Packing List: Island Hopping in Greece

This packing list for a Greek getaway is a companion to the Travelling in Style series about building a fashionable onebag travel capsule wardrobe and the lessons I learned along the way.

Agkali Bay in Folegandros might be one of the most beautiful places ever.

Greece was my first international trip, and I was immediately in love with the vibe, the food, the stunning views, the clear waters, and the beautiful sunsets. I can't wait to go back and explore more of the islands.

I'm going to break down what I packed for 11 days in Greece, island hopping between Santorini, Folegandros, and Milos in the Cyclades and then spending one very hot (this was during the 2021 heatwave) night in Athens before heading back home.

On this trip, we ended up taking planes (budget airlines and major carriers), ferries, taxis, shuttles, and buses, so packing light was crucial to being able to get around easily. We hiked, swam, lounged on the beach, tasted wine at a vineyard, ate at nice restaurants, and took a boat tour on each island.

I carried an 18L backpack (the Matador Beast 18), and it worked out perfectly. I didn't research the weather properly and brought a light raincoat (apparently, it rarely rains in the Cyclades) and my leather travel shoes instead of the more comfortable, packable, and casual suede ones.

Warm weather trips make it easier to pack light because you aren't bringing as many layers and your clothes will generally be made from lightweight materials.

This trip took place in the Summer of 2021 and lasted 11 days.

You have to stop constantly to enjoy the views between Imerovigli and Oia.

Itinerary

  • 3 Days in Imerovigli, Santorini
  • 1 Night in Chora, Folegandros
  • 2 Nights in Agkali Bay, Folegandros
  • 3 Days in Adamantas, Milos
  • 1 Night in Athens

Transportation

We flew into Santorini, took ferries between the islands, used taxis and buses on the islands, and then flex back into Athens. We took a boat trip while on each island.

Activities

  • Boat Tours: We took a boat trip on each island; one was a laid back catamaran with wine and sunset views, one was a small boat we had to ourselves and involved snorkeling into some caves and visiting remote beaches, and one was a larger all-day boat tour to several spots on the island only accessible by boat.
  • Light Hiking: The walk from Imerovigli to Oia is a bit of a hike and invovles some steep paths of loosely-packed rocks.
  • Wine: We enjoyed a few bottles of Greek wine at vineyards, restaurants, on boats, and lounging on the beach.
  • Swimming & Beach Days: Relaxing on a beautiful beach with the crystaline blue and green waters of Greece is a great way to spend a day.
  • Exploring: Each town in each island has something unique to offer and just wandering around in search of good food and good vibes is a great way to get to know the area.
  • Dining: We explored some of the best restaurants on each island. We experienced a delicious lunch that I still think about in a restaurant tucked into the alleys of Oia, dinner in what is basically a Greek grandmother's house turned into a restaurant with a small pantry and no written menu, a fantastic dining experience that kept us coming back to one restaurant with a handwritten menu in almost a dozen languages 3 nights in a row, and everything in between.
All packed and ready.

Packing List

Bags

  • Matador Beast 18L
  • Sea to Summit small dry bag

Shoes

  • Merrel Trail Glove 5 Leather in Black
  • Nissolo Travel Derby in Brown
  • Olukai Nalukai Leather in Brown

Outerwear

  • Relwen Windsurf Pocket Crew in Seafoam
    • A sweater in Greece in the Summer probably sounds ridiculous, but this lightweight one from Relwen was perfect for sitting outside and enjoying some wine in the evening.
  • Chrome Industries Storm Salute Commute

Tops

  • Mission Workshop Long Sleeve in Blue
  • Proof 72 Hour Merino Henley in Navy
  • Proof 72 Hour Merino Henley in Stone
  • Royal Robbins Merinolux Polo
  • Chrome Industries Merino Henley in Navy
  • Chrome Industries Merino Henley in Gray
  • Hurley Dry Fit Lagos Henley in Ocean

Bottoms

  • Proof Kyoto Pants
  • Faherty All Day Shorts
  • Good Threads Shorts in Light Pink
  • Kahin Porto Boardshorts

Activewear

  • On Running Hybrid Shorts in Black
  • On Running Comfort Tee in Purple
  • On Running Socks

Basics

  • Hanes Polyblend boxer briefs
  • Vans no show socks

Accessories

  • Orion Leather Belt
  • Richardson Trucker Hat
  • Seiko PADI Turtle on metal bracelet
  • Knockaround Mount Evans

Technology

  • iPad Mini
  • Sony a6000 w/ extra battery
  • Anker PowerPort III 2 port GaN USB-C charger (w/ EU adapter)

Miscellaneous

  • Chrome Industries Merino Gaiter
  • Klean Kanteen Insulated 32oz Wide Mouth
  • Black Diamond Locking Carabiner
  • Eagle Creek Pack-it Clean Dirty Cube Large
  • KN95 Mask & Fabric Mask

Toiletries

This was all stuffed into a 1qt Ziploc Freezer Bag and just fit into the top pocket of the pack for easy access going through airports

  • Razor
  • Deodorant
  • Toothbrush with integrated toothpaste tube
  • Duke Cannon Solid Cologne (Bourbon)
  • ThinkSport SPF 50+ Sunscreen in an Eagle Creek Pack-It Silicone travel tube
Lunch at To Spitiko in the town of Chora on the island of Folegandros.

Lessons Learned

I can pack less.: I can fit a lot more than I thought into a lot less space. I originally had a 34L bag fully packed, but then my partner wanted to downsize from a rollaboard and asked if they could borrow my 34L backpack, so I decided to challenge myself to reduce my pack size, too.

Good socks are worth so much.: I needed a quicker-drying more odor-resistant sock that I could wash and dry overnight, but every other "no show" that I had tried was either too tall or slid down my heel all day.

Always triple-check the weather; give it one last look the morning of your flight, too.: I always try to be prepared for rain so it won't ruin my day, but it turns out that was highly unlikely in this case. It also got so hot from the unexpected heat wave that even in shorts, flip-flops, and a lightweight henley, I was drenched in sweat. It was hard to get my clothes clean enough to not stink by the end of the trip.

More is okay sometimes.: If I hadn't slightly overpacked, I would have been a sweaty, smelly mess by the end of the trip. Having a couple of shirts and a pair of shorts more than I thought I needed was a blessing in disguise.

Backpacks are better.: Ferries, shuttles, and taxis are so much easier to deal with when you're only carrying a backpack. You can keep your pack with you and not have to deal with the chaos of trying to get your luggage out of the massive pile that builds up on the ferries.

I'm lazy.: I brought some running shorts and a top to pair with my trail runners and head out for a run, but that never happened. I think I need to look at the Strava Global Heatmap before a trip and actually plan a route because having to plan it in the moment gives me too many excuses to skip a run.

Olukai's are impressive.: I've never worn a more comfortable sandal and I've never had one that I would have felt comfortable scrambling on rocks in, but these Nalukai sandals are awesome. The medium brown leather looks nice, too.

Agkali Bay is one of my favorite beaches ever. The mask I'm wearing on my arm here was necessary at seemingly random times. Pandemic travel was weird.

Highlights

There was so much to love on each island, but here are a few of my favorites that I still think about years later.

  • Sunset: Greek sunsets are spectacular and we watched the sunset every day. Each island has it's own vibe for sunset, from climbing up a paved path of switchbacks to the Church of Panagia in Folegandros with the rest of the town to everyone pausing for a few minutes wherever they happen to be in Santorini.
  • Roka: If you've found yourself in Oia on the island of Santorini and the crowds are a bit much, look for a little sign near an alley that says "Roka" and start following it. You'll be lead off the main drag and down a few side streets, and the meal you find at Roka will be amazing. It stays pretty busy, so be sure to secure your table ahead of time.
  • Hatzidakis Winery: This is the best Greek wine I've ever had, and some of the best wine I've had in general. Hatzidakis make organic wines and put a lot of effort into respecting the natural landscape and native flora. Skip the big wineries and check out this hidden gem.
  • Kleftiko: This otherwordly rock formation with a unique history on the southwestern edge of the island of Milos was absolutely stunning. If you're in Milos, be sure to arrange a boat tour that stops here. There are so many amazing places in Milos, but Kleftiko was the most impressive.
Klekftiko is stunning.