Guests ask us things a search engine cannot answer — what a week of food really costs in a staffed villa, whether a beach club is walkable from a particular bay, which house holds thirty people without anyone sleeping on a sofa. Here are five of the questions our specialists have fielded most often this year, answered the way we would answer them on the phone.
TuscanyWhich villas in Tuscany work for a large group?
Five in our collection take twenty or more: Villa Zietta (22), Villa Maria II (18), and Villa Daniela, Villa Elsa and Villa Rinascimento, each of which can hold thirty or more when the guest house is included. Zietta and Daniela are the easiest to run as a single party; Rinascimento is a hamlet rather than a house.
“Large group” is really two questions — how many beds, and whether everyone eats at one table. A property that sleeps thirty across four buildings is a different holiday from one that sleeps eighteen under a single roof. Our Tuscany villa rentals collection covers both, and the distinction is worth deciding before you look at pictures.
A main villa and two guest houses, fully renovated in 2021, ten minutes from Castellina in Chianti. Three hectares of private land planted with olive trees, and a west-facing pergola terrace with a table for twenty — so dinner arrives with the sunset. The most straightforward of the five to run as one party.
View Villa Zietta ›An eighteenth-century property in the countryside outside Lucca, with grounds running to two hectares — a swimming pool, a private lake, and enough separate outdoor rooms that a group of eighteen naturally spreads out before dinner pulls it back together.
View Villa Maria II ›Eleven traditional bedrooms and a newer wing of five more, set in an Italian garden with a fenced pool and a shaded patio. The practical detail that decides it for families: local shops and a grocery store are a short walk away, and Lucca is a ten-minute drive.
View Villa Daniela ›A grand estate in Chianti near Siena, restored, with the scale Italian and foreign noble families once used for celebrating — which is what it still does best: reunions, anniversaries, Tuscan weddings. Note the capacity carefully: published rates are for up to 26 guests, and 32 requires taking the guest house as well.
View Villa Elsa ›Fourteenth-century, and not a villa in the ordinary sense — a hamlet and a working farm that presses its own olive oil, in the Chianti countryside a quarter of an hour from Florence. It was owned by a family of painters and hosted Raffaello, Pontormo and Botticelli. For forty guests it is the only realistic answer in our Tuscan collection.
View Villa Rinascimento ›
Further reading: Large villas in Tuscany for family and friends’ reunions and the ultimate Tuscany itinerary.
FlorenceIs Florence worth it at New Year — and where do we stay?
Yes, and the reason is counterintuitive: Florence in late December belongs to Florentines. The summer crush is gone, the Uffizi is walkable, and the city celebrates New Year outdoors in the piazzas rather than behind a hotel ballroom door. Stay in a Chianti estate fifteen to thirty minutes out rather than in the centre — you get the space and a driver, and the city is a short ride each way.
The trade is weather for access. Expect cold, crisp days, some rain, and a genuine chance of frost in the hills; expect also to book a table at short notice, walk into churches you queued an hour for in July, and see the Duomo without a crowd in front of it. Christmas markets run through December, and the city’s New Year concerts and piazza gatherings are free and public.
For a group, a countryside estate is the better base at this time of year — a fire, a kitchen and a chef beats four hotel rooms and a restaurant booking, and the drive in is twenty minutes on empty winter roads. Villa Rinascimento sits a quarter of an hour out; several of our Chianti houses are similar. What matters is heating, which is not universal in old Tuscan buildings: ask us to confirm it property by property, because a fifteenth- century house with underfloor heating and one without are different holidays in January.
Further reading: Florence: a travel guide to experience the best of it.
Punta CanaWhat does food actually cost in a villa?
Three tiers, per person per day: cooking for yourselves from local markets and supermarkets; a mid-range private chef including groceries and preparation for two or three meals; or a high-end gourmet chef where the menu drives the number. Most luxury villas in Punta Cana come with chef service, so in practice you are choosing between the second and third.
An honest note on the figures. This answer used to quote precise dollar ranges — roughly $20–40 for self-catering, $50–100 mid-range, $100–200 and up for gourmet. Those were set in 2024 and food costs have not stood still since, so treat them as the shape of the decision rather than a quote. For a real number against your dates and party, ask us: your chef’s rate and a grocery estimate come back in writing before you book, which is more useful than any range on a blog.
What the tiers actually buy, which has not changed:
- Cooking yourselves. Eggs, bread, fruit and coffee for breakfast; sandwiches or salads at lunch; pasta, grilled meat or local dishes at dinner. Perfectly good, and a real saving on a long stay — but somebody in the party is shopping and cooking.
- Mid-range chef. Two or three meals prepared, groceries handled, kitchen left clean. This is where most guests land, and it is the point at which a villa starts to feel like a hotel that happens to be yours.
- Gourmet chef. Menu design, harder-to-source ingredients, wine pairing, courses. Worth it for a celebration dinner or two rather than every night of a week.
Add dining out to any tier and the total moves quickly — the restaurants in Punta Cana are worth several evenings. Our Punta Cana villas each list what is included, and the concierge arranges the chef either way.
Further reading: The best restaurants in Punta Cana.
Turks & CaicosWhen is the best time to go?
Mid-December to mid-April. Dry season, 75–85°F, low humidity, and the hurricane risk that runs June to November is effectively behind you. It is also peak season, so rates and crowds are at their highest — if that matters more than certainty, late April to early June and late November to early December give you nearly the same weather for noticeably less.
- Peak · mid-Dec to mid-Apr. The reliable window, and the festive weeks inside it are the island’s liveliest. Book festive 12 to 18 months out; the best beachfront houses go first.
- Shoulder · late Apr–early Jun, late Nov–early Dec. Still warm, still dry enough, fewer people, better rates. Our specialists’ own preference.
- Summer · Jun–Aug. The lowest rates of the year. Higher humidity and a real if modest chance of tropical weather — worth insuring.
Grace Bay’s calm shallow water is the reason this island suits families and first-time villa guests better than almost anywhere in the Caribbean. See the Turks & Caicos villa rentals collection for what is open on your dates.
Further reading: Our seven favourite beaches in Turks & Caicos.
MykonosWhere should we stay to be near Scorpios?
Paraga, and it is not close — Scorpios sits on Paraga Beach, so staying there makes the club a short walk rather than a drive. After that: Agios Ioannis at about ten minutes by car, Mykonos Town at ten to fifteen, and Ornos at roughly fifteen. All four are practical; only Paraga removes the car from the evening.
- Paraga Beach — walking distance. The closest, and the most relaxed of the four in daytime. Choose it if the club is central to the trip.
- Agios Ioannis — about 10 minutes. Quieter than town, upscale houses, the best sunset views on this side of the island.
- Mykonos Town, Chora — 10 to 15 minutes. Restaurants, shops and nightlife on your doorstep, the club a short drive away. This includes the Alefkandra waterfront, better known as Little Venice, which is part of Chora rather than a separate area.
- Ornos — roughly 15 minutes. The family-friendly option, with a good spread of dining and an easy beach.
Worth knowing: our Mykonos villas are spread across all four, and the difference between a ten-minute drive and a walk matters more here than the map suggests — Mykonos evenings run late and the roads to the south-coast clubs are busy at the wrong hours. Scorpios takes reservations well in advance in high season; the concierge handles it with the villa.
Further reading: New large Mykonos villas for group getaways.
However specific or niche — capacity, heating, chef rates, a beach club table — a specialist will answer it properly. That is one of the advantages of being part of our community.
