Best 7-Day Cyclades Catamaran Itinerary: Paros Round Trip

Route Overview

Yacht Charter Day 0 – Arrive in Paros

Yacht Charter Day 1 – Paros to Naxos

Yacht Charter Day 2 – Naxos to Ios

Yacht Charter Day 3 – Ios to Santorini

Yacht Charter Day 4 – Santorini to Folegandros 

Yacht Charter Day 5 – Folegandros to Sifnos 

Yacht Charter Day 6 – Sifnos to Mykonos

Yacht Charter Day 7 – Mykonos to Paros

Day 1 – Paros to Naxos

The short passage to Naxos is an ideal first sailing day: steady breeze, islands on the horizon, and an easy run for a modern catamaran.

Naxos is the largest and highest island in the Cyclades and often described as the breadbasket of the group – unusually green, with fields, citrus groves, vineyards and olive trees supplying much of the region’s produce.

The medieval Kastro and the great marble gate of the Portara give the arrival real drama, especially at sunset.

Highlights

• Swim off long sandy beaches like Agios Prokopios or Plaka
• Sunset walk to the Portara above the harbour
• Tasting Naxian cheese, potatoes and local dishes in a family taverna

Day 2 – Naxos to Ios

The route south to Ios often passes close to the Small Cyclades; in settled weather it’s possible to break the sail with a lunch stop near one of these smaller islands.

Ios combines broad sandy beaches with a lively Chora and some surprisingly interesting cultural spots, including the hilltop Odysseas Elytis theatre.

Highlights

• Swimming and anchoring at Manganari, one of the best beaches in the area
• Evening wander through Ios Chora with its viewpoints and windmills
• Excursion to the supposed Tomb of Homer for big Aegean views

Day 3 – Ios to Santorini

Sailing into Santorini feels like entering a flooded volcanic crater: sheer cliffs and white villages perched along the rim. The island is the remnant of a major Bronze Age eruption that buried the city of Akrotiri, often linked to the Atlantis myth.

From a yacht, Santorini is about smart logistics: limited anchoring in the deep caldera means using Vlychada or organised moorings and exploring the island by road.

Highlights

• Caldera-side sunset from Oia or Fira, looking down at the anchored ships
• Guided visit to Akrotiri, with its remarkably preserved streets and houses
• Tasting crisp Assyrtiko and sweet Vinsanto at a caldera-view winery

Day 4 – Santorini to Folegandros

From Santorini, the route shifts into quieter territory with Folegandros. The cliff-edge Chora and its old Kastro quarter offer one of the most atmospheric evenings in the Cyclades.

The zigzag path up to Panagia church gives wide views back across the sea, and the coastline is dotted with simple, unspoiled coves.

Highlights

• Evening in Chora, with tavernas strung along the clifftop squares
• Sunset walk up to Panagia church for views over the island and sea
• Swim and snorkel stop at Katergo or other wild beaches with minimal development

Day 5 – Folegandros to Sifnos

The sail north-west to Sifnos brings you to an island known across Greece for its food and pottery. Slow-cooked chickpeas (revithada) and clay-pot stews are part of the local identity.

During the day, the catamaran can drop anchor in bays like Vathi or Faros before moving round to Kamares for the night.

Highlights

• Long lunch and swim at Vathi or Faros, ideal catamaran anchorages
• Evening visit to Kastro and the Church of the Seven Martyrs on its rock outcrop
• Tasting traditional revithada and other Sifnos dishes in a local taverna

Day 6 – Sifnos to Mykonos

This is the longest leg of the week, heading towards Mykonos. On a catamaran, it’s a rewarding open-water sail when the Meltemi cooperates.

Mykonos itself is a sharp contrast to the quieter islands: iconic windmills, Little Venice, galleries, designer shops, and a highly polished hospitality scene.

It also offers easy access to the archaeological site of Delos and the swimming bays of Rhenia.

Highlights

• Open-sea sailing day that shows what a cruising catamaran is built for
• Strolling past the Kato Mili windmills and along Little Venice at golden hour
• Optional Delos and Rhenia excursion for temples, ruins and clear-water swimming

Day 7 – Mykonos to Paros

The final hop back to Paros closes the loop. It’s usually a relaxed sail with time for a last swim at anchor before returning to Parikia for disembarkation.

Many guests choose to spend a final night on Paros ashore, which takes the pressure off flight and ferry connections and gives a softer landing after a week at sea.

Highlights

• Final sail between Mykonos and Paros with open Aegean views
• Last swim stop and lunch onboard before returning to base
• Farewell dinner in Parikia or Naoussa rather than rushing straight home