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14-Day Itinerary

14 Days in Santorini
🌅 Complete Itinerary & Cost Guide

14 days in Santorini lets you go beyond the highlights — take day trips, revisit favourites, and enjoy slow mornings. Here's a realistic day-by-day plan plus what it costs.

Trip length
14 days
Est. cost per person
$2,240
Best months
May, June
Region
Europe
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Day-by-Day Itinerary

This plan covers the essentials without burnout. Adjust based on opening hours, weather, and your stamina. Most days are 4–6 hours of activity with long meals and downtime built in.

Day 1Arrival + Oia

Settle into your hotel, grab a light lunch, then ease into Santorini with Oia sunset (arrive 90 min early). Don't overbook day one — jet lag is real.

Day 2Red Beach + Akrotiri

Red Beach + Akrotiri ruins. Pair it with a sit-down lunch nearby and an evening walk through a different neighbourhood.

Day 3Wine tasting at Santo

Wine tasting at Santo Wines. Take the morning slow and use the afternoon to explore a quieter district away from the tourist core.

Day 4Catamaran cruise around the

Catamaran cruise around the caldera. Pair with a long lunch — Try fava (yellow split pea purée) — Santorini's PDO speciality. Best at Metaxi Mas.

Day 5Hike from Fira to Oia

Hike from Fira to Oia along the rim (3 hours). This day usually involves a longer journey so start early.

Day 6Day trip or Santorini deep dive

For trips of 14+ days, take an external day trip (mentioned in the highlights) or revisit Oia sunset (arrive 90 at a slower pace.

Day 7Day trip or Santorini deep dive

For trips of 14+ days, take an external day trip (mentioned in the highlights) or revisit Red Beach + Akrotiri at a slower pace.

Day 8Day trip or Santorini deep dive

For trips of 14+ days, take an external day trip (mentioned in the highlights) or revisit Wine tasting at Santo at a slower pace.

Day 9Day trip or Santorini deep dive

For trips of 14+ days, take an external day trip (mentioned in the highlights) or revisit Catamaran cruise around the at a slower pace.

Day 10Day trip or Santorini deep dive

For trips of 14+ days, take an external day trip (mentioned in the highlights) or revisit Hike from Fira to at a slower pace.

Day 11Day trip or Santorini deep dive

For trips of 14+ days, take an external day trip (mentioned in the highlights) or revisit Oia sunset (arrive 90 at a slower pace.

Day 12Day trip or Santorini deep dive

For trips of 14+ days, take an external day trip (mentioned in the highlights) or revisit Red Beach + Akrotiri at a slower pace.

Day 13Hidden gems + slow day

Use this day for whatever you didn't get to: a museum, a hammam, a long lazy lunch. The best memories come from unplanned hours.

Day 14Last day in Santorini

Hit one final must-see (Hike from Fira to Oia along the rim (3 hours)), pick up souvenirs, and leave time for a relaxed lunch before your flight or onward train.

What does 14 days in Santorini cost?

Estimates below are per person, including accommodation, food, local transport, and ~1 paid activity per day. Flights to Santorini are not included — they vary wildly by origin.

Budget
$1,260
Hostels, street food, public transport
Mid-range
$2,240
3-star hotel, casual restaurants, 1 paid tour
Luxury
$4,620
4–5 star hotel, fine dining, private guides

Santorini survival tips

🚇 Transport

Local buses (€1.80) connect main villages. Renting an ATV is fun but accidents are common.

🍽 Food

Try fava (yellow split pea purée) — Santorini's PDO speciality. Best at Metaxi Mas.

⚠ Watch out

Cruise ship days (check schedule) make Oia unbearable midday. Go early morning or after 7pm.

When to go

May, June, September, October are the best months for Santorini — the climate is at its best and crowds haven't peaked. Avoid July–August (overrun + expensive) and November–March (many closures).

See full month-by-month guide →

Other Santorini trip lengths

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More on Santorini

🌅 Full Santorini guide💰 Santorini trip cost📅 Best time to visit
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