Girls Trip: Under the Tuscan Sun & Sea

Girls Trip: Under the Tuscan Sun & Sea

Hosted By:

Jenn Hilchey

 🚨Sold Out | Waitlist Open
 

May 23–28, 2027

A small group of 10–12 women

$3,750 pp double  | $4,250 pp single

Tuscany is calling again!

I’m so excited to be heading back to one of my favorite places for another Girls’ Trip filled with incredible food and wine, beautiful days in the Tuscan countryside, charming towns, and a really fun group of women to share it all with.

This small-group getaway is all about experiencing the best of Tuscany together—from winery visits and long lunches to exploring some of my favorite places in the region, with plenty of time to slow down and enjoy where we are.

Join the Waitlist!

Itinerary

Arrival & Welcome in Florence 🇮🇹
1
May 23

Arrival & Welcome in Florence 🇮🇹

Meet Jenn and the group in Florence, then travel together through the countryside to our Tuscany hotel. That evening, get to know your fellow travelers over a multi-course welcome dinner and guided wine tasting at Tenuta Torciano Winery!

Truffle Hunt, Cooking Class & Lunch 🍄🍝🍷
2
May 24

Truffle Hunt, Cooking Class & Lunch 🍄🍝🍷

Join expert guides and their trained dogs for a truffle hunt, followed by a hands-on Tuscan cooking class. Enjoy your creations over lunch paired with local wines, then spend the afternoon at leisure before dinner at the winery.

Excursion onboard of the SanLorenzo Yacht 🛥️🌊
3
May 25

Excursion onboard of the SanLorenzo Yacht 🛥️🌊

Spend the day aboard a private SanLorenzo yacht, exploring the Tuscan coast toward Elba Island with time to swim and relax. Enjoy a chef-prepared four-course seafood lunch and a guided wine school featuring 10 wines, including rare reserve vintages. Back at the hotel, we’ll finish the day with a casual pizza and wine night.

Tuscan Jeep Vineyard Tour & Wine School 🚙🍇🍷
4
May 26

Tuscan Jeep Vineyard Tour & Wine School 🚙🍇🍷

Explore the estate’s vineyards and olive groves by 4x4 jeep while learning about Tuscan winemaking. Enjoy a countryside aperitif, traditional lunch, and guided wine tasting, followed by free time at the hotel and dinner at the winery.

Day Trip to San Gimignano & Siena 🏰🇮🇹
5
May 27

Day Trip to San Gimignano & Siena 🏰🇮🇹

Explore San Gimignano and Siena, with time to wander historic streets, browse shops, and enjoy lunch at a restaurant of your choice. Lunch is at your own expense. That evening, celebrate our time together with a farewell dinner among the vineyard rows.

Breakfast & Check-Out
6
May 28

Breakfast & Check-Out

Enjoy breakfast before checking out. Scheduled group transfers to Florence Airport (FLR) and Santa Maria Novella train station are included.

Girls Trip: Under the Tuscan Sun & Sea Price

Trip Deposit & Payment Schedule

Non-refundable deposit:
$750 per person due at registration.

Final Payment Due:
90 days before trip start date.

$3,750 pp Double Occupancy 

$4,250 pp Single Occupancy


For guests booking together: Double occupancy pricing is based on two guests sharing a room. If one guest cancels, the remaining guest may find another traveler to take their place or, if available, be paired with another solo traveler. If neither option is available, the single occupancy rate will apply, as accommodations are priced per room rather than per person.

Included In Price

  • All meals included daily—breakfast, plus multi-course lunches and dinners expertly paired with regional wines and served in elegant, authentic settings. One lunch during free time in Siena and San Gimignano is not included and is at your own expense.
  • Private luxury transportation for all scheduled experiences and group activities
  • 5 nights at Torciano Boutique Hotel, an elegant countryside stay nestled among vineyards and olive groves
  • A private yacht experience on the Tuscan coast — sun, sea, and serious celebration
  • All curated excursions and cultural experiences listed in the itinerary — no surprise costs, just seamless enjoyment
  • On-site host and dedicated concierge — I’ll be with you every step of the way to ensure seamless coordination, personalized support, and an unforgettable experience
  • Tips for drivers, guides, and servers. — Additional gratuities are always welcome at your discretion for exceptional service, but are never expected.

Excluded In Price

  • International flights: We’re happy to assist with flight recommendations based on your arrival and departure.
  • Travel insurance (required): We can help you secure a policy tailored to your trip.
  • Visa fees (if applicable)
  • Lunch during free time in San Gimignano and Siena. Additional meals or alcohol outside the itinerary during free time are not included.
  • Taxis or transportation for personal leisure
  • Optional add-on activities and excursions
  • Personal items such as souvenirs
Cancellation Policy:
Cancellations will be evaluated individually in accordance with the terms of your mandatory travel insurance policy, (which The Travel Box International can assist you in obtaining). For cancellations outside of insurance coverage, please review the standard cancellation policy  HERE. Travelers seeking the flexibility to cancel for any reason are strongly encouraged to purchase additional travel insurance.
Our Stay: Tenuta Torciano Hotel

Our Stay: Tenuta Torciano Hotel

For our time in Tuscany, we’ll stay at Tenuta Torciano Hotel, a boutique property near San Gimignano, just minutes from the family’s winery. It’s a charming base for our adventures, with a quieter countryside setting to return to after days spent exploring, tasting, and enjoying the region together.

Our stay is connected to a family story that began in 1720, when Bartolomeo Giachi founded Tenuta Torciano. Thirteen generations later, the Giachi family continues to share its love of Tuscan wine, food, and hospitality with visitors from around the world.

That connection is part of what makes this stay so personal. From our welcome dinner and wine tasting to the experiences we’ll share throughout the week, we’ll get to know Tuscany through the people and traditions behind it.

Optional Florence Pre-Extension

Optional Florence Pre-Extension

May 22, 2027 | Florence, Italy

Want to start the trip a little early? For those who would like extra time in Florence before our Tuscany Girls’ Trip begins, an optional one-night stay will be available at Porta Rossa Hotel Firenze.

Located in the heart of Florence, this historic 5-star hotel dates back to the 13th century and is considered one of the oldest hotels in Italy. It combines original Florentine character with modern, upscale accommodations and puts you within easy walking distance of Ponte Vecchio, Piazza della Signoria, the Uffizi Gallery, Via de’ Tornabuoni, and plenty of restaurants, cafés, and shops.

Arriving a day early also gives you a little extra time to adjust to the time change, settle in, and start the trip at a more relaxed pace. It also provides some added breathing room in case of unexpected flight delays or travel disruptions before we meet as a group and head into the Tuscan countryside.

Optional Room Rates:

Superior Double Room

  • One queen bed:  €581 EUR per room

Premium Room

  • One queen bed or two separate beds:  €637 EUR per room
Solo Travelers: Welcome to Your Community!

Solo Travelers: Welcome to Your Community!

Embrace the freedom of solo travel and join a supportive, vibrant community! This trip is designed to warmly welcome and embrace solo adventurers. We believe traveling solo on a group trip is an incredible way to build confidence, make new friends, and create truly personal memories.

If you're interested in sharing a room and wish to be paired with another solo traveler at the double occupancy rate, we strongly encourage it! Please note that while we'll do our best to find a compatible match, pairing is not automatically guaranteed until confirmed. We'll provide a separate questionnaire to help us make the best possible match for you. Get ready to forge incredible bonds and experience Tuscany with new amazing friends!

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FAQ’s

Yes, it is

All adult ages are welcome! Past groups have typically ranged from their 30s-50s.

10-12 Guests Only!

Airfare is NOT included. We’re happy to assist with flight recommendations based on your arrival and departure.

All meals are included (with wine) minus ONE lunch during free time in San Gimignano and Siena Additional meals or alcohol outside the itinerary during free time are not included.

Travel insurance is required for all travelers. It helps protect your investment and gives you peace of mind in the event of unexpected changes, delays, or emergencies. Please plan to purchase your travel insurance within 7 days of your deposit to take advantage of the best possible coverage options. Proof of travel insurance must be submitted no later than 90 days prior to departure. The Travel Box International is happy to assist you with this—I’ll send over a quote link from our trusted partner, TravelSafe Insurance, right after your deposit is processed.

Complete the registration form, and I’ll be in touch to confirm availability, answer your questions, and send the deposit payment form. Your spot is confirmed once availability has been verified and your $750 non-refundable deposit has been received. The remaining balance is due 90 days before the trip begins.

All trip payments, including the deposit and final balance, are non-refundable. Travel insurance is required. If you need to cancel, any reimbursement must be sought through your insurance provider and is subject to your policy’s terms, covered reasons, and exclusions. Purchasing insurance does not guarantee reimbursement.

Embrace the freedom of solo travel and join a supportive, vibrant community! This trip is designed to warmly welcome and embrace solo adventurers. We believe traveling solo on a group trip is an incredible way to build confidence, make new friends, and create truly personal memories.

$3,750 per person for double occupancy (two people, sharing one room with two twin beds) $4,250 per person for single occupancy (one person, one double bed)

Yes! Dietary restrictions and allergies can be accommodated. Please include any dietary needs when registering.

Florence Airport (FLR) is the most convenient option. Rome Fiumicino (FCO) and Milan Malpensa (MXP) are also good alternatives if you’d like to spend more time in Italy, with onward train travel to Florence. Group transfers operate at preset departure times. A full, detailed itinerary with meeting information and timings will be shared privately with confirmed travelers. Please check with me before booking flights to ensure they align with the group schedule.

Absolutely! I recommend arriving at least one night before the trip begins to settle in, adjust to the time change, and allow extra breathing room for possible flight delays. Our optional Florence pre-extension on May 22 includes a one-night stay at Porta Rossa Hotel Firenze, giving you time to enjoy the city before we head to Tuscany together. If you’d like a longer stay, I can arrange additional nights and plan as much of your time in Italy as you’d like, before or after the group trip. Select the pre-extension when registering, or let me know what else you have in mind!

For cancellations outside of insurance coverage, please review the standard cancellation policy HERE. Itinerary subject to change.

Make Your Reservation Now!