Santorini – A Classic Beginning

With only two nights on the island, I based myself in Fira, close to the airport and perfectly placed for everything I wanted to see.

Settling In

My hotel was just five minute walk from the centre,  with a great pool and those very comfy sun loungers, perfect for unwinding after the flight before strolling safely into town.

That first evening I set out to find the perfect restaurant with a view of the renowned Santorini sunset. There was a moment’s hesitation about seating a solo diner, something I had read might happen, but I got what I wanted,  a glass of wine, a beautiful fresh fish dinner, views looking out over the caldera, pure magic.

Fira is a lively mix of cobbled lanes, tiny chapels, boutique stores, ice‑cream bars and artisan shops,  a charming place to wander. As the sun drops and the lights come on it is the most wonderful place to wander and people watch. Yes it is very busy and some would say over-commercialised but when there is views like there is from Fira it will always be popular resort. 

Day two : The Famous Fira–Oia Coastal Walk

I set off early so to avoid the high temperatures,  the route takes approx  10 km  along a trail to Oia, with a scenic detour to Skaros Rock which adds on another 1.5 hours to the walk.

Leaving Fira, there is a very clear path and hard to go wrong.  The trail winds past luxurious properties perched on the cliffside: private pools, dreamy terraces and uninterrupted volcanic views. First stop is Firostefani, which feels like a quieter extention of Fira. A small clifftop village of whitewahsed houses, blue domes churches and a handful of tavernas.  Continuing on into Imerovigli,  often discribed as the "balcony of Santorini" here the crowds melt away and the landsacpe grow wilder and more dramatic, stunning hotels with infinity pools facing out to sea.  From Imeroviglia you can branch off to Skaros Rock, a steady hike rewarded with sweeping views. It is well worth the effort but try to tackle in the morning or later in the afternoon rather than in the full glare of the midday sun.

My finish line is Oia, I didn't get to spend a lot of time here but first impression was of a very upmarket village that still felt genuinely welcome. Even in my walking gear I was made to feel very welcome as I settled in for a late afternoon lunch with the most incredible views. 

Oia is the quintessential Santorini scene. Whitewashed cave houses, blue-domes churches, bougainvillea spilling out over balconies . It is a place of artisan boutiques, stylish cafes and sunset terraces but I had no problem finding a quiet corner to sit and look out at the caldera and understand why Oia is one of the most photographed places in Greece. 

Paros – Slower Pace, True Greece Charm

On day three I headed to the port for a pre‑booked ferry to Paros. Bags are stored in the lower deck, its important to store your bags at the marked sections  labelled at what ever island you are disembarking, as ferries usually stop at multiple islands.  

On arrival I didn't book a transfer on arrival, but would advise to prebook as the queues were very long, I ended up getting the public bus which was waiting just at the exit and cost a fraction of a taxi but packed like sardines.

Staying in Naoussa

Paros immediately feels calmer than Santorini. I based myself in Naoussa, a gorgeous harbour town that comes alive in the evening with traditional tavernas, boutique shops and very pretty lantern lit cobbled streets. 

Beach Days & Exploring in Paros

The beaches were breezy during my stay, so with the advise from my hotelier I hopped on a water taxi to a more sheltered bay for a perfectly lazy, sun‑soaked day.

On Day 2 in Paros I took the local bus to Lefkes,  a traditional mountain village, where life moves slowly and stone houses sit framed by rolling hills. It was a lovely change of pace from the coast and a reminder that Greek island life is as rich inland as it is by the sea.

My suggestion is to get there early, I arrived around 9am and by 11.30 it started to get very crowded.

Naxos – Warm, Authentic & Full of Character

My final island was Naxos, after a quick  ferry ride from Paros I checked into a charming family run hotel just two minutes walk from the lovely  beach of Agios Georgios Bay. With serviced beach clubs, tavernas and warm shallow waters, it was everything a Greek island should be.

It was a pleasant 15‑minute stroll into the lively centre, where modern bars sit beside the old market district, full of character, history and little alleyways that were such a pleasure to explore. 

Hiking the Highest Peak in the Cyclades

I had pre‑booked a guided hike with Hellenic Hiking to the highest point in the Cyclades. The walk was relatively easy, and the guides were full of fascinating island history, from ancient myths to modern life. Could it be done alone? Absolutely.  But on holiday, it is a treat to let someone else take the reins and just enjoy the journey. We even finished with a little Greek picnic compliments of our guides – perfect day.  

A Flying Finish – Athens & The Acropolis

After Naxos I had one night in Athens, just enough time to finally tick the Acropolis off the list.

I chose to fly rather than take the ferry. With crossings taking 4–5 hours and worsening weather on my last day, many ferries were cancelled, so the flight was definitely the right choice.

With only 24 hours in the city, I joined a half‑day guided tour to make the most of my time. The Acropolis was breath taking: ancient marble glowing in the sunlight, the city spread out below, and a genuine sense of standing where history was written.

Looking Back

Four hotels, three flights, two ferries – and everything ran perfectly because it was booked in advance. I chose centrally located hotels so I never had to worry about costly transfers or late‑night taxis.

Travelling Solo

It turned out to be one of the most relaxing holidays I have ever taken. Yes, dining alone takes a little getting used to, but a good book, delicious food and a glass of wine soon take care of that.

What surprised me most was how empowering it felt: setting my own pace, choosing where to linger and when to move on, and knowing I could trust my own company.

Travel Tips 

Solo Travel Tip
Choose hotels close to the centre. Being within walking distance of restaurants and the harbour at night makes a world of difference. 

Ferry Tip
Always place your luggage in the section labelled for your destination. Ferries usually stop at multiple islands, and this simple step keeps everything stress‑free.

Dining Alone
Ask for a table with a view, order a glass of wine and open a book. After the first night or two, it starts to feel less like a challenge and more like a little luxury of its own.

Why the Greek Islands Work for Everyone

Whether you are travelling solo, planning a romantic escape, off on a girl's trip, a sea-view addict, a hiker, a history lover....the Greek Islands just work.

The ferry system is beautifully organised, making island‑hopping easy and stress‑free.

Santorini is extremely popular and welcomes plenty of cruise traffic, so Fira and Oia can get busy. If I return, I may choose a quieter part of the island, but for a first visit I was more than happy with my base. 

Naxos stole my heart, it felt like a home from home and everyone I met was so genuinely welcome.

A trip of sunshine, warm hospitality, beautiful villages and the kind of sea views that stay with you for life – everything a Greek island journey should be.  If this sounds like your kind of escape, contact me to start planning your own tailor-made Greek island hopping adventure, designed around exactly how you love to travel.