Oia, Santorini at night, Greece

Custom Trips› Greece

Custom Trips to Greece

Greece,
Your Way.

Tailor-made Greece itineraries built around you — from the Acropolis and the backstreets of Athens to hidden Aegean islands, the Peloponnese, and Crete's rugged south coast.

Plan My Greece Trip See Sample Itinerary
25+Years Experience
6,000+Greek Islands
All StylesBudget to Luxury
Overview Regions Who It's For Itinerary When to Go FAQ

Why Greece

Ancient, sun-drenched, and endlessly surprising.

Greece has been drawing travellers for millennia — and it still manages to exceed expectations. The challenge isn't finding something remarkable to do; it's knowing which island to choose, which villages to seek out, and how to avoid the well-trodden paths that leave visitors feeling like they've seen a postcard rather than a place.

We've spent years in Greece — on the water, in the mountains, in the villages that don't appear in glossy brochures. We know which experiences are genuinely special and how to sequence them so your trip flows rather than rushes — the same approach we bring to every custom trip we design. The result is a Greece that feels personal, unhurried, and deeply yours.

Group of travellers at Santorini viewpoint, Greece
10,000+ Happy Travelers

The Country

Greece is far more than the islands.

Most visitors come for the Cyclades and leave without touching the mainland, Crete, or the Ionian coast. We design trips that show the full range — from ancient ruins and mountain villages to volcanic caldera sunsets and hidden coves that take a water taxi to reach.

Acropolis, Athens, Greece
Athens & the Mainland
Athens rewards those who go beyond the Acropolis. The neighbourhood of Monastiraki, the galleries of Psiri, a rooftop dinner with the Parthenon lit above — the city has a layered, lived-in energy that surprises most visitors. The mainland also hides Meteora's monastery-capped rock towers, Delphi, and the wild Peloponnese coast.
Paddleboarding in the Greek islands
The Cyclades
Santorini and Mykonos are famous for good reason, but the Cyclades hold a dozen quieter islands — Naxos, Paros, Folegandros, Milos — that offer the same Aegean beauty with a fraction of the crowds. We help you find the right combination and the right time of year to visit each one.
Turquoise bay with flowers, Rhodes, Greece
Crete & the South
Greece's largest island is a destination in itself — wide enough to spend two weeks without retracing a single step. The Samaria Gorge, the Venetian harbour of Chania, the Minoan ruins of Knossos, the palm-fringed beach at Vai. Crete has a distinct identity and cuisine that sets it apart from the rest of the country.

Choosing the Right Island

Not all Greek islands are the same.

This is where most Greece trips go wrong — picking islands based on name recognition rather than fit. We match islands to who you are and what you want from your trip.

Santorini
Couples · Luxury · Sunsets
Deservedly iconic. The caldera views, the cave hotels, the volcanic beaches. Best experienced slowly, with the right property, outside of peak August crowds.
Naxos
Families · Food · Authenticity
The Cyclades' best-kept secret for families and food lovers. Long sandy beaches, a working agricultural interior, great local cheese and wine, and far fewer tourists than its neighbours.
Milos
Adventure · Scenery · Swimming
Volcanic geology has given Milos an astonishing variety of rock formations, sea caves, and coloured beaches. The boat-accessible coves at Kleftiko alone justify the trip.
Crete
History · Hiking · Everything
For those who want it all in one place. Ancient ruins, mountain gorges, excellent food, long beaches, and an island culture that feels entirely its own.

Who It's For

Greece works beautifully for all kinds of travellers.

We've planned Greece trips for couples on honeymoon, families with young children, groups of friends celebrating milestone birthdays, and solo travellers who want company only when they choose it.

Couples & Honeymoons
Greece may be the world's most naturally romantic destination. We know which cave suite in Santorini is worth the price, which island dinner is the one to remember, and how to sequence your trip so it builds rather than peaks on day one. One of our most-requested honeymoon destinations — and we understand why.
Families With Kids
Greece is brilliant for families — the food is accessible, the beaches are safe, and the history comes alive in ways that actually engage children. Naxos and Crete work particularly well for families. We've done this ourselves and know the practicalities: ferries, timing, and which ruins hold a ten-year-old's attention.
Groups & Special Occasions
A Greek island birthday, a bachelorette in Mykonos, a group villa on Corfu — Greece lends itself beautifully to group travel. We handle the villa sourcing, the boat charters, the restaurant takeovers, and the logistics that make group trips either brilliant or exhausting.
History & Culture Travellers
The depth of Greek history is staggering. Athens, Delphi, Olympia, Knossos, Mycenae — and that's before you reach the Byzantine churches and Venetian fortresses layered on top. We pair the right private guides with the right pacing so the history enriches rather than exhausts.

Sample Itinerary

12 Days in Greece — Athens to the Islands.

This is how we typically design a first Greece trip — starting in Athens, moving through Crete, then north through the Cyclades. Every itinerary we build is shaped around your pace and travel style — this is a starting point, not a fixed plan.

Jump to 1–3 Athens 4–6 Crete 7–9 Santorini 10–12 Naxos
1–3
Athens
The city that started everything
Athens rewards those who go slowly and with the right guide. The Acropolis before the crowds, history that feels alive rather than recited, evenings in the neighbourhoods most visitors never find. We know where Athens keeps its best — the rooftop dinner, the taverna that's been there for generations, the museum room that stops you in your tracks. Three days here gives the city the time it deserves before the islands.
AcropolisPrivate GuidePlakaLocal Dining
4–6
Crete
Greece's largest island — and its most underrated
Crete is a destination in its own right — wide enough to spend two weeks without retracing a step. Three days here is enough to get a real feel: the Venetian harbour of Chania, the Minoan ruins of Knossos, the food culture that sets Crete apart from the rest of the country. We know which version of Crete fits who you are and build accordingly.
ChaniaKnossosCretan FoodBeaches
7–9
Santorini
The caldera — done properly
Santorini is easy to get wrong — the wrong property, the wrong part of the island, the wrong restaurants. Done well, it's genuinely extraordinary. Three days here moves slowly: mornings on the water, afternoons with a glass of the island's volcanic wine, evenings at a dinner that earns its view. We know which experiences live up to the setting and which are simply trading on the postcard.
OiaCaldera ViewsVolcano Boat TripWine Tasting
10–12
Naxos
The perfect close
Naxos is the Cyclades' largest island and its most self-sufficient — it doesn't need tourists the way the others do, and it shows. Long beaches that don't fill up. A mountainous interior with marble quarries, Byzantine churches, and Venetian towers. A food culture that's entirely its own. Ending here rather than Santorini is a deliberate choice — it leaves the trip on something genuine rather than something famous.
Naxos TownBeach DaysMountain VillagesLocal Food

The specific properties, guides, boat captains, restaurants, and timings that make each of these days work — that's what we bring. This is the shape of the trip; what fills it is what we build together when you reach out.

And some of our favourite stops in Greece aren't on this page at all. Over 25 years we've found places that don't appear in guidebooks, that most visitors never reach, and that consistently become the moments people talk about most when they get home. Ask us about them.

When to Visit

Shoulder season Greece is the secret.

July and August are peak season — hot, crowded, and expensive. The travellers who know Greece best visit in May, June, or September. The sea is warm, the light is extraordinary, and you can actually get a table at the restaurant you want.

Jan
Off
Feb
Off
Mar
Quiet
Apr
Good
May
Peak
Jun
Peak
Jul
Busy
Aug
Busy
Sep
Peak
Oct
Good
Nov
Quiet
Dec
Off
Our favourite months
Great conditions
Quieter / cooler
Most things closed
May & June: Our Top Pick
Warm enough to swim, cool enough to walk comfortably. Wildflowers still on the hillsides. Restaurants fully open and not yet overwhelmed. Ferry schedules in full swing. This is Greece at its best.
September: A Close Second
The summer crowds begin to thin after the first week. Sea temperatures are at their warmest of the year. The light turns golden and the pace slows. September is the favourite month for many regular Greece travellers.
July & August: Still Worth It
Greece in peak season is still Greece — spectacular and memorable. We help you navigate it: the right islands, the right time of day for the famous spots, and the right properties that offer a quiet retreat from the bustle.
Sunset viewpoint over Greek island village
Our Greece Expertise

We know Greece island by island.

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Island Selection That Fits You

The biggest mistake in Greece trip planning is picking islands by name recognition. We match your group, your pace, and your interests to the right combination — so you're not fighting August crowds on Mykonos when you'd love the quiet coves of Folegandros.
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Contacts That Open Doors

The cave suite that's always booked. The private boat captain who knows Milos's hidden coves. The Athens chef who doesn't take walk-ins. These relationships take years to build and make a real, tangible difference to your trip.
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Seamless Ferry & Island Logistics

Greek island-hopping involves ferries, flying dolphins, timing, and luggage — and it's easy to get wrong. We handle all of it, including the backup plan when the summer meltemi wind delays services. You focus on enjoying it; we handle everything else.
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With You Throughout

Our team is available via WhatsApp from the moment you land in Athens to the moment you fly home. Ferry cancelled? Restaurant closed? Something unexpected? We sort it immediately, wherever you are in the country.

What Travellers Say

Greece trips they'll never forget.

Very responsive and very knowledgeable. They helped me and my partner plan a private trip to Greece and tailored it to our liking. They were with us through text the whole way — whenever we needed help booking taxis on the fly. Couldn't have asked for a better trip.

Lee Yeung · Greece, 2024

Being in our 40s, we do not travel the way 20-year-olds do. It was so great to be able to trust Free & Easy to look after all the details. No matter where we were, we were just a quick message away from any help. On a scale from one to ten, we give them fifteen!

Tammy & Robert Bell · 2026

Common Questions

Everything you need to know.

For a ten-day trip, two or three islands is the right number. More than that and you spend more time on ferries than on beaches. The instinct to see as many islands as possible is understandable, but the trips that feel most satisfying are the ones that slow down and go deeper. We'd rather you have three days on Naxos than one day each on five islands.
May, June, and September are the months we recommend most consistently — warm enough to swim, dry, and without the peak August crowds and prices. The light in these months is extraordinary, the sea is calm, and you can actually get a table at the restaurant you want. July and August are peak season — busier and more expensive, but still spectacular if you book early and plan well. Winter closes most island businesses entirely, though Athens is worth visiting year-round. We factor your timing into the itinerary so you're on the right islands at the right time of year.
Greece is part of the Schengen Area. Citizens of EU countries and many others (including the US, Canada, Australia, and the UK) can enter visa-free for short stays. The UK now has slightly different arrangements post-Brexit, and ETIAS is expected to come into effect for visa-exempt travellers at some point — we always confirm the current requirements for your specific passport when you enquire.
Greece is excellent for families with children of almost any age. Greek culture is genuinely welcoming to children — you'll rarely feel unwelcome at a restaurant, regardless of the hour. The food tends to be accessible. The beaches are some of the safest in the Mediterranean. We recommend Naxos and Crete for families over Santorini and Mykonos, which skew more toward couples and nightlife.
Greece has an extensive ferry network connecting the islands. Routes range from fast catamarans to slower overnight ferries. In summer, schedules are frequent and reliable; in winter, services reduce significantly. We handle all ferry bookings and build sensible timing into your itinerary — including buffers for the occasional delay.
Santorini is about the scenery — the caldera, the sunsets, the wine, the dramatic geology. It's more romantic and more suitable for couples. Mykonos is about atmosphere and nightlife — it's louder, more social, and better suited to groups and party-minded travellers. Both are genuinely beautiful. Which one fits you depends on what you're looking for.
Greece can cost as much or as little as you make it — and the range is significant. The shoulder months deliver the same scenery, the same sea, and the same food at meaningfully lower prices with far fewer people around. As for what a custom trip with us costs — that depends on who's travelling, for how long, and what kind of experience you're after. We don't work from a price list. We'd rather understand your trip first and design to your budget from there. Flexible payment plans are also available — just ask. For a full breakdown of day-to-day costs, see our Greece Spending Money Guide.
Absolutely. Greece pairs naturally with Turkey (Istanbul is a short flight from Athens), Croatia, Italy, and Portugal for a broader Mediterranean trip. We design multi-country itineraries regularly and can build a route that makes geographic and experiential sense rather than just stitching destinations together.

Let's Start Planning

Ready for your
Greece trip?

Tell us which islands you've dreamed about, how long you have, and what kind of trip you want. We'll take it from there.

Flexible payment plans available — just ask.

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