Sketching and Painting Holidays in Italy

Uncountable islands on an endless expanse of blue; fishing boats bobbing in colourful harbours; beckoning tavernas and hidden, rocky coves: Greek island hopping through the charming, historic Dodecanese

Introduction Trip - Realm of the Nesoi Your sketching day Are these holidays for me? How to book

Introduction

What’s the first thing that comes to mind when you hear the words, Greek Islands?

Is it the infinity of blue, from the water to the sky to the serenely painted chapels, perched on high above rocky bays? Is it a wizened fisherman, mending his nets beside brightly coloured boats in the harbour in timeless fashion, while the buzz of the new world hurries, unnoticed, around him?

A fig tree, dripping with plump deliciousness, draped across a taverna table laid with a tempting mezze, perhaps a glass of retsina on the side? Towering cliffs above the clearest water, goats among the olive trees, whitewashed villages clinging to the hillsides, the smell of wild oregano as you stroll sandy paths?

You will find all these things on a trip to the region. Yet with up to six thousand islands and islets, and over two hundred which are inhabited, it might be surprising to learn that each one has a character all its own, along with an unmistakeably Greek flavour. One could spend a lifetime carrying a sketchbook from island to island; every one of them bursts with subjects just begging to be splashed onto the page, and it must be almost impossible to choose just one.

In the Eastern Aegean, nudging up to the Turkish border, lie the sun-drenched Dodecanese. These include the well-known tourist meccas of Kos and Rhodes, along with some lesser known but stunningly iconic islands such as Symi, and quieter, peaceful havens which have so far avoided the ravages of mass tourism. The beauty of this group, in particular, is the weather, which stays warm into late September and October, long after schools have returned and the crowds have dissipated. This is when we will travel, with the aim of sitting outside to paint in comfortable, not stiflingly hot, sunshine and swimming in a wonderfully warmed-up sea.

From ancient ruins to rocky hillsides, hidden coves and sparking seas, the Dodecanese have everything a visit to Greece should provide, along with delicious regional food, and sights you might never have imagined – or painted.

Trip - Realm of the Nesoi

Realm of the Nesoi - Greek Island Hopping:

Sketchbook Journey

Next Trip(s): September 17th 2026

Duration: 15 nights from Kos to Rhodes, Greek Dodecanese

Price: £3400 (Two sharing a room: £2700. Non-painting partners: £2600)

The Nesoi, in Greek mythology, are the primordial goddesses of the islands. Daughters of Gaia, they began as mountains, but were cast into the sea by Poseidon in a fit of rage. Each island has its own goddess, worshipped by ancient Greek seafarers as providers of safety, shelter, and orientation.

In all the islands, ties to history and mythology are strong, and traditions hold fast, despite their more recent popularity with visitors from all over the world. The Greek hospitality is also legendary; the pace of life is relaxed, the climate mostly kind, the living easy. Being islands, one is never far from the sea, and we will be spending most of our time on it, in it or beside it, as well as painting it.

We visit as many islands as we can squeeze into our time in the Dodecanese. We aim for a comprehensive flavour of the region, encompassing as many facets of the landscape, culture and history as possible in a relatively short journey, without rushing from one place to another. Despite the distance covered and variety of locations, there is plenty of relaxation on this itinerary with time for swimming, paddling or just soaking it all in. There will be painting opportunities every day, and with subjects ranging from simple to challenging there really is something for everyone here, whether your interest lies in landscape, seascape, boats or buildings.

Highlights:
Tranquil, timeless Telendos; fascinating Asklépion; gorgeous Symi with its iconic harbour and colourful buildings; refreshing swimming in clean, clear water; history and alleyways of Rhodes Old Town

Please ask for a detailed daily itinerary for this trip

Day 1: On arrival to Kos, make the short journey to Kéfalos, a beach town on the southwest coast

Day 2: In Kéfalos, sketch the pretty offshore islet then take a boat to visit its little church and crystalline waters

Day 3: Afternoon in Kos old town with its historical sites

Day 4: Sketching at the atmospheric ruins of Asklépion

Day 5: Ferry to Kalymnos and bus to Masouri; paint Telendos from the mainland

Day 6: Visit the remotest village on Kalymnos with its blue-domed church

Day 7: Boat to Telendos, and a change of pace in this laid-back, authentic location

Day 8: On Telendos. Paint chapels, beaches, flowers and all things Greek

Day 9: On Telendos. Sunset boat trip.

Day 10: Back to Kalymnos, visit Agios Savvas high above Pothia, then catch the ferry to Symi

Day 11: Explore the stunning harbour area with its pastel-painted merchants’ houses; visit Pedi, a peaceful fishing village

Day 12: Full day boat trip around the island with lots of swimming interspersed with sketching

Day 13: Visit the monastery at Panormetis in the south of the island in a beautiful bay

Day 14: Morning painting around the beautiful town; afternoon ferry to Rhodes

Day 15: Day trip by boat to Chalki, or sketching around the historic Rhodes Old Town

Day 16: Fly back from Rhodes

(There is also the possibility of shortening this trip and making one of two circuits: Kos-Kos 10 days, or Rhodes-Rhodes 7 days. These might suit those with less time or a smaller budget. Please enquire about these shorter itineraries which are strictly number-dependent.)

The price for this holiday includes:

All accommodation on a bed & breakfast basis. Dinners in self-catering accommodation (Kos town). All ferries between the islands and on day trips (boat to Kastri from Kéfalos; Telendos sunset cruise; Symi island boat trip or water taxi; day trip to Chalki from Rhodes). Buses where they form part of the itinerary (Kéfalos to Kos town; Emboriós/Masouri from Pothia on Kalymnos; Panormítis trip; bus to Chorio/Pedi on Symi). Taxis to/from Asklépion archaeological site and entrance fees. Set of watercolours and brush suitable for the holiday. Ongoing painting tuition/guidance as required, advice and frequent sketchbook appraisals. Farewell drinks and dinner on final night in Rhodes

The price does NOT include:

Flights. Taxis/buses to/from the airport (taxis may be shared if others are arriving at the same time). Lunches and dinners (except when stated in the itinerary); drinks, refreshments, snacks. Optional entry fees to archaeological sites, museums, monasteries. Some art materials, most notably an appropriate sketchbook (a list will be sent upon booking). Extra nights before or after the trip in Kos or Rhodes.

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Your sketching day

Every day on this holiday will have an opportunity for painting. You can even sketch from the ferries!

We do not need particularly early starts on this trip. Even on days when we are moving islands the ferries are not at an antisocial hour, and we will begin whatever we are doing after a decent breakfast.

Despite the apparent ‘busyness’ of the itinerary you will find the days quite relaxing, and once we have found a good spot to paint we won’t be as rushed as we are on some Vistas trips. Although I encourage sketchbook work, to keep a pictorial record of our special journey in one place, this itinerary is better suited than most to the completion of more traditionally ‘finished’ watercolour paintings, if desired. Just bear in mind you’ll probably need a drawing board for this, which will have to be carried – in your lightweight hand luggage.

An opportunity for swimming will be provided on most days. In many cases we’ll already be painting from the beach, so from sketchbook to sea to taverna and back is often the order of the day.

Guidance, instruction, demos and exercises will be available at all times, and if you are a novice, this is a wonderfully unintimidating environment for developing your technique.

The more experienced may choose to go follow their own path, though this is a watercolour-based trip.

In practical terms, sketching and painting in Greece is not taxing. Even in hot weather we can find shade, and often there will be a bench, a seat at a beachside taverna or a broad, stone step to sit on. You won’t attract much attention, either, unless it’s from a genuinely interested fellow artist seated next to you in a restaurant. Apart from the busiest places – Symi harbour, Rhodes Old Town, Asképion – we will be able to tuck ourselves away, virtually unseen. The Greeks themselves are far too busy to be interested in what we’re doing – unless you want to show them, of course!

The most iconic subjects include dazzling white churches with cobalt domes against a background of deep turquoise sea; prettily painted, small fishing boats full of buoys and nets bobbing beside the jetties; dry, rocky mountainsides plunging down to pale pebble beaches and the stack of pastel-coloured sponge-merchants’ houses around Symi and Chalki harbours. In addition, we have the chance to sketch famous archaeological sites in Rhodes and Kos, testing your perspective skills with all those archways.

We end the day with dinner together at a local restaurant, perhaps watching the sunset with a glass of something cold in hand. Every few days we’ll have a sketchbook appraisal where we can provide encouragement and constructive input for each other, while marvelling at how much we have managed to achieve in such a short space of time!

Are these holidays for me?

Greece, with its islands, is no stranger to tourists of all types, including the package variety, and it is regarded as a welcoming, family-friendly destination. Most of the locals we encounter speak at least a little English, are well-used to foreigners and to providing warm hospitality.

On this itinerary we fly into one airport and out of another (unless taking a shortened version). It entails frequent sea travel between the islands, and we will use the public bus to get around while we are on land. So, while our time in the main locations will be slow-paced and relaxing, there is much to see and many places to reach. Therefore, this must be thought of as an adventurous, energetic trip.

It involves lots of boats of all sizes, sea crossings of up to three hours and walking up and down a considerable number of stone steps. Most of the island towns are built into the hillside, and many of the streets are too narrow for cars (i.e. taxis). Our accommodation must be reached on foot, with our luggage. Sometimes it may be at the top of the hill. A small backpack is by far the most practical solution, and you should pack light for this trip.

You will also get more out of this itinerary if you like the water; there will be lots of opportunities to swim between making sketchbook entries, and the water, in September, is glorious.

Accommodation in the islands varies from basic (i.e. a bit spartan and rather old-fashioned) to luxurious. On this itinerary we will experience a mixture of the two as I attempt to provide comfortable, attractive sleeping environments whilst keeping the cost affordable. All your accommodations will be safe and clean with a private bathroom. In many cases they will be beautifully presented, and some will have a pool. As with travel everywhere, we must be willing to adapt if our room is not of a 5* standard. Wherever possible I choose smaller, family-run, authentically Greek places, helping the local economy.

In common with many parts of southern Europe, a mañana approach often prevails, and it can help to embrace that philosophy. Greece is not a ‘risky’ destination, but nor is it Switzerland: it’s best if you can learn to shrug if things seem to be a bit more casual than expected.

In terms of painting, there are a wide variety of subjects ranging from simple seascapes where the hardest part is capturing the clear, clean, bright colours in the water, to the very challenging jumble of merchants’ mansions stacked up above Symi harbour. You will become accomplished at depicting the shadows on whitewashed chapel walls, the vivid violet bougainvillea and the scrubby brown hillsides, and you’ll want to tackle the colourful fishing boats bobbing in the harbours. A Sketchbook Journey is about capturing the moment, the feeling of a place. On this trip there may be time to complete one or two more ‘finished’ paintings, also, if this is your preference.

Pure landscapists who dislike painting manmade structures of any kind may struggle here, as it’s difficult to avoid them completely. While many will be in their element within the villages and harbours, if this doesn’t sound like you, you might want to consider the Italian Dolomites or Canary Islands itineraries instead. Please ask me if you are in any doubt as to which trip is right for you.

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How to book

You may reserve a place on any trip with payment of a 10% deposit. Trips run subject to a minimum number of participants being reached, which will be confirmed before a deposit is taken. Until then you may register your interest, to be notified once the trip is confirmed.

Firstly, please use the contact form to send an e-mail to me, and let me know which trip you are interested in. I will send you more information to make sure it's the right trip for you. If you are unsure which will suit you best, we can go through the options.
When you are ready to make your booking I will send you a booking form and payment details so that you can pay your deposit.
I will send you essential information about how to join the group if you are not being met at the airport; advice on choosing flights (if applicable) and what you need to bring with you on your holiday, as well as a Useful Information fact-sheet for the country you will be visiting, if you have not already requested this.
The balance of your payment is due in British pounds, 2 weeks before the commencement of your Sketching Holiday. You may make a bank transfer (recommended), via PayPal or Wise, or if you prefer to pay by cheque (in pounds sterling), this must be presented and cleared in my account well before the commencement of the holiday.

Non-UK residents may choose to pay in cash on arrival at the destination but please speak to me about this first.

By making your booking you are agreeing to our 'Terms and Conditions' which can be found by clicking here.

Contact information:
Email: [email protected]
Phone: 00 44 (0)798 281 2842 (active only when I am in the UK or via Whatsapp).
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Sketching & Painting Holidays in Greece