arrive via ferry, you will be at the bottom of the mountain. There is literally nowhere to go but up. We decided to rent a dune buggy and 4-wheeler (Quad) because you can drive the entire island in less than half an hour. All of the quads will be by the port along with a few cafes. There is also plenty of cargo space behind the quad and in the dune buggy so you should be able to fit all of your suitcases in your ride up the mountain. Once we made it to our bed and breakfast, we decided to walk around a bit before our only reservation. We stayed in Pyrgos neighborhood. We walked around the different shops, churches, even walked in the middle of a rap music video being filmed! You will see a lot of the classic white cyclade buildings and a blue domed church.
After walking around a bit, we freshened up for our 16 (full glass) wine flight dinner at Santos Winery. Make sure you make a reservation via the website and bring the printout confirmation with you! We were able to snag a great window seat because of it. The winery is located right at the top of the long winding hill from the port. The view there is pretty amazing. You can see the entire west coast of the island, as well as an unobstructed view of the sunset. The wine itself was delicious and the staff were very friendly.
The next day, we rode our ATVs up to Oia. You can definitely see the difference in money between Oia and Pyrgos. Walking around the shops at Oia had more name brand stores as well as the Greek famous marble sidewalks. It was very beautiful and had many great photo ops from “rooftop” angles. After walking around Oia, we went to the “old port” in Fira via the cable car. At the bottom of this port, you are able to rent a boat and visit the volcanoes across the way. Depending on how much you want to spend/how much time you have, you can opt for longer tours where you can snorkel and swim beside the volcano, or hike along the volcano. We did not bring our swimsuits, so we just opted for the boat ride which i believe was around 60 Euros.
After a long day of exploring, we went back for a nap and then headed over to Monolithos beach on the east side of the island. Here, you can find the black sand associated with volcanic islands. We then went to one of the restaurants by the beach before heading out for a night on the town at a local hangout bar called Tranquila.