What I’m Packing for Tuscany

and the parallels with Leadership

Joya Dass
8 min readApr 4, 2023

A travel operator once asked me, “Why do I pick foreign countries versus say — -Colorado? to host retreats?” My 3 reasons I believe travel leads to better leadership.

For now, if you are going to Tuscany with me for the Mastermind retreat, you might be thinking “What to pack?”

Imagine showing up to climb Mt. Everest and all you had was ballet flats. You would be ill equipped to do the thing you came thousands of miles to do. I prepare for a trip much in the way I prepare for leadership.

Here are three things I consider the minute I buy my plane ticket:

#1 Temperature at the destination. Tuscany will be a low of 54. High of 74. Overcast.

#2 Activities. We will be in a cooking class. Biking and wineries. Dining. Writing. Leading.

#3 Fashion. It’s key to be deferential to the culture I am visiting.

Now lets dig in to what I am packing in my suitcase.

Electronics

I post alot of stories on Instagram when I’m travelling. I love documenting the minute to minute developments. This charger from Anker carries me through the day both here and abroad.

In the hotel room, I plug alot of electronics into the socket. I mean, alot. Hair dryer, flat iron, phone charger, phone, Kindle, computer. I bring this Anker power strip, featuring both traditional plugs and USB ports. In hotel rooms, sometimes the mirror is too far from the electrical outlet, so this strip comes in handy. With a power strip, I also only need to use one converter.

Packing cubes

Away Luggage makes 4 packing cubes in several sizes. One for socks. One for lingerie. One for sweaters. I like how they fit, like Lego blocks, into the larger carry-on from their line.

For toiletries, I love the Sezane Mini Travel Bag. It features a top-zip functionality. I used to be someone who carried alot of little bags, but I ended up rummaging for ages to find scissors, for example. With this bag, I open it. I see everything.

I also love these Clarity Jet Set Cases from Truffle, which have a transparent window, allowing you to see everything you have inside, but made of a durable leather.

CLOTHES

Day 1 is a travel day. Its a long day. I’ll be travelling with at least one member of the Mastermind because god knows I don’t want to be in a 900 year old castle in the middle of Tuscany by myself.

She said, “ghosts?”

I said, “No, i’m more worried about plumbing and toilet paper.”

It’s a 10 hour flight New York to Florence with a stop in Brussels.

Lets talk base layers: Commando makes a great non underwire bra that gives me the right support, but are “pajama like” enough to sleep in. For bottoms, I’m gonna get a little vulnerable: I’m approaching menopause. My periods are tough. I mean really tough. So for a long haul flight, I’m wearing these boyshorts from Ruby Love. I want the confidence to move around and know that I am protected. Ruby Love products are designed to offer that confidence.

My standard travel gear for long haul flights are a scoop neck tee from Marine Layer. On top, I wear a navy blue sweatshirt and matching blue joggers from Athleta. The joggers are made of an athletic wicking fabric that pulls sweat away from the body to the surface so it can evaporate. I contain messy plane hair with my black NY Yankees hat. All my essentials (passport, wallet, earbuds) stay on my person in my Athleta excursion bag.

Footwear: I wear Nike sneakers and Balega socks.
Skincare: Once on board, I remove makeup using Neutrogena hydroboost makeup wipes, apply astringent wipes from Thayer, and moisturize, moisturize, moisturize. I brought back a prickly pear moisturizer from Morocco last year. This website features a similar product.

We will be landing at breakfast time with a long day ahead. We pick up the car rental, grab lunch in town and head to the villa an hour outside of Florence. To freshen up, after long haul travel, I use these Yuni Beauty “Shower sheets.” I got the Peppermint and Citrus flavor. (Psst. They are paraben free). The founders are a husband and wife duo, both yoga teachers and at least one of them born in India. I’ll change into a long sleeved scoop necked top from AG Jeans, AIRSTRETCH pants from Banana Republic. They are light as air and sustainable, made from recycled polyester and spandex. I’ll top it all off with a quilted padded vest from Barbour, which takes me from city to country and back again. For the hour drive to Chianti,, I’ll have driving loafers from M.Gemi on my feet.

Chef Antonella will be making us dinner at the villa. Temperatures drop come night time, so this navy blue cashmere sweater from Reset and black jeans from Banana Republic will come in handy for sitting by the fireplace

Day 3 Welcome everyone to the villa

While I’m arriving early to make sure everything at the villa is in order, everyone is arriving on Tuesday. Folks are coming via train, by car, via Milan, via Florence. By aperitivo hour, I hope to be welcoming everyone to the house. For the welcome dinner, I want to be casual but polished. I’m wearing this funnel neck sweater from Reset (I found the brand in Sicily when I was there in January and am a little obsessed) paired with the Alessia silk slip skirt from Italian brand Ravella.

My super comfortable Kurt Geiger mules are my walking duds for the day. The crystal and bead embroidery on the toe features a fun eye motif.

Day 4 Kick off with exercises. Drone photographer. Cooking Class

Wednesday, after breakfast, we are digging in to the writing exercises for the Mastermind, Keep in mind, everyone in the mastermind is building a personal brand in 2023, culminating in giving a TedTalk on a New York City stage. So, this is a time to really write and think about what stories will map to the message they want to share on stage. Everyone is speaking to an aspect of leadership.

The day is bookended by two main events: A drone photographer is coming by in the morning 10am-12pm to capture us at work. We are going to be deep in the hills of Tuscany and I don’t know that you can truly capture the magic of the place, unelss you capture it from the air. In the evening, Chef Antonella will be hosting a cooking class where we will be making a 4 course meal of ravioli, ragout, pork loin and tiramisu.

I did a color analysis last year and learned that “Royal Blue” is my power color. So, I’m doffing my traditional “New York black” in exchange for more royal blue. This cotton scoop neck top from British retailer Boden, paired with my AIRSTRETCH pants will carry me through the shoot and the day.

Day 4 is the wine and bike

We will be biking from winery to winery. A van will follow us in case someone tires. For this day, layers are key. I’ll wear this short sleeve t shirt from Lululemon’s The Swiftly Tech collection. Again technical fabric great for wicking moisture away or my AG Jeans long sleeve tee, weather depending. Pairing this with my Salutation Stash ⅞ tight from Athleta in black, my Uniqlo vest, socks from Balega, sneakers.

Day 5 Olive oil tasting and Retreat Dinner

The last day, we head to a local olive oil mill Frantoio Doglia for a tasting and lunch.

For this, the Vivienne Noir dress from Tuckernuck (it has a hint of shimmer in it), with a scarf from the mills of Cambodia (gift from my friend Kelly), paired with these Felize Suede loafers from M. Gemi It transitions well to the evening festivities. Over the closing dinner, we will opening letters everyone wrote to themselves back in January when the Mastermind kicked off and reflect on the week.

Day 6 Drive Chianti to Florence

We are out of the villa by 10am. Driving back to the City, black jeans, purple top and Barbour gilet

One of my highlights of the trip will be doing yoga overlooking the Duomo

For this, i’m bringing my yoga gear for sure.

Over the last 10 years, I’ve built a business mastermind with an element of adventure.

My mission is to help women build a powerful personal brand.

I help both corporate women and business owners tell better stories about themselves

I am the founder of the Women’s Leadership Lab.

My portfolio

  • I am the founder and CEO of the Women’s Leadership Lab, a 12 month business mastermind with a goal to build a powerful personal brand, culminating in a Tedx style talk on a NYC stage.
  • I work with women seeking a promotion to the C Suite
  • I work with business owners who need to tell better stories to get clients
  • I work with women to pitch to investors
  • I work with former executives launching consultancies
  • I work with artists looking to command a higher price point in the market, by telling better stories
  • I help women land their TedTalk

My results

  • 1 Got the job with a 15% pay bump
  • 1 got the promotion to the C Suite with a 10% pay bump
  • 1 built a $50MM real estate fund
  • 1 said ‘yes’ to live television interviews
  • 1 got her first check for her startup from the community
  • 1 went from commanding $500 to $5000 for her art
  • 9K followers on LinkedIn
  • 8K followers on Instagram
  • 5K followers on Facebook

If you would like to enroll in my Mastermind, join the waitlist here.

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Joya Dass
Joya Dass

Written by Joya Dass

If you have a goal and want the steps to make it your reality, I have a solution. www.joyadass.com

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