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I was so excited when Nicole Dean agreed to share some nuggets about her recent trip to Italy. (And that was before I heard her story about the extradited prisoner getting shoved up the stairs onto her plane. #teaser)

Nicole is a fabulously successful businesswoman and explorer extraordinaire. I wanted to share her travel story not only because it was a super cool trip, but also because Nicole is a great example of someone who has truly created a lifestyle business.

Her trip to Italy may have been her first, but this isn’t one of those once-in-a-lifetime stories. Nicole has traveled extensively around the world and around the country — and as you’ll learn here, she leaves her laptop at home when she does. She isn’t chained to her businesses. Sign me up!

Nicole is the co-founder of CoachGlue.com, a business that designs and creates high-end coaching programs, workshops, and content for business coaches that they can license, brand, and sell to their own clients.

You can also find Nicole kicking butt on the beach during Beachpreneurs, a ladies-only mastermind retreat that she co-owns along with the fabulous Kelly McCausey of Love People and Make Money. And you can find out more about Nicole — and the word “awesomization” — at NicoleDean.com.

Nicole lives with such joy and has a huge heart. You’ll see it radiate from the smile in her photos and from her sincere devotion to causes that she supports.

So it is with an abundance of gratitude that I thank Nicole for taking the time to talk about her trip to Italy and share some of her fabulous photos! (I’m totally going with her next time. Wanna come?)

How did this trip come about?

It was a serendipity kind of thing. I had been invited to a Mastermind in Tuscany and really wanted to go but the dates conflicted with an event that I was co-hosting (Beachpreneurs Beach Camp in Daytona Beach), so I obviously wouldn’t have felt right to leave those people in order to go to another event. 

So I was bummed because I had no idea when I would be able to go. I had always wanted to go to Italy. I mean, who doesn’t? Under the Tuscan Sun? The culture, the men, the wine, the art, the history, the nature? I mean, what’s NOT to love?

So I figured Italy was out for awhile and that was just that. 

Then I was at an event / business conference in March with my friend Kelly McCausey, who is the co-owner of Beachpreneurs (and my dearest, smart friend). This event was new to us and we only knew 3 people. So Kelly went into the event’s Facebook group and saw that a woman, Marie Fratoni, had posted that she was at the resort and was up for fun.

We met for dinner, where Marie mentioned that she takes groups to Italy as one of her businesses and that she’d be taking her ninth trip there in September.

Her trip was called “Living La Dolce Vita” or “The Sweet Life” and it looked relaxing and lovely for unwinding. There wasn’t quite as much adventure in the schedule as I would have liked if I’d planned it myself, but for a first-timer to have a trip already planned and organized — and to be going with someone I really LIKED and looked forward to spending time with? This might work.

I love to travel but I don’t love to travel alone (at least not the first time going to a new country), so I asked Marie if I could fly over with her and she said, “Yes but I’ll be going a few days early to explore Florence and staying a few days after to explore Venice. You can join me if you’d like.” 

I obviously jumped on that and voila. The trip was planned.

Can you give a brief overview of what you did and saw?

We flew into Florence, which was an adventure in itself as we were on a flight with an extradited prisoner who was forcibly brought on the plane by armed guards while struggling and getting shoved up the stairs (which we watched from our bus). And then he was obviously drugged, as he was out for the remainder of the flight. 

The flight was gorgeous. We flew over the Alps en route from Amsterdam to Florence. I couldn’t get enough of it, other than I knew we were almost there! 

We landed in Firenze (Florence), got a cab and settled into our hotel. Then we had a few days to explore the great city and fall in love.

We saw the Duomo and the Santa Croce, where we saw Michelangelo and Galileo’s tombs (among others). The next day I easily spent 5 hours going through the Uffizi Gallery where I was able to see original Michelangelo, Botticelli, and da Vinci paintings.

Firenze to San Fedele

From Firenze we took a bus to Tuscany, specifically to San Fedele,  a12th-century monastery where we stayed for the next week. San Fedele was where the “Living La Dolce Vita” part of the trip happened. Breakfast and gourmet dinner were provided every day, including lots of chianti that was grown in vineyards nearby.

During the drive down, we were introduced to the rest of our group. It was a diverse bunch and I wondered how we would all get along. As I mentioned, I host retreats and events myself so it’s always fun and interesting to see who ends up together and how that unveils into relationships. It was as it was meant to be and everyone, as always, brought smiles, laughter, stories, and memories to the group.

We stayed at San Fedele with another group and they were wonderful traveling companions who became friends. The organizer, Rebecca, is an artist and her event was meant to be a painting workshop. But Rebecca is such a love that everyone (not only painters) wanted to spend time with her so she ended up with a very diverse group as well.

Two of my new companions were a grandmother in her 80s named Barb (or Gramma B as I called her) and her adventurous, spirited adult granddaughter, Rya. I just adored them both.

During our week at San Fedele we took trips each day for a few hours to see the nearby sights and tour our surroundings. Each town had its own unique charm and personality that I couldn’t help but want to breathe in so that I didn’t forget a thing. Ask me to choose my favorite place and it would be like choosing the favorite of my three children or my three dogs … but we all know how that is.

There’s so much more to tell, but I know this is running long. Every morning at San Fedele I got my coffee and did yoga between the olive trees. Every night was spent enjoying an unbelievable 4 course dinner cooked by Andrea, our private chef, and lots of chianti and laughter and stories.

San Fedele to Venice

After 7 beautiful, soul-filling days, I packed up and walked away from San Fedele with tears in my eyes and gratitude in my heart, and focused on my excitement to be heading to Venice.

We got a ride to the train station and then boarded the train in Florence. When we arrived in Venice, we met our porter, who was basically a guy with a flat wheelbarrow who hauled our luggage and walked us to our hotel (while we ran through the crowd trying to keep up with him). There aren’t many cars in Venice because it’s a series of 118 islands, so transportation is pretty much by foot or boat.

The first place we saw after we checked into our hotel was Piazza San Marco, which was stunning. It’s so nautical and it reminded me very much of CS Lewis’ The Voyage of the Dawn Treader.

After exploring that and figuring out how the water taxis and water buses worked, we were ready for more exploring the next day. Our travel agent had arranged for a walking tour, a gondola ride, and a boat ride out towards the Adriatic Sea to explore the islands of Murano, Burano, and Torcello. The boat ride was a highlight of my trip. I love being on the water.

I wish we’d had more time to explore Venice as there is so much more to see there. Next time. 🙂

After our time in Venice, we took the train back to Florence, and had one more night to go see our favorite things again and then it was off to the airport to head home.

In your airport selfie the day you left, you said you were “feeling lots of feelings.” Can you elaborate?

I was feeling excitement, overwhelm, guilt for leaving my family, and wonder and extreme gratitude. I was also curious about the people I would be spending time with. I hoped they would be positive, laid back and fun.

I had intentionally not done a lot of research as I wanted to go in with an open mind. That worked for and against me in the end, but at the airport, part of my facial expression was “I have NO idea what I’m getting into!”

You took your yoga mat and left your laptop behind. What was that like?

That is just how I travel. I rarely bring my laptop with me. My team and partners can handle anything that comes up and I structure as much as I can so that even on work trips, I’m networking, not sitting in front of a computer answering emails.

You seemed to do really well finding gluten-free food. How did you do that?

Italy is actually at the forefront of the Celiac movement and in understanding the need for many of us to eat gluten-free. I am not Celiac, but I have an autoimmune disorder (Hashimotos) and my doctor said to treat my body as if I do have Celiac.

I do not worry personally about cross contamination because I have that luxury, but I do not intentionally eat gluten. I ran into a few difficulties where I ended up with meals of just grilled veggies with balsamic vinegar on them, which was fine, but most places I could say “sans gluten” and they were very accommodating. I also kept a few snacks in my purse at all times just in case.

Thankfully, my travel buddies were willing to walk a bit further to find a place where I could eat. That made it easier for me, too. Even the hotels brought me special crackers and muffins since they knew I couldn’t eat the others. It was really nice.

The only problem I had was my KLM flight back, as I wasn’t able to request a meal through Delta (which is their partner) so I had nothing to eat on the return flight. I had packed a few snacks, though, so I made it ok without getting too hangry.

What did you learn for the next trip to Italy?

I would definitely use a travel agent again. The portions of the trip that she arranged were so nice and I would have been lost without that assistance. From the hotels to the trains to the tours to the museum tickets to the crazy porter experience, she made it all pretty seamless.

You’re a seasoned traveler. Where does Italy rank for you?

That’s a tough one. 

My daughter lives in Latvia and was born there, so that’s always my #1 location to visit. My granddaughter’s smile is better than any sunset or art gallery I’ve ever seen. And Latvia has become a second home for me. The culture and people? It does’t get any better than that for me. 

But that aside.. of all of the countries I’ve been, I honestly see such beauty in all of them that it’s hard to rank them. I guess I’ll just have to go back and see. 

That said… 

I adored the 10 days I spent in Costa Rica. It was a life-changing trip and I would go back there in a heartbeat. Just like Italy, I left a piece of my heart there. 

I was absolutely blessed to tour Ireland with friends who live there, so I was totally spoiled to be able to see the REAL Ireland and also stay in a castle and do the touristy things and I would go back there in a heartbeat, too. 

Snorkeling in the Bahamas was so beautiful. And I love island life.

And Mexico, the culture and energy and people? Climbing the pyramids? So cool. 

But yes, I will be going back to Italy. I have so many places yet to see and now so many places I must go back to. There’s a reason people flock there. It’s awe-inspiring.

Can you choose 2 Favorite Parts of this trip?

The food. Obviously. How can I possibly have a personal professional master chef in Italy who creates gluten-free masterpieces just for me and NOT say the food was my favorite? Definitely, the food.

I also truly loved my morning yoga. Looking out at the hills rolling in every direction, the cypress trees in the distance, the olive trees beside me, the sun on my face… I felt so grounded and at peace. The grounds of San Fedele have had nearly 800 years of births, weddings, and funerals. Wars raged right where I was standing and so many souls prayed and felt deeply in that church. There were centuries of hope, worries, laughter, promises, fears, joy and pain. It put things in my day to day into perspective really well.

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So who else wants to join Nicole the next time she heads to Italy? (or Latvia, or the Bahamas, or Mexico, or ….)

If you want to learn more about Nicole Dean and what she offers — and you should! — then check her out at Coach Glue, NicoleDean.com, or scope out her and Kelly’s unique retreat (and become a beachie!) at beachpreneurs.com.

And for a different spin on traveling, check out my post about the “Gnomad Family,” who travel with their young children.

Have you been to Italy? Please share a little about your experience!

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