Two-Week Itinerary for Italy & Santorini

Ever since my husband and I got engaged, we’ve been dreaming about an extended honeymoon somewhere in Europe. We’ve both traveled to Europe separately, but couldn’t wait to experience its magic together. I spent four years in Paris growing up and planned a trip to Barcelona after graduating from college, while he had studied abroad in Madrid. With our hectic schedules, we couldn’t make a honeymoon work right after the wedding, but boy was it worth the two-year wait.

We explored a couple different countries while researching for our trip, and almost decided against Italy. We were worried it would be too touristy, and it just felt so cliched to travel to Italy for our honeymoon after seeing so many of our friends doing the same. We’ve both also been to Italy during our younger years, and considered traveling somewhere more off the beaten path. Alas, our love for fresh pasta, vino and Italian culture was too strong, and I’m SO glad we decided to spend the majority of our trip in Italy. It’s simply exquisite. Santorini has always been at the top of my bucket list, so I convinced my husband to spend the last few days of our vacation there since we were going to be so close. I definitely need to plan a separate trip to Greece to experience its culture in its entirety, but we’re incredibly grateful that we got to spend a few days in Santorini during our honeymoon. It is beyond words.

Here’s how we laid out our two weeks in Italy & Santorini. September is the perfect time to visit Italy, because it’s at the end of tourist season and the weather starts to cool down ever so slightly (but still warm enough for beaches). We wanted to get a good feel for the country by visiting a variety of different cities, but we also didn’t want to be overwhelmed by packing our bags every 1-2 days. We wanted a good mix of beach towns, wine country, big cities, culture and adventure with things to constantly do. We like to be on the go when we’re on vacation rather than beach bumming for a week straight, so this itinerary worked really well for us and gave us a sense of places we want to visit again for a longer period of time. We also LOVED all the hotels/B&Bs that we stayed at, so I’ve linked details to our accommodations. Okay, enough rambling – here we go!

  • DAY 1: Fly into Naples, rent a car (with a driver – you don’t want to be driving on your own here) and drive directly to the picturesque town of Positano for two days. We’re not huge beach people and wanted to spend more time in other places in Italy and in Santorini, so we decided to spend all our time in Positano rather than town-hopping around the Amalfi Coast.
    • Positano accommodation: Villa La Tartana  (cute little no-frills B&B steps away from the Spiagga Grande)
    • Tip: Visit Le Sirenuse for a gorgeous view of Positano’s colorful homes. Rent a private speed boat at Spiagga Grande (super affordable for just an hour or two) for the most breathtaking and luxurious views of the Amalfi Coast. You can drive around the coast with a bottle of Prosecco, visit private beaches, and go swimming. The views of Positano from the boat just can’t be beat.
    • Foodie highlights: We weren’t super adventurous with food in Positano because we were there for such a short period of time but we liked Chez Black for fresh seafood and a stellar waterfront view. Yes, it’s super touristy and on the pricey side, but worth it for one meal.
  • DAY 2: Positano – sight seeing, beach bumming
  • DAY 3: Positano in the morning, then take a car back to Naples and a train to Florence
    • Florence accommodation: Le Stanze di Caterina (steps away from the Duomo with beautiful, art-inspired rooms)
  • DAY 4: Florence – sight seeing (Uffizi Gallery, Scuola del Cuoio – Florence’s leather school with amazing leather products, and sunset at Piazzale Michelangelo)
    • Foodie highlights: Osteria Santo Spirito for a more local feel and Trattoria ZaZa for unbelievable truffle pastas.
  • DAY 5: Florence – sight seeing till the late afternoon (Mercato Centrale for fabulous lunch options and Accademia for the gorgeous David), then rent a car to drive to Tuscany
    • Tuscany accommodation: Fonte de Medici (We got an incredible deal through Jetsetter– the most gorgeous Tuscan villas EVER! A little remote, but totally worth it for the property)
    • Foodie highlights: Lamole di Lamole. Must visit for the most mouthwatering Florentine steak ever. Amazing spot.
  • DAY 6: Tuscany – wine tasting and visiting little Medieval towns
  • DAY 7: Tuscany/day trip to Siena
  • DAY 8: Tuscany, then drive to Rome
    • Rome accommodation: Augustana House (Super clean, no-frills B&B located on a quieter, less touristy part of the city. Nicest staff!)
    • Foodie highlights: We arrived in Rome with pretty low expectations (“It’s too hot! Too touristy!”) but we absolutely LOVED the city. The food in particular was absolutely stellar; the best we had in the country. Highly recommend following Romewise.com for restaurant suggestions and making reservations EARLY – I’m still dreaming about my pasta dishes from Osteria del Sostegno and Roberto e Loretta. Rome is heaven for pasta, bacon and tiramisu lovers. Mmm!
  • DAY 9: Rome – sight seeing (Trevi Fountain and the Caesar Shuffle – Colosseum, Roman Forum, and Pantheon)
  • DAY 10: Rome – sight seeing (the Vatican – absolutely incredible)
  • DAY 11: Rome in the morning, then flight to Santorini
    • Santorini accommodation: The Majestic Hotel (just outside Fira)
    • Tip: Best way to explore the entire island is by renting an ATV! So much fun, and you come across so many lovely little private beaches with family-owned seafood restaurants. Some of the spots we stumbled upon were just magnificent. Santorini is too beautiful for words.
  • DAY 12: Santorini – sight seeing (Sunset Cruise)
  • DAY 13: Santorini – sight seeing (exploring the towns of Fira, Imerovigli, and Oia)
  • DAY 14: Santorini, then flight back to the U.S. via Rome

Sigh, can I please go back already? Hope this itinerary was helpful for your planning – leave me a comment if you have any questions! And just so this post isn’t ALL words, here are some of my favorite pictures from our trip:

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The adorable town of Positano in the Amalfi Coast

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Sunset in Florence from the Piazza Michelangelo 

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View of Firenze from the Uffizi Gallery

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Rolling hills of Tuscany. View from Fonte de Medici. No words. 

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Trevi Fountain, Rome

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Santorini views from Imerovigli 

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Sunset at Oia, Santorini

Travel Diaries: Kauai

The lush, amazing, beautiful Garden Island of Kauai was Part II of my recent Hawaii adventure. If you haven’t read Part I yet, go read it first!

While Maui was all about family, Kauai was perfect for some alone time with my husband. I knew that Jurassic Park was filmed here, so I was expecting greenery, but was still completely blown away by how visually stunning this island is. I’m talking palm tree after palm tree, gorgeous waterfalls everywhere, and the most unbelievable scenery I have ever seen in my life. It’s true what they say – Kauai is just the prettiest.

We stayed at a vacation rental at the Hanalei Bay Resort, which we absolutely loved. It looks like a five star resort with a beautiful lagoon-style pool, has the most stunning views of Hanalei Bay, and shares its beach with the St. Regis (minus the St. Regis prices). I mean, you really can’t beat that. Every night, we would pour ourselves a glass of white wine, sit on the hills facing the bay and enjoy the most spectacular sunsets. I so wish we could be back there!

I’m so excited to share some of my favorite images from the trip – it was incredibly difficult to edit these down, because every part of Kauai is so picturesque. These pictures do a great job of highlighting some of our favorite things about the island – Hanalei Bay sunsets, hiking part of the beautiful Napali coast, kayaking to the secret waterfalls, feasting on incredible sushi, and just the sheer amazingness of Mother Nature.

The beautiful grounds at Hanalei bay resort
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Admiring the bay at sunset, just steps away from our room at the resort…truly breathtaking. 

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The view from St. Regis’s outdoor patio – an amazing place to grab a glass of champagne right at sunset

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We hiked the first two miles of the Napali Coast. The full 11 hike mile is considered to be one of the most scenic (and dangerous) hikes in the country and requires overnight camping and permits. The first two miles to a secluded beach is supposed to be the “easier” portion, but it was still challenging for me – lots of ascending and descending on muddy trails with absolutely stunning views. Many hikers do an additional two miles to the waterfalls, but this takes the entire day. We were plenty satisfied with our three hour adventure and recommend this for less experienced hikers.

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I mean, just look at those turquoise waters – just gorgeous! We were lucky to do this hike on a clear, sunny day. 

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The delicious sushi burrito from Sushi Girl! A must visit for anyone visiting Kauai- it’s a little hole in the wall stand en route to the Napali Coast with the freshest selection of take out sushi. We went here three times in four days – that’s how good it is (plus the food selection in Kauai is pretty limited). Especially good after hiking. 

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Our third day in Kauai, we signed up for a kayaking tour with Ali Kayaks on the Wailua River. This consists of fairly easy and relaxed kayaking for two hours, a moderate hike through a VERY muddy rainforest, and splashing around in a pool by the beautiful secret waterfalls that’s only accessible by kayaking. Such a fun morning adventure!  

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Lazing around on Hanalei Bay beach on our final day in Kauai 

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Shave ice from Hee Fat, considered to be the best ice on the island! I had no idea what to expect, but this stuff is AMAZING. We got the strawberry and coconut real fruit syrup with macadamia nut ice cream on the bottom. So, so good. 

Hope you enjoyed this peek into our Hawaii trip! Be sure to follow me on Instagram @mrsgcg if you’d like to see more snapshots from our trip. And don’t hesitate to leave a comment if you have any questions or need advice about traveling in Maui and/or Kauai.

Travel Diaries: Maui, Hawaii

Aloha! I just got back from an incredible eight-day trip to Hawaii (four days in Maui, four days in Kauai), and have never felt more refreshed and rejuvenated. Aaand…depressed about being back in concrete jungle Chicago. I. love. the. island. life. Take me back already!

This was my first trip to Hawaii and my expectations were set pretty high, for obvious reasons. Having spent much of my formative years in Indonesia, I felt completely at home in the tropical climate the minute we landed in Maui. The warm air, the exquisite greenery, the dynamic landscape–I just couldn’t wait to soak it all up. The Maui leg of the trip was spent with my immediate family to celebrate my dad’s 60th birthday, so it made the whole experience all that more special. My parents and brother love traveling as much as we do, and we were adamant about making the most of our four short days on the island.

In no particular order, I’ve recapped my top five moments in Maui below. Not featured but also deserving special mention: sipping on Mai Tais and listening to the sound of crashing waves from our Maalaea Banyans lanai every night, sunset dinner at Kimo’s, and just the beautiful quietness of island life. Such a necessary break from a busy, stressful summer.

The Old Laihana Luau: Rated one of the best and most authentic luaus on the island, the Old Laihana Luau was a fantastic family experience. We booked the luau for my dad’s actual birthday, and it was the perfect celebration. Gorgeous venue right by the water with a spectacular sunset view, incredible service, traditional Hawaii cuisine (which was pretty good for a buffet meal), fabulous entertainment, and an open bar. All for hundred bucks per person. Not a bad deal and definitely worth it, especially during your first few days on the trip to really get in the Hawaiian state of mind.

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The feast at Old Laihana Luau: Fried rice, roasted pork, mahi-mahi, ahi poke, and stir fry veggies

Snorkeling on Kaanapali Beach: I’m a snorkeling newbie, so my husband and I were really, really excited to to check out Maui’s beaches. We didn’t want to waste a whole day on a snorkeling trip (though I now regret not doing Molokini Crater), but we heard that Kaanapali Beach’s Black Rock is perfect for a quick morning snorkeling dip. We had so much fun swimming side by side and saw a ton of little colorful fishies, including a baby sea turtle! It was amazing and an experience I’ll never forget. I just wish we had a GoPro!

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The unfiltered beauty of Kaanapali Beach – no underwater pictures, but you can see the Black Rock in the distance

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Giddy after encountering a baby sea turtle!

Road to Hana: Road to Hana is probably the most popular drive in Maui – I have major motion sickness and can barely drive, so I didn’t think I would enjoy the long, winding roads as much as I did. With some Dramamine in tow and my road trip-loving husband behind the driver’s seat, the entire fam left early in the AM for the spectacular journey to Hana. As my dad kept saying “it’s about the journey, not the destination” because the various stops along the way are just awesome. My favorite stop was the black sand beach at Wai’anapanapa National Park – we even brought home a lava rock for our home 🙂 Nature is so freaking cool, especially in Hawaii.

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Salted caramel coconut ice cream from Coco Glen, the cutest little stand on the Road to Hana. So delicious and necessary after the winding roads.

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Feelin’ victorious after reaching the black sand beach!

Sunrise at Haleakala Crater: This was actually a little disappointing for us, because the morning we decided to make the one hour drive up to Haleakala Crater was a foggy one and we didn’t see the full sunrise that most tourists rave about. BUT, the experience is still one that I’ll fondly look back on – we all woke up at 2:30 am, bundled up in sweaters and blankets (it’s 40 degrees up there, especially in the early morning!) and drove up to the crater in eager anticipation of sunrise. The atmosphere was really cool and we felt like we were floating in the cloud with other freezing cold tourists. If we could do it again, I’d go for sunset or check it out during the day so you can actually see the crater. Oh, well.

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…Ahi Poke: Is it weird that one of my top five moments is food-related? If you know me at all, then no. One of our first meals on the island was at Maui Fish Market, after snorkeling on Kaanapali Beach. The food options in Maui and Kauai (especially in Kuauai) are limited–at least compared to big cities in the mainland–but the seafood is incredible. We feasted on baja fish tacos, shrimp, and AHI POKE. Maui Fish Market is where we first tried ahi poke, and it became our standard go-to meal for pretty much the rest of the trip. You just can’t beat that fresh island taste. Nom nom.

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So. fresh.

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Mahi-mahi sandwich. Drooling again.

Hope you enjoyed the pictures and stay tuned for my Kauai post, coming next!