Let me start by saying we only visited a few of the most popular Greek islands. That being said, places like Santorini are frequently visited for a reason, they are incredible. From Greece's largest and less touristy island, Crete, to the picturesque cliffs of Santorini, to the endless beaches of Mykonos, there are still atypical experiences to be had. In all of these places we stayed in unique Airbnbs (including a literal cave-house!), highly recommend going this route. Bonus Athens favorites at the bottom!
CRETE
EXPLORE
Old Venetian Harbor and Lighthouse is the heart of Chania. The waterfront offers amazing views, great seafood, shopping, and people-watching. Stop into the Hassan Pascha Mosque right on the water. It's a Turkish style mosque, very different from anything else you'll see in the area.
Golden Beach aka Hrissi Akti is a nearby beautiful beach that's generally pretty quiet. If you're looking for something a little more special, head to Elafonisi Beach, which is further from town but has pink sand.
EAT
Chatzimichali Ntaliani serves up the best tzatiki we had in Greece. Tucked in a little side street, this restaurant is the perfect place to spend an evening drinking wine (or ouzo) and relaxing. No website, address is 46, Chania 731 32.
Ta Neoria (Neoria Seaside Tavern) offers fresh-caught seafood, directly from the marina. The atmosphere is authentic, dining to the tune of fishing boats clinking in the harbor. An Anthony Bourdain recommendation, and don't leave without getting the grilled octopus.
DRINK
Sinagogi Bar is an open air bar and lounge with a cave style interior. Located in an old synagogue, this spot is great for a little more lively night out.
SANTORINI
EXPLORE
Spiridakos Sailing Cruise is the best way to spend an afternoon. Take a half-day catamaran ride for five hours of sailing, swimming, and dinner. The waters can be rough in spots (especially for people prone to sea-sickness like me) but worth it. Easy pick up via personal shuttle from Fira.
Kamari Beach features the black volcano sand and is only an easy ride by bus, taxi, or for the more adventurous, ATV.
EAT
Kastro Restaurant is known for it's spectacular views of the sunset as it wanes over Oia. Head over early or expect to wait for a table.
DRINK
Santorini Brewing is know for its Yellow Donkey and Red Donkey brews. Come for the beer and appetizers, stay for the views of Oia on their little rooftop patio.
Two Brothers Bar in Fira is a good stop on a mini bar-crawl. A bit of an ex-pat vibe, plus dancing.
MYKONOS
EXPLORE
Paraga Beach is one of the most lovely beaches I've encountered. A total antidote to the party beaches (ie. Paradise Beach, which has its time and place). Snag a cheap lawn chair and be prepared to stay all day (and snack at the beach-side cafe).
ATV Rental is probably the best way to get around Mykonos. Much flatter than some of the other islands, navigating on ATVs is totally doable and makes any beach an easy destination. Double up for nervous riders, you can pick them up almost anywhere.
EAT
I Scream is a must stop in Mykonos town. Amidst all the lovely dinner fare, don't pass on the pistachio gelato for a delicious treat.
SHOP
Mykonos Town offers tons of adorable shops, including handmade linens, bright jewelry and more.
DRINK
Scandinavian Bar for drinks and dancing, and probably some shots. Just saying...
ATHENS
EXPLORE
The Acropolis is a classic, with good reason. There's nothing like it. While some tours might suggest hours, it really only warrants about 90 minutes. Afterwards, walk down to town center.
Constitution Square or Syntagma Square is a central square, adjacent to the Parliament Building. Catch the changing of the guards on the hour for a unique (and free) mini-show. Grab a gelato from across the street first to cool yourself while you wait.
EAT
Galaxy Restaurant located in the Hilton Hotel, has spectacular views of the city (and the Acropolis) plus delicious food.
SHOP
Melissino's, The Poet Sandal Maker is a legend and certainly a destination shop. Custom leather sandals come in seemingly endless styles. For about 30-40 euros you can take home a pair fitted right to your foot. Be warned the shop-keeper likes to keep people moving, so make your selection and get helped quickly. A totally unique shopping experience.