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Greece · 5 days · luxury · November 2026

Santorini & Milos

Caldera-view suites, a private catamaran among volcanic islets and Milos's lunar beaches and sea caves make this a romantic yet kid-easy Cycladic escape.

Your city → JTR MLO → Your city

Read the Santorini & Milos travel guide →Santorini & Milos agency packages →More trip inspiration →

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Overview

Total trip cost

Santorini & Milos · Santorini → Milos · 5 days · 4 nights

Estimated

$2,770

Accommodation · 4 nights$1,520Estimate for your budget
  • 2 stays via Booking.comCheck in at Andronis Boutique Hotel · Check in at Milos Cove Suites$1,520Book
  • 2 flights via AviasalesFly your city to Santorini · Fly Milos to your citySee partnerBook
  • 1 ferry via FerryhopperHigh-speed ferry to MilosSee partnerBook
  • 1 transfer via Welcome PickupsTransfer to Milos Airport$90Book
  • 3 activities via GetYourGuideStroll Imerovigli's clifftop paths · Private catamaran sailing from Vlychada · Explore Akrotiri archaeological site$360Book
  • 3 activities via ViatorBoat tour to Kleftiko sea caves · Walk Sarakiniko's moonscape · Morning at Adamas harbour$360Book
  • 4 meals via Google MapsEstimate · Sunset dinner at Ambrosia · Dinner at Metaxi Mas · Dinner in Plaka village · Seafood dinner in Klima$440Book

Estimates based on your budget. Final prices are confirmed on partner sites. Flights priced on the partner site. Wandr may earn a commission when you book through partner links, at no extra cost to you.

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01

Arrival & First Caldera Sunset

1
morninghotelBooking.com

Check in at Andronis Boutique Hotel

Imerovigli

Family suite with private plunge pool and caldera views, perched on the cliffs of Imerovigli.

2
morningflightAviasales

Fly your city to Santorini

Thira Airport

Short domestic hop from your city International to Santorini's Thira airport, arriving mid-morning.

3
afternoonactivityGetYourGuide

Stroll Imerovigli's clifftop paths

Imerovigli

Easy walk along whitewashed lanes and chapels overlooking the caldera, gentle pace suited to the whole family.

4
eveningrestaurantGoogle Maps

Sunset dinner at Ambrosia

Oia

Clifftop terrace in Oia serving Cycladic seafood with front-row views of the famous sunset, child-friendly menu available.

02

Private Catamaran & Ancient Akrotiri

1
morningactivityGetYourGuide

Private catamaran sailing from Vlychada

Vlychada Marina

Half-day charter around the caldera with swim stops at Red Beach and White Beach, crewed for families with kids.

2
afternoonactivityGetYourGuide

Explore Akrotiri archaeological site

Akrotiri

Walk through the excavated Bronze Age town preserved under volcanic ash, a hit with curious kids and history lovers alike.

3
eveningrestaurantGoogle Maps

Dinner at Metaxi Mas

Pyrgos

Beloved family-run taverna in Pyrgos plating slow-cooked Santorinian classics in a vine-shaded courtyard.

03

Island-Hop to Milos

1
morningferryFerryhopper

High-speed ferry to Milos

Athinios PortAthinios Port, Santorini → Adamas Port, Milos

Sail from Athinios Port to Adamas Port on a high-speed catamaran ferry, roughly two hours across the Aegean.

2
afternoonhotelBooking.com

Check in at Milos Cove Suites

Adamas

Boutique seafront suites just outside Adamas with a pool and easy access to the harbour's tavernas.

3
eveningrestaurantGoogle Maps

Dinner in Plaka village

Plaka

Climb to Milos's hilltop capital for grilled octopus and Venetian castle ruins glowing at dusk.

04

Sea Caves & Lunar Landscapes

1
morningactivityViator

Boat tour to Kleftiko sea caves

Kleftiko

Small private boat glides into turquoise caves and rock arches, with safe shallow swim stops for kids.

2
afternoonactivityViator

Walk Sarakiniko's moonscape

Sarakiniko

Explore the white volcanic rock formations and natural pools of Sarakiniko, a favourite photo stop for all ages.

3
eveningrestaurantGoogle Maps

Seafood dinner in Klima

Klima

Colourful fishing village of boat garages (syrmata) hosting a simple waterfront taverna serving the day's catch.

05

Farewell Milos & Flight Home

1
morningactivityViator

Morning at Adamas harbour

Adamas

Easy final stroll past fishing boats and bakeries, picking up local honey and thyme before departure.

2
afternoontransferWelcome Pickups

Transfer to Milos Airport

Adamas

Short taxi ride from Adamas to Milos Airport ahead of the return flight to your city.

3
afternoonflightAviasales

Fly Milos to your city

Milos Airport

Quick connecting flight back to your city International, closing out the island escape.

Before you go

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