The Ultimate Greece Trip Itinerary: Which Islands to Visit

One of the hardest parts about planning a trip to Greece is deciding which Islands you want to go to and how you are going to travel between them. We met so many people on our journey and everyone does Greece differently. After our trip, I was really so happy with where we went and how long we stayed. The only thing is, Greece has so many islands and places to visit, you’d need years to explore all of the amazing spots! For us, we chose two popular places and two more quiet islands that are still easy to get to. Read below to hear more details about the trip!

• Day 1-2: Athens & Nemea Wine Country
• Day 2-5: Milos
• Day 5-8: Santorini
• Day 8-10: Paros
• Day 10-12: Mykonos

What to Pack for Greece

For our Greece trip, I brought one pair of heels and never wore them, lol. Most of the streets and places you’ll be walking are cobblestone, hilly, and sandy, so there is absolutely no reason to wear heels! I did bring small block wedges which I wore a lot and other than that it was tennis shoes and sandals.

For clothing, it depends on the time of year, but most likely you’re going when it’s warm/hot. Swimwear, sundresses, shorts, hats, sunglasses, all of that good stuff is necessary. Make sure to bring a scarf or shawl situation you can wear when it’s windy or the nights get cooler. I wish I would’ve had a fanny pack or some easy small purse to have with me at all times.

You can check out all of the links to my trip under my favorites tab!

Athens & Nemea Wine Country

Where to Stay in Athens

In Athens, you have tons of choices, all pretty reasonably priced as well. We chose the Niche Hotel and loved it. You can’t beat the location which is within walking distance to the Acropolis and many great restaurants. However, if you’re more into the nightlife scene I recommend staying on the other side of the acropolis near more of the late-night bars.

What To Do in Athens

From what I’ve heard, most people choose to skip Athens on their Greece trip or only spend one night here. Well, we spent two but I’m so glad we had a little extra time to explore this awesome, historic city! There are so many fun bars and restaurants, I actually could’ve stayed here a little longer if we were able. Obviously, you have to visit the Acropolis and see the Parthenon. There are a bunch of other historic sights all over the city.

My favorite part though was our wine tour through Nemea Wine Country. Known for its Agiorgitiko grape, this mountainous region in the Peloponnese Peninsula is a beautiful place producing exceptional wines.

We did our wine tour through Ancient Greece Tours with Tas, our awesome Greek-Australian guide who drove us through the region and shared some interesting history with us along the way. You are able to stop to see the Corinth Canal, see the ancient Zeus Temple of Corinth, and then continue on to wine country. We had the pleasure of visiting a few different wineries which included Palivou, Gaia, and Lafazanis Winery. If you’re interested in learning more about Greek Wines, check out my blog post here!

Our last stop was dinner in Ancient Corinth at a small restaurant balcony overlooking the Ancient Temple of Aphrodite.

If you are interested in checking out some nightlife, we visited a few cool bars that made some delicious cocktails: Baba Au Rum, Juan Rodriguez Bar, and The Clumsies.

Milos

Milos was such a dream! This should definitely be on your list of islands to visit. We flew from Athens to Milos on a quick 30-minute flight and it was seamless! This island has it all, without being overly touristy and busy. Don’t get me wrong there definitely were still tourists, but nothing like Santorini and Mykonos (more on that later). Milos is unique because it’s mountainous, yet has gorgeous beaches, cute fishing towns, and delicious and authentic restaurants.

Where to Stay in Milos

We stayed at the Milos Breeze Boutique Hotel. To be honest, we didn’t do much research before booking, but we ended up loving the location of our hotel, plus the staff and accommodations were lovely. This hotel is located right up the hill from a little village called Pollonia where there are tons of restaurants and little shops. I also heard Milos Cove Hotel and White Pebble Suites are great.

Where to Eat in Milos

O! Hamos! In all my research for our Greece trip this place came up as the best restaurant in Milos so I knew we had to go. We showed up at 8 pm and waited for 1 hour and 45 minutes… they don’t take reservations. Was it worth that long of a wait? Mmm idk because that was a super long time to wait haha, but the food was seriously incredible and so authentic. Plus it was one of our cheapest meals. We ordered like 6 things plus a bottle of wine and spent 80 euros. If you are able to go during lunch hours or for an early dinner, the wait shouldn’t be as bad!

Gialos. This restaurant was in Pallonia right on the water and is known for its fresh seafood. Everything else on the menu was also so fresh and delicious. I highly recommend eating dinner here one night.

What to Do in Milos

Take a boat tour of the island. Whether it’s a private boat or a group boat, this is a great way to get a different perspective of the island! Plus, some things like the caves and Kleftiko beach are only accessible by boat. There are a lot of different companies to book through, but I’d recommend checking out Naya Yachting or Excellent Yachting.

Visit the beautiful beaches. There are so many unique beaches in Milos, these are a few I recommend: Sarakiniko, Firiplaka, Tsigrado, Provatas, and Papafragas.

Watch the sunset at Plaka. This experience came highly recommended and I can honestly say it was one of my favorite parts of the trip! First of all, Plaka is the cutest town situated on top of the highest mountain in Milos. Once you’re in the town center, you have to walk up quite a ways, but it’s so worth it. Everyone gathers near the old churches to watch the sunset each evening. They even have cocktails to go to if you want to bring something up with you!

Wine Tasting at Kostantakis Cave Winery. This winery near Pallonia where we stayed is the only winery on the island. It’s family owned and each year they only produce about 1,000 cases of wine. It’s a fun little hang-out spot around 5 pm, perfect for a tasting before heading out to dinner.

Santorini, Greece

Where to Stay in Santorini

The Andronis Boutique Hotel was my favorite place we stayed the entire trip! Everything from the staff, the rooms, service, views, location, concierge service, etc could not have been more perfect. Andronis has many locations on the island of Santorini, but I believe we chose the best place for us to stay. The Boutique Hotel is located right in Oia, so you don’t need to leave the hotel to get incredible views and enjoy the landscape. This was especially important to us because of how busy and touristy the island can get.

Where to Eat in Santorini

Lycabettus Restaurant. This cliff-side dining experience was surreal. We enjoyed the full tasting menu and I did the wine pairings while Mo did the cocktail pairings. It was such a fun experience to do one of each, the dishes were creative and delicious, and the ambiance was spectacular.

Ammoudi Fish Tavern. This was such a cool experience. We walked down 300 steps to visit this seafood restaurant right on the edge of the bay. I highly recommend making a reservation to watch the sunset.

Pacman. By this point of the trip, I was kind of craving a different type of cuisine, and Pacman was perfect for sushi. This restaurant has more of a lively boho vibe. It was a little expensive, but it is Santorini after all.

What to Do in Santorini

Wine tasting on Santorini. Doing a wine tour is a must for your Greece trip when you visit the island of Santorini! It was so fascinating seeing the vineyards and hearing all about the viticulture and production of wines on the island. Santorini Winetopia took good care of us and made sure we had plenty of wines to taste, small bites throughout the experience, a variety of wineries, and a lot of education.

Sunset Boat Cruise. If you have time, doing a boat tour in Santorini is a fun experience and you can visit the white, red, and black sand beaches and the natural hot springs you wouldn’t be able to otherwise. We booked through Caldera Yachting and were so impressed by the quality of the catamaran and the food they served on board.

Paros, Greece

Paros is such a lively island with lots going on, without the overwhelming crowds of Santorini. It’s much more affordable than Milos, and not overpriced like Mykonos and Santorini. I wish we would’ve had more time here on our Greece trip, but at the same time, I felt like two nights was enough!

Where to Stay in Paros

We stayed at the Cove Hotel near Naoussa. This brand-new place has a quiet, chill vibe that is perfect for relaxing during the daytime. The food and cocktails were awesome, and the accommodations were comfortable. They even had a small spot for massages that we enjoyed by the pool, and a cute little gym we actually used (once haha).

Where to Eat in Paros

Siparos Restaurant was probably one of my favorite meals from our entire Greece trip. It was only about a 5-minute drive from our hotel and it’s situated right in front of the water. This is another epic spot to watch the sunset. We ordered their famous salted, grilled fish and loved everything from this place.

Mario was listed as one of the top places to eat on the island, and for the atmosphere, I definitely see why. It’s situated right near the boats in downtown Naoussa, and you are in this awesome little courtyard that’s hustling with people. We felt like we were sitting down for a big family meal, and the food seemed authentic. It wasn’t my favorite food we’ve eaten on the trip, but the service was great and the atmosphere was fun!

Check out Agosta Bar for an awesome late-night vibe and great cocktails. Fotis All Day Bar was also a sweet spot for drinks and shisha 🙂

Mykonos

Mykonos… okay, it is what people say it is! It’s definitely the party island with lots going on. We felt like for our Greece trip, two nights were for sure enough for us. And honestly, if you don’t care to experience the nightlife of Greece, you could skip this island. However, a lot of the other islands don’t have late nightlife or clubs so if you want to experience that for a night or two it is worth the stop!

Where to Stay in Mykonos

We stayed at the Aeonic Suites & Spa, and aside from our hotel in Santorini, this was my favorite place we stayed! It’s a brand new 5-star hotel and the service and accommodations did not disappoint. It’s also a great location, about a 5-minute drive from Old Town Mykonos.

What to Do & Where to Go in Mykonos

For your Greece trip to Mykonos, Scorpios is a must. We went for the sunset which was a great time to go and it really starts getting busy and fun. Cocktails and food are delicious but prepare to spend money.

SantAnna Beach Club was also such a vibe! We got a cabana for the day and lounged with cocktails, sushi, and shisha. We went after the super busy season so the vibe was pretty chill, but you can check their calendar for events and DJs! This place also had great service, cocktails, and food, but prepare to spend!

If you have time, definitely walk the streets, go shopping, and explore the old port of Mykonos.