Cycladic Express: Paros, Naxos, Mykonos, Milos & Santorini – 11 Days

Fast-paced but meticulously planned 10-night itinerary is designed for couples who want to experience the diversity of the Cyclades without the stress of overwhelming research. By visiting Paros, Naxos, Mykonos, Milos, and Santorini, you will witness everything from traditional marble-paved villages and ancient ruins to dramatic volcanic sea caves.
11 Days

Overview

Highlights

Locations

Day 1
Arrival in Paros

Arrival in Paros

Free Afternoon in Naousa
Paros
Arrival in Paros
Day 2
Morning Horseback Ride
Paros
Day 3
Ferry to Naxos

Ferry to Naxos

Old Town Sunset Walk
Naxos
Ferry to Naxos
Day 4
Farm Visit & Lunch at Chalki Village
Naxos
Day 5
Ferry to Mykonos

Ferry to Mykonos

Guided Mykonos Town Walking Tour
Mykonos
Ferry to Mykonos
Day 6
Beach Day (free time)
Mykonos
Day 7
Ferry to Milos

Ferry to Milos

Evening Stroll in Plaka
Milos
Ferry to Milos
Day 8
Full-Day Catamaran Adventure to Kleftiko & Sykia Cave
Milos
Day 9
Ferry to Santorini

Ferry to Santorini

Luxury Sunset Catamaran Cruise
Santorini
Ferry to Santorini
Day 10
Private Guided Village Highlights & Oia Sunset
Santorini
Day 11
Departure

Departure

Fly to Athens International Airport
Departure

Table of Contents

Detailed Itinerary

couple holding hands walking by the beach

Day 1

Your adventure begins on the elegant island of Paros. A private driver will meet you for a transfer to your accommodation. Spend your first afternoon relaxing by the sea or exploring the narrow streets of Parikia independently.

Day 2

Follow an experienced instructor through tranquil countryside trails and distinctive rugged terrain. The ride offers unmatched views of Paros’s heart, including ancient olive groves and charming stone walls.

Day 3

Take a short ferry ride (approx. 25–45 minutes) to the fertile island of Naxos. After a private transfer to your hotel, walk to the iconic Portara (Temple of Apollo) to watch the sun set over the Aegean

Portara of Naxos

Day 4

Your journey begins with a scenic drive to the village of Kaloxylos to visit a century-old olive press factory and explore the island’s oldest olive grove, which boasts trees over 800 years old.

Day 5

This walking tour covers the landmarks and hidden gems of Mykonos Town, including the iconic Windmills and the historic Armenistis Lighthouse. You will also stroll through Little Venice and Manto Mavrogenous Square while learning the island’s rich history from a local expert.

beach party Mykonos at sunset

Day 6

Enjoy a completely free day to follow the island’s traditional rhythms.

Balcony view Heraklion town in Crete

Day 7

Depart Mykonos for the volcanic island of Milos on a high-speed ferry (approx. 2h 45m). After checking in, head to the hilltop village of Plaka to witness one of the most celebrated sunsets in the Cyclades.

Day 8

Set sail from Adamas to the legendary Kleftiko Bay, a former pirate haven. You will have the opportunity to snorkel through breathtaking arches and caves, enjoy a hearty Mediterranean lunch on board with local wine, and take a dinghy ride inside the open-roof Sykia Cave.

Day 9

Travel to the iconic caldera island of Santorini. In the evening, you will sail past the Red and White Beaches for snorkeling. The cruise includes a dip in the volcanic hot springs and a fresh BBQ meal with an open bar as you watch the sun dip below the caldera cliffs.

couple holding hands strolling in OIa, Santorini

Day 10

This tour takes you through the quintessential villages of Oia, Firostefani, and Imerovigli for panoramic views. The journey concludes at the highest peak of the island, Prophet Elias Mountain, for a final sweeping view of the Aegean.

Day 11

Enjoy a final breakfast overlooking the caldera before your private transfer takes you to the airport for your flight home

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