Greek Islands in 8 Days
the backstory
We were looking for a fun way to celebrate Tori’s 30th birthday which is in late October. October is not when we typically travel – April/May is usually our sweet spot for trips to Europe so we have the nice weather and avoid the peak season crowds.
To plan an October vacation, we wanted to come up with somewhere where we would still have great weather with the pretty sea views that we love. We landed on Santorini and Crete as our perfect Island duo – because they are further South, they are warmer in October and things stay open a little longer (Islands further north begin closing the first couple of weeks of October).
Our two main hubs for this trip were Chania on the Island of Crete and Santorini, but since we had never been to Greece before, we included a little bit of time to see Athens too. If you have more time and this is your first trip, it might be worth giving Athens some more time than we did in our itinerary. If you are thinking about traveling in October too, I’d consider moving the trip just a little earlier in the month as places start to close down for the season towards the end of the month – check before you go!
Itinerary overview
Chania – Crete
Day 1: Arrive & Settle
Day 2: Balos Beach
Day 3: Samaria Gorge Hike & Agia Roumeli
Day 4: Day Trip to Elafonissi Beach
Santorini
Day 5: Wine Tour
Day 6: Boat Day
Day 7: Fira to Oia Hike & Spa
Athens
Day 8: Quick visit to Athens
Day 9: Going Home
OUR FAVORITE ACTIVITIES
While Santorini is popular for a reason – it is stunning and has some killer sunsets against the whitewashed landscape – Chania was our favorite. Chania has a tiny, adorable old town on the Island of Crete right on the harbor. While there weren’t a ton of sights in the old town itself, it was the perfect hub for our visit to Crete to enjoy the mountains, beaches, and just wander around the harbor and shops. It was a lot less touristy compared to Santorini, home to some amazing food, and we found really good value here (good prices for amazing quality). If we were going to add a couple more days to this trip, we’d spend a few nights in Elounda (also on Crete) before going to Santorini.
Click the pictures below to book some of our favorites from this trip.
samaria gorge hike & AGIA ROUMELI
HARBOR VIEWS IN CHANIA
BOAT DAY IN SANTORINI
HOTEL WITH PRIVATE HOT TUB & VIEW
WINE TASTING EXPERIENCE
SCENIC HIKE TO BALOS BEACH
detailed itinerary by day
DAY 1: ARRIVE & Settle
Sleep in Chania
PLANNED ACTIVITES
ARRIVE & SETTLE
10:00AM | Land and connect flights to Chania
2:00PM | Land in Chania and pick up rental car
3:00PM | Check into hotel and get settled (we stayed at Residenza Vranas Boutique Hotel and loved it)
Afternoon | Get acclimated
6:00PM | Dinner at Salis (cute restaurant, easily walkable, delicious food)
TIPS
CHANIA
We loved it here – it is a tiny, adorable old town on the Island of Crete right on the harbor and was the perfect hub for our visit to Crete to enjoy the mountains, beaches, and old town. If we were going to add a couple more days to this trip, we’d spend a few nights in Elounda (also on Crete) before going to Santorini. We especially loved our hotel – it was a small boutique place with just a few rooms, great service, amazing breakfast included. We booked the suite which had awesome views overlooking the harbor, and it felt like a great value for the price we paid.
GETTING THERE
We had not visited Greece before, so opted to book roundtrip flights to Athens (plus there were the most economical and direct flight options this way). Plus, this gave us an opportunity to see the city and at least visit the Acropolis. We opted to fly from Athens to Chania and booked another flight from Chania to Santorini for this trip. Flights within Greece were relatively economical and easy to navigate.
TRANSPORTATION
We opted to get a rental car through Hertz since Crete is a huge Island. This was a great way for us to explore.
DAY 2: bALOS bEACH
Sleep in Chania
PLANNED ACTIVITES
BALOS BEACH
9:00AM | Grab some breakfast at the Ginger Concept
10:00AM | Pick up something to take for lunch at xx
10:30AM-11:30AM | Drive to Balos Beach and spend the day
11:30AM-3:00PM | Spend the day enjoying Balos
3:00PM-4:00PM | Drive back to Chania
4:00PM-8:00PM | Get ready for dinner walk around Chania and enjoy the shops
8:00PM | Dinner at Oinoa (loved this place, truly delicious food, romantic patio)
TIPS
BALOS
Balos is a beautiful, shallow, clear turquois lagoon and beach in the middle of a national park with panoramic views and an exotic feel. We decided to rent a car and drive ourselves to Balos which worked out great. Be ready to endure a very bumpy dirt road drive to get there, but it is totally worth it. Once you are parked, the hike down to Balos takes about 25 minutes down 850 steps, so make sure to wear appropriate shoes (I recommend sneakers).
SHOPPING
Chania Old Town has some great shops throughout the backstreets. Theotokopoulou, Chatzimichali Daliani, and Daskalogianni are good places to look for some authentic souvenirs.
Day 3: sAMARIA GORGE HIKE & AGIA ROUMELI
Sleep in Ronda
PLANNED ACTIVITES
SAMARIA GORGE HIKE & AGIA ROUMELI
6:00AM | Meet at pick-up spot for hike transportation
6:00AM-7:00AM | Bus ride from Chania to Samarian Gorge
7:00AM-12:00PM | Hike down the Samarian Gorge from starting point (Omalos plateau)
12:00PM-1:30PM | Conclude the hike in the coastal village of Agia Roumeli and have some lunch (there are several small restaurants to choose from)
1:30PM-4:30PM | Enjoy the beach, swim, and hang out
4:30PM-6:00PM | Take the ferry back to the bus pick-up spot; then the bus back to your drop-off in Chania
7:00PM | Get ready for dinner
8:30PM | Dinner at Tamam (classic restaurant in Chania Old Town)
TIPS
THE HIKE
The hike is amazing – would highly recommend. It is a very strenuous ~10-mile hike down a steep ravine with many loose stones, a lot of climbing, walking on uneven stones etc. If you are well equipped to walk through some challenging terrain, it is worth it. Just make sure to wear the right shoes, comfortable, layered clothes (the temperature can vary greatly from the top of the ravine to the bottom) and pack sunscreen, a swimsuit, beach shoes, a towel, water, and snacks. The hike ends at a pretty little village (Agia Roumeli) located right between the mountains and the sea.
LOGISTICS
We booked this excursion which made sense because the ride to the beginning of the gorge is long, narrow and curvy – beware if you experience motion sickness. Because we did a tour, the pick-up was very early in the morning and we had to drop others off, but it did take out a lot of the coordination to get back to the car. The alternative option would be to drive your own car, park it at the entrance, hike, take the ferry back to where the buses pick everyone up, then take a taxi back to your parked car. Regardless, I would recommend starting very early to avoid the crowds.
Day 4: DAY TRIP TO ELAFONISSI BEACH
Sleep in Chania
PLANNED ACTIVITIES
DAY TRIP TO ELAFONISSI BEACH
9:00AM | Breakfast through the hotel or grab something light
10:00AM | Pick up some lunch and snacks to bring
10:30AM | Drive to Elafonissi for the day
4:00PM | Drive back to Chania and get ready for dinner
6:00PM | Have a cocktail at Woodstock
8:00PM | Palazzo Almare for dinner
TIPS
ELAFONISSI
This beach is famous for its pick sand and clear water and is considered one of the most beautiful beaches in the world. There are chairs and umbrellas to rent or you can just bring your own towel and umbrella (the hotel provided these for us).
Day 5: arrive in santorini
Sleep in Santorini
PLANNED ACTIVITES
ARRIVE & WINE TOUR
10:15AM | Flight from Chania airport to Santorini
2:00PM | Check into hotel
2:00PM-3:30PM | Relax at hotel pool/hot tub, settle in
4:00-7:00PM | Santo Wines tour and tasting
7:30PM | Kapari Wine Restaurant for dinner
TIPS
GETTING THERE
We chose to book a flight from Chania which was relative quick and easy (3 hour duration including a quick layover); the alternative would be to book a ferry (provided you don’t go too late in the season). There aren’t ferries directly from Chania; you’d have to drive two hours to Heraklion to catch the ferry there.
STAYING
We stayed in Imerovigli right on the caldera edge pathway in between Fira (the main town) and Oia (the more expensive northern part of the island).
WINE TOUR
Greece has some amazing wine, and we loved visiting the winery and booked ours for sunset (which Santorini is famous for) and loved the wine so much, we shipped some home. You can book it here.
GETTING AROUND
We booked a rental car and had it dropped off at our hotel so we could get around – the hotel helped us with this when we got there, but you could do this ahead of time as well. If it had been a little warmer, we would have considered a scooter rental for fun (just know it requires the right kind of license).
Day 6: boat day
Sleep in Santorini
PLANNED ACTIVITES
BEACH DAY
10:30AM-3:30PM | Boat Day Cruise, Snorkeling, and Lunch
3:30PM-5:00PM | Get back to hotel and ready for dinner
5:30PM | Head to Oia for some exploration before dinner
7:00PM | Dinner at Sphinx on the rooftop for sunset
TIPS
BOAT TOUR
We booked the Caldera Yachting Gold Day Cruise. Next time I would try a different company (this one has a ton of great reviews) because some of the crew seemed generally annoyed much of the time. Despite that, the overall the experience was fun. They picked us up at our hotel, cooked us a full lunch onboard and provided snorkel gear when we stopped to swim. The water was pretty cold in October, but we loved it still. We were with a small group of other people (~20 of us in total). We had plenty of space and enjoyed seeing the sights. We learned a few facts from the boat crew, but it was mostly time to relax, enjoy the views of the Islands, and swim.
Day 7: Fira to Oia Hike & Spa
Sleep in Santorini
PLANNED ACTIVITES
FIRA TO OIA HIKE & SPA
7:00-11:00AM | Hike from Imerovigli down to Fira and up to Oia
11:30AM | Get some lunch at a fish taverna on the water in the cute fishing village of Ammoudi (down 300 steps from Oia)
2:00PM | Head back to hotel
3:00PM | Spa experience at hotel
7:30PM | Dinner at Selene
TIPS
THE HIKE
Start early as possible as the pathway gets super crowded. The cruise ship port lets out in Fira, and the path gets more congested with people as the day goes on. Starting early also helps with avoiding the heat of the day depending on the weather.
SPA
Santorini has some wonderful resorts and ours offered a wellness cave experience which we took full advantage of and enjoyed massages there as well. This was amazing after a long day of hiking. Alternatively, just enjoy the pool or hottub (many of the resorts in Santorini have hot tubs looking right over the caldera)
EATING
This is a splurge restaurant for sure but worth it – we enjoyed the fixed price menu and wine pairing and it was a full experience. The service, food, and atmosphere were the best. There is a Meze & Wine Bistro downstairs without the price tag if you are looking for a good alternative.
Day 8: Quick visit to Athens & Home
Sleep in Santorini
PLANNED ACTIVITES
ACROPOLIS & DINNER
11:00AM | Check out of hotel & head to airport
1:00PM | Flight from Santorini to Athens
1:00PM-3:00PM | Land in Athens and take metro or taxi to hotel and settle in
3:30PM | Visit the Acropolis
6:30PM | Drinks
8:30PM | Dinner at the Tudor restaurant
TIPS
ACROPOLIS
Since this was just a quick visit to Athens, we built in time to visit the top site there – the Acropolis (home of the Parthenon). It worked out great to visit here late in the day because we missed most of the crowds this way. You can buy your tickets there or ahead of time online here. You can get through the whole site in 90 mins or so. The last entrance is typically 4:30PM.