Santorini - Mykonos - Milos
Day 1
Santorini (Vlychada Marina) - Folegandros
Day 2
Folegandros - Milos (Adamantas Port)
Day 3
Milos - Paros (Parikia Harbor)
Day 4
Paros - Paros
Day 5
Paros - Syros
Day 6
Syros - Tinos
Day 7
Tinos - Mykonos (Tourlos Marina)
Day 8
Mykonos - Mykonos
Day 9
Mykonos - Amorgos (Aegiali Harbor)
Day 10
Amorgos - Irakleia
Day 11
Irakleia - Naxos
Day 12
Naxos - Ios
Day 13
Ios - Santorini (Vlychada Marina)
Day 14
Santorini - Check-out
Detailed Itinerary by days
Day 1Santorini (Vlychada Marina) - Folegandros
Sail to the untamed beauty of Folegandros and forget about the volcanic drama of Santorini. Set sail for the hidden nook of Katergo Beach, where the pristine waters and pebble beach await. Eat matsata (hand-cut pasta) with wild goat ragù under strings of lamps after hiking the cliffside walk to Chora, a settlement that clings to the rocks like a seabird's nest.
Day 2Folegandros - Milos (Adamantas Port)
Send it to Milos, a rainbow of volcanic hues. After kayaking Sarakiniko's bone-white moonscape, snorkel the Papafragas Caves and then dock in Klima's candy-colored syrmata. Feast on grilled octopus in Mandrakia; twilight fishing camps glitter here.
Day 3Milos - Paros (Parikia Harbor)
Early morning: sail to Sifnos's Kamares, then hike to the arched seafront Chrysopigi Monastery. Lunch at Artemonas on mastelo, or clay-pot lamb. Glide to Paros' Parikia afternoon, where the fourth-century Panagia Ekatontapiliani church guards whitewashed alleyways. Swimming in Kolymbithres' lunar rocks at sunset will cap the day.
Day 4Paros - Paros
Free day to really enjoy Paros! Bike to Lefkes's jasmine-scented alleyways, or explore Naoussa's trendy waterfront for octopus souvlaki. Relax at Golden Beach (windy but well worth it) or sip Assyrtiko from a Marpissa winery.
Day 5Paros - Syros
The neoclassical city of Ermoupoli on Syros is a sight to behold, with its pastel houses and marble streets. While perusing the rosewater loukoumi at a shop that dates back 150 years, ascend Ano Syros to take in the sunset views. Final drink: Ouzo at a seedy rembetiko establishment.
Day 6Syros - Tinos
Tinos calls with a spiritual mystery. Pilgrims crawl to the Panagia Evangelistria, although Pyrgos village has marble marvels for hunting. Lunch on artichokes à la polita in a patio surrounded with bougainvillea, then surf Kolymbithra's windswept waves.
Day 7Tinos - Mykonos (Tourlos Marina)
Trade custom for the electric pulse of Mykonos. From Paradise's DJ rhythms to Agios Sostis's secret peace, dock in Tourlos then beach-hop. Dine in Little Venice, the sea licking your toes, on lobster spaghetti.
Day 8Mykonos - Mykonos
I am free to enjoy today! Discover the old remains of Delos, peruse the lanes of Mykonos Town for linens, and relax on Super Paradise Beach. At Scorpios, you must have a sunset cocktail while you watch the Aegean turn golden.
Day 9Mykonos - Amorgos (Aegiali Harbor)
See the wild soul of Amorgos. Clutching cliffs like a holy daredevil, hike to the Monastery of Hozoviotissa then dive the turquoise depths of the Olympia shipwreck. Dinner is coming. Under a star-blanketed sky, psimeni raki, honey-spiced spirit.
Day 10Amorgos - Irakleia
Sail for Irakleia, the mystery of the Small Cyclades. Trekking olive orchards to Kastro's pirate remains, snorkel the sparkling waters of Blue Cave, then eat grilled gouna (sun-dried mackerel) at a beach shack.
Day 11Irakleia - Naxos
The green monster of the Cyclades, Naxos welcomes you. After eating kitro-glazed pork in a highland taverna, climb Mount Zas, Zeus' legendary birthplace. Swim under the moon in Agios Prokopios to cap the day.
Day 12Naxos - Ios
Race to the gorgeous dunes of Ios. Snorkel Manganari Beach, climb to Homer's Tomb for sunset panoramas, then plunge into Chora's electrifying alleys—ouzo shots, rembetika melodies, starlit anarchy.
Day 13Ios - Santorini (Vlychada Marina)
Go back to Santorini, docking in the lunar marina of Vlychada. At a caldera-edge taverna, eat fava with capers after kayaking the rust-hued rocks. On last night, toast your trip as Oia's domes sparkle like pearls.
Day 14Santorini - Check-out
One last dip in Ammoudi Bay, where volcanic black blends with blue. Breakfast at a cliffsidecafé on Greek coffee and spanakopita, with the caldera below. Disembark with hair stained with salt and a heart full of Aegean brightness.
