Santorini suits a first Greek island trip, with caldera views, cliffside Oia sunsets and an airport plus regular ferries from Athens.
Mediterranean islands for a first trip
Five of our Top 21 islands sit in the Mediterranean. If it is your first island trip in the region, these are the ones to compare, grouped by country, with two Italian mainland hotels from our Hotels list as add-ons. Scores map Tripadvisor traveler ratings to 1–100. Only Santorini represents Greece in our current list.
Greece & Croatia
2 picks; highest score here: Santorini (90).
Hvar is often billed as Croatia’s sunniest island, pairing lavender fields and a Venetian-era harbour town with fast catamarans from Split.
Italy
2 picks; highest score here: Sicily (90).
Sicily packs Greek temples at Agrigento, Baroque Noto, Palermo street food and Mount Etna into one island rewarding a longer stay.
Sardinia rewards a first visit with turquoise Costa Smeralda coves, quieter southern beaches and mountain villages best explored by rental car.
Spain
1 pick.
Mallorca works for almost any first-timer, combining Palma’s cathedral and old town with Serra de Tramuntana mountain drives and quiet coves.
Italian mainland add-ons
Two Italian hotels from our Hotels Top 21 that pair naturally with an island week.
Belmond Hotel Caruso sits high above the Amalfi Coast in Ravello, a mainland splurge that pairs well with a Sicily trip.
Borgo Egnazia is a white-stone resort village in Puglia, a relaxed mainland finale before flying home from Bari or Brindisi airports.
How these scores work
Every card line is exactly 21 words, written for this guide from facts in our data and public records (founding dates, prizes, episode counts); each pick’s full verdict sits on its category Top 21. Scores (1–100) are mapped from named public aggregates, last checked 2026-11-02:
Links go to each subject’s official site. Disclaimer.