Santorini and Mykonos in five days: caldera-view sunsets and a wine tasting on volcanic soil above Oia, a catamaran run past the volcano to hot springs and Red Beach, a fast ferry to Mykonos for windmill views over Little Venice, a half-day crossing to the ancient ruins of Delos, and a beach club afternoon at Psarou — with real hotels, licensed operators, and 2026 prices for every stop.
Day 1Arrive in Santorini
Land at Santorini’s small clifftop airport and settle into Oia in time for the island’s famous sunset, followed by dinner at one of its best-known caldera-view tables.
🚕 Private Airport Transfer — Santorini Transfer
~40 minutes · From $75 USD, private car for 2
A locally run transfer service meets arrivals at Santorini (JTR) airport for the drive north to Oia, winding along the caldera rim road with sea views most of the way.
Santorini Transfer · +30 697 228 7072 · santorinitransfer.eu
🌅 Sunset at the Oia Castle Ruins
~1 hour, self-guided · Free
The ruined 15th-century Venetian kastro at the edge of the village is Santorini’s most famous sunset perch, its stepped terraces filling with visitors as the sun drops behind the caldera — arrive at least 45 minutes early to find a spot.
🍽️ Dinner — 1800 Floga Restaurant
~1.5 hours · $70–$95 USD / person
A restored 1800s captain’s mansion turned fine-dining room on Oia’s main pedestrian street, pairing modern Greek plates with one of the island’s deepest Assyrtiko wine lists.
1800 Floga Restaurant · +30 22860 71800 · www.oia-1800.com
🛎️ Overnight — Katikies Hotel
From $650–$850 USD / night, for 2 people
A cliffside icon of Cycladic architecture stepping down the caldera in tiers of white cave suites, several with private plunge pools, just a short walk from central Oia.
Katikies Hotel · +30 22860 72382 · www.katikies.com/katikieshotelsantorini
Day 2Wine & the Caldera by Boat
A full day split between Santorini’s volcanic vineyards and the water below the caldera, ending back in Oia for a second sunset.
🍷 Wine Tasting — Santo Wines
~1.5 hours, guided tour + tasting flight · $50 USD / person
A clifftop winery built into the caldera wall above Pyrgos, pouring Assyrtiko and other native varieties grown in the island’s ash-black volcanic soil — the guided cellar tour ends on a terrace with sweeping views back toward Oia and Nea Kameni.
Santo Wines · +30 22860 22596 · www.santowines.gr
⛵ Catamaran Cruise — Volcano Yachting
~5 hours, semi-private · $145 USD / person, lunch & drinks included
A day sail from Ammoudi Bay out to the still-active Nea Kameni volcano for a short hike to the crater, a swim in the sulfur-warmed hot springs, and a stop at Red Beach and White Beach before returning under sail.
Volcano Yachting · +30 22860 21673 · www.volcanoyachting.com
🛎️ Overnight — Katikies Hotel
From $650–$850 USD / night, for 2 people
Second night at the cliffside suite, with the caldera lit up by a last Oia sunset before tomorrow’s crossing to Mykonos.
Katikies Hotel · +30 22860 72382 · www.katikies.com/katikieshotelsantorini
Day 3Santorini to Mykonos
A morning high-speed ferry crossing to Mykonos, with the afternoon free to wander Little Venice before dinner on the water.
⛴️ High-Speed Ferry — Seajets
~1 hour 50 minutes · From $88 USD / person
Seajets’ high-speed catamarans link Santorini’s Athinios port directly to Mykonos several times a day in season, with air-conditioned lounges, an open deck and a snack bar on board.
Seajets · +30 210 710 7710 · www.seajets.com
🏘️ Little Venice & the Windmills
~1.5 hours, self-guided · Free
Pastel-colored captain’s houses lean directly over the water along Mykonos Town’s most photographed stretch, a five-minute walk from the row of restored 16th-century windmills on the hill above.
🍽️ Dinner — Cocco Mykonos
~1.5 hours · $60–$85 USD / person
A waterfront table in Little Venice with chairs set right at the water’s edge, serving modern Mediterranean seafood as the sunset colors the bay.
Cocco Mykonos · +30 22890 22458 · coccomykonos.com
🛎️ Overnight — Bluetopia Suites
From $350–$450 USD / night, for 2 people
A Little Venice hotel with balconies that hang directly over the sea, a short walk from the windmills and the bars along the harbor.
Bluetopia Suites · +30 22890 24034 · bluetopiamykonos.com
Day 4Delos & Psarou Beach
A half-day boat trip to one of the Aegean’s most important archaeological sites, followed by an afternoon at one of Mykonos’s best-known beach clubs.
🏛️ Half-Day Guided Tour — Delos Tours
~4 hours, guided, includes boat & site entrance · $79 USD / person
A short boat crossing from Mykonos’s Old Port to the uninhabited island of Delos, a UNESCO World Heritage site and, according to myth, the birthplace of Apollo, with a guide leading the way past the Terrace of the Lions and the Sanctuary of Apollo.
Delos Tours · +30 22890 28603 · www.delostours.gr
🏖️ Beach Club — Nammos, Psarou Beach
Afternoon · Sunbeds from $75 USD, food & drink minimum spend applies
One of the Mediterranean’s original beach-club-as-destination spots, with white loungers on the sand at Psarou and a Mediterranean menu that runs well past lunch — reservations recommended in peak season.
Nammos · +30 22890 22440 · www.nammos.com/mykonos
🛎️ Overnight — Bluetopia Suites
From $350–$450 USD / night, for 2 people
Second night in Little Venice before tomorrow’s departure.
Bluetopia Suites · +30 22890 24034 · bluetopiamykonos.com
Day 5Little Venice & Departure
A last quiet morning among the windmills before the short transfer to the airport.
☕ Morning in Little Venice
~1.5 hours, self-guided · Free
The waterfront cafés open early and the crowds haven’t arrived yet — a good last morning for coffee at the water’s edge and a final walk past the windmills before checkout.
🚕 Private Airport Transfer — Mykonos Cab
~20 minutes · From $40 USD, private car for 2
A local transfer service collects you from the hotel for the short drive to Mykonos International Airport (JMK).
Mykonos Cab · +30 694 654 0444 · www.mykonoscabservice.gr
✈️ Departure — Mykonos International Airport (JMK)
Self-guided
Closes a five-day loop that ran from Oia’s blue domes and volcanic vineyards to Mykonos’s windmills, ancient Delos and a beach club afternoon at Psarou — check international carriers’ recommended arrival times, typically 2–3 hours before departure.
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