5 Day Tuscany Golf Itinerary
Tuscany is golf with the volume turned down and the scenery turned up, a touring trip through cypress avenues, Brunello vineyards and walled hill towns, with the courses a graceful accompaniment to the food, the wine and the art. Five days runs a relaxed line from the Maremma coast up to Florence. Here is a day by day plan around Argentario, Toscana at Il Pelagone, Royal Golf La Bagnaia, Castiglion del Bosco and Ugolino, with drive times, the season and where to stay.
Photo: The Club Castiglion del Bosco via Google.
Who this trip suits
This is a trip for golfers who travel as much for the table and the landscape as for the card, and who will happily trade a championship test for a round through olive groves and vines with Siena on the skyline. The courses here are a pleasure rather than a punishment, played at an unhurried Italian pace, and they leave plenty in the tank for a long lunch and an afternoon in a hill town. It works beautifully as a couples trip, an anniversary or a small group who want golf, wine and culture in equal measure.
The one thing to accept is that Tuscany is a touring trip, not a single base, so you will drive between regions on good but winding roads. The plan below runs one logical line, south to north, from the Maremma coast through the Siena hills to Florence, so you are always moving forward rather than doubling back. Fix Castiglion del Bosco first, since it is private and arranged through the estate, then build the rest of the week around it.
The 5 day plan
Argentario Golf Club
Open on the Maremma coast at Argentario, the PGA National Italy course designed by David Mezzacane and Baldovino Dassu, threaded across the hills of the Monte Argentario promontory above Porto Ercole. It is a handsome, undulating layout with sea glimpses and a fine resort and spa attached, an easy first round to shake off the flight. Settle into the rhythm of the trip with a swim and a seafood dinner on the harbour afterwards.
Toscana Golf Club at Il Pelagone
A short drive north into the Maremma hills brings you to the Toscana Golf Club at Il Pelagone, a Keith Preston design that opened in 1999 and rolls through olive groves and macchia near the medieval town of Gavorrano. It is wide, friendly and quietly strategic, the sort of course that flatters a holiday swing while still asking smart questions around the greens. A relaxed second day before you turn inland toward Siena.
Royal Golf La Bagnaia
Move inland to the rolling Siena countryside and Robert Trent Jones Junior's course at La Bagnaia, laid lightly across the hills around a restored borgo resort just south of the city. The routing follows the land rather than fighting it, with the tower of Siena never far away, and the estate makes a natural base for the central leg of the trip. Play in the morning, then take the short drive into Siena for the Campo and an evening among the lanes.
Castiglion del Bosco
The jewel of the trip. Tom Weiskopf's course at Castiglion del Bosco is Italy's only private club, set inside the UNESCO listed Val d'Orcia near Montalcino on a Brunello producing estate, and it is played as a guest of the resort rather than on a public sheet. The holes flow through vineyards, woodland and wildflower meadows with the hill towns on every horizon, a round to savour. Pair it with a cellar visit and lunch on the estate, and confirm access directly before booking.
Golf Club Ugolino
Finish in the Chianti hills just south of Florence at Ugolino, the oldest course in Tuscany, designed by Cecil Blandford and Peter Gannon and opened in 1933. It is a charming, old fashioned parkland of tight tree lined corridors, maritime pines and vineyard views, full of period character and a fitting last round before the city. Play in the morning, then drive into Florence for the Duomo, the Uffizi and a final Tuscan dinner.
Drive times and logistics
| Leg | Indicative drive |
|---|---|
| Rome Fiumicino Airport to Monte Argentario | Around 1 hour 45 minutes |
| Argentario to Toscana at Il Pelagone, Gavorrano | Around 45 minutes to 1 hour |
| Gavorrano to La Bagnaia, near Siena | Around 1 hour 15 minutes |
| La Bagnaia to Castiglion del Bosco, Montalcino | Around 45 minutes |
| Montalcino to Ugolino, near Florence | Around 1 hour 30 minutes |
| Ugolino to Florence city centre | Around 30 minutes |
Drive times are indicative and traffic dependent. A car is essential for this touring route. Green fees and visitor days change, so always confirm directly before booking. Find places to stay across Tuscany.
Where to stay and how to play it
Tuscany rewards two or three bases rather than one. Open with a night or two on the Argentario coast near the golf and the harbour, move to a Siena or Val d'Orcia base for the central rounds at La Bagnaia and Castiglion del Bosco, where staying on an estate is the simplest route to the private course, then finish near Florence for Ugolino and the city. Hire a car, keep the daily drives modest, and let the order flex around confirmed tee times and a private course slot. If you prefer to anchor in one place, a Siena base reaches most of the rounds within a comfortable drive, at the cost of a little more time on the road each day.
Plan your Tuscany golf trip
We arrange the Castiglion del Bosco round through the estate, secure the rest of the tee times, set the route to keep the driving easy and sort the villas, the hotels and the wine. Tell us roughly when and who is travelling, and one concierge costs it to the head, with no obligation.
Tuscany golf trip questions
How many days do you need for a Tuscany golf trip?
Five playing days lets you run a relaxed line from the Maremma coast up to Florence, taking in Argentario, Toscana at Il Pelagone, Royal Golf La Bagnaia, Castiglion del Bosco and Ugolino, with time for Siena, Montalcino and a long lunch between rounds. Tuscany is a touring trip rather than a single base, so plan on driving, and a week leaves room for wine, the hill towns and a rest day.
What are green fees in Tuscany in 2026?
Tuscan green fees are moderate by world standards, with most clubs indicatively in the region of 70 to 150 euros for an 18 hole round in the 2026 high season, and the resort courses at the upper end. Castiglion del Bosco is private and played only as a guest of the estate, so it sits apart and is arranged through the hotel. Rates ease in spring and autumn. Always confirm current fees and visitor access directly before booking.
When is the best time to play golf in Tuscany?
Late spring, from May to June, and early autumn, in September and October, are the sweet spots, with warm settled days, the countryside at its best and the courses in fine condition. High summer is hot and busy on the coast, while winter is quiet and mild with softer ground. For golf paired with the vineyards and the harvest, late September into October is hard to beat.
Is Castiglion del Bosco open to visitors?
Castiglion del Bosco is Italy's only private golf club, the Tom Weiskopf course set inside the UNESCO listed Val d'Orcia near Montalcino, and it is played as a guest of the estate rather than on a public tee sheet. The simplest route is to stay at the resort or to arrange access through a trip planner, which also opens the cellar, the spa and the wider estate. Always confirm access directly before booking.
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Researched and written by the GolfForKings editorial desk. Course facts and indicative green fees verified June 2026. Last reviewed June 2026.