Guided Cyclades Island Hopping in Luxury Bike and Boat Tour

This tour is rated Level 4 out of 5. It involves hilly to mountainous terrain with some steeper ascents of up to approximately 500 metres. Confident riding on winding descents, uneven asphalt, and occasional gravel paths is required. Daily distances range from 25 to 42 km, with elevation gains of 250 to 800 metres per day. All tours can be more comfortably managed using the E-bike's electronic assistance.

E-bike rental is available as an optional service at €252 per week, including an Ortlieb pannier bag. Optional limited insurance covering theft and damage (excluding gross negligence) is available for an additional €28 per week.

Meals are provided on a half-board basis starting from Day 2. The on-board chef prepares a generous breakfast each morning and one warm meal daily. Meals begin with dinner on board on Day 2 and conclude with breakfast on the departure day (Day 9). Dinner on Day 1 and all meals and beverages ashore are not included.

Yes. The Cyclades are one of the windiest regions in Greece, which can occasionally affect the planned route. The tour runs during months when lighter winds are expected, but conditions cannot be predicted with certainty. If an island cannot be visited as planned, the yacht will remain longer at another island. Appealing alternative activities and day trips by regular ferry to other islands are also possible.

Yes. Helmets are mandatory on all rides. Participants are asked to bring their own well-fitting helmet. Rental helmets are available upon request when making a reservation.

This tour is primarily a guided group experience. However, upon consultation with your tour guides, independent cycling along recommended routes may be arranged. You are also free to spend a half or full day swimming or relaxing on board instead of joining a planned bike tour.

Complimentary Wi-Fi is provided on the yacht, though connectivity may be limited while at sea. For a more reliable connection, visiting a café or bar in port — where free Wi-Fi is widely available — is recommended.

Given the international nature of the tours, journeys are typically conducted bilingually in German and English.

Yes. A 3-day Athens extension and a 4-day Santorini extension are both bookable before or after the main trip. The Athens extension includes 2 hotel nights, Acropolis entrance, a guided activity (E-bike, culinary tour, or walking tour), and a dinner. The Santorini extension includes 3 nights in a 3-star boutique hotel and a choice of guided activity. Prices vary by room type and season.

The maximum number of participants for this tour is 12 people.

Special dietary needs including lactose-free, gluten-free, and vegan options can be accommodated for an additional fee of €70. This must be requested in advance and is payable on board.

A guided bike tour includes a professional local guide who rides with you throughout the trip. The guide handles navigation, manages daily logistics, ensures safety, and shares cultural insights. In addition to the guide, you also have a support vehicle that transfers luggage, provides water/snacks, and offers on-route assistance or a lift whenever needed. You simply follow the guide and enjoy a fully supported experience.

Your guides are local cycling experts, fluent in English, with deep knowledge of the region’s history, culture, and food.

On our guided tours, we ensure you begin your ride feeling comfortable and well-supported. Your guide and local team play an active role in getting your bike properly set up. **Before Your Tour** When you book, we ask for your height. This allows our local partners to select the correct frame size and prepare the bike in advance so it’s close to your ideal fit when you arrive. **At the Start of the Tour** You’ll receive a full in-person bike fitting with your guide or local representative. This typically includes: - Adjusting saddle height - Moving the saddle fore–aft (small adjustments to move the saddle forward or back for better balance and comfort) - Fine-tuning handlebar height and reach (where adjustable) - Confirming pedal preference — flat pedals are provided by default. If you bring your own clip-in pedals, our guide will help install and adjust them - A short test ride to check comfort Your guide will ensure everything feels right before the tour begins. **During the Tour** Throughout the trip, your guide will make additional adjustments whenever needed. This is especially helpful if you discover new comfort preferences after a few hours of riding. **What to Expect** Our guided tour bike fitting is hands-on, comfort-focused, and practical, ensuring you ride safely and enjoyably each day. It’s not a detailed workshop-level fit, but it covers all essential adjustments for multi-day touring.

For guided tours, we do not provide GPX files separately, as navigation is handled by your guide. On certain occasions, if you prefer more independence, we may offer app-based navigation access with the daily routes loaded. However, please understand that this may not always be possible and depends on the specific tour setup.

Our support vehicle is always close by to make your ride worry-free. It carries your luggage, water, snacks, and spare parts, and is there if you need a quick lift or just want to rest for a while. You’ll see it at regular intervals along the route and during meal or refreshment stops. The vehicle is also used for scheduled transfers and to ensure safety and comfort along the route.

The fitness level required for each trip is indicated by the "level" of the tour, which in turn is mentioned on each tour page right next to the price and the trip duration. **Easy**: The terrain is mostly flat with a few gentle climbs. **Moderate**: The terrain is either mostly flat or consists of rolling hills with a few challenging climbs. There could also be a few days with longer riding distances of up to 75 kms (45 miles) **Difficult**: The terrain is mostly hilly with strong elevation gains and/or has long days on the bike. Such trips are recommended for intermediate to advanced cyclists. Please note that we usually bike around 4-5 hours per day irrespective of the level of the trip.

We’ve carefully planned the route so that most rides follow peaceful countryside roads, scenic bike paths, and quiet lanes well away from heavy traffic. On rare occasions, short stretches on busier roads may be necessary, but your guides will ensure these sections are managed safely.

While your tour price covers most of the main expenses, including accommodations, daily breakfast, and many meals, you may wish to budget for a few lunches or dinners not included in the itinerary, as well as drinks, snacks, or personal treats along the way. As a general guide, allow around US $20–40 per person per day for these additional expenses.

Our guided bike tours typically have 6–14 guests, allowing for a personalised experience.

Airport transfers are not included unless specifically mentioned in your trip inclusions. For airport pickup, we recommend booking directly from the airport upon arrival — most airports have reliable taxi, shuttle, or app-based options. For airport drop, please book a transfer through your last hotel — they can easily arrange it for you.

We focus on delivering exceptional experiences during your tour. For logistical simplicity and flexibility, we do not handle pre- or post-tour hotel bookings. However, we’re happy to share a list of recommended hotels near the starting and ending points of your trip so you can plan your stay independently.

We are happy to pass on your room preference for a twin or double setup, and our hotel partners do their best to accommodate these requests. However, room configurations are always subject to availability at each property. On some of our trips—especially those that travel through remote regions or small boutique inns—room types may be limited. In such cases, despite our best efforts, you may need to stay in a double room instead of a twin, or twin instead of a double, depending on what is available. Given the nature of our journeys and the unique places we visit, we kindly ask for your understanding and support if such adjustments are required. We will always inform you in advance wherever possible and work closely with our partners to ensure the most comfortable arrangement for your stay.

You can exchange currency at the airport itself, or at ATMs in larger cities. Most commercial establishments will accept international credit cards for payments, though its good to carry some local currency with you at all times.

Tours run rain or shine, but we may adjust the route or schedule for safety. The support vehicle is always available.

Popular tours can sell out months ahead, especially in summer. Booking at least 9 months in advance ensures best availability.

We require a 10% deposit at booking. The balance is due 60 days before departure.

For full details, please see our [cancellation policy here](https://www.artofbicycletrips.com/terms-conditions/).

Yes. About 4 weeks before your trip, you’ll receive a Pre-Departure Information Pack with daily ride profiles, packing tips, meeting locations, and detailed itinerary.

The meeting time on Day 1 is mentioned in your travel planner shared with you. You can arrive either on the morning of Day 1 depending on the meeting time, or book a pre-tour night to arrive a day earlier.