Launching 6-Nights, 7-Days in Tuscany
Experience authentic Tuscan living with a perfect balance of rich cultural heritage, architectural wonder, and stunning natural beauty. Join us for specialized guided museum visits, unique culinary and cultural experiences, private wine tastings and vineyard tours, shopping at the world-class designer outlets, the best in local dining, and stay at two of the region’s most charming, boutique hotels, all while creating lifelong memories while in good company.
Day One:
Private transfer from your arrival point (Santa Maria Novella Train Station or FLR airport) in Florence to the hotel for check-in.
Meet your hosts and co-travelers at an evening aperitivo showcasing local, Tuscan snacks, cocktails, and wine.
Group dinner at an authentic trattoria.
Day Two:
AM: Private guided tour of Florence’s cultural, historical, and architectural gems led by an art historian.
Lunch at a local cafe.
PM: Walking food-tour with a stop at Florence’s famous food market, local bakery, and wine tasting.
Group dinner highlighting Florentine specialties.
Day Three:
AM: Private outing in a black car service to the famed designer outlets.
PM: Walking-tour of culturally significant sights, gardens, and artisanal boutiques, including a local Florentine leather shop.
Group dinner in the heart of Florence.
Day Four:
AM: Florence departure with private group transfer in a black car service.
Exceptional culinary lunch experience in a charming village located outside of Florence.
Arrival at a boutique hotel in the Tuscany countryside nestled in the hills of Val d’Orcia.
Group dinner at the hotel featuring local Tuscan fare.
Day Five:
AM: Transfer in a black car service to a family-run agriturismo for a hands-on pasta making class followed by lunch prepared by the group, local cheese tasting, and wine pairing.
PM: Stop in the picturesque town of Pienza, a UNESCO World Heritage Site. Explore the local cheese makers, cafes, and shops with the group or at your own pace.
Group dinner in authentic osteria in the charming village of Bagno Vignoni.
Day Six:
AM: Transfer in a black car service van to the wine region of Montalcino. Home to Brunello di Montalcino. Visit a biodynamic vineyard for a unique wine tasting experience, including a vineyard tour and wine pairing with local meats and cheese.
PM: Stop in the iconic hilltop village of Montalcino to explore the local shops and wine tasting rooms, lunch, and discover and taste additional wines at a historic fort in the center of town.
Farewell group dinner at the hotel.
Day Seven:
Hotel Check Out and complimentary timed group departure in a black car service to either FLR airport in Florence or FCO airport in Rome.




What is Included?
- Daily hotel breakfast (Days Two - Seven)
- Daily group, prix fixe dinners (Days One - Six)
- Prix fixe lunch included (Day Two and Four - Six)
- Six night boutique hotel stay
- Upon arrival, private black car transfer from either Santa Maria Novella train station of FLR airport in Florence
- Upon departure, one-time private group departure in a black car service to FLR in Florence and FCO in Rome
- Arrival aperitivo, inclusive of traditional Tuscan snacks, cocktails, and wine
- Privately guided historical tours and admissions
- Private food market tour with a wine tasting
- Private group excursion to designer outlets, including round-trip private group transfer *purchases excluded
- Private group transport from Florence to Tuscan countryside boutique hotel
- Private group excursion to Pienza with private group transportation, including a pasta making class with cheese and wine pairings at a family-run agriturismo
- Private group excursion with transportation to Montalcino inclusive of vineyard visit, tour, wine tasting, lunch in Montalcino with visit and wine tasting at a historical fort
- One-time assistance with airfare planning and/or point maximization *cost of airfare not included
- Assistance with travel arrangements to the meeting point in Florence *cost of transportation not included
What is Not Included?
- Airfare or other transportation arrangements
- Client requested room upgrades, subject to availability
- Hotel incidentals, room charges, minibar, room service
- Transportation, dining, and experience expenses, not listed in the itinerary
- Transportation arrangements to Florence, if not from Florence Santa Maria Novella Station or FLR Airport
- Transportation arrangements from Tuscany that are separate from the one-time transfers to FLR and FCO Airport
- Purchases made on shopping days or tours
- Mandatory travel insurance
- Gratuities at your discretion
*Minimum group size must be met before travels are confirmed. The minimum group size is 8. If 8 guests are not reached, this tour will be refunded, with the option to reschedule.
*Itinerary inclusions based on availability and schedules may vary accordingly.


reserve your spot for TUSCANY 2024
Yes, currently our Custom Group Travel is limited to those clients 21 years of age or more. For travel with young adults or children, please contact The Destination Designer for custom travel planning.
Custom Group Travel is a small group, curated experience. To ensure this, group sizes start at eight and are limited to twelve travelers.
Minimum group size must be met before travels are confirmed. The minimum group size is eight. If eight guests are not reached, the tour will be refunded, with the option to reschedule.
Deposits required pursuant to the terms and conditions of the Custom Group Tour are required at the time of booking.
Final payment is due to The Destination Designer 45 (forty-five) days prior to the trip departure. Failure to complete full payment at the designated time will result in booking cancellation without notice, will be considered a client cancellation, and cancellation fees will apply.
If you are a United States citizen and traveling internationally, a US passport is needed. Please ensure that your passport is valid for at least six months beyond the completion of your trip to ensure entry into your destination country.
Check destination specific visa requirements at the time of booking.
If you are not a United States citizen and traveling internationally, check with your consulate or embassy as well as the destination country’s consulate or embassy to determine necessary travel documents.
If traveling internationally with children under the age of 21 without both parents or as a legal guardian, check with your travel advisor regarding necessary documentation to comply with international travel regulations.
Prior to departure, make at least two photocopies of your passport and other necessary travel documents and leave one copy at home. Additionally, make a digital copy of said documents and store them in your smartphone or tablet.
Please Note: The Destination Designer is not liable or responsible for any disruption of travel due to inaccurate, false, incomplete, or improper travel documentation needed throughout your journey.
Yes, for Custom Group Travel, travel insurance is required and proof of said coverage is required as per the terms and conditions of your contract with The Destination Designer.
Yes, we understand the task of booking airfare can be overwhelming whether paying in cash or redeeming miles and we are happy to assist you with airfare searches, airfare bookings, and showing you how to maximize your points for mileage tickets. This is all included in the cost of your Custom Group Travel.
Yes, subject to availability and at the sole cost of the client. Please contact The Destination Designer to submit your request prior to your travel departure date.
We will do our best to accommodate early check-in and late check-out requests, however such requests are not guaranteed, subject to availability, and at the sole discretion of the hotel.
Please feel free, however all incidentals, meals, drinks, or any other services outside of the scope of included items enumerated in the custom itinerary are at the sole cost of the client.
Please note, upon check-in at your designated hotel, each client will be required to provide their own credit card to the hotel for any additional charges/incidentals/damage incurred. Failure to do so may result in a violation of the terms and conditions of your reservation for your accommodations and the terms and conditions of your Custom Group Travel contract resulting in cancellation of said contract with all applicable penalties the sole responsibility of the client.
We are excited to offer additional opt-in activities that we will happily arrange for you during your Custom Group Trip. This allows you the flexibility to choose exactly what you want to do during your free time.
Please note that the cost of the opt-in activities are a separate and an additional cost and are subject to availability. Availability is on a first come, first service basis. Please reach out to your Travel Designer for additional information regarding the opt-in activities.
Yes, we are happy to make additional dinner reservations for you during the duration of your Custom Group Tour. Please note that deadlines apply to dinner reservations requests, so please check the terms of your agreement/contract.
Please check the specifics of your Custom Group Itinerary to determine if there are any luggage restrictions while traveling with the group.
Prior to travel it is the client’s responsibility to check and comply with airline luggage restrictions and/or regulations. The Destination Designer is not liable for any travel disruption or delay due to the client’s failure to comply.
Yes, we will do our best to accommodate any special requests or dietary restrictions of our clients but please note that as a result meal choices may be limited.
The Destination Designer wants you to enjoy the experience of their Custom Group Tours. In order to do so, you should be in good health and must be able to walk a reasonable distance on different surfaces. Much of the tour is accessible solely on foot and often pathways and roads are narrow and uneven. Additionally, traveling up and down steep steps is often required.
We are sorry to inform you that at this time, our Custom Group Tours are unable to accommodate wheelchairs, motorized scooters, or provide walking or other individual assistance to those with specialized needs. Travelers who require such assistance are free to bring a companion to provide assistance at the sole cost of the traveler.
If you have a medical condition that may impact your ability to travel or participate in activities while traveling, please contact your physician for medical advice and medical clearance to travel and notify The Destination Designer as soon as possible.
When traveling please ensure that you have packed in your hand luggage enough required medication and/or prescriptions for the duration of your tour and extra in case of trip delays.
If you suffer from any allergies, please notify The Destination Designer at the time of booking.
Prior to booking your tour, carefully review the travel itinerary and should you have any questions, please contact your Custom Travel Planner.