Greece Getaway Guide: How We Planned the Dream Trip (Honeymoon or Not)
Shoulder-season Greece travel guide with our exact route, travel agent secrets, and stress-saving tips for couples and first-time visitors.
After back-to-back snowstorm weekends here in Iowa, daydreaming about Greece feels like a full-time job—but the upside of being snowed in is finally having time to write about it.
It was our first European trip together, and there was a tiny part of me that wondered if our energy levels would sync up—would one of us want to go nonstop while the other hit a wall by midafternoon? Instead, we eased into the exact same rhythm so naturally. Greece ended up being the perfect mix for us: ancient history for Emory, ocean views and island wandering for me, and plenty of space for both adventure and rest.
Whether you’re planning a honeymoon, a first big trip together, or just a long-overdue adventure, this guide walks you through our itinerary, what we’d repeat in a heartbeat, what we’d tweak if we were to do it again.
Why Greece Was “The One”
Greece had been on both of our bucket lists for years—but for totally different reasons, which is exactly why it ended up being the perfect fit.
For Emory, it was all about the history: ancient civilizations, mythology, battlefields, temples, and actually standing in the places he’d only ever read about. For me, it was the promise of both beachy, blue-water relaxation and European city energy with cobblestones, café patios, and old-world charm.
If you and your partner have different travel styles, Greece is a dream compromise. You can climb ancient ruins one day, swim in crystal-clear water the next, and eat your way through every moment in between.
Trip Logistics: Timing and Travel Agent Help
We traveled in late September into early October, right in the shoulder season, and it was absolutely perfect. Everything was still open, the days were warm enough for beach time, and nowhere felt overly busy or crowded—just lively in the best way.
How We Chose Our Islands
Choosing islands was honestly the hardest part because there are so many good options. We ultimately landed on Paros and Milos because they gave us the classic whitewashed, blue-water look of places like Santorini and Mykonos without the big crowds or price tag. We briefly debated squeezing in a third island, but I’m so glad we didn’t. Sticking to two let us actually settle in and enjoy them, and we have zero regrets about the ones we chose.
When Should You Book Your Honeymoon? I Think ASAP!
We didn’t jet off the day after our wedding. Instead, we took a week—which meant unloading a semi trailer’s worth of wedding décor and slowly attempting to get our lives back in order. It gave us space to catch our breath, see loved ones who stayed a little longer, open gifts, and actually process the day.
After a week, our newlywed energy was still buzzing, and it felt fun to ride that high straight into a big trip. Money was going to be tight right after the wedding, but I knew if we pushed the honeymoon too far out, we’d keep finding reasons to say “not yet.”
Honeymoon Tip: If you’re debating timing, ask yourself: Do you want to ride the wedding high into vacation mode, or do you need a serious decompression week (or two) first? There’s no wrong answer—just make sure you give yourselves at least a few days to recover, do laundry, and find your passport.
Why We Used a Travel Agent (and Why Type A Me Loved It)
My biggest fear about going on a honeymoon was 100% the planning and decision-making on top of wedding prep. We did not have the time or mental energy to research walkable neighborhoods, compare hotel reviews, and coordinate ferry and plane schedules like a beautiful little spreadsheet.
I’m very Type A and love being in control, so handing that over stressed me out at first. But working with our travel agent, Allison, ended up being the opposite of stressful. We told her our goals and vision for the trip, and she turned that into an initial plan, we tweaked it, she revised it, and then suddenly… it was booked. Major transportation, stays, and smart excursion suggestions. It was the perfect balance of “this is handled” and “we still have room for spontaneity.”
Here’s what she handled so we didn’t have to:
Mapping our route so the trip actually flowed
Helping us decide how many days to spend in each place based on budget and logistics
Finding nicer accommodations at better prices than we found on our own
Identifying safe, walkable areas with plenty of restaurants and things to do
Pointing us toward tours and experiences we never would’ve uncovered just scrolling
Coordinating flights, ferries, and timing around potential European strikes
For a honeymoon—when you’re planning a wedding, managing family, and juggling work—outsourcing those moving pieces is truly a gift to yourselves. It let us show up as relaxed, excited versions of ourselves instead of two burned-out project managers trying to troubleshoot in real time.
Stop One: Athens
Two Nights, One Day - Food, history, and a city that deserved more time
Accommodation: Titania Hotel (PS: Absolutely incredible 10/10 would recommend. They are so hospitable!)
We heard the same advice from so many people: “See the Parthenon, but don’t stay in Athens too long.” I strongly disagree. From the moment we stepped off the plane after our Des Moines → Chicago → Athens marathon, the city felt oddly familiar but still thrilling.
Athens has this warm, sun-soaked energy—European but with little flashes that reminded me of Southern California. If someone had told me we were just outside LA in places, I would’ve believed them.
Historical Tour: Easing Into Vacation Mode
On our first morning, we did a guided historical tour booked through our travel agent. It was the ideal way to:
Fight jet lag without having to make a single decision
Actually learn what we were looking at instead of just snapping photos and moving on
Connect with other travelers who were just as excited to be there
Standing at the Parthenon was a true goosebump moment. It felt like stepping onto a page of a textbook.
Food Tour: Best First-Night Move
That evening, we decided at the last minute to join a Greek Food Walking Tour despite being exhausted, and ended up being one of our favorite memories from the entire trip. We tried dishes we never would’ve ordered on our own, wandered through charming streets, and spent hours eating and laughing with people from all over the world.
If you do one thing in Athens, make it a food tour. It’s the fastest way to figure out what you like, learn practical local tips, and have a shared experience right away.
Honeymoon Tip: Book at least one guided activity your first full day. It takes the pressure off planning when you’re tired and gives you instant shared memories.
Stop Two: Roadtrip through the Peloponnese
Two Nights, One Full Day, 2 Travel Days to and from - - Beaches, mountain monasteries, and main-land Greece
Accommodation: MENELAION (PS: The location was perfect & Sparta has free parking!)
After Athens, we picked up a rental car and drove toward Sparta, with a stop in Corinthia. I had done exactly zero research on Corinthia—and it ended up being one of the most stunning surprises of the whole trip.
Corinthia: The Beach We Didn’t See Coming
We parked in town to grab lunch, walked a few minutes, and suddenly were standing in front of one of the most beautiful bodies of water I’ve ever seen. Because it was the end of the season, the beach was nearly empty and felt like a secret. If we did this trip again, I’d absolutely spend a night or two here at a place on the water.
Sparta: Historic Small-Town Vibes
When Emory first said he wanted to go to Sparta, I was skeptical. It sounded like a “boy thing”—like he wanted to go just to say he went. But I was so pleasantly surprised. I had no expectations, so everything felt special and intimate, and it was a part of Greece I hadn’t really heard much about.
Sparta felt like a real town where people live, work, and gossip at the same café every morning. It was slower paced and less flashy—exactly what we needed between the bustle of Athens and the islands.
Highlights you might want to copy:
Surprisingly great local shopping
Tiny mom-and-pop restaurants where the “menu” was basically recommendations, Highlights Include: Kapari & Ministry Music Hall
A hike to an ancient monastery that was harder than expected but came with incredible views
A restaurant built into the side of a mountain with Italian food and great service
Stop Three: Paros
Three Nights, 4 Days, Our longest stay - ATVs, Beaches & Authentic Greek Experiences
Accommodation: Mr & Mrs White Paros (PS: The best complimentary breakfast!)
From Athens, we flew to Paros and instantly understood why people romanticize the Greek islands. Our hotel sat just off the main town, Naousa, where stone-paved streets were car-free and the buildings were the exact whitewashed charm you see on Pinterest, covered in bougainvillea (my favorite) with cats sunbathing in doorways.
The Unplanned Recommendation That Became “The Meal”
On our first night, hungry and tired, we set out for dinner without much of a plan—which is my personal nightmare as a Type A foodie in a new town. Instead of wandering aimlessly, I pulled out a list of recommendations a friend had shared. We picked one, set it in the map, saw the whole town on the walk over, and ended up having our favorite meal of the entire trip at Taverna Glafkos!
Spontaneity is fun, but when it comes to dinner, I want an experience. When Yelp isn’t really a thing, having a short list from friends, locals, or a blog post is gold.
Greeka, however, is like the Greek Yelp and it came in handy many times!
ATVs and Beach Hopping
The highlight of the whole trip for me was renting ATVs and spending our days hopping from beach to beach, exploring little towns and coves, and pulling over whenever something looked pretty—which was always. It was affordable, convenient, and gave us enough independence to feel adventurous without needing a rigid schedule.
Fishing Boat and Greek BBQ Day
My second favorite highlight was the fishing boat and Greek BBQ tour (Antiparos & Despotiko Kaiki Cruise). We swam off tiny islands, I snorkeled for the first time where there were actually fish, and we had an authentic BBQ picnic I’m still dreaming about. We met the most incredible people and even had goats casually wandering the shoreline.
Overall thoughts on Paros, I also just loved wandering Naousa itself. I could’ve spent a whole week there trying new restaurants and blowing my budget on shopping. The town has this buzzing, casual nightlife and such a fun vibe. Parikia, on the other hand, felt more like a busy port city—worth a visit, but if you’re choosing, stay in Naousa.
Stop Four: Milos
Two nights, One day - Rough ferry ride, colorful fishing villages, and our most adventurous meal
Accommodation: Santa Maria Village Resort & Spa (Stunning pool, I wish we had time to enjoy it!)
We took a ferry from Paros to Milos, and the seas were not playing around. Even with motion sickness meds and wrist bands, it was… a lot. But Milos itself made every queasy minute worth it.
More ATVs, More Magic
With only one full day, we rented ATVs again and hit some of the island’s biggest highlights:
Colorful fishing villages with houses right on the water
A scenic lunch at Medusa Restaurant where we tried sun-dried octopus and swordfish souvlaki
Firiplaka Beach with pink-tinted cliffs that looked almost unreal
That night, we found a tiny family-run restaurant, O! Hamos!, offering farm-fresh, homemade food that nailed the indoor–outdoor atmosphere and storytelling. The space was beautiful, the hospitality was warm, and the food made us quietly happy in the best way.
My biggest regret is that we didn’t have more time here. Milos is known for having incredible, totally different-feeling beaches all over the island, and we only got to fully enjoy one. Our hotel was also stunning, and I would’ve loved at least one full day of spa time and pool lounging with that view.
Honeymoon tip: If you’re like us and get FOMO about “seeing it all,” try to add one or two pure relaxation days to your trip. I wouldn’t trade any of our experiences, but I absolutely would’ve added another day or two for slow mornings and pool time.
Going Home: Lost Luggage, Low Stress
On our way home, we flew back to Athens, only to realize our luggage had not flown back with us.
We had packed AirTags (a must-have for your registry) in our checked bags, so we could see exactly where they were and watch them slowly catch up to us. We stayed at the airport hotel which was SO convenient, worth it, and ended up being one of the nicest of the whole trip, Sofitel Athens Airport,ordered room service, watched Netflix, and flew Athens → Chicago → Des Moines the next morning. The luggage arrived a few days later without any drama.
Travel Tip: No matter where I’m going, domestic, international, direct flight, I always assume my bag, even a carry-on isn’t going to make it. So I pack essentials in my backpack, a casual outfit, underwear, PJs, any special attire for a formal or a swimsuit, and key toiletries like a toothbrush, toothpaste, deodorant, and a hairbrush. Stores exist everywhere, but having your basics you love on hand can be the difference between “mild inconvenience” and “full meltdown.” For Greece be sure to also pack motion sickness meds, a portable charger, and this bag was essential for ATV days.
Practical Tips and What We’d Do Differently
Here’s what we’d tell any couple planning a Greece honeymoon, friend-to-friend style:
Add the hotel breakfast option. If your hotel offers an add-on breakfast, do it! We were on the fence because we usually like to explore local spots, but every hotel gave us a genuinely good, authentic breakfast with tons of variety. It was such a gift to sleep in, stay in comfy clothes, wander down to the lobby, and not have to hunt for food or pay for yet another meal out. It was one of those small choices that made the whole trip feel easier and more relaxing (thanks to the travel agent again!)
Go a little longer if you can. We wished we’d stretched our trip to a full two weeks. Greece takes time to travel around, and it’s a place you want to linger—slow mornings, long lunches, and extra beach days.
Rent ATVs on the islands. They’re the most fun, flexible way to explore Paros and Milos. Pack layers, wear helmets, and build in time for spontaneous stops.
Don’t skip Athens. Give it at least one or two full days. It has far more personality, history, and food than the “just see the Parthenon and leave” if you enjoy city life.
Seriously, consider a travel agent. Especially when you’re planning a wedding at the same time. Having someone map your route and handle logistics lets you show up as the fun version of yourselves, not the stressed-out project manager version.
If You’re Planning Your Own Greece Vacation…
Greece ended up being everything we hoped for and more: a chance to exhale after the joyful chaos of wedding week, explore somewhere brand-new together, and collect the kind of stories we’ll be telling for years—lost wedding ring and all.
If you’re dreaming up your own Greece itinerary or trying to decide when to travel, which islands to pick, or whether to use a travel agent, drop your questions and share what kind of honeymoon you want (more adventure or more naps), and we can start shaping your perfect route.
With love,
It sounded so lovely Jae Jae. Trip of a life time. So happy you enjoyed so much and shared it all with us.