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.