Blue-domed churches above the caldera in Oia, Santorini
← All trips Santorini · Mykonos · the Aegean

The Greek Isles

Whitewashed villages spilling down cliffs, impossibly blue water and sunsets that stop entire crowds in their tracks.

The vibe Cliffs, sunsets & seaside tavernas
Weather Warm, dry and sunny May–October
Perfect for Cruise incentives & top-tier rewards
Bonus A new island every morning

The sunset everyone applauds. Literally.

In Oia, hundreds of people gather on the castle walls every evening to watch the sun sink into the Aegean, and when it disappears, they clap. That’s the Greek Isles in a nutshell: places so beautiful they feel unreal, served with grilled octopus, crisp local wine and a warm “yamas!”

Hop from Santorini’s volcanic cliffs to Mykonos’ windmills and waterfront bars, swim in hidden coves straight off the side of a boat, and wander 3,000 years of history between lunch and dinner. Arrive by cruise ship and you wake up somewhere new and gorgeous every single morning.

The famous row of windmills above Mykonos town Waterfront tables in Little Venice, Mykonos A seaside taverna table set beside the Aegean
Don’t miss

Six moments your team will never forget

01

Watch the sunset in Oia

Claim a spot on the old castle walls, glass in hand, and join the crowd as it cheers the sun into the sea.

02

Sail the Santorini caldera

A private catamaran to the volcano’s hot springs, swim stops in red and white sand coves, dinner cooked on board.

03

Taste wine grown on a volcano

Santorini’s vines grow in woven baskets on the ground to survive the wind. The crisp Assyrtiko is unforgettable.

04

Cocktails in Little Venice

Mykonos’ waterfront bars sit so close to the sea that waves splash the tables, right below the famous windmills.

05

Step back 3,000 years

Explore sacred Delos, the Acropolis of Lindos on Rhodes or the Palace of Knossos on Crete.

06

Linger over a taverna lunch

Grilled octopus, just-caught fish, horiatiki salad and a very long, very happy lunch with your toes near the water.

Best time to go

Late spring and early fall.

May, June, September and early October are the magic months: warm sea, golden light and room to breathe. July and August are hot, crowded and breezy. From November to March, many island hotels and restaurants close for the season.

Jan Quiet
Feb Quiet
Mar Quiet
Apr Quiet
May Sweet
Jun Sweet
Jul Peak
Aug Peak
Sep Sweet
Oct Sweet
Nov Quiet
Dec Quiet
Sweet spot for groups Peak season Quiet season

One trip, many islands

A small-ship cruise turns one booking into four or five islands, with no packing and unpacking.

Something for everyone

History buffs, foodies, beach lovers and night owls all find their thing, often on the same island.

Room to celebrate

Private caldera sunset sails, vineyard dinners and cliffside terraces made for an awards night.

Take your team to the Greek Isles.

We’ll build the whole program around your goals and budget, then travel with you to run it.

Plan a Greek Isles program
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