Sydney Hubbard
I’ve spent a lot of time traveling around Greece, from sailing between islands to exploring some of the quieter places that don’t always make the typical itineraries. That firsthand experience, along with lots of behind-the-scenes research, helps shape the trips I design.
I really enjoy the planning process and helping make a big trip feel manageable and exciting. I’d love to help you plan a Greece adventure that feels just right for you! 🇬🇷💙
How did you get involved in travel?
"I really fell in love with travel right after high school, when I challenged myself to visit one new country every year. I’m 15 countries in now and definitely not slowing down.
I’ve traveled solo, with friends, and spent years planning trips for the people around me. At this point, I’m the default travel planner in my group. What keeps me excited about travel is how much it gives back on both sides. I’ve seen how thoughtful, sustainable tourism can directly support local communities, and I’ve also felt how stepping into new cultures shifts your perspective in ways that stick with you.
For me, travel is really about connection, between people, cultures, and those small, meaningful moments that stay with you long after you’re home."
Please share a unique travel experience you will never forget.
"On my last trip to Greece, one of my favorite surprises was a day trip to Aegina, known as the pistachio capital of the country. We visited a small, family-run farm that’s been passed down for generations, and it was my first time seeing pistachios growing in real life. I had no idea how much hands-on work goes into cultivating them.
The family explained how Aegina’s soil and climate are what make these pistachios so special, and then came the fun part: tasting. Pistachio pesto, brittle, baklava… and the standout was the pistachio butter.
It’s now my top recommendation for a Greek souvenir (so delicious and easy to bring home!). If you love pistachios, Aegina is one of those underrated stops that’s absolutely worth it."
Sydney's favorite itineraries and travel advice
Top itineraries and travel advice
With 10 days in Greece, you can choose between an island-hopping adventure, a historical highlights tour, and a fast-paced road trip itinerary. The islands of Santorini, Naxos,...
Cyclades, Saronic, Dodecanese, Sporades: to plan an island-hopping trip around Greece, you'll need some background on each of the island groups. Read on to learn what to expect,...
Family itineraries
Bring the whole family for 13 days of exploring the ABCs of Crete with this itinerary. After discovering the myths of the Acropolis in Athens, you'll fly to Greece's largest...
Get out into the Greek islands with your school-age children on this 10-day trip. You'll start with an introduction to some of the country's most famous myths and landmarks in...
Luxury itineraries
Ten days in Greece is an excellent amount of time to delve into a highlights tour that features Athens, Crete, and three picturesque Cyclades islands. You can also cater the...
This lavish 10-day exploration of Greek food and wine starts in Athens, where you'll stroll through historic neighborhoods and visit the towering Acropolis. Then, you're off to...
Road trip itineraries
Honeymoon itineraries
Dive into pure luxury on this romantic escape to Greece. Start in Athens, where you'll stroll through the charming neighborhoods of Plaka and Psyrri and cruise the hidden coves...
Greece is one of the most irresistible honeymoon getaways on Earth. Relax on Europe's best and most diverse range of beaches on one or more of the nation's 6000-odd islands,...
Recent trip reviews for Sydney
A three generations family trip to Greece...
Greece
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May 30 - Jun 9, 2026
Mark,
Thanks so much for your kind words! I love hearing that the trip was a great fit for all three generations + that the Naxos farm visit/cooking class was a family favorite! I’ve done that one myself and loved it too, so it’s always extra fun when travelers connect with it as much as I did. It was such a pleasure helping plan your family’s time in Greece! 🩵
Our Amazing Trip to Greece
Greece
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May 23 - Jun 1, 2026
Aaron,
I’m so glad you were able to experience such a beautiful mix of Athens, the islands, and Crete, and that the private experiences helped make the trip feel extra special. I'm excited to see where you and Cher go next! 🩵
Exceptional diverse trip to Greece
Greece
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May 17 - May 27, 2026
Thank you, Susan! It's great to hear you had such an amazing experience with your guides. Having knowledgeable local guides really makes such a difference when traveling, so I love hearing this feedback 🩵
Overall, we had an amazing trip! Everyone was...
Greece
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May 19 - May 27, 2026
Rana - thank you for taking the time to leave a review. I’m really happy to hear you overall had such an amazing trip and found the itinerary easy to follow!
I’m really sorry to hear about the frustrating situations with the Mykonos transfer and the unexpected power outage in Santorini. Thank you for bringing these to our attention. We’ll be reaching out to both the transfer company and hotel directly to better understand what happened during your trip and help make sure future travelers don’t run into similar issues.
Thanks again for trusting myself and kimkim with your Greece trip 🩵
We were paired with Sydney as our Greece spec...
Greece
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May 4 - May 14, 2026
We were paired with Sydney as our Greece specialist. It was the trip of a lifetime and I can’t stress how great Sydney was! EVERY place we stayed was in the perfect area. EVERY tour we went on was amazing! EVERY ride showed up right on time! We couldn’t have used a more knowledgeable and helpful planner. Perfect to a tee. Already thinking about what other country we will use KimKim for. Can’t wait!
Thank you so much, Bill! I’m happy to hear you had such an awesome trip. It was a pleasure helping you plan everything, and I’m glad all the hotels, tours, and transfers worked out so smoothly for you guys. Can’t wait for kimkim to help with the next adventure whenever you’re ready! 🇬🇷💙
Spectacular Trip to Greece
Greece
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May 5 - May 15, 2026
After arriving in Athens on Day 01, we rested briefly in the hotel and took pictures of the view out the window. It took us a day to confirm that we were seeing the Acropolis – but not the Parthenon because a building rose to... Read more
Regis,
I loved reading through your daily reflections (I can picture it all through your storytelling!). I’m so glad Lana’s birthday trip was a success and that so many experiences were highlights for you both. It was a pleasure helping bring this trip to life! 🩵
Sydney
Where do I begin? From the very start of the ...
Greece
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May 5 - May 15, 2026
Lana,
Thank you for such a thoughtful review. One of my favorite parts of this job is creating trips that feel highly customized to each traveler, so hearing which moments stood out to you both means the world! It sounds like you and Regis truly embraced Greece in the best way. Thank you for letting me be even just a small part of it 💙
Sydney
Amazing Vacation!
Greece
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May 4 - May 14, 2026
Kristina,
I’m so happy to hear the trip felt seamless and that everyone found something they loved. From the food experiences to the history and time on the water, you guys experienced everything I love about Greece! Thank you for trusting me with such a special trip, and I’d love to help with your next adventure someday! 🩵
Sydney
Fabulous Greece trip!
Greece
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Apr 29 - May 8, 2026
We loved every place we visited
The rooms were all great and located in the heart of things easy to get around. All breakfast that was included was great except our place in Santorini could have been improved it lacked in... Read more
Tricia,
It was such a pleasure helping plan your Greece adventure. I’m so glad the weather hiccup in Santorini didn’t keep you from enjoying that sunset cruise, and that your guides, hotels, and experiences made the trip so memorable. Thank you again for trusting kimkim. We’d love to help you plan your next adventure! 💙
Sydney
We fell in love with Greece after we met Geor...
Greece
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May 3 - May 10, 2026
Patty,
Thank you for your kind words! It was a ton of fun planning your Greece adventure together.
Local guides can make such a meaningful impression during travel, especially when they share a personal love for their country and it's culture. Thank you again for trusting us with your travels, and I hope we'll have a chance to plan more together soon!
Sydney