Pour yourself a cup of coffee or tea and come travel with Tim and me through our beautiful celebration vacation.
Boston • Sicily
Celebrating 70 in the Best Way Possible
What an unforgettable three-week adventure we had celebrating my 70th birthday! Our original plan was to go to Greece however the logistics of going to Greece and then to Paris became challenging. We decided on Sicily for the diverse culture, the most Greek ruins in one place and the ease of travel — not too much time on planes or ferries. It turned out to be an incredible choice, driving ourselves around this beautiful island.
We started our travels celebrating with friends, which made the beginning of our trip so much fun. Then we were off on our own to discover new places we had never been to before. From the breathtaking coastlines of Sicily to the charm of the French countryside. Every stop was filled with incredible food, beautiful scenery, wonderful friends, and memories we’ll treasure forever.
It felt like the perfect way to welcome this new decade of life.
I’ll be sharing the first half of our travels in this blog of Boston and Sicily of our favorite restaurants, hotels, day trips, travel tips, and a few “lessons learned” that might make your own travels a little easier.
Packing for 3-Weeks in a Carry-On…
I’m happy to report that everything I took in my Away carry-on I packed perfectly. I honestly did a great job and wouldn’t have changed much.
Here’s what worked beautifully:
Shoes
I brought
- Nice white sneakers
- Black sandals for evenings
- Casual Taos walking sandals
- Havana Flip-flops
- Water shoes for Sicily’s rocky beaches
- Altra shoes on planes and for long walks/hikes. LOVE.
Clothing
Packing pieces that serve multiple purposes is one of the best travel tips: The simple black dress worn to both the Boston wedding and to our elegant dinner in Paris was perfect!
Here’s what I packed:
- Plenty of white and navy t-shirts (although I definitely packed too many navy shirts—I reached for white almost every day!)
- Two casual short sleeved linen dresses
- Three linen blouses
- One pair of linen shorts
- One pair of hiking shorts
- Lightweight cropped white jeans
- My favorite everyday Ruti pants
- One pair of dressier Ruti linen pants
- A sleeveless linen top by Ruti
- Vuori travel joggers
- Organic Black wide-leg travel pants and sweater by PACT worked beautifully on flights and for dinners.
Beach & Evening Essentials
For beach days and relaxing by the pool, I packed:
- Swimsuit
- Beach cover-up
- Foldable sun hat
- Lightweight sweatshirt
For evenings:
- Mid-length black sweater
- Shawl + 2 neck scarves
- Small Kate Spade gold handbag
These few pieces easily dressed up casual outfits and worked for everything from elegant dinners to leisurely lunches.
The Little Things
I packed:
- One pair of cotton pajamas
- 14 pairs of organic cotton underwear. Love Pact undies!
- Eight pairs of socks (many tucked inside my tennis shoes!)
- Three bras- 1 organic “airplane” bra from Pact. I LOVE this bra so much I’ve been wearing it at home!
Once we reached our home in France, I washed underwear and socks using laundry detergent sheets I’d packed. They took almost no room and were incredibly handy.
What’s in My Backpack?
My backpack is my travel command center.
Inside I carried:
- Three weeks of vitamin packets
- My emergency health kit (I’ll share everything that’s inside below!)
- Toiletry bag
- Makeup + hair clips and ties
- Phone cords
- Travel water bottle
- Reusable compact shopping bag
- Compression socks
- European travel blow-dryer
- Journal and pens
- Printed itinerary with hotel addresses and phone numbers
- Umbrella
- Playing cards
- Farkle
- Travel backgammon
I carry my bag with food as if I bought it at the airport so they don’t bother you along with my cross-over anti-theft travel bag.
What’s in my Food Bag?
Traveling gluten-free always requires a little planning.
Normally I pack enough food for long international flights because I never know what will actually be available.
I brought these snacks: Elemental Superfood Bars, Perfect Bars, Siete Dip chips, Mamana Tempeh Chips.
I made a wrap to bring on flight to Boston: Used Largest Coyotas wrap.
This trip surprised me.
British Airways did an excellent job with gluten-free meals. We actually found it worked better not to preorder. The flight attendants had complete ingredient lists available, and every meal we received was clearly labeled.
That said…I’m still glad I packed backup snacks “just in case.”
Because, as you’ll soon read…
Sometimes travel doesn’t go exactly according to plan.
And sometimes…
Neither does pizza.
One travel habit that came in handy
On our last leg of our travels home! I always carry an extra t-shirt, leggings, underwear, and a fresh pair of socks in my backpack.
That little habit paid off when we missed our connecting flight on the way home after checking our carry-on bags. Having a clean change of clothes made an unexpected overnight stay so much more comfortable.
First Stop: Boston
Our adventure began in Boston as we celebrated the wedding of our dear friends’ daughter. What a joyful weekend! Even though it rained on the wedding day, it didn’t dampen the celebration. Spending time with lifelong friends made the weekend extra special. We had so much fun walking the Freedom Trail and visiting the Isabella Stewart Gardner Museum! We also took a beautiful walk around the Wharf District and Boston Gardens, the Back Bay. While everyone else flew back to California, we waited to board the evening flight to Sicily. While waiting, we visited Boston’s great Aquarium. We packed in a lot on 3 days!
We stayed at the Boston Harbor Hotel. Of course, we also made it our mission to find great gluten-free restaurants. Some were absolutely outstanding…others, not so much! The restaurants that truly understood gluten-free dining are definitely worth sharing because they’re gems for anyone traveling with food sensitivities.
Our favorite restaurant that we ate at for dinner was just down the street from the hotel, it was NEBO Enoteca. So good, especially their fried calamari!
Next day’s lunch, we had delivered the most delicious gluten free Lobster Roll and Boston Clam Chowder from Luke’s Lobster restaurant!
Sunday morning, we all got up early and walked to breakfast at Cafe Bonjour, a family owned restaurants in downtown Boston. The food was delicious and the father and daughter were just so accommodating, kind, and adorable, they couldn’t do enough for us. Plus they have a great menu gluten free or not!
Off to Sicily…
One of the biggest advantages of starting our trip on the East Coast was how easy it was to fly to Europe. From Boston we took a short overnight flight to London, followed by another flight to Palermo, Sicily.
Surprisingly, jet lag never really caught up with us while traveling. This is what I took to help with jet lag.
The Weather Couldn’t Have Been Better
Travel timing is everything.
We arrived just before the record-breaking heat wave that swept through Italy and France. For almost our entire three-week trip we enjoyed beautiful temperatures around 80°F (26°C), sunny skies, and cooler evenings.
It honestly couldn’t have been more perfect.
Our First Stop Palermo
After our five-hour layover in London (the lounge food wasn’t anything to write home about, although they did have gluten-free bread!), we boarded our British Airways flight to Palermo.
We landed around 7:00 p.m., where our hotel had arranged a driver to meet us at the airport. It was such a nice way to begin our Sicilian adventure—no worrying about directions or transportation after a long day of traveling.
Our arrival to Sicily was the best possible first impression for a new city experience. Our first two nights in Palermo, we stayed at Palazzo Sovrana Boutique Hotel, and I couldn’t have picked a better location. Our spacious room overlooked the beautiful Teatro Massimo, Palermo’s famous opera house, and we were only about a 20-minute walk from the train station.
The icing on the cake?
The hotel’s rooftop restaurant, DOBO.
The hotel staff highly recommended it, and wow…what an introduction to Sicily!
Our dinner began at 9:00 p.m. as the sun slowly set over Palermo, colorful lights lit up the theatre and a beautiful orange moon began rising in the opposite sky. It couldn’t have been more magical.
Chef Domenico Basile welcomed us with warmth that immediately made us feel at home. Once he learned we were both gluten-intolerant, every course became a personal labor of love.
As the evening unfolded, he came to our table several times, sharing stories about Sicilian cooking, his family, his passion for cooking and each beautiful dish he had prepared. We lingered over dinner until nearly midnight.
It wasn’t just one of our best meals in Sicily…
It was one of our most memorable dining experiences of the entire trip.
A true gastronomic symphony.
Cefalù
Sicily’s National Holiday
The next day we took an early train to the small beach village of Cefalu. It happened to be a National Holiday, Day of Republic so we hopped on a 7am train and enjoyed a few hours of quiet before the crowds came. That was a great decision.
In Cefalu we got amazing gluten free sandwiches at La Cefalu Nostrana with the freshest ingredients! We lounged on the beach, swam in the ocean and explored the town. And of course we ate gelato and a gluten free cannoli. Highly recommend a visit or a longer stay here!
Simple.
Fresh.
Perfect.
One Perfect Beach Day
Sometimes the best days aren’t filled with sightseeing.
Sometimes they’re filled with…
Absolutely nothing.
We rented loungers.
Read our books.
Floated in the crystal-clear Mediterranean.
Warm sunshine and Backgammon…
And yes…
Gelato and Canollis.
It doesn’t get much better than that.
If I had one piece of advice about Cefalù, it would simply be this:
Don’t rush.
There isn’t a checklist here.
The town itself is the experience.
Back in Palermo
We took a relaxing jacuzzi tub before walking to dinner at Trattoria Corona. Another excellent gluten-free recommendation.
One thing we noticed quickly while traveling throughout Sicily was how similar many restaurant menus were. Most offered wonderful fresh fish, a beef, a pasta, and endless plates with tomatoes and burrata or ricotta.
Delicious?
Absolutely.
But I’ll confess…
By the end of ten days, I was dreaming about a big green leafy salad with lettuce!
Thankfully, Chef Domenico at DOBO had spoiled us on our first night by preparing the most beautiful salad we’d had in Italy.
Cooking with “The Duchess”
One experience I’d been especially looking forward to was spending the morning with Nicoletta—known affectionately throughout Palermo as “The Duchess.”
Friends had recommended her.
Rick Steve’s recommended her.
The reviews were glowing.
Sometimes, though, travel teaches us that even highly recommended experiences don’t always become our favorites.
Nicoletta welcomed us warmly into her historic family villa, and hearing the stories of the home and gardens was fascinating. We visited a few market vendors she knew personally before returning to her beautiful kitchen to prepare lunch together.
Was it enjoyable?
Absolutely.
Was it everything I’d imagined?
Not quite. She was simply having an off day.
I had envisioned wandering through Palermo’s bustling outdoor markets, discovering local produce and seafood while soaking in the energy of everyday Sicilian life. Instead, the market portion felt rather limited.
Travel is like that.
Even wonderful experiences don’t always unfold exactly as we imagine.
Sometimes the places you don’t see become the reason to return.
If I were planning this trip again, and had limited time in Palermo, I would probably skip the cooking class and head to Monreale, just twenty minutes outside Palermo. The cathedral there is world-famous for its breathtaking gold mosaics, and I was sorry that we missed it.
If you’re visiting Palermo…
Put Monreale on your list.
Castellammare del Golfo
After our cooking class, we picked up our rental car from SixT, and I have to say—it was a wonderful experience. We were given a brand-new Volvo that was a dream to drive.
Soon we were off, excited to begin exploring more of Sicily.
By mid-afternoon we were winding along the coastline toward Castellammare del Golfo.
Almost immediately, the pace of life slowed.
Our next stop was the charming seaside village of Castellammare del Golfo where we stayed at the delightful Hotel Cala Marina. This sweet little hotel sits right on the harbor, and it couldn’t have been a prettier introduction to Sicily’s coastal villages.
After checking in, we wandered up the ancient stone steps into the old town. The views overlooking the harbor were absolutely beautiful. Families filled the piazzas, children played, and everyone seemed to be out enjoying the warm evening at 10 pm. There was such a wonderful feeling of community everywhere we went.
Dinner that evening was one I’d been looking forward to. Grani.Da Re Pizza e bottega had excellent gluten-free reviews, even celiac friendly. After talking with the staff about our gluten intolerance, we felt a sense of comfort that the staff understood.
Tim’s gluten-free pizza arrived first. It was delicious! My pizza followed shortly after. Everything looked perfect.
Unfortunately, one simple mistake happened—I forgot to ask the one last question when the pizza arrived.
“This is the gluten-free pizza…right?”
Instead, caught up with excitement, I happily dug in.
A few bites later, Tim looked at my pizza, then looked back at me.
“I don’t think that’s gluten-free.”
My heart sank.
Sure enough…
It wasn’t.
UGH! I was so disappointed, and truthfully got a bit freaked out.
Thankfully, after calming myself down, I reminded myself that I had packed everything I needed to help support my body. More about what’s in my travel emergency kit later—because it truly saved me during the rest of our trip!
Instead of letting it ruin our evening, we took a slow walk through the village beneath a warm, star-filled Sicilian sky while Tim happily enjoyed a gelato. (I wisely decided to skip dessert that night!) It turned out to be a peaceful ending to a day that hadn’t gone exactly as planned.
The one item that’s been especially helpful for me is Nux Vomica 30C, a homeopathic remedy I use after, overeating, digestive upset while traveling or in this case accidental gluten exposure.
I also bring anti-inflammatory supplements, electrolyte packets, and know to drink plenty of water to hydrate my intestines and help lessen the inflammatory response that I get…Painful Bloating.
Panicking never helps the body. Yes, I was so bummed. Yes, I let my guard down. And yes, I did get bloated most days after eating during the rest of the trip. I took my homeopathic remedy after most meals and still enjoyed every bite while away!
Travel can be unpredictable.
Being prepared lets us enjoy the adventure instead of fearing the unexpected.
Menfi
The next morning we enjoyed another wonderful breakfast overlooking the harbor before heading about an hour south to Menfi.
And then…
We arrived at La Foresteria Planeta Estate.
WOW.
Of all the wonderful places we stayed during our three weeks away, this may have been the one where we both looked at each other and said,
“I wish we had booked four more nights.”
This beautiful winery estate was everything we love—peaceful, elegant, yet rustic chic without being pretentious, surrounded by vineyards, with sweeping views all the way to the sea. It was exactly our cup of tea.
Our spacious room overlooked the vineyards, and after settling in, we headed to Selinunte. Excited for our first Greek Ruins!
Selinunte.
Time to explore one of Sicily’s many great treasures…
If you enjoy history, don’t miss it. It’s one of the main reasons we chose Sicily instead of Greece! It has more Greek ruins all in one place!
Walking among these ancient Greek ruins overlooking the Mediterranean was unforgettable. There is something incredibly humbling about standing where people walked thousands of years ago. The scale of the ruins is breathtaking, and the setting beside the sea makes it even more remarkable.
WHAT. A. DAY!
It was hot walking around the ruins, so once back at our hotel, we went directly to the infinity pool where we spent a wonderful time relaxing, swimming in the cool pool and reading…and enjoying one of our favorite travel traditions—a game of Backgammon.
That evening we dined at our hotel for one of the second finest dinners of our trip.
Nearly everything served comes directly from the estate or nearby local farms and fishermen. The vegetables were freshly harvested, the seafood was incredibly fresh, the wines were exceptional, and every course celebrated the flavors of Sicily.
One of the unexpected joys of travel is meeting people along the way.
That evening we met a lovely couple from Australia seated next to us. As we talked, we laughed when we realized we had planned almost the exact same itinerary—staying in a different town nearly every night, exploring during the day, and slowly making our way across Sicily.
By the end of dinner it felt less like we had met strangers and more like we’d made new friends.
Travel has a wonderful way of doing that.
The next morning’s breakfast was every bit as memorable.
Honestly…I don’t think I’ve ever seen a breakfast buffet quite like it!
The long dining table overflowed with beautiful fresh fruit, local cheeses, homemade pastries (yes—even gluten-free surprises!), eggs, breads, yogurt, and every delicious thing you could imagine.
We lingered over breakfast much longer than we normally would.
Some places simply invite you to slow down. La Foresteria was one of them.
If Tim and I ever return to Sicily—and I truly hope we do—this is the place where we’ll stay a little longer.
Agrigento – The Valley of the Temples
Eventually it was time to continue our adventure.
We packed the car and headed toward Agrigento, home to the spectacular Valley of the Temples.
Thanks to Siri, our drive became a bit longer than expected! She managed to send us well out of our way through the Sicilian countryside. Fortunately, the scenery was beautiful, so it wasn’t exactly a hardship. We learned Siri can make mistakes! We didn’t listen to our intuition!
By mid-afternoon we arrived at the Villa Athena Resort, one of the most unique hotels we’ve ever experienced.
The hotel sits inside the archaeological park, just a short walk from the ancient Greek temples. Looking out from the property and seeing these magnificent ruins rising in the distance was simply extraordinary.
We spent several hours walking through the Valley of the Temples. It was hot—but absolutely worth every step. The ruins are immense, beautifully preserved, and amazingly reconstructed…and unlike anything Tim had ever seen before. I spent time in Greece after college… I was so excited for him to experience these ruins!
After our walk, we happily returned to the hotel, changed into our swimsuits, and spent the rest of the afternoon relaxing by the pool while gazing toward the temples.
It was the perfect way to unwind.
Dinner that evening, at the hotel restaurant, was another highlight.
Exceptional food.
Exceptional service.
An unforgettable view.
And if you’re spending the night, don’t miss walking back through the Valley of the Temples after dark. Seeing the ancient ruins illuminated beneath the night sky is simply magical.
Some places leave you impressed.
Others leave you inspired.
Agrigento somehow managed to do both
Ragusa Ibla
Our next stop was the beautiful hill town of Ragusa Ibla, one of Sicily’s UNESCO World Heritage treasures.
We checked into our lovely Dimora Bonafede Ibla Design Rooms, a charming boutique hotel tucked into the heart of the old town. Even though the room was small, the view from our outdoor deck was spacious and wonderful! The people over seeing the rooms were so helpful and kind and had great suggestions as to what to see and where to eat too! From there, we spent the afternoon doing exactly what we love most—wandering and eating gelato!
Ragusa Ibla is built on a hillside, with narrow cobblestone streets, beautiful churches, hidden stairways, and breathtaking views around every corner. OMG the drive into Ragusa had us hysterically laughing. Who would have thought San Francisco’s hilly streets looked mild compared to Ragusa!
Because it was quite warm that afternoon, we decided to hop aboard the little tourist train that winds through town.
I’ll admit…
At first, we thought it looked a little silly—almost like something you’d find at Disneyland.
But…
It turned out to be one of the best decisions we made!
It gave us a wonderful overview of the town, helped us appreciate just how hilly Ragusa really is, and allowed us to discover places we later explored on foot.
Sometimes the “touristy” thing ends up being the smartest thing!
That evening we enjoyed a wonderful dinner at That’s A Moro, one of the best gluten-free restaurants we found in Sicily. If you’re visiting Ragusa, I highly recommend it.
Right next door is Trattoria La Bettola, another excellent choice. Both restaurants were warm, welcoming, and wonderfully accommodating for gluten-free dining.
It was another perfect Sicilian evening.
Breakfast the next morning was simple, however they outdid themselves with the abundance of gluten free breads and pastries! Oh MY!
Ortigia
The next morning, after another glorious breakfast at Hotel Ortegia, we met up with Chef Alessia, we went to the farmers market to find and pick up the ingredients for our cooking class. What I loved is that she allowed us to create our own menu cooking her family’s Sicilian favorites. We got to choose the fish, the vegetable and she insisted we make traditional arancini! It was so much fun! We made sardines, a special Mackerel, leafy greens that I’ve never cooked before and the rice balls! Oh what a wonderful experience we had!
Well…
Almost.
Siri had other plans!
Somewhere along the way she decided to send us on an unexpected scenic tour through the Sicilian countryside, adding nearly an hour and a half to our drive.
Thankfully, the scenery was beautiful, and by then we had learned that in Sicily, sometimes the detours become part of the adventure.
Before arriving in Ortigia, we stopped in the delightful town of Modica, famous throughout Sicily for its unique chocolate. It ended up being part of our detour thanks to Siri…
Our home for the next two nights was the Algilà Ortigia Charme Hotel, and we loved our hotel and our view of the ocean. We fell in love with Ortigia!
The location of our beautiful hotel couldn’t have been better, and if you stay there, do yourself one favor…
Don’t skip breakfast!
Honestly, it was one of the finest hotel breakfasts of our entire trip.
Our first evening included dinner at AreaM on the waterfront followed by a leisurely stroll through Ortigia’s charming streets.
This little island completely captured our hearts.
A Day We’ll Never Forget
The next morning became one of the true highlights of our Sicilian adventure.
We spent the morning on a family-owned farm with the wonderful Chef Alessia. We got to learn how to make traditional Sicilian ricotta from fresh goat’s milk! I was IN Heaven!
What an experience!
We actually got to make goat ricotta! We did the entire process, and while it was still warm, we tasted it. Then after our fun making ricotta, we had a fun olive oil samplings, visited with the goats and then had such a lovely picnic sampling all their incredible goat cheeses, yogurts, olive oils, wines, and meats, and learned so much about Sicilian farming traditions.
And then…
We visited all the goats and we got to hold two-day-old baby goats.
I was completely smitten.
If you’ve been reading my blog for very long, you probably know how much I love experiences like this. Being welcomed onto a working farm, meeting the people, learning their traditions, and sharing a meal together—that’s the kind of travel that stays with you long after you’ve returned home.
If this sounds like your kind of adventure…
Don’t miss it.
It was truly one of our favorite experiences in all of Sicily.
Reach out to Chef Alessia and see all her many wonderful offerings! alessia@smileandfood.com
Later that Afternoon at Sea
After returning to town, we decided to experience Ortigia from the water.
Alessia made a call to her friend, and we hired a small private boat with a local skipper. It was that easy! Before long, we were cruising along the island’s rocky coastline, exploring sea caves that glowed brilliant shades of blue.
Then…
We jumped in.
The Mediterranean was crystal clear, refreshing, and absolutely beautiful.
The crystal-clear azure blue water was thoroughly refreshing.
Tim later said this was his favorite experience of the entire trip, and I completely understand why.
It’s those simplest moments that become the ones we remember forever.
Our Last Day
The next morning, after another glorious breakfast at Hotel Ortegia, we met up with Chef Alessia, we went to the farmers market to find and pick up the ingredients for our cooking class. What I loved is that she allowed us to create our own menu cooking her family’s Sicilian favorites.
We got to choose the fish, the vegetable and she insisted we make traditional arancini! It was so much fun! We made sardines, a special Mackerel, leafy greens that I’ve never cooked before and the rice balls! Oh what a wonderful experience we had!
Taormina
After our last Sicilian cooking class, we packed up and drove to Catania airport to return our wonderful Volvo. Again, SixT made everything with our car so easy. A driver from Hotel Ashbee picked us up, and once we arrived, we were happy not to have our car in Taormina!
From the moment we arrived, it was easy to understand why people from all over the world fall in love with this spectacular hilltop town. What we didn’t know until we arrived was it was the start of Taormina’s International Film Festival! Crowded, yes, but we had fun walking in the street in the upper city of Taormina.
Our hotel was perfectly situated, just walking distance from town and outside enough from the busy-ness the film festival brought to town. We spent two wonderful nights at The Hotel Ashbee, a beautiful stunning family owned hotel overlooking the sea.
Our final day we went to visit the Greek theater, Teatro Antico di Taormina. Afterwards we decided to have a beach day in Sicily. It was a short walk to ride the funicular down to the beach. Everything changed. The sea, the water, the view, was so relaxing.
Within minutes we found ourselves beside the sparkling Mediterranean, enjoying the beautiful cove. It was what we saw in so many photos of what Sicily’s special beaches have to offer.
It’s also where many scenes from The White Lotus were filmed, so it was fun recognizing the area.
If we return someday, I think we’d stay closer to the beach itself.
It was absolutely glorious.
Our final evening in Sicily ended with an unforgettable Michelin-starred dinner at St. George by Heinz Beck, located in our hotel.
What an incredible way to celebrate the final chapter of our Sicilian adventure.
Every course was beautifully presented, every bite was memorable.
As we lingered over dinner, Tim and I found ourselves talking about everything we’d experienced over the past ten days.
Ancient ruins.
Seaside villages.
Jumping into the Mediterranean ocean.
Some amazingly unforgettable meals.
Baby goats.
Blue caves.
Even a gluten pizza.
We laughed.
We reminisced.
And we both agreed…
Sicily had completely stolen our hearts.
As we packed our suitcases that night, the next morning we headed for the airport. We knew we weren’t simply leaving another vacation behind.
We were leaving a place we thoroughly fell in love with.
Arrivederci, Sicilia.
