Island Hopping in May: Greek Isles, Azores & Lesser-Known Gems

May is one of the best months for island hopping—crowds are still thin, temperatures are warm but not scorching, and nature is in full bloom. Whether you're dreaming of the iconic Greek Isles, the wild beauty of the Azores, or hidden island paradises, this guide will help you plan the perfect island-hopping adventure.

5/6/20253 min read

Amazing tranquil landscape of Santorini caldera and sea view
Amazing tranquil landscape of Santorini caldera and sea view
Why Island Hopping in May?
  • Perfect Weather: Warm, sunny days with cooler evenings—ideal for exploring.

  • Fewer Crowds: Beat the summer tourist rush and enjoy a more relaxed experience.

  • Lower Prices: Flights and accommodations are often cheaper before peak season.

  • Lush Landscapes: Spring blooms make islands even more picturesque.

Now, let’s dive into three incredible island-hopping destinations for May!

1. The Greek Isles: A Classic Island-Hopping Paradise

Greece’s islands are legendary for their whitewashed villages, turquoise waters, and vibrant nightlife. May is the perfect time to explore before the summer crowds arrive.

Top Islands to Visit:

  • Santorini: Famous for its stunning sunsets and cliffside villages like Oia.

  • Mykonos: Chic beach clubs and lively streets—great for early-season parties.

  • Crete: Rich history, rugged landscapes, and secluded beaches.

  • Milos: A quieter alternative with surreal rock formations and crystal-clear waters.

  • Naxos: Authentic Greek charm, ancient ruins, and long sandy beaches.

Island-Hopping Tips:

  • Ferries: Book early—routes become more frequent in May.

  • Itinerary: Stick to 2-3 islands per week to avoid rushing.

  • Must-Do: Visit ancient ruins in Delos, swim in Santorini’s volcanic hot springs, and try fresh seafood in small tavernas.

2. The Azores: Europe’s Best-Kept Secret

For nature lovers, the Azores—a Portuguese archipelago in the Atlantic—offer dramatic volcanic landscapes, hot springs, and lush greenery. May brings mild weather and blooming hydrangeas.

Top Islands to Visit:

  • São Miguel: The largest island, home to Sete Cidades crater lakes and Furnas hot springs.

  • Pico: Dominated by Mount Pico (Portugal’s highest peak) and famous for whale watching.

  • Terceira: UNESCO-listed Angra do Heroísmo and unique lava caves.

  • Faial: The "Blue Island" with a stunning marina and Capelinhos Volcano.

Island-Hopping Tips:

  • Flights: SATA/Azores Airlines offers inter-island flights (quicker than ferries).

  • Activities: Hiking, whale watching (peak season starts in May), and soaking in geothermal pools.

  • Local Eats: Try cozido das Furnas (meat stew cooked underground by volcanic heat).

3. Lesser-Known Island Gems for a Unique Escape

If you want to avoid the usual tourist trails, these underrated islands offer untouched beauty and authentic culture.

Hidden Paradise Picks:

  • Vis, Croatia: A secluded Adriatic island with pristine beaches and historic military tunnels.

  • Lofoten Islands, Norway: Arctic beauty with dramatic fjords and midnight sun in late May.

  • Isles of Scilly, UK: A subtropical British archipelago with white-sand beaches and rare wildlife.

  • La Gomera, Canary Islands: A hiker’s dream with misty forests and rugged cliffs.

Why Visit in May?

  • Tranquility: These islands are rarely crowded, even in peak season.

  • Wildlife Spotting: Ideal for birdwatching and marine life.

  • Adventure: Kayaking, hiking, and diving without the summer heat.

Final Tips for Island Hopping in May

  • Pack Layers: Evenings can be cool, especially in the Azores and northern islands.

  • Book Early: While May isn’t peak season, popular spots (like Santorini) still fill up.

  • Stay Flexible: Weather can be unpredictable—have backup plans for outdoor activities.

Conclusion

Whether you choose the classic Greek Isles, the wild Azores, or a hidden gem, May is the perfect month for island hopping. You’ll enjoy ideal weather, fewer tourists, and unforgettable landscapes—all before the summer rush begins.

Which islands are calling your name? Let us know in the comments!


Greek island of Mykonos, Greece - beautiful white buildings and blue sea
Greek island of Mykonos, Greece - beautiful white buildings and blue sea
Amazing Landscape of the Lakes of Sete Cidades
Amazing Landscape of the Lakes of Sete Cidades
Views of Henningsvaer in the Lofoten Islands in Norway
Views of Henningsvaer in the Lofoten Islands in Norway
Island of Vis bay aerial drone view , Croatia.
Island of Vis bay aerial drone view , Croatia.