Tuscan Cycling & Fitness Retreat: Bike, Cook & Taste Your Way Through Chianti

The retreat runs for six days and five nights in the Chianti Classico region of Tuscany, based the whole time at Borgo Sicelle, a former small Chianti farm that now operates as a private villa with nine apartments. It sits between Florence and Siena, surrounded by vineyards, olive groves and cypress trees. Because the group stays in one place and everything is included from the moment you land in Florence, the week is built around riding and eating rather than packing and moving.

Cycling is the backbone of the trip. There are four guided rides, all levels welcome, and daily distance sits between 15 and 30 miles. The local guide rides with the group and a support van is available on request. Routes take in towns like Castellina in Chianti, San Donato in Poggio and Radda in Chianti. The first ride happens on the opening afternoon, an introductory loop through the countryside after you have settled in. Tuscany is rolling hill country, so expect climbs — this is not a flat route. Bikes are provided: either a 27-speed hybrid or an e-bike, plus a helmet, so you do not need to ship your own.

One day the bikes stay parked and the group does a guided hike in the Tuscan hills instead. Daily fitness classes run alongside the riding, led by the retreat leaders who hold numerous certifications between them — the classes may cover core training, yoga, Pilates, BodyBalance and stretching, and they are adapted to the people in the room rather than following a fixed script. Two winery tours and tastings are scheduled during the week, along with an Italian cooking class where the group prepares one of the meals with guidance from a local chef. The villa's host also puts on an authentic Tuscan BBQ.

Between sessions, afternoons are deliberately free. The villa has a swimming pool that looks out over the valley, a garden, and a terrace with tables and lounge chairs. The common room is where the fitness classes happen. The rhythm of the day follows the local habit of an afternoon siesta, so there is real time to rest before dinner.

Meals included are daily breakfast and dinner, with most lunches also covered during the week. By the end of the trip you will have eaten a meal you cooked yourself in the cooking class, a BBQ cooked by the villa host, and whatever you choose to order around the winery visits. Supplemental meals, snacks, alcohol outside the wine tastings, souvenirs, airfare, taxes and gratuity are not included. Group transfers run from Florence International Airport to the villa on the first scheduled day and back to Florence at the end.

The group is limited to 14 travellers, so it stays small enough that the guides can adjust pace and the fitness sessions to the people who are actually there. Single travellers are paired in a two-bedroom apartment with another solo guest based on availability; couples get priority for single-bedroom apartments. Single occupancy can be arranged for an additional fee. This is an active holiday with a lot of rewards built around food and wine — the riding is real, but so is the eating.

What's included

- 5 nights' accommodation at Borgo Sicelle, including all taxes and fees - Daily breakfast and dinner at the villa - Most lunches during the retreat - 4 guided bike tours (15–30 miles per day) - 27-speed hybrid bike or e-bike with helmet rental - Support van available on request - Local cycling guide - 2 winery tours and tastings - Italian cooking class - Guided hike in the Tuscan hills - Authentic Tuscan BBQ prepared by the villa host - Daily fitness classes led by your retreat leaders - 1 complimentary 15-minute percussive therapy session per person - Group transfers from/to Florence on the first and last scheduled days of the programme - All entrance fees and services of local guides as per the itinerary - Use of the villa pool, garden, terrace and common room

What's not included

- Airfare - Pre- and post-trip accommodation and associated expenses - Air and land transportation to/from host cities - Gratuities for travel director, local guides, drivers, porters and hotel staff - Costs associated with necessary travel documentation (passport, visa) - Porterage fees - All types of personal insurance - Personal expenses - Beverages during meals (coffee and tea are included) - Alcohol outside the included winery tastings - Supplemental meals and snacks - Souvenirs - WA State sales tax