Cyclades Island Hopping

ACTIVE PERIOD: May - October
DIFFICULTY LEVEL: 2

DURATION: 9 days
NUMBER OF PARTICIPANTS: 2

Cyclades Island Hopping

Price from €2540

Overview

Cyclades Island Hopping is an unforgettable active escape across Greece’s most iconic islands, Paros, Naxos & Santorini, combining expert-led adventures with the freedom and flexibility of semi-guided travel.

The iconic Cycladic Islands are what Greece is all about. Traditional fishing villages, whitewashed flat-roofed houses and narrow streets, hundreds of beautiful little chapels, rugged, sun-drenched landscapes contrasting with the deep blue sea, and spectacular bays with powdery white sand beaches.

Travel beyond the usual tourist paths by boat, on foot, or by sea kayak, and experience the Cyclades from a truly unique perspective.

Discover the Cyclades through local eyes, embracing island traditions, everyday life, and the hidden corners that reveal each island’s soul.

Nine days filled with movement, beauty, and authentic Greek moments in one of the country’s most captivating regions - guided where it counts, free where it fuels your curiosity.

Day 1: Arrival in Paros Island
Day 2: Paros - Byzantine Trail Hike
Day 3: Paros - Day Cruise on a traditional fishing boat
Day 4: Paros to Naxos
Day 5: Naxos - Inland Hike among villages, Kouroi statues & Apano Castle
Day 6: Naxos – Rhina Cave Sea Kayak
Day 7: Naxos to Santorini & Hike the Caldera Trail
Day 8: Santorini - Sea Kayaking
Day 9: End of Trip

Activities / Schedule

Arrival in Paros Island

Our trip starts in Paros.

You can reach the island by plane or by ferry, with several departures available depending on the season. The ferry ride takes about three to five hours and brings you straight into the heart of the Aegean. Once you arrive, a short transfer takes you to your hotel in Naousa, one of the loveliest seaside towns in the Cyclades.

The rest of the day is yours to explore Paros, wander through Naousa, or spend some time by the sea.

Overnight in Paros Island.

Paros Byzantine Trail Hike

Our day begins with a drive to the traditional village of Lefkes, where we’ll wander through its narrow streets and alleys lined with whitewashed houses. From there, we’ll set off on a hike along the island’s most well-known route, the herb-scented Byzantine Way. This historic path, constructed during Byzantine times, once served as part of a central road that traversed the entire island. The route takes about an hour and a half, offering a pleasant walk through the Parian countryside, with just a few gentle uphill sections, making it accessible to everyone. Our hike ends in the village of Prodromos, where a traditional Greek coffee and local sweets offer a warm and relaxed finish to the experience.

Overnight in Paros.

Paros Day Cruise on a traditional fishing boat

A wonderful day of fun and relaxation awaits aboard a traditional boat. We’ll discover the caves of Mastichari, where bright white rock formations and small openings create a unique coastal landscape to experience. You can swim, float in the bright blue water of the Blue Lagoon, or snorkel and enjoy the calm sea.

Fresh local food and drinks will be served onboard, with plenty of time to enjoy the sun and the breeze. It’s a day to slow down, connect with nature and the people you’re traveling with. A day to remember!

Overnight in Paros.

Paros to Naxos

After breakfast, you’ll be transferred from your hotel to the port of Paros to board the ferry to Naxos, the largest and and most fertile of the Cycladic islands. Once you arrive, a short transfer will bring you to your hotel, giving you time to settle in. The rest of the day is free to enjoy Naxos in your own way.

Overnight in Naxos.

Naxos - Inland Hike among villages, Kouroi statues & Apano Castle

Enjoy your breakfast and then depart for your hike through three different villages, each with its own atmosphere and small details that make Naxos so special. Along the way, you’ll also come across local antiquities that highlight the island’s long history. At the end of your hike, you'll visit a local distillery producing Kitron, Naxos’ citrus-based liqueur, where you can taste this specialty and discover the story behind it.

Overnight in Naxos.

Naxos – Rhina Cave Sea Kayak

After breakfast, set out on an unforgettable sea kayaking adventure, an eco-friendly and exciting way to explore Naxos’ intricate coastline from your kayak. Paddle through the crystal-clear, blue-green waters of the Aegean Sea and snorkel among vibrant marine life. Discover Rhina Cave, known for its delicate stalactite formations and enjoy homemade snacks prepared with local ingredients. End the day with a swim in quiet, boat-access beaches with clear blue water.

Overnight in Naxos.

Naxos – Santorini Caldera Hike

After breakfast, depart for your transfer to the port of Naxos to board the ferry to Santorini. It is time to head to the most famous Cycladic island, known around the world for its views and unique landscape. When you arrive in Santorini, you will be transferred to your hotel and have some time to settle in.

In the evening, you will enjoy the Caldera Hike. While walking along the rim of the volcanic Caldera, you’ll experience the breathtaking, panoramic views of the Aegean Sea, the Mediterranean islands and whitewashed, blue-topped Cycladic chapels.

Overnight in Santorini.

Sea Kayaking in Santorini

After breakfast, depart for your sea kayaking adventure. Paddle along Santorini’s coastline and take in the striking views of the Black, White, and Red Beach. You will also have the chance to snorkel near Kampia Beach and explore the coastline from the water. The experience includes a delicious lunch at a traditional tavern, the perfect reward for a morning full of activity.

Overnight in Santorini.

Your Cyclades adventure ends

Enjoy your final breakfast in Greece. Check-out is available until 11:00. A departure transfer will take you from your hotel to Santorini Airport or the port according to your travel plans.

Important Info

In a glance

CURRENCY: euro (€)
TIMEZONE: UTC+02:00 (EET)

Highlights

Paros is renowned for its superb sandy beaches, great beach bars, and the lovely town of Naousa.
Naxos, the biggest and most fertile of the Cycladic islands, has some amazing inland villages and important cultural sites like the impressive Portara and the Kouros statues which we will see while hiking.
Last but not least, Santorini, the princess of the Greek islands, is where we choose hiking and paddling to experience the authentic and less touristy side of this truly unique landscape!

Price

Semi-Guided Mode:

2.540€/person for 4-6 participants
2.730€/person for 2-3 participants

Single supplement:

660€/person

Important Note

This program is offered as a semi-guided experience, giving you the perfect blend of support and independent exploration. A fully guided version is also available upon request.

Semi Guided Mode:

The following activities with all necessary equipment included, led by expert guides:
- Lefkes & Byzantine Hike in Paros
- Boat tour in Paros
- Inland Hike among villages – Kouroi in Naxos
- Rhina Cave Sea Kayak in Naxos
- Caldera Trail hike in Santorini
- Sea Kayak in Santorini with lunch
Arrival/Departure transfer Paros airport – hotel and from hotel to Paros port
3 nights accommodation in double/twin rooms in a 3* hotel in Paros, including breakfast
Arrival Departure transfer from Naxos port to hotel and from the hotel to Naxos port
3 nights accommodation in double/twin rooms in a 3* hotel in Naxos, including breakfast
Arrival/Departure transfer Santorini port – hotel and from hotel to Santorini airport
2 nights accommodation in double/twin rooms in a 3* hotel in Santorini, including breakfast
Ferry tickets Paros – Naxos, Naxos – Santorini
All necessary transfers to and from the starting and ending points of the activities
Liability insurance
VAT and all legal taxes

Semi-Guided Mode:

Full-Time Tour Leader
Accommodation tax to the hotels (payable on the spot by the guests)
Accident insurance (+3 euro/person/day)
Air or ferry tickets to Paros and from Naxos
Meals
Alcoholic drinks, soft drinks/beverages during meals
Anything not mentioned in the inclusions

Equipment

Day pack 13-20l
Comfortable light clothing suitable for outdoor activities
Rain jacket and rain pants for spring and fall
Mid-weight polar fleece sweater for spring and fall
Long-sleeve shirt for sun protection
Swimsuit & beach towel
Beach sandals
Sun hat & Sunglasses
Lightweight and supportive hiking shoes
High protection sunscreen
Trekking poles
Motion sickness remedies (if needed)
Personal first-aid kit
Insect repellent
Your own personal water bottle. As part of our environmental policy and actions, we are committed to eliminating the use of plastic water bottles.

Reviews

One of the greatest experience! A must do in island! Great work to Sebastian and his team! Special thanks to panos and Kostas!

Great experience!

My family (kids 6 & 8) and I, throughly enjoyed this experience. Personally I have been to this area with catamarans and boats several times but from the kayak perspective it was a completely different level of experience. Adding to the pluses very friendly, professional & experienced staff, not to mention the breathtaking setting. Definitely recommended! Thank you guys!

Amazing experience!

It was absolutely amazing!! The team was very friendly, I enjoyed every minute of it and i will definitely visit again!!

Amazing!!

Gallery

Cyclades Island Hopping

Explore Paros, Naxos and Santorini, three of the Cyclades’ most iconic islands!

Price from €2540

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FAQs

What should I bring with me?

What is listed above in Equipment section

What's the meeting point & time?

Meeting Point: At your hotel in Paros

Time: 05:00pm

When is the activity available?

The activity is available from March to November.

What weather can be expected?

During spring and autumn, there is a possibility of rain, so it is recommended to pack a raincoat or waterproof poncho. In the summer period, temperatures can range between 30 and 40 degrees Celsius during the daytime.