Antiparos, Greece

ITINERARY INSPIRATION: Greek Island Itineraries

7 Greek Island Itineraries for 10 Days in Greece

If you’ve read my guide to one month in the Cyclades you may already have some inspiration on how to spend one month in Greece and perhaps how to reasonably break down that itinerary into more bite-sized chunks. We were fortunate to have a month to explore the Greek isles in 2020 which gave us an opportunity to pop around to lesser-visited islands like Sifnos and Antiparos; islands we would have likely skipped given a shorter time frame to play with. At Compass & Vine, I’ve been designing Greek itineraries for a range of travelers and overwhelmingly I’m working with people who have around 10 days to dedicate to Greek island itineraries. With that in mind, I’m sharing some inspiration for 10 days in Greece with island pairings below. Where possible, I’m including my Virtuoso links for anyone that’s a DIYer looking to book on their own. For anyone else wanting some guidance and a tailored itinerary, reach out to me to say hello so we can chat!

Worth noting: these combinations are island-based. For anyone who hasn’t been to Greece previously, you’ll want to carve out two nights with at least one full day in Athens to visit the Acropolis and take in the core of the country’s history as a base to your time in the region. Full disclosure: Athens isn’t my favorite city but it’s a history-lovers haven and a couple of nights provides a decent primer before moving onto islands.

Rhodes + Symi

Exploring Rhodes Old Town

3 Nights Rhodes Town ⇢ 4 Nights Symi ⇢ 3 Nights Lindos

1A few years back I wrote about our family trip to the region, spending 10 days in Greece split between Athens, Rhodes, and Symi. My family hadn’t yet been to Athens so our two nights there were fairly obligatory. International flights transit in and out of Rhodes which means many travelers can skip Athens altogether if desired. For those who can enjoy 10 days dedicated to the Dodecanese island chain, Rhodes + Symi are a fabulous pairing. For first-timers to the region, I would allocate 3 nights in Rhodes Town for a history fix, 4 nights in Symi to enjoy the charm of this tiny island + 3 nights in Lindos on Rhodes to end with a lovely beach fix. Starting and ending in Rhodes makes flights in and out of Rhodes airport a breeze.

👉🏼 Read more on visiting Rhodes and Symi.

Naxos + Paros + Antiparos

Things to Do in Naxos

4 Nights Naxos ⇢ 4 Nights Paros ⇢ 2 Nights Antiparos

2In the not-too-distant past, Naxos and Paros were considered ‘off-the-beaten path’ and ‘up-and-coming’. In all honesty, I think we’re well past that. Naxos and Paros are both well-known beloved islands in the Cyclades and they each offer their own flavor, which makes them a particularly wonderful pairing. Naxos feels more authentically Greek with a slightly more rustic slant and a bigger focus on historic sites and agriculture. It’s arguably the best island for a food tour as it’s the only island that can be truly self-sustaining with its food production, and many families would argue it’s one of the most family-friendly as well. Paros, by contrast, feels more upmarket and slightly more glam, particularly in the harbour town of Naousa where good shopping and nice restaurants are readily available. Antiparos, accessible only via Paros, is a great inclusion as it provides the addition of an island that is truly on the rise, offering a slightly more low-key laid back vibe in an idyllic setting. Many visitors to Antiparos visit solely on a day trip from Paros, but giving yourselves a couple of nights to enjoy Antiparos Town and all of its charm makes for a memorable itinerary.

👉🏼 Check out my mini guide to Paros for some inspiration!
👉🏼 Read about our day exploring Antiparos by boat.

Mykonos + Naxos + Paros

4 days in Mykonos

4 Nights Mykonos ⇢ 3 Nights Naxos ⇢ 3 Nights Paros

3Mykonos is a fan-favorite for a reason and while it’s a polarizing destination, I truly think it has something on offer for everyone. Its hard-partying reputation does the island a disservice. For as international as the island is and scene-y as it can be, there’s a lot on offer that makes it alluring: some of the region’s best hotels and resorts, a slew of incredible restaurants, sunsets in Little Venice, shopping and wandering Mykonos’ Town’s labyrinth of streets, upscale day clubs, great boating opportunities, and some charming tavernas. I love this itinerary in this order as well because these islands provide a beautiful contrast with different experiences. If Mykonos and Naxos were on opposing ends of the glam scale, Paros would probably be the Goldilocks island perfectly positioned in the middle with a palpable blend of village charm pumped up with a dose of glitz.

👉🏼 Read more on 4 days in Mykonos.

Milos + Santorini

Boat Trip to Kleftiko, Milos

5 Nights Milos ⇢ 5 Nights Santorini

4When it comes to Greek island itineraries, this is a great duo if you have 10 days in the Cyclades focused on R&R at a slow pace. To start, fly into Milos via Athens. If you haven’t yet been to Milos, you’ll get to meet my favorite island in the region. What Milos lacks in traditional Cycladic charm, it makes up for with the most dramatic coastline imaginable. We spent 4 nights in Milos and were so sad to leave. I could spend a week on the island, but for a comfortable pace, I’d suggest five nights. From Milos, take a ferry to Santorini (about two hours).

There’s no doubt about it: Santorini is one of Greece’s stars. Nearly every client I talk with about the Greek islands includes Santorini as one of their must-visits. If I’m being totally honest, Santorini isn’t my personal favorite as far as the Cyclades go, but I do understand why it’s a must-see for visitors to the region. The island is a stark contrast to many of its neighbors, and while most people vaguely understand Santorini’s volcanic makeup, a boat cruise inside the caldera gives you perspective on the island. Oia is dotted with stunning resorts carved into the cliffside and restaurants bathed in a sunset glow. For wine lovers wanting to go wine tasting in the Cyclades, Santorini is the epicenter as one of Greece’s most famous wine-producing regions with 18 wineries to visit. We spent five nights in Santorini, which I’d recommend for anyone looking for a slowed-down enjoyable pace.

👉🏼 Read about our day wine tasting in Santorini.

Crete + Santorini

Places for Sunset in Santorini

5 Nights  Santorini ⇢ 5 Nights Crete or 4 Nights Santorini ⇢ 6 Nights Crete (Two Hubs)

5For anyone out there looking to travel to the Greek isles later in the season (think early October), this is the combo for you. I’ve had a couple of clients leaning towards the fall to avoid crowds and peak season pricing, but the biggest challenge is that many of the islands further north begin closing down during the first couple of weeks of October. For more activities and regular programming, Santorini + Crete are a perfect pairing. Begin in Santorini, and then take the ferry over to Crete for the latter half of your trip (note that ferries typically stop around 10/10).

Crete is a massive island (over 3200 square miles) so your time in Crete would likely be dedicated to one primary hub. If you spend 5 days in Santorini, choose a single hub for 5 days in Crete (e.g. Elounda or Chania). To get a better taster of Crete, spend 4 nights in Santorini with a split stay in Crete (3 nights in Elounda + 3 nights in Chania, for example). Reach out and we can discuss which Cretan hub is the best fit based on your personal style and preferences!

👉🏼 Read about our time boating in Santorini.

Mykonos + Paros + Santorini

Greek Island Itineraries

3 Nights Paros ⇢ 3 Nights Mykonos ⇢ 4 Night Santorini

6Classic. This is my go-to Greek island itinerary for folks wanting a classically beautiful trio. Depending on your vibe and preferences you can use your 4-night stay in either Mykonos or Santorini (Santorini for romance, wine tasting, etc.; Mykonos for beaches and day clubs). All of these islands bring a glamorous edge, but Mykonos brings a more international high-energy feel, which contrasts with Santorini’s romantic slant and Paros’ upscale village vibes. Paros easily connects to Mykonos by ferry, and there’s a fast ferry that travels from Mykonos to Santorini making the connection a breeze (about two hours).

👉🏼 Read about our self-guided ATV Tour of Mykonos. 
👉🏼 Read my mini guide to Paros for some inspiration.

Milos + Kimolos + Sifnos

One Month in the Cyclades

4 Nights Milos ⇢ 2 Nights Kimolos ⇢ 3 Nights Sifnos

7For travelers wanting something off-the-beaten-path when putting together their Greek island itineraries, this is a super unique combination that will leave your friends wondering where in the world you’re off to. To start with, for food lovers it’s hard to beat Sifnos. You’ll find amazing fare everywhere in Greece but Sifnos has upped the ante with more gastronomic outposts putting out inventive fare.  Our go-to was Omega3, which has become a bit of a Sifnian institution, but there are a range of exceptional options in Platis Yailos offering creative takes on Greek inputs.

The order of this itinerary can be easily flip-flopped to start in Sifnos instead (ferries available from Athens, about 3 hours on a fast boat). 3 nights in Sifnos allows a bit of island exploration and plenty of wonderful meals. Sifnos and Milos are connected by ferry making the transfer simple and allowing 4 nights in Milos to enjoy this stunning island by land and by sea. Kimolos, which is accessible by a ferry from Milos (30 minutes from Apollonia), is a wonderful little gem that flies under the radar. Here you’ll find some gorgeous beaches (home to one of my favorite beaches in the Cyclades), a charming town, and a great little hub to explore for a couple of nights.

Hotels in Greece to Consider by Island

Places for Sunset in Santorini

The potential combinations are endless in this region with a ferry system that connects islands in an efficient way. If you’re mapping out Greek island itineraries and have 10 days to spare, it’s worth noting that less is more. It’s tempting to cram in as much as possible but 3 islands is really the max I’d suggest doing so you can have the time to appreciate what you’re seeing and experiencing. Not featured here are the Saronic islands, Ionian islands, or the Sporades; this solely touches on the Cyclades with a dash of the Dodecanese but the inspiration is endless. Want to collaborate on an itinerary that’s uniquely yours? Reach out to me at Compass & Vine so we can plan. ✨

What’s your favorite Greek island itinerary combination?

Shannon Kircher, The Wanderlust Effect

More about Shannon Kircher

Shannon Kircher is the founder and editor of The Wanderlust Effect. Founded in 2009, she has continued to document her international escapes as an expat in Europe and the Caribbean. Additionally, Shannon is the founder of Compass & Vine, a luxury boutique travel design firm, and is the Director of Marketing for the Frangipani Beach Resort. Shannon holds an MSc in Social Policy and Development from the London School of Economics and is a current candidate for WSET Level 3 in Wines & Spirits.