In the summer of 2025, I did a 3-island solo trip ending out with 2 nights in Santorini. I had incredible experienced in Mykonos and Athens prior! While I enjoyed my time in Santorini, I definitely made a few mistakes with my trip that impacted my experience.
While I would definitely go back, I would certainly do a few things differently. Read on to prevent making the same mistakes as me on your trip to Santorini.

loved: watching mamma mia on a cliff
Anytime someone asks what my favorite part of Greece was, I always say it was watching Mamma Mia on the side of a volcano as the sun set. This experience is priced really well and so worth it. It is hosted by Volkan on the Rocks in Fira and they provide headphones, blankets, and light bites as you watch.
I would recommend the earlier sunset time for views and vibes. However, it is important to note that if you are planning on using public transportation to get back to your accommodation (anywhere outside of Fira), the earlier time ends too early to make it for the last bus, which brings me to my first hate…
hated: the public transit scene
The big reason that I struggled in Santorini was the location of my hostel. I did not do my research ahead of time, so I figured booking in Perissa on the East side of the island would be no problem.
While it technically isn’t that far from the main cities of Fira and Oia, what I failed to take into account was the giant volcano in the middle of the island that meant getting from one side to the other was a 1-2hr trip. Ubers were faster, but very expensive.
Perissa was a nice area to maybe take a day trip to, but I just found myself frustrated with how much time I was wasting getting places each day.
If you are interested in using the public transportation, be super attentive to the bus schedules BEFORE booking anything in advance. Even getting from Oia to Fira is about 30 mins. While it is very cheap to use the bus, my best recommendation would be staying somewhere that most of your activities are centered from with Ubers for daily excursions.

loved: my hotel experience
In case you didn’t put the two and two together above, I booked Mamma Mia before realizing I wouldn’t make the last bus back to Perissa. Thankfully, I realized this the day before and also had stayed under-budget for my entire trip.
I decided to splurge on my last day by booking a closer hotel to be able to watch the full movie. I stayed at Sole d’Oro Luxury Suites solely because it was the cheapest I could find. I was pleasantly surprised to be greeted with a welcome cocktail, bottle of wine, private rooftop hot tub, and a beautiful room.
I typically prefer hostels while solo travelling to make friends and save money. However, as my last night in Greece, this was the perfect way to relax and unwind. I think if you are staying in Santorini, the best route here is to go for the hotel versus the hostel.

loved: getting lost exploring the streets
I think one of the biggest appeals of Santorini (and maybe Greece as a whole) are the beautiful white buildings and winding stone streets. I loved spending my time wandering down alleys and around corners.
You don’t need to have plans booked out to the minute in this city. I highly recommend saving at least a full morning or evening to just shop and explore. Some things I came across without a plan included: handmade necklace of my name in Greek, dozens of cutie cats, a really cool lookout point at the northern tip of Oia, and lots more.
hated: cruise dumps mid-day
The one barrier to having your Greek explorer girly moment down the streets is when the cruises dump thousands of people onto the island mid-day. I’m not being dramatic, it is CRAMMED in the little streets, bodies on bodies. You can tell they are cruise people because they will have a little colored sticker on them (and hot take, they’re usually rude…).
I tried to focus my planned excursions to be during the time the cruises were dropping people off so I wouldn’t get stuck in the crowds. It also may be a good idea to plan your trip here during shoulder season (late spring, early fall) for a little bit less people.

loved: hiking to the cliff jump
One of the ways that I avoided the crowds was by trekking all the way down to Amoudi Bay and cliff jumping here. This hike was long and steep so bring a LOT of water. You could pay for a donkey ride down, but the donkeys looked really sad so I felt bad and opted to walk.
Once I got to the bottom it’s about a 10 minute easy hike to the left of the restaurants to get to the jumping areas. I would be a bad physical therapist if I did not remind you to always be cautious cliff jumping and ensure the water is deep enough before swimming.
This was a great way to cool off and avoid crowds! And feel like I was exercising while otherwise stuffing my face with tzatziki and pita…
hated: rainy weather
My view of Santorini may also be tarnished by my first day experience. Let me set the scene: I had just partied in Mykonos for 12 hours straight, slept for 4 hours, hopped on a choppy ferry, arrived in Santorini to a torrential downpour, and had to wait outside in the rain for 2 hours with all of my luggage and no rain jacket. Then as soon as I ate I got food poisoning…. lol
Of course, controlling the weather is impossible. However, it is important to know that there really is not much to do in Santorini when it is rainy. Pretty much everything revolves around being outdoors. So just be forewarned, if there is a rainy day in your forecast, get ready to spend a lot of time at your accommodation!

loved: catamaran tour
Finally, one of my top experiences I had in Greece was booking a day-long catamaran tour with Vista Yachting. I love myself an all-inclusive and this was absolutely perfect in every way.
The cruise includes hotel pick-up/drop-off, unlimited wine, snorkeling, swimming, REALLY good food, and the perfect Instagram-worthy sites and photo-ops. I thought it was a really great deal for everything you get!
If I were to go back to Santorini, I would just book one of these cruises every day and not worry about any of the details 🙂














