A proposed eight-day journey from Florentine art and workshops to Siena and time in the Tuscan countryside.
A thoughtful starting point. Room for everything that matters to you.
Keep the moments you love. Change the pace, the hotels or the route. Tell us about special requests and anything already booked; we will shape the proposal around you.
- Four proposed nights in Florence and three in the Chianti countryside, with one hotel change
- One focused Uffizi visit and time in the Oltrarno
- A Siena outing balanced with rest at a country hotel
- A proposed Tuscan food or wine experience shaped around your tastes
- Restaurants and travel details organized with your itinerary
Preview itinerary. No hotel, guide, ticket or table is confirmed by this page. The written proposal confirms the arrangements, availability and conditions.
Three ways to make it yours.
Compare hotels and experiences, not levels of service. Personal planning, restaurants, approved reservation requests and the Chic Trip app are part of every journey.
7 nights · Two adults sharing one double room · Illustrative budgets, USD.
Charm
Boutique Florence and country-house Chianti, with private guiding for the Uffizi and Siena.
Around $5,990 USD per person · $11,980 total for two
- 4 nights in Florence: Characterful four-star boutique hotel. Classic double room. Area to consider: The historic center or Oltrarno. 3 nights in Chianti: Four-star country hotel or an explicitly agreed country-house equivalent. Classic double room. Area to consider: The Greve or Castellina countryside, after checking the Siena route.
- Private Uffizi visit and private Siena town introduction. An independent Oltrarno route with an artisan-visit request, plus one hosted winery tasting on day 7; day 4 stays free. Transport: Private arrival, Florence-to-Chianti and departure transfers. Private return transport for Siena and the winery; city outings otherwise planned around walking and independent local journeys.
Signature
Five-star city and country hotels, a guided Oltrarno outing and a private Tuscan tasting.
Around $9,990 USD per person · $19,980 total for two
- 4 nights in Florence: Selected five-star hotel. Superior or deluxe double room. Area to consider: The central Arno or historic-center area. 3 nights in Chianti: Selected five-star country hotel. Superior or deluxe double room. Area to consider: One Chianti country base with the Siena journey checked.
- Private Uffizi, Oltrarno and Siena visits, with an artisan appointment sought for the Oltrarno day. One private winery tasting or private cooking session on day 7; choose one, with day 4 and the quiet afternoons preserved. Transport: Executive-car arrival, hotel-change and departure transfers. Private vehicles for the Siena outing and selected food or wine experience, with pickup, waiting time and return stated.
Exceptional
A Florence suite and a Chianti suite, with specialist guiding and privately hosted Tuscan flavors.
Around $16,990 USD per person · $33,980 total for two
- 4 nights in Florence: Distinctive luxury hotel. Junior suite or suite; river views requested separately by room category. Area to consider: A central Arno or historic address chosen with you. 3 nights in Chianti: Luxury country hotel. Suite with a sitting area; outdoor space checked individually. Area to consider: A single Chianti estate, selected for setting and access.
- Private art-focused Uffizi guiding, a privately guided Oltrarno walk with a requested artisan meeting, and a private Siena introduction. One private chef-led Tuscan cooking experience on day 7; a private winery visit may replace it, not accompany it automatically. Transport: Premium arrival, hotel-change and departure transfers. A private vehicle for the agreed Siena and culinary outing blocks, including waiting time; the free Florence day has no scheduled car or visit.
The hotel and room shown belong to that proposed style; further changes beyond it are quoted separately. A private guide does not mean private access to a venue.
These are indicative budgets, not confirmed offers or guaranteed availability. Dates, season, room choice and experiences affect the final total. International flights and meals excluded unless specified.
What we confirm before you book
These are proposed configurations, not confirmed bookings. Your written proposal names the hotels, room categories, guides, admissions and transport, with the complete price and cancellation conditions for your dates. A private guide does not mean private access to a venue. Requests depend on availability; no special entrance, room feature or restaurant table is guaranteed.
Hotel categories describe the selection we would propose, not a confirmed property. Room size, bed setup, views, air conditioning, lifts, step-free access, breakfast, taxes and facilities are checked for the actual hotel and room.
Optional enhancements are outside the configuration shown until selected and priced in your proposal. International flights, ordinary restaurant meals, drinks and table deposits are separate unless expressly itemized. A tasting or class includes only the food and drinks listed in the proposal.
Something particular in mind?
Mix these ideas or start from scratch. Tell us what matters to you and we’ll prepare a personal quote.
Tell Fred about your wishes
Your days, at your pace
Illustrative days, not fixed dates. Opening days, transfers and your preferences will shape the final order.
- Florence
- Oltrarno
- Chianti
- Siena
Day 1: A gentle arrival in Florence
Florence
Settle into your proposed Florence hotel after the arrival transfer. Take a short walk near your base and enjoy dinner close by, leaving the first day flexible around travel and check-in.
- Proposed arrival transfer
- Neighborhood dinner planning
Time for yourself: Rest at the hotel after travel before choosing whether to go out.
Day 2: Florentine art, with room to breathe
Florence
Make a focused Uffizi visit the main proposed experience, with admission, guide and artworks to be discussed for your dates. Lunch stays in the center, followed by a gentle walk toward the river if you wish.
- Proposed guided Uffizi visit and admission
- Nearby lunch selection
Time for yourself: Keep the afternoon free for the hotel, a cafe or a short riverside stroll.
Day 3: The Oltrarno and its workshops
Florence
Explore the Oltrarno at a measured pace. A proposed artisan introduction can be included only after a host and appointment are confirmed. Allow time for a neighborhood lunch and return to your hotel before dinner.
- Proposed Oltrarno neighborhood walk
- Artisan-visit request and restaurant planning
Time for yourself: Browse independently or spend the later afternoon resting at your hotel.
Day 4: Your own Florence morning
Florence
Leave a lighter day for the cathedral neighborhood, shopping or a cafe, with no additional museum assumed. This is an exterior city walk; cathedral, dome and bell-tower access would need a separate choice and admission arrangements.
- A flexible self-guided neighborhood plan
- Restaurant selection and reservation requests
Time for yourself: Keep a full afternoon free before changing hotels the next day.
Day 5: Into the Chianti countryside
Chianti
Travel by proposed private transfer to one country hotel for three nights. A village stop can be planned around the chosen property and check-in. Door-to-door timing will be checked once the route and hotel are known.
- Proposed Florence-to-Chianti transfer
- Country-hotel and en-route lunch planning
Time for yourself: Settle in and enjoy the country setting without another scheduled outing.
Day 6: A considered day in Siena
Chianti
Propose a Siena excursion with private transport and a focused guided introduction. Cathedral access, if wanted, is subject to the admissions actually quoted. Keep lunch in town and return to the hotel with time to relax.
- Proposed Siena excursion with transport and guide
- Lunch suggestions along the route
Time for yourself: Leave the late afternoon and early evening free at your country hotel.
Day 7: Tuscan flavors and a quiet afternoon
Chianti
Choose one proposed winery or cooking experience, with provider, format, menu and transport to be confirmed. A non-alcoholic alternative can replace the wine focus. Leave room to enjoy the hotel rather than adding multiple village visits.
- One proposed food or wine experience to be selected and quoted
- Farewell restaurant planning
Time for yourself: Spend the afternoon at the hotel, with time for rest and packing.
Day 8: Onward from Tuscany
Chianti
Plan a departure transfer to the agreed airport or station. The final connection and timing depend on your booked onward travel, with additional nights quoted if they make the departure more comfortable.
- Proposed departure transfer
- Connection planning
Time for yourself: Enjoy a last breakfast if the confirmed schedule allows it.
The right restaurants. The details in your pocket.
We suggest restaurants for your tastes and budget, refine the choices with you, then handle approved reservation requests. Tell us about dietary needs, celebrations and the atmosphere you enjoy.
Your day-by-day itinerary, maps and reservation information live together in the Chic Trip app. You can discuss the trip without creating an account.
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