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Ah Greece, the incredible history, the food, the islands, the food, the culture (did I mention the food?)- it’s hard to not fall in love with this country. This was a blended vacation- some of us were working remotely in Greece (very feasible) and some of us were in full vacation mode (beach day, anyone?) As such, this itinerary, and our travel recommendations, work well no matter what kind of trip you’re looking for.

As with all of my vacations, I try to blend luxury with affordability. I use points for amazing experiences I outright would never be able to afford (i.e. business class flights), and choose budget-friendly but beautiful accommodations when I’m paying cash. Especially in Greece, you can leverage both strategies to travel in style and not break the bank.

I know this guide is long, but it contains an Athens itinerary + Greek Islands itinerary – really everything I wish I knew ahead of time. Feel free to jump to whichever section is most interesting to you!

Note: This post contains affiliate links. If you click an affiliate link or book through an affiliate program, I receive a small commission at no cost to you. This helps keep my work free, and I promise I only share links I actually recommend!

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How to Book Flights to Greece on Points ✈️

Flying to Athens on Points

By the time I officially picked Greece for a vacation destination and rallied my (incredible) friends, flights were expensive. Flights from NYC to ATH were $1,000 in economy, so I booked an overnight flight with United for 30,000 points per person transferred from my Chase account.

My boyfriend has the the Chase Sapphire Preferred® Card (my recommended starter card with a 60,000 point bonus – learn more) and I have the Chase Ink Business Preferred® Credit Card (currently offering a 75,000 point bonus – learn more) and the Chase Sapphire Reserve® card (also offering a 60,000 points bonus – learn more), so it was easy to earn more than enough points to cover this flight. If you’re new to points and miles, I recommend starting with the Chase Sapphire Preferred. Thanks to it’s low sign up fee, it’s my favorite entry card.

As an aside, this is why I think the credit card fees are totally worth it. Are fees high? Sometimes. Are they cheaper than buying two $1,000 flights? Yes.

Flying Business Class from Greece on Points

For the return, we wanted to fly in business class 🥂

We snagged two tickets in business class for 70,000 points each, also on United, from Santorini to NYC. Now, I think you could probably find an even cheaper deal (see some of my favorite tools for finding award availability here), but your points are YOURS to decide how to spend.

This is also typically a minimum $3,000 flight. So $3,000/70,000 points x100 = 4.3¢/point redemption. Considering 2¢ is typical, I’ll take it!

Two Week Greece Itinerary: Athens–>Paros–>Mykonos–>Santorini

You can interact with this map! If we stayed in a hotel (vs an Airbnb), I’ve marked it on the map in Purple

Most Greece itineraries often lean either towards history or towards island hopping. I wanted to do both (maximizer over here ‍🙋‍♀️) and you’ll see that reflected in the cities/timelines below. Here’s how much time to spend in each island/city in Greece:

• Athens: 4 – 5 Days
• Paros: 4 Days
• Mykonos: 3 Days
• Santorini: 3 Days

4 – 5 Days in Athens: The History

TL;DR Athens Recommendations:

• Plaka is the best neighborhood in Athens for tourists
• For a budget hotel in Athens that’s still nice, stay at the Moxy. Otherwise, there are tons of options on VRBO and Airbnb
• These are best Athens guided tours of the Acropolis, Delphi, Mycenae
• So many good restaurants and bars (including a “World’s 50 Best Bar“)

We were flying into Athens and I’d encourage you to give yourself a day to adjust to the timezone and then have a few days to explore.

Best Affordable Hotels in Athens:

Funnily enough, the week of the trip I realized that we were arriving a day earlier than I thought (and had booked accommodation for), so I used a free night award from my Marriott Bonvoy Boundless® Credit Card to stay at the Moxy for a night. It was a cute hotel in a great location, so I would highly recommend it! Check out the latest rates here.

Following that, we had a friend joining us who was working remotely, so we opted for an apartment which you can book on VRBO or Airbnb. We each had our own space, a kitchen/work area, it was affordable, and you can earn airline miles when you book Airbnbs, so it felt like a win all around.

If you’re wondering where to stay in Athens, the Plaka neighborhood is your go to! Check here for apartments in Athens you can rent in Plaka.

Best Tours in Athens:

For our time in Athens, we focused on history. So we did day trips and small guided tours through the Acropolis, Delphi, and Mycenae/Epidaurus. I honestly love guided tours because I get so much more out of it when someone can explain the history and answer my questions.

We also went to The Clumsies, one of the World’s 50 Best Bars. Beautiful cocktails in a very cool bar setting. Get there early if you can.

10 Days in the Greek Islands 🏝️

You might be wondering, can you really do the Greek islands in 10 days? You definitely can’t do all of them, but I assure you, you can still have an incredible time.

4 Days in Paros: The Best Island

TL;DR Paros Recommendations:

• The Best Hotel on Paros: Stay at Zefi Hotel
• Explore:
  • Kolymbithres beach
  • Antiparos

Let’s hop on to the island part of the trip, shall we? We visited 3 islands during our stay, but Paros was by far my favorite. It was beautiful, it was fun, and it was a little less crowded and “party-ey” than Mykonos. But let’s keep it between us. Don’t want it to get too crowded.

Getting There:

We booked a short flight for €186 on Sky Express from Athens to Paros:

It was a small plane and I’ll note you board from the back on this airline, so no need to pay for up-front seating

Hotels in Paros:

We stayed at the Zefi Hotel and Suites and I honestly can’t recommend it enough. It’s truly the best affordable, luxury hotel in Greece that I stayed in. The rooms were beautiful, the pool was stunning, the snacks were amazing (order the greek yogurt parfait and thank me later), it was a short walk into town, and the staff were incredibly kind. Our room in particular had two bedrooms, a balcony, and a gigantic bathtub. I want to go back immediately, if not sooner. Check out the latest prices and more details.

Activities and Restaurants in Paros:

For a fancier meal, make a reservation at Barbarossa (no one eats before 10pm, so take an early nap around 7pm) and head to Sante after dinner for cocktails in the courtyard (we went here every night we were in Paros).

Take the fexrry to Kolymbithres beach– it has giant rocks, beautiful water, and you can rent a beach chair for ~$20 (worth it- stay out of the sun and look young forever).

I also spent one day with my sister touring Antiparos, the small island across the way, via ATV. We picked up an ATV at a shop down the street from the hotel, and I probably drove 10 miles under the speed limit the whole time because my sister is precious cargo. I will say the ATVs come without gas, and we mistakenly filled ours all the way up. You absolutely only need maybe 1/2 tank (depending on how much driving you’re doing), so learn from our mistakes (but we’ll consider it a donation to the local economy).

We visited the Cave of Antiparos and had lunch by the ocean followed by a beachside nap. Life is rough.

You can also do an Antiparos tour + swimming cruise which I would 100% do the next time I’m back.

3 Days in Mykonos: The Party Island

TL;DR Mykonos Recommendations:

• The Ilio Marais is the best affordable hotel in Mykonos that still feels luxurious
• Wander through the cute town streets
• Tropicana Beach Club (fun and dancey)
• Scorpios ($$$)

Ah Mykonos, does it even need an explanation? It’s beautiful and the music and DJs are phenomenal. We visited in shoulder season (June) so we were too early for the most famous DJs, but still had a phenomenal time with smaller crowds (I’d recommend it. I chose this timeline specifically).

Getting to Mykonos by Ferry:

We headed to Mykonos by 1-hour ferry booked on SeaJets. Yes, it is chaos. I recommend booking early, arriving early, and being prepared to wait. But honestly it was a pretty smooth sailing trip (see what I did there? ).

Affordable Hotels in Mykonos:

Mykonos is pricey and we were trying to find accommodation for ~6 people. We stayed at the White and Grey apartments. Each one is a cute little apartment surrounding a beautiful pool. The staff was very kind and I think it was a solid, budget-yet-beautiful choice.

I will say it’s not super walkable to town if it’s remotely hot. You’re better off with a car or you’ll need a $40 taxi when you want to leave the property. If I were to go back, I would stay at the Ilio Maris. Much more centrally located, it has a beautiful pool and every room has a balcony.

Best Beach Clubs in Mykonos:

Wandering through the town of Mykonos is actually quite lovely (if not touristy). There are tons of little shops nestled along the coast and some massive windmills. Expect pricier meals here.

The real draw of Mykonos though is the beach clubs, and we did 2, with different vibes and price points.

Tropicana Beach Club:

• Gorgeous water. I want to live in it.
• We did not make a reservation, but it was off season so it wasn’t too full.
• The host is wild (there’s a scandalous outfit involved) and the music was great. This was a serious day-dancing party by 3pm.

Scorpios Beach Club:

• Reservation absolutely needed.
• Beautiful setting and services.
• $$$$

I think Scorpios is amazing, don’t get me wrong, but with the price point I might not go out of my way to go back a second time.

3 Days in Santorini: The Most Incredible Views

TL;DR Santorini Recommendations:

• We booked a Villa in Santorini. You’ll be aways away from the major tourist sites, but I think it’s worth it so long as you also rent a car.
• Chef Spiros Cooking Class (or catering) is a must-do

Getting To Santorini:

You can take a ferry from Mykonos to Santorini (about 3 hours). Same as before, a bit chaotic so book early and get there early. Nothing to be scared of though; I’d do it again.

Best Affordable Villas in Santorini:

Since we were a group of 6 people we did things a little differently. Instead of staying at a hotel in the city center, we opted for a villa on the hillside. I will 100% say it was worth it. Our views weren’t all the white walls and blue rooftops, but it was absolutely stunning. You can find a ton of the best Santorini villa options here that won’t break the bank.

What to Do in Santorini:

We rented a car for Santorini (absolutely worth it and very easy driving) and drove to a nearby hike one day and local winery another day. There are also numerous highly-rated wine tours where they do all the planning (and driving) for you.

We also set up a cooking class with Chef Spiros and it was the highlight of the trip. Normally, he does catering, but he walked us through how to cook 4 dishes (which I have since made at home!), taught us about the local ingredients, and he even did the dishes (what a guy). I cannot recommend him highly enough.

But honestly, most of what we did in Santorini was sip wine and enjoy the view.

Heading Home

All flights back from Santorini to NY required an overnight in Athens, so we flew back and stayed at an Airbnb near the airport before heading out the next day. We also booked our flights home as a 2-stop trip (Santorini to Athens, Athens to Vienna, Vienna to NYC). However, we would have had to fly back through Athens anyway, so this paid for our Santorini –> Athens leg, and made the flight cheaper because it was 2 stops.

There’s 4,000 things on my Greece bucket list I haven’t done yet, so I can’t wait for my next trip back!

Hope this helps and let me know if you have any questions!

Cheers to your next adventure ✈️🥂

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