This itinerary includes Santorini, Mykonos and Athens, arriving by flight and then traveling via ferry in between destinations. This guide is tailored to friends or solo travelers – people that want to spend more time exploring, and not necessarily in romantic hotels and restaurants (though everyone deserves a nice meal and sunset cruise!)
Total Days: 8 Days | Accommodations: Recommended Hotel in Thira, Santorini, Mykonos Town in Mykonos and Monastiraki in Athens | Transportation: Walking and occasional cab or bus | Traveled: Solo| Type of Trip: Exploring scenic locations, ancient Greece and food/wine along the way | Highlights: Thira to Oia Hike, Sunset Cruise in Santorini, ATV ride in Mykonos, Acropolis visit
DAY 1
At a glimpse: Explore Thira
Travel agenda: The small Santorini airport is easy to navigate, with buses and cabs available outside so that it shouldn’t take more than 15 minutes to arrive in Thira. Once settled into your hotel, head to lunch at Lucky’s Souvlakis. Enjoy the Greek version of a gyros pita with french fries (because you’re on vacation). From there, wander the streets of Thira, weaving in and out of the restaurants and shops. You’ll get good views of the Caldera, the sea lagoon that was created after a volcanic eruption occurred 3,000 years ago.
Half an hour before sunset, find a place to perch on Nomikou M and set up shop (destination Da Costa will put you in the right area). If you’ve come across any convenience shops, pick up some snacks and Donkey Brewery beers for an unofficial picnic. Have a camera ready for that famous waterfront mise en scène.
Post-sunset, work your way back to the main road and get a 10 minute taxi from Mitropoleos Street (the main transportation square) so you can high tail it over to the Open Air Cinema in Kamari. A unique setting to relax and enjoy an English-speaking movie with Greek subtitles.
DAY 2
At a glimpse: Hike from Thira to Oia, then spend the day exploring Oia
Travel agenda: Set the alarm for an early 7am wakeup. Don your sneakers and start the day with a big breakfast at Magma City Cafe. Then it’s time to hit the 6 mile Thira to Oia trail that takes you along the caldera cliff. Walk 4 minutes west to start at the Atlantis Hotel and then walk north with the water on your left at all times.
About 1/4 of the way in, you’ll come across Skaros Rock. Walk down to see the little Church of Christ chapel and then scramble your way to the top of the Rock. The last few steps up you’ll have to channel Alex Honnold, but the 360 view at the top is worth it.
Head back to the main path and you’ll hit the town of Imerovigli. Keep trekking north! Parts of the dirt path turn hilly and then stop altogether, so that you’re walking on the paved street. This ends at the snack shop if you need water or sustenance. Don’t miss the Profitis Ilias church along the way. It’s around the Panagia church that views of Oia come into view. You’re in the home stretch when you hit the stunning marble road that leads into the main streets of town.
At this point you’ll also see all the fabulous people and Instagram models sauntering by. Not everyone just hiked 6+ miles! So book an Oia or Volcanic Hot Stone Massage at Caldera Massages Studio & Spa. This and a shower after will have you feeling refreshed and invigorated!
Now you’ve earned lunch! Head 4 minutes east to Karma for a cool atmosphere, unique seating and a bar if you prefer to eat your lunch there. Wander, get lost, explore! It’s an incredibly beautiful area and its easy to find a new favorite view everywhere you look. There are also some great boutique stores here, though they will cost you! For an early dinner head down to Ammoudi Port. Get your seafood fix at Ammoudi Taverna (the calamari is a must!).
One hour-1.5 hours before sunset, walk back up to Sun Spirit for cocktails. This is where you will watch the sunset. Here’s the key: once the sun has set, hoards of people will leave the area. But this is when the sky turns pink and the city glows. This is your chance to head to the Oia Castle! After a full day in Oia, head back to Fira via a local bus. It’s easy and inexpensive at €1.60 a ride which you pay on the bus.
Tip: Wait until most people have left Oia Castle for the sunset view. Yes, you’ll question everything as the hypothetical salmon fighting the departing crowds to the old castle ruins. At this point, spots along the wall should be opening up and you can enjoy the post-sunset glow until dark! The lines for cabs/buses to Thira will also be much shorter.
DAY 3
At a glimpse: Stroll through Pyrgos, a winery and sunset cruise in Santorini
Travel agenda: Start the day with Greek yogurt at Lila Cafe. Then from Thira, take the local Perissa bus with stop in Pyrgos village. Roam the roads and enjoy the lack of crowds here. Stop at the Castle of Pyrgos at the top for views of the whole island.
Lunch should be on the quaint outdoor terrace at Franco’s Cafe. From there, meander 30 minutes Southwest to the water and you’ll be at Venetsanos Winery. Stop in and order a flight tasting.
Tip: Santo Wines is even closer and also a cool spot. However it’s on the cruise ship circuit and can be a bit crowded. If you’re not a wine drinker, the other option would be to rent an ATV to explore the father parts of the island, including the Akrotiri Lighthouse.
End your Santorini experience on the water with a Sunset Cruise. There are dozens of options for boats, and your best bet is to go to a local travel office/desk and ask what is available while comparing rates. Make sure to reserve one that includes: a view of White Beach, Red Beach, a stop at the volcanic hot springs for swimming, dinner and beverages, and of course a sunset view. Most include pickup and drop-off from your hotel, so all you have to do is book! The shuttles leave between 3:00pm and 4:00pm so you’ll want to be back at your hotel by then to grab your bathing suit, sunblock and a change of clothes.
DAY 4
At a glimpse: Ferry to Mykonos, explore Mykonos Town and the waterfront
Travel agenda: Book the earliest high-speed ferry to Mykonos. The 2 hour ferry ride offers comfortable seats and a snack bar. Once in Mykonos, there are buses in the New Port parking lot that will take you to Mykonos Town, or Fabrika.
Tip: Navigating the ferries can be difficult. Lines are formed and then forgotten as soon as a ferry approaches. People and cars board and deboard at the same time. You’re supposed to leave your luggage with the cars on the lower level so arrange your bag along the wall and make a mental note of what permanent sign it is closest to! Don’t stress about the confusing ticket seating and find any available seat on the ferry. If an attendant asks you to move, just politely ask where your section is.
After checking into the hotel, head to Mykonos Town. Get lost in the cobblestone alleys and narrow side lanes. Captain’s is for a waterfront meze dinner but save dessert for the loukamades or the Greek doughnuts, at Yassou Snack Bar. See the sunset near the famous Windmills (Kato Mili) and wander Little Venice, a picturesque shoreline. Caprice Bar is a fun waterfront spot for cocktails!
DAY 5
At a glimpse: Beach hop around Mykonos via ATV
Travel agenda: The best way to explore the island is by ATV! Mykonos is spread out enough where you won’t encounter much traffic and there’s less of a chance of getting lost. Rent an ATV in the morning at one of the many rental spots in Mykonos Town, then head to Central Cafe for breakfast.
Tip: For 24 hours, the ATV should be about $100. All you need is a driver’s license for a larger quad bike (150 and 310cc). Slow down on corners and pull over if there’s a car behind you. Otherwise its just common sense!
Now begins the beach-hop. Head north to Fokos Beach to enjoy some time exploring. Then on the way down head to Mykonos Vioma Organic Farm for some snacks and maybe a glass of wine! Next up: Ftelia beach, a windsurfer spot on the bay.
From there, head west to Agios Sostis Beach. Relax and sunbathe on one of the best local beaches in Mykonos. Even better, when you’ve had enough sun, turn left to Kiki’s Tavern for a low-key but very good food spot where you’ll be welcomed by the owner.
Cut south across the island with Paraga Beach Bar as your destination. The beach is clear, clean and there are a few bars in the area that make it a fun stop. If you want to step it up a notch, Paradise Club and Tropicana Beach Bar are just a few minutes away! The local bus can take you back from there and you can pick up the ATV in the morning!
DAY 6
At a glimpse: Ferry to Athens, Ancient Greece intro and markets
Travel agenda: Arrive and take a taxi to your hotel. Once settled in, stop to get a traditional coffee at Mokka. Then walk 4 minutes to lunch at Falafellas, a street vendor with wonderful takeaway falafels. From there it’s 5 minutes to Monatriraki Flea Market. Explore and do some souvenir shopping.
Get your first dose of ancient Greece at the Ancient Agora of Athens with several landmark sites like the Stoa of Attalos, the Temple of Haephestus and the Church of the Holy Apostles all located in the same area. Next, head to the A for Athens roof deck for apps and drinks (but really the view of the acropolis).
Tip: At the Agora, purchase the combined ticket option, which is valid for admission to the Acropolis and Slopes, Ancient Agora, Roman Agora, Hadrian’s Library, Olympieion, Kerameikos and Aristotle’s School.
DAY 7
At a glimpse: A full Athens day starting with walking tour
Travel agenda: This is a long day so start with a big breakfast at IF Espresso Bar for specialty coffee, eggs and Greek specials. Then at 9:30am walk just around the corner over to Hadrian’s Arch to meet a new crew for a free walking tour of Athens. It’s a 2.5-3 hour walk and highlights both the modern and ancient Greek sites with additional myths, facts and legends. This is a fascinating introduction to the city and the guide will also make local and insider recommendations for the rest of your trip. Get lunch at To Kafeneion, a little oasis in the Plaka and explore the quaint area.
After 3pm and once the crowds have died down, the time has come to experience the Acropolis. It’s about a 20 minute walk up from the southeastern corner of the Dionysus Theater entrance (this is not the main entrance which means there’s usually a shorter queue). Set out to explore the Propylaea or grand entrance, the smaller Temple of Athena Nike, the Grand Parthenon, and the Erectheion, not to mention all of the ruins scattered around the hill. Don’t miss the short climb up the nearby rock of Areopagos for a cool view of the acropolis and the Odeon of Herodes Atticus Roman theatre.
Tip: The Herodes Theatre still offers concerts and festivals during the summer so check the schedule to see if your stay lines up with a show.
You’ve earned a good dinner and beverage at Filippou, a local spot with great Moussaka and reasonable prices. If you have a sweet tooth end the night at Bougatsa Thessaloniki, a dessert cafe open 24/7.
DAY 8
At a glimpse: A short hike and museum trip
Travel agenda: On your last day in Greece, start with a coffee and breakfast at the adorable Lotte. Before the city wakes up, hike to Filopappou Hill for another stunning view of the city. From the bottom of the hill, walk 8 minutes to the Acropolis Museum. The new museum is beautiful and worth at least 2 hours.
Tip: It’s best to visit the Museum after the Acropolis. After seeing the real thing, the museum’s architecture is designed to feel like you’re on the Acropolis so you can visualize where the statues and reliefs would be.
For lunch, walk 10 minutes to Maiandros for some authentic local cuisine and a final cheers to Greece.
