- There are a few ways to get to the island of Santorini, either by regular boat, high speed boat, or plane. I would highly recommend taking a flight from Athens - it's only about 30 minutes in the air and can be quite cheap, even roundtrip.
- You can take taxis around the island no problem, it's not too pricey, but the best ways to get around are either by local bus or by renting an ATV. You need a valid driver's license - a Canadian license works well - it doesn't need to be international.
- Staying in Santorini can vary a lot. There are a ton of villas in Oia, but if you stay there, you will definitely be paying a premium. If budget is no concern, there are many luxury villas here. The island is also dotted with mid range hotel, all the way to cheap shared hostels. I would recommend staying in Perissa - there's a beautiful and much less crowded beach there.
Lunch at Gyros Time ($)
Depending on when you get to the island, stop in at Gyros Time in Perissa for some cheap and delicious gyros. Make sure you get a large Mythos beer and fries to go with it. This place is legit!
Black Sand Beach in Perissa (Free)
This gorgeous stretch of beach in Perissa is less frequented by tourists since it's a bit out of the main area in Oia. It's worth a visit to see the black volcanic sand and swim in the clear waters. You can rent chairs for a small fee, but it's just as good to lay your towels out if you're on a budget.
To Psaraki for Dinner ($$)
One of the best establishments in Santorini and regularily makes "best of" lists. The view here is just as good as the fresh food being served up. Sample some Greek wines from the area and eat your way through multiple courses. Finish the night off with an ouzo, a classic Greek liqueur.
Rent an ATV ($$)
Although buses are a great way to get around the island, it's nice to have the flexibility to move aroudn on your own without having to fully rent a car. As long as you have a valid driver's license from your hoem country, you should be good to go. There are a number of ATV rental places - ask you hotel for one that's close by. Spend some time driving around the island and taking some pictures.
Red Sand Beach (Free)
While you're touring around on your ATV, head over to the famous Red Sand Beach. The beach is famed for its titular red-hued sand, and is a noted for being popular tourist attraction. It does get busy, but it makes for a fun afternoon in the sun.
Venetsanos Winery ($$)
A perfect dinner and evening! This family owned and operated winery since 1947 has unique architecture, a sun terrace, a cafe, guided tours, and events. Book in advance to secure a spot. I also recommend doing a tour of the estate. It's small but has a very interesting history. Dinner here overlooks the sea and comes with delicious wine pairings. You can also buy bottles here to take home with you.
Touring Around Oia (Shopping)
If you're in Santorini, you absolutely can't miss going to the picture-perfect Oia. Spend some time walking around this area, stopping into the many bookshops, cafes, antique shops, souvineer stores, art stores, glass shops, and everything in between. This area is full of photo opps.
Atlantis Books E.E. (Shopping)
While you're touring around Oia, book lovers need to stop in at Atlantic Books. The front of the store is beautiful, but head downstairs into the labrynth of books, both old and new. This is a bit of a haven for rare and antique books, and well as some more modern favourites. English books are available.
Sunset in Oia
Santorini is famous for its beautiful sunsets. There are many ways to see the gorgeous view, including sunset boat cruise (on the more expensive end), to dinner and wine at a cafe by the cliffs (mid-range), to just finding a nice spot to sit and relax (free). Make sure you don't miss this!
Akrotiri was a Cycladic Bronze Age settlement that was destroyed in the Theran eruption sometime in the 16th century BC and buried in volcanic ash, which preserved the remains of fine frescoes and many objects and artworks. The settlement has been suggested as a possible inspiration for Plato's story of Atlantis! Tour this wonderful museum for a great price. You can buy tickets at the door here no problem.
Take a Caldera Cruise (Varies)
There are a ton of options for a boat cruise that can range from one hour, to a full day sail around the island. Again, some are private or semi-private tours, some are with a group. Group tours tend to be cheaper. Always book these tours in advance to secure your spot and a much better price on a ticket! I recommend this Caldera Cruise which goes for about $150 CAD per person, which is great deal considering it comes with food and drinks and lasts about 5 hours. It also includes a sea-side sunset!