Cruising & cycling holidays

Cruising and cycling holidays work really well. They encourage travellers to take their time and dine out in locally owned restaurants. There’s nothing like a well-deserved seafood lunch in a traditional taverna to complement a cycle ride before returning to your yacht for a swim or a laze on deck.

This type of holiday is also low impact environmentally, so you can be confident that your visit will tread lightly on the landscapes that you’ve built your experience around. By eating locally, buying locally and travelling with local hosts you will be supporting communities away from the main tourist hotspots and in some cases contributing to their survival.

Two such locations that give themselves effortlessly to cruising and cycling are Montenegro’s Adriatic coast and the islands of the Greek Cyclades. Bracing offshore breeze and the warmth of the Mediterranean sun are never in doubt and evenings spent at different anchorages encourage even more opportunities to experience life on land, as well as at sea.
Both activities allow you to explore further and cover longer distances, giving you freedom to really become immersed in surroundings and get to know settings, intimately. Your expert local guides will take you to uninhabited coves, small fishing villages by sea; on land they’ll talk you through seasonal landscapes and introduce you to remote scenic viewpoints and out of the way deserted beaches.
You’ll recognise the benefits of travelling with hosts that really know the region, indeed live there, in every aspect of your holiday. They’ll know how to avoid the crowds, where to find the most authentic food, the best angles for your photo. They’ll also introduce you to local people and provide you with the context and history that will really bring locations to life.
Below is a brief guide to cycling and sailing holidays in Montenegro and Greece with information on where you’ll be sailing and cycling as well as the best time to go.

Cruising & cycling in Montenegro

Although you might consider a sailing holiday to have a few ups and downs, it’s actually the cycling side of this holiday that provides the undulations. Montenegro’s mountains make amazing places to pedal, with ancient olive groves and vineyards offering all manner of excuses to pause, catch your breath and enjoy the twinkling waves of the Adriatic from on high.
Powell Ettinger from our specialist cycling & sailing tour suppliers, the Small Cruise Ship Collection: “The combination of cycling and sailing works very well together. Not only does it appeal to guests wishing to relax onboard but it also lends itself to those wishing to get some exercise and explore on land for a few hours before rejoining the boat for a relaxing swim or bite to eat.”

Where will we sail?

The Bay of Kotor makes an excellent location to start a sailing trip in Montenegro with the tiny island of Sveti Marko and the coastal town of Herceg Novi allowing ample excuses to enjoy the tranquillity of the Adriatic before setting sail for the bright lights of Budva and Bar further south along the coast.

Lesser-known locations, such as the traditional fishing village of Bigova and the beautiful blue bays of Zanjice, are ideal for soaking up some sun prior to setting sail for Tivat and Perast. After overnight anchorages in both locations you'll sail back to Kotor from where your voyage first started.

Where will we cycle?

There are some superb cycling routes in Montenegro that will take you winding uphill to the Mausoleo di Njegos at the top of Mount Lovćen and down to riverside towns, such Rijeka Crnojevića, and the west coast wineries situated along the shores of Skadar Lake.

From olive groves and stone built fishing villages on the Lustica Peninsula to the strategic, yet easily accessible, setting of Vrmac ridge, separating Tivat from the Bay of Kotor, cycling in Montenegro is as enjoyable as life on the ocean. Average daily distances of 30km allow for relaxed two to three hour rides before re-boarding the boat for a swim, sunbathe and generous glass of Vranac red wine.

When’s the best time to go?

Either side of July and August is the best time to go on a cycling and sailing holiday in Montenegro with May offering less humidity and greener landscapes whilst September promises warmer waters to coincide with grape and olive harvests. You’ll also miss the peak summer tourist season.
Find out more in our Montenegro cycling guide

Our top Unusual combinations Holiday

Sailing and cycling Cyclades holiday, Greece

Sailing and cycling Cyclades holiday, Greece

Self guided or guided (upon request) tour in the Cyclades

From €1500 8 days ex flights
Small group travel:
2023: 1 May, 1 Jun, 1 Jul, 1 Aug, 1 Sep
Travel Team
If you'd like to chat about Unusual combinations or need help finding a holiday to suit you we're very happy to help.

Cruising & cycling in the Greek Cyclades

Island hopping in Greece is tried and tested, but add a bike to the mix and you’ve got all the makings of a legendary cycling and sailing Cyclades holiday. Watch whitewashed windmills slide gently into view as you navigate rocky coastlines, then hop on to land to explore tiny hilltop villages and take lunch in traditional tavernas all against a deep blue backdrop where the sky melts into the sea.

Where will we sail?

Setting sail from the port town of Laurium on the Greek mainland’s southeast coast allows easy access to the islands of the Aegean with the cobbled streets of Ioulida on the island of Kea providing your first taste of the Cyclades.

From Kea you can set sail to the islands of Syros, Paros and Signos where neoclassical buildings combine with whitewashed windmills, churches and monasteries. Different lunch stops every day take you to a range of rustic tavernas serving seaside specials and the freshest of fresh local catches.

Of course, sailing around the Cyclades always evokes a few epic tales and where better than Serifos, the birthplace of Greek hero Perseus, and the pirate caves of Kythnos, from where to conclude a legendary sailing holiday in the Cyclades.

Where will we cycle?

Average daily distances of roughly 30kms ensure the cycling on the Cyclades is just as laid back as the sailing. Even steep ascents are met with rich rewards upon reaching the top. Self guided cycling in the Cyclades also allow you to choose a distance, and gradient, that suits your fitness levels.

Often routes start from that night’s anchorage in port towns, such as Finikas on Syros and Merichas on Kythnos, from where roads lead up and over island summits before descending to beautiful beaches and bays via lunches in locally owned hilltop tavernas.

When’s the best time to go?

Late spring in the Cyclades, May and June, finds green hillsides and wildflowers as well as comfortable temperatures and calm sea conditions. July and August are usually way too hot to even think about cycling but wait for September and October and you’ll find the best time to go for cooler temperatures as well as fewer crowds in seaside towns.
Find out more in our Cyclades travel guide
Written by Chris Owen
Photo credits: [Page banner: David T] [Top box (Montenegro): Steph Smith] [Cycling (Montenegro): theavoae] [Best time to go (Montenegro): Boudewijn "Bo" Boer] [Cyclades: Klearchos Kapoutsis] [Best time to go (Cyclades): Swtiria ]