Santorini & the Greek Isles
Known for: Caldera views, island-hopping, honeymoon-favorite scenery
Santorini’s blue-domed churches over the caldera are exactly what they look like in photos, and exactly why it’s one of the most requested honeymoon and anniversary destinations Dave books.
Most Greek Isles trips work best combined with at least one other island (Mykonos, Naxos, or a mainland stop in Athens) rather than a full week in one spot: Dave typically builds a short island-hopping itinerary using ferries rather than trying to do it all by cruise ship alone.
Best time to visit Santorini and the Greek Isles
Late May through June and September are the best windows for a Santorini and Greek Isles vacation, with warm weather, swimmable water and fewer crowds than July and August. Peak summer is hot, busy and expensive, and Oia in particular can feel packed at sunset. Spring brings wildflowers and cooler temperatures, but some businesses and ferries run limited schedules. Winter is very quiet and many hotels and restaurants close.
Top things to do in Santorini and the Greek Isles
Watch the sunset from Oia
Oia's white buildings and blue domes are the classic Santorini image. Arrive well before sunset for a spot, or watch from a quieter point like Imerovigli.
Walk the caldera path from Fira to Oia
The scenic trail runs along the cliff edge with sweeping views. Go early, bring water and sun protection, and allow several hours.
Tour a winery
Santorini's volcanic soil and old vines produce distinctive white wines, and tastings often include caldera views.
Take a caldera boat tour
Sailings visit the volcanic islands, hot springs and red and black beaches, usually with swim stops.
Add another island
Mykonos, Naxos and Paros pair well with Santorini and offer different styles, from lively beaches to quiet villages.
Spend time in Athens
Many itineraries start or end in Athens for the Acropolis and the city's food scene.
Where to stay in Santorini and the Greek Isles
Caldera-view hotels in Oia, Fira and Imerovigli are the most scenic and the most expensive. Beach areas like Kamari and Perissa offer easier access to black-sand beaches and lower prices. Because the island is full of stairs and hills, check accessibility if anyone in your group has mobility needs. For a Greek Isles trip, consider a short route of two or three islands rather than trying to see everything.
Getting to Santorini and the Greek Isles and getting around
Santorini (JTR) has flights from Athens and seasonal flights from other European cities. Most U.S. travelers connect through Athens or another European hub. Ferries link the islands, and schedules vary by season, so build in buffer time before flights home. Rental cars and ATVs are common on the island, but many visitors rely on taxis and transfers. A passport is required.
Planning tips for your Santorini and the Greek Isles vacation
- Book caldera-view rooms as early as possible.
- Allow buffer time for ferries and weather delays.
- Pack shoes with good grip for stairs and uneven paths.
- Consider a pre- or post-trip stay in Athens.
- Keep island-hopping realistic. Two or three islands is plenty for most trips.
Santorini and the Greek Isles travel FAQs
How many days do you need in Santorini?
Three to four nights is typical for Santorini alone. Plan 7 to 10 days if you are adding other islands.
Is Santorini good for a honeymoon?
Yes. It is one of the most requested honeymoon and anniversary destinations in Europe.
What is the best time to visit the Greek Isles?
Late May, June and September balance good weather with manageable crowds.
Is island-hopping hard to do?
It is straightforward with planning, but ferry schedules change seasonally, so it helps to have the route mapped out.
Can 7220 Travel plan a Greece itinerary?
Yes. Dave builds island-hopping itineraries with flights, ferries, hotels and tours.
Plan your Santorini and the Greek Isles trip with 7220 Travel
7220 Travel is a family and group travel agency based in Laramie, Wyoming, serving travelers nationwide. Dave Engel builds each trip around your group, your dates and your budget, then keeps watching for eligible savings after you book. Request a free quote or call 307-314-2517.
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