
Cortona, Italy
9 Nights ... May 2-11, 2026
13,250 Euro (excluding flights)
Solo In Style:
Women over 50 travelling solo and loving it!
Join our Living In Style Getaway in Cortona, curated and hosted by Deborah Ives, founder of Solo In Style, and Laura Cozik, founder of Team Lipstick and Mallorca by Design.
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5 Women are Welcome
What is "Living In Style"...
Living In Style events are curated for a particular place. When we come across the most exceptional accommodation in the most spectacular location, we feel compelled to design an experience. Santa Croce will take your breath away for nine spectacular nights. It sits at the tippy top of the hill, with views over beautiful Cortona and the Val di Chiana. This expansive property was originally an ancient monastery owned by the local church. It has very recently been renovated to the highest standards of authenticity and comfort. Think luxury linens, frescoes on the ceiling, and chandeliers in the trees. The villa comes with an exceptional all-female staff to boot. Elena is our private chef, Sophie is our concierge and house manager, and there is daily cleaning by a team of local women. You won't ever want to leave! Living In Style also presents a spectacular program for our guests to luxuriate in ... one in which quality of life reigns supreme.
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Our Private Villa...
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The Six Elements of Living In Style...
1. ENCHANTING ACCOMMODATIONS
This is the magic of Living In Style, the place you will call home for 9 beautiful days and nights. Our goal is for you walk through the door and think "how did they ever find this place?!". Living In Style villas are not chosen, they are discovered. When we come across something so enchanting that it begs to be the center of the most extraordinary experience, that is when we begin to plan.
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2. ULTRA-INCLUSIVE
This means you won't have to reach into your pocket unless purchasing presents for yourself. The house has a fully stocked wine bar, guest refrigerator, all complimentary. Meals, beverages, experiences ... even gratuities are taken care of. Think being spoiled by "all encompassing luxury".
3. ONLY FIVE GUESTS
Living In Style welcomes just 5 Solo In Style guests. Think one dining table and one conversation.
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4. JUST ONE LOCATION
Slow down and immerse yourself in Cortona, Italy. Instead of hopping from one one city to another, packing and unpacking, stay put and live the place you're in. The idea is to get to know one area and one way of life extremely well, as opposed to scratching the surface of many. ​
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5. ACTIVE WELLNESS
Living In Style infuses a luxurious wellness program into each and every day, one where you learn the simple skills needed for a high quality life beyond 50. We present self care necessities like strength, balance, flexibility, skincare, and the importance of sheer happiness. Living In Style is for active women, as our itinerary presents a good amount of walking, hiking, biking, and fun adventures.
6. LOCAL PEOPLE / EXPERIENCES
Mixing with local people, participating in their customs and traditions, joining them for a sunset aperativo, and doing things they do, going places they go ... this is Living In Style. ​​​​​​​​
Villages You Will Explore...
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Cortona
Montepulciano
Bagno Vignoni
Arezzo
Anghiari
Lake Trasimeno
Your Hosts...
How often is it that you go on holiday with the founders of your chosen tribe? Solo In Style has more than 620,000 members, and Deborah Ives, the woman who caught lightning in a bottle, will be joining this experience with you. Also looking after you will be Laura Cozik, the founder of Team Lipstick and Mallorca by Design. Her focus is always on the most unique experiences.
Join Us...
This Living In Style Getaway is limited to just 5 amazing women. Each guest has their own room with private bath. Rooms are first come, first served ... the sooner you submit your deposit, the more choices you have. Join us as we enjoy each other’s company, share our stories, forge new friendships, and have an insane amount of fun to boot. Laughter and curiosity will be our guides.
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5 Women are Welcome
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Itinerary...
Day 1, Saturday - May 2 - Villa Santa Croce
Total Driving Time: Florence Airport 90 minutes
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Under The Tuscan Sun...
Arrive to Florence Airport, meet your driver, and check in to the most spectacular villa in Cortona, located in a converted monastery at the top of the hill with breath-taking views over the Val di Chiana. This extremely luxurious property is the reason you join our event ... we will live like locals in the most prestigious part of the village. Solo In Style has private use of the entire property, with expansive gardens, salt water swimming pool, hot tub, massage cave, and more. For your pleasure, there is a private chef and daily cleaning staff. Cortona itself is where the book "Under The Tuscan Sun" was inspired, and where the movie was subsequently filmed. Our welcome dinner is under the stars, surrounded by twinkle lights.
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Day 2, Sunday - May 3 - Cortona
Total Driving Time: 0:00 hours
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Walking Tour, Cortona Jewelry, Dinner in the Village...
Blissful morning stretch and gentle barefoot training, coffee and breakfast. Next we have a walking tour through the precious village of Cortona, a medieval hilltop town whose soaring position offers 360° views of the incredible Val di Chiana. Spend time surrounded by beanstalk-like cyprus trees, sunflower fields, and the most intriguing history and architecture. An ancient tour with Valeria teaches us about the Etruscan civilization that founded this walled town. Discover the stories, art-filled spaces, palaces, churches, monuments, along with a visit to the museum. We head back to our Santa Croce for lunch and a dip in the saltwater pool. Just before dinner, we visit the most stunning jewelry showroom, in one of the oldest and most beautiful buildings of Cortona. In this ancient space, glasses of Prosecco are laced with flakes of silver as the owners share generations of stories. A special gift awaits each guest. Dinner is then served at the famous La Loggetta Restaurant in the town square.
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Day 3, Monday - May 4 - Bike Tour / Local Wineries
Total Driving Time: 0:00 hours​
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Pedal, Sip, Dine...
Blissful morning stretch and barefoot training, coffee and breakfast. This morning we set off for a full day of touring the local wineries, and a fantastic lunch on a vineyard. The bike pace is slow and easy, as we make several stops along the way to sample some of the best wines in Tuscany. At one special vineyard, a delicious lunch is prepared in our honor. There is then a bit of relaxation back at our villa. In the early evening we have a lesson in basic Italian phrases, which you can then practice throughout your stay. Dinner is served by Chef Elena.​​​​
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Day 4, Tuesday - May 5 - Montepulciano
Total Driving Time: 1:20 hours​
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Historic Walk, Underground Wineries...
Blissful morning stretch and barefoot training, coffee and breakfast. A long walk above the clouds jumpstarts our body and awakens our mind. On our route we see the ancient walls built to protect the city, the Basilica of Santa Margarita, and the Fortress of Girifalco. Together we prepare lunch at the villa. In the afternoon we visit another hilltop town that is full of history and art, surrounded by olive trees, vineyards and chestnut forests. The town is Montepulciano. Valeria takes us on a guided tour through ancient times, then an escort leads us through secret passages along a monumental path of the fifteenth century "Underground City". Through spectacular brick vaults and tunnels dug into the tuff, we find gigantic oak barrels in which the famous Vino Nobile di Montepulciano and Rosso di Montepulciano reside. Enjoy a tasting of these exceptional wines, with an explanation of their characteristics. Spend time wandering and shopping before we all meet for dinner in Montepulciano. ​
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Day 5, Wednesday - May 6 - Cortona
Total Driving Time: 20 minutes
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Under The Tuscan Sun, Cheese Making Workshop...
Blissful morning stretch and barefoot training, coffee and breakfast. This morning we hike to see the original Bramasole villa that inspired the popular "Under The Tuscan Sun" book by Frances Mayes ... she still lives here. This exceptional book was turned into a beloved movie that was filmed in Cortona. The story represents freedom, change, a new chapter in life, foreign exploration, and a leap of faith. A short drive down the hill takes us to the most beautiful farm with an abundance of animals ... ponies, sheep, chickens, hens, geese, ducks, turtledoves and more. Here we learn the "Art of Pecorino" via a cheese making class with Ilaria. We will produce three types of cheese with Ilaria - raveggiolo, pecorino, and ricotta. The ricotta from this farm is actually mentioned in the Under The Tuscan Sun Cookbook. The experience ends with a wonderful tasting of Tuscan bruschetta, pecorino cheese, pasta, and ricotta with jam ... all accompanied by good wine. Dinner is at our Santa Croce.
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Day 6, Thursday - May 7 - Bagno Vignoni
Total Driving Time: 2:20 hours
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Hot Springs, Unforgettable Spa Day...
Blissful morning stretch and barefoot training, coffee and breakfast. Today we prepare to be blown away by the wonders of Bagno Vignoni, a tiny hamlet with a population of just 17 year-round residents. The entire village revolves around a natural hot spring that takes up the entire town square. Guests check in for their spa services (massage or facial), then head to the geothermal pools, waterfalls, Roman sauna, steam room, and light therapy room, for a soothing renewal of energy. A spa lunch is served in the dining area. In the late afternoon we disappear into nature where there are natural hot pools waiting to be experienced. Enjoy the silence. Prior to dinner, we all enjoy a walk around the square to discover the book store, mother and daughter owned clothing shop, home goods store, woman owned herbal shop. By now we come to realize how truly miraculous Bagno Vignoni is. Dinner is then served in the village.
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Day 7, Friday - May 8 - Cortona
Total Driving Time: 0:00 hours
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The Roman Road, Shopping, Hat Party...
Blissful morning stretch and barefoot conditioning, coffee and breakfast. Today we are trekking a well preserved section of the Roman Road. The Roman Road was an extensive network of pathways built by the Roman Empire for military, communication, and trade purposes. A beautiful picnic lunch is enjoyed with the most fabulous views. Tonight we walk into town to embark on a fashion reconnaissance. It begins with choosing a special hat for our evening celebration ... this is our gift to you. All of the hats at Annie Hall Hat Shop are made by women, and fun fact ... Lady Gaga has one! Don your hat for an Italian Negroni cocktail making demonstration at a local bar. We then dip in and out of local shops you will only find in Cortona. From designer clothing to elegant shoes, handcrafted bags, artisan ceramics, olive wood products, exclusive jewelry, locally inspired perfumes, organic skincare products, and authentic works of art. A well deserved dinner is served in the square.
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Day 8, Saturday - May 9 - Arezzo / Anghiari
Train Ride: 20 minutes / Total Driving Time: 1:30 hours​
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Hop The Local Train...
Blissful morning stretch and barefoot training, coffee and breakfast. Today we board the train to Arezzo, where Valeria will show us Piazza Grande, The Cathedral, the green park of Il Prato, Il Corso with it's many stores, the Parish Church of the 13th Century, and the well preserved medieval walls. We have light lunch in the town square before our driver comes to fetch us. Next we visit Anghiari, rated "one of the most beautiful villages in Italy". Here we have a private tour of the incredible Busatti Linen Factory, which has been in operation since 1842, slowly taking over all 5 floors of the palace. It all began in 1797 when Napolean's army was stationed at the Busatti house in Anghiari. They began making blankets, uniforms and clothing for the soldiers. We will visit their store for a bit of shopping ... where a special gift is waiting for each guest. Busatti's high quality, organic linens can be found in the bedrooms, living rooms and dining rooms of our Santa Croce villa. Anghiari itself is stunning and we will be sure to walk the village, before sitting down to a delicious dinner.
Day 9, Sunday - May 10 - Cortona
Total Driving Time: 1:00 hour
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Our Final Day...
Sleep in for a bit of recovery, coffee and breakfast. This morning we visit Lake Trasimeno for a lovely boat tour. We have been enjoying the view of this lake from our terrace since they day we arrived ... it's time to take a closer look. After a bit of time on the lake and a beautiful lunch, our driver will bring us back to Santa Croce. Relax by the pool or in one of the many peaceful places at this gorgeous villa. It will be missed. Our farewell dinner is served in the garden by Chef Elena. A big thank you to Frances Mayes for writing such a beautiful book full of dreams and possibilities. It's never too late to move, change, or simply add the most wonderful experiences to your life.
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Day 10, Monday - May 11 - Home Sweet Home
Total Driving Time: Florence Airport 90 minutes
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Until Next Time...
Bid a reluctant yet grateful farewell to Cortona. You leave with the most exceptional memories, a Living in Style outlook on the future, and an all new set of FANTASTIC FRIENDS to boot! Transport to Florence Airport will be arranged.
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Accommodations
This exceptional property was originally a monastery, set high on the hill, over-looking the beautiful village of Cortona and the Val di Chiana. You will feel like royalty.
There are three structures ... the main house with four ensuite rooms on the upper most floor, a small stone building with an ensuite duplex room, and another stone building with two ensuite rooms. All of the rooms are gorgeous, all have views, each is unique in color and decor, some have frescoes. Ammenities in all rooms include luxurious bath products, robe and slippers, and hair dryer.
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The private property includes a salt water swimming pool, hot tub, numerous outdoor lounge areas, outdoor dining, an edible garden, a massage cave, pizza oven and barbecue in the grass, a complimentary wine vault with a copious selection of Italian wines, and the most magnificent views. There is no other property in Cortona that can hold a candle to this one. Here you will feel like the queen of Italy.
Your Hosts

Deborah Ives
Founder, Solo In Style
Deborah has always loved to travel and when she found herself suddenly divorced at age 50, her response was to go it alone. It was scary, fabulous, and empowering, in equal measure, and she was instantly hooked. As a solo female traveler over the age of 50, a huge and growing demographic, Deborah felt ignored by the travel industry. This prompted her to create Solo In Style with the idea of connecting like-minded women through their solo travels. Alongside a successful 30-year career in marketing, fine wine and culinary arts, Deborah, now aged 64, continues to expand Solo In Style globally to encourage and support as many women as possible to fulfill their solo travel ambitions.

Laura Cozik
Founder, Team Lipstick, Mallorca by Design
Laura has always been passionate about encouraging women to push their boundaries in order to become powerful. She truly believes this can only be done when you align yourself with other capable women who are willing to support each other. Laura is 58 years old, a group fitness instructor, a nationally ranked ballroom dance champion, a triathlete, an entrepreneur, and an extroverted introvert who loves to travel solo. She has been published in Cosmopolitan, Competitor, Shape, Triathlete, and New York Magazine for her accomplishments in the fitness and travel industries. Her celebrity clients include Nicole Kidman, Dr. Sanjay Gupta, Keith Urban and Soledad O'Brien.
Pricing and Details
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Pricing Per Person - 9 Nights - May 2 thru 11, 2026
This intimate event welcomes just 5 spectacular women.
€13,250 euros per person - Private room and en-suite bath for 9 nights.
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€5,000 euro deposit due at the time of registration – Payment due in full by January 1, 2026
Rooms are FIRST COME, FIRST SERVED. The earlier you book, the more options to choose from.​
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Included ​
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9 nights accommodation
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All transportation in Italy​
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All meals
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Tips and gratuities
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Activities...​​
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Blissful morning stretch sessions and barefoot conditioning​
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A daily dose of wellness and self care for women 50+ (varies day to day)
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Private tours - art, history, architecture, culture
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Cortona Village
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Montepulciano
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Arezzo
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Anghiari
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Jewelry experience
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Bicycle tour of local wineries
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Lunch at a local winery
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A lesson in basic Italian phrases ​
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Wine tasting in Montepulciano
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Cheese making workshop with a local family
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Massage or Facial
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Historic walks and invigorating hikes
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A special picnic lunch
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Boat tour
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2 dedicated hosts to look after and celebrate with you
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Living In Style gifts from DelBrenna Jewelry, Annie Hall Hat Shop, Busatti Linens, and the famous Santa Maria Novella Perfumes.
Not Included
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Flights
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Alcohol - other than wine
Questions and Information
Please contact Laura for more information… laura@mallorcabydesign.com
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Cancellation Policy
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€5,000 euro penalty if cancelled prior to January 1, 2026
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No refund if cancelled on or after January 1, 2026
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We will assist you in re-selling your spot to another Solo In Style member, but this is not guaranteed. If we manage to re-sell your spot, there is a €500 euro cancellation fee.
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Subject To Change
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All details are subject to change, in order to enhance the client experience
Terms and Conditions
There is some important information to note before we get to the fun part. Please read our terms and conditions below, as it is your responsibility to be entirely aware of our policies and what to expect.
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Physical Ability and Health Requirements
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Living In Style events are for active women over 50. Women who wake up each morning ready for a bit of physical training and self care. Women who enjoy activities such as slow hiking and gentle biking. Our program is not strenuous, it is simply about moving your body. There will be steep hills in Cortona, plus stairs and cobblestones, and it is entirely possible that we may walk 5 miles per day or 10,000 steps. We require all guests to have an appropriate level of fitness that allows them to do that. We will provide plenty of downtime for rest and recovery and you are welcome to skip activities ... we just ask that you are cognizant of the itinerary prior to registering.
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If you have special health issues or take medications, we ask that you advise us prior to registering for our getaway so we can ensure that there are no red flags and you are a good fit for the planned itinerary.
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Booking Flights
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Flights should not be booked until we approve your registration and application, and until we officially host our meet and greet on Zoom with your fellow travelers. This is when we discuss the best options.
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Methods of Payment
We accept bank transfers in EURO. Credit cards will be accepted with a 4% fee added, also in EURO.
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Cancellation Policy
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€5,000 euro penalty if cancelled prior to January 1, 2025.
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No refund if cancelled on or after January 1, 2026.
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We will assist you in re-selling your spot to another Solo In Style member, but this is not guaranteed. If we manage to re-sell your spot, there is a €500 euro cancellation fee.
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Application Process
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Our goal is always to ensure the best possible experience for our guests. Because of this, our process is to ask you to be very sure that the itinerary is suited to your preferences. Once it is determined that our program is a good fit, you RSVP, fill out our application, pay your deposit, and schedule a one-on-one call so we can get to know you better. This process is not only FUN, it is also designed to ensure that every guest has a spectacular experience.
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Weather
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Fall is so lovely in Tuscany, as wildflowers bloom and temperatures average 60-70 during the day (16-20 celcius), and 50-60 in the evenings (10-16 celcius). Global warming may have something to say about this as the years tick by. A light sweater or jacket is recommended for evenings.
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Maximum Group Size
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We are accepting just 5 women for this event.
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Eligible to Attend
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This trip is exclusively for Solo in Style members ... women 50+ years of age with a brilliant outlook on life, who love to travel and want to meet like-minded as well as diverse women.
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Pack List
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A pack list will be sent to every guest prior to travel. Casual clothing throughout, comfortable walking footwear, swimwear for the pool and spa, and workout gear. The pack list will be much more detailed.
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Room Selection
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All rooms are private with private bathroom, for maximum comfort and a bit of solo time. They are each uniquely beautiful in layout and decor ... reserved on a FIRST COME, FIRST SERVED basis. The earlier you reserve your spot and pay your deposit, the more choices you’ll have. The selection process begins once full payment has been received by every guest.​
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Room Sharing
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Solo In Style is exactly that ... your room is just for you. All rooms are solo occupancy with private bathrooms.
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Mandatory Travel Insurance
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Solo in Style requires each guest to purchase full personal travel insurance for the duration of the trip. It's the safest and best way to travel. We will ask for proof of insurance prior to the event and reserve the right to deny any participant who has not obtained this. Any fees paid towards the event will be non-refundable.
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Dietary Requirements
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Most requirements are possible, although pure vegan and gluten free may be limited. When booking restaurants, we will be sure to give them a heads up with regard to your preferences.
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Photos and Videos
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One of the most fun aspects of any travel event is the photos and videos taken. We provide a shared folder where everyone can drop and download media. Guests are welcome to post these images on social media. You may not sell or otherwise use any of the images taken by us or our photographers or other guests for commercial purposes. When registering for our event you agree and acknowledge that your image and likeness may be used in future promotional material, both by Solo In Style, and our partner companies. We only use the "good ones" where everyone looks great! If you prefer not to be photographed or to appear in any videos, simply let us know.
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Waiver
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Please be prepared to sign a ‘Waiver of Responsibility’ form before you begin your tour. This form is an understanding that all guests need to exercise judgement and care at all times to ensure their own safety and that of their fellow travelers.
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Airport Transfers
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There are two transfers on arrival day and two on departure day. One is always earlier, while the other is later. We will do our best to plan around everyone's schedule. We discuss flights during our first meet and greet Zoom call.
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Luggage Limitations
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Each guest is permitted one suitcase and one carry-on bag or backpack. You must be able to transport and carry your own luggage at all times, as there is no guaranteed assistance. This may very well mean up flights of stairs.
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Alcohol and Other Substances
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If you plan to drink, we ask you to do so responsibly. The idea is to enjoy, but not to become inebriated. Drugs and illegal substances will never be tolerated.
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Force Majeure
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In case of a Force Majeure event, we are not responsible for performing our obligations and will not be responsible for any resulting damages. A Force Majeure Event is any circumstances beyond our reasonable control, including without limitation acts of nature, terrorist activities, insurrection, explosion, flood, earthquake, tempest, forceful wind, fire or accident, war or threat of war declared or undeclared, sabotage, civil disturbance, labor strikes, requisition, pandemics, sickness, quarantine, government intervention, weather conditions, and unforeseen circumstances. If we, and/or our partners or agents, are affected by a Force Majeure Event, we, and/or our partners or agents, may vary or cancel any itinerary or activity without any obligation or liability.
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Disclaimer
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Solo In Style along with Mallorca by Design and all our representatives, act only in capacity as agents for the guest in all matters connected with travel, sight-seeing journeys and transportation. You agree that we are held free of responsibility for any damage occasioned by any cause. These causes will be laid out more fully in our waiver, which you are required to sign prior to travel. Additionally, we reserve the right to alter our itinerary ​in order to provide the best experience for each and every guest. The bespoke nature of our itineraries means that they may be subject to minor changes, updates and additions as we get closer to departure.

The Process...
RSVP, fill out the application, pay your deposit, then schedule a private Zoom chat so that we can get to know you, and so that we can strive to meet and exceed your expectations. After that, we invite everyone to a Zoom meet and greet. Solo In Style events are about travel, but we also want to share our stories and forge new friendships with like-minded women.