Tuscany: The Slow Way

Arrive in Florence and transfer to your boutique hotel in the city center during the group arrival window. Today is a soft landing — check in, freshen up, and take your first walk across the Arno.

In the evening, gather for a welcome dinner at a curated local restaurant. Good wine, good food, and the beginning of a week that moves at your pace.

Included: Group arrival transfer window · Welcome dinner Not included: Airfare · Meals outside the welcome dinner · Airport transfers outside the group window

Begin with one of the world's great museum experiences: a guided Uffizi Gallery highlights tour. The planned experience is a small-group Uffizi visit focused on the museum's most celebrated works — Botticelli's Birth of Venus, Raphael, Caravaggio, and the Florentine masters — in a guided format that keeps the experience focused and absorbing rather than overwhelming.

After the museum, the afternoon is entirely yours. Walk across the Ponte Vecchio, climb to Piazzale Michelangelo for the view, browse the San Lorenzo market, or find a café and stay there. This is a Slow Wanderer trip — the afternoon is not scheduled on purpose.

Included: Guided Uffizi highlights experience · Group transportation as needed Not included: Lunch · Personal shopping · Optional photo walk

The hands-on day. A Tuscan cooking class with a local chef — the planned experience is a small-group session that covers fresh pasta, a seasonal main, and a traditional dessert. You'll cook together, eat together, and leave with recipes you'll actually use at home.

The afternoon is free for last Florence wandering — the Oltrarno neighborhood, the Boboli Gardens, or a final gelato by the river. In the evening, the group transfers to the Tuscan countryside for the second half of the trip.

Included: Tuscan cooking class with local chef Not included: Lunch · Personal shopping

The signature day. A full Chianti wine tour through the Tuscan countryside — vineyard visits, cellar tours, and multiple tastings at one or two estates. The planned experience is a small-group Chianti day trip that includes roundtrip transportation, guided vineyard and cellar visits, and wine tastings with local food pairings.

Afterward, settle into your agriturismo or countryside property for the second half of the trip. Long table dinner, open sky, and the kind of evening that makes you want to stay another week.

Included: Chianti wine tour with vineyard visit and tastings Not included: Additional wine purchases · Guide/driver gratuities

A day in two of Tuscany's most beautiful medieval towns. The planned experience is a guided Siena and San Gimignano day trip — Siena's Piazza del Campo, the Duomo, the medieval towers of San Gimignano, and the kind of streets that make you forget what year it is.

This is the most structured day of the Tuscany half of the trip — a guided experience with a clear arc. The rest of the week is yours to fill as slowly as you like.

Included: Siena and San Gimignano guided day trip · Group transportation Not included: Lunch · Entrance fees not included in the tour · Guide/driver gratuities

The most intentionally unscheduled day of the trip. Sleep in. Walk the property. Read in the garden. Take a solo drive through the back roads. Visit a local market. Do absolutely nothing and feel completely fine about it.

In the evening, the group gathers for a farewell dinner — either at the agriturismo or at a nearby trattoria, depending on the final property and vendor. A long table, good wine, and a group that has spent a week moving slowly through one of the most beautiful places on earth.

Included: Farewell dinner Not included: Lunch · Additional drinks · Gratuities

After check-out, transfer back to Florence Airport during the group departure window. One last espresso, one last look at the hills, and a group chat that will outlast the trip.

Included: Group departure transfer window Not included: Airfare · Transfers outside the group window

Not at all. The Slow Wanderer itinerary builds in natural connection moments throughout the week — a welcome dinner, a cooking class, the Chianti wine tour, and a farewell dinner. The pace is intentionally unhurried, which means the group has time to actually get to know each other rather than just moving from one activity to the next.

This trip requires 8 paid travelers to operate at the planned price and experience level. Major non-refundable supplier commitments will not be fully confirmed until the trip minimum has been met or a contingency plan is in place. If the minimum is not met, Vacay With Friends may revise the itinerary, adjust pricing, offer a trip credit, or cancel the trip and refund eligible payments according to supplier terms.

The $700 deposit is non-refundable and non-transferable. Cancellations before May 26, 2027 may have additional payments refunded less supplier penalties and unrecoverable costs. Cancellations May 27, 2027–July 25, 2027 may have up to 50% of payments made non-refundable depending on supplier terms and replacement traveler availability. Cancellations on or after July 26, 2027 are fully non-refundable.

Travel insurance is strongly recommended for every traveler. Consider coverage that includes trip cancellation, trip interruption, emergency medical coverage abroad, travel delay, baggage protection, and emergency assistance. Cancel For Any Reason coverage is worth considering when available.

Late September and early October is one of the most beautiful times to visit Tuscany — harvest season. Expect warm, golden days with highs of 18–24°C (64–75°F), dramatically lower crowds than summer, and the countryside at its most atmospheric: vineyards turning amber, truffle season beginning, and long evenings that feel like they belong in a film. Pack light layers for cooler evenings and comfortable walking shoes. Rain is possible but rarely prolonged.

The Chianti wine tour includes roundtrip transportation from the Tuscan property, guided visits to one or two Chianti estates, cellar tours, and multiple wine tastings with local food pairings. The final vendor will be confirmed closer to the trip date and shared with all travelers in the pre-trip guide.

No. The Slow Wanderer itinerary is designed for a comfortable, accessible pace. The Uffizi and the Siena/San Gimignano day trip involve walking on uneven cobblestone streets, but there are no hikes, climbs, or physically strenuous activities. If you can walk a city comfortably, you'll be fine.