Florence & Chianti · best April to June, September to October
Renaissance Florence, cypress-lined Chianti roads and long lunches at wine estates. Most guests split their time between the city and a countryside base.
- Getting there: Florence (FLR) is 20 minutes from the city; Pisa (PSA) is about 1 hour by train or car.
- Car needed: Mostly yes, or book drivers
- Activity prices: Pricier
- Group favorites: chianti wine tour with tastings at two estates; florence highlights walking tour; skip-the-line Uffizi Gallery guided tour
Things to do · Weekend itinerary · Where to stay · Welcome dinner
Positano, Amalfi & Ravello · best May to June, September to early October
Pastel villages stacked above the sea, lemon groves and boat days to Capri. Expect stairs, winding roads and spectacular views from every terrace.
- Getting there: Naples (NAP) is about 1h30 by car to Positano or Amalfi. Many guests book a private transfer.
- Car needed: Not usually
- Activity prices: Mid-range
- Group favorites: capri boat day trip with a Blue Grotto stop; private boat along the Amalfi Coast; path of the Gods guided hike
Things to do · Weekend itinerary · Where to stay · Welcome dinner
Bellagio, Varenna & Tremezzo · best May to September
Villas, gardens and ferries crossing between pastel villages. The central lake around Bellagio, Varenna and Tremezzo is where most weddings happen.
- Getting there: Milan Malpensa (MXP) or Milan Linate (LIN), both about 1h15 by car to the central lake.
- Car needed: Not usually
- Activity prices: Mid-range
- Group favorites: private speedboat tour: Bellagio, Varenna and Villa del Balbianello; villa del Balbianello and Villa Carlotta gardens; italian cooking class in a lakeside home
Things to do · Weekend itinerary · Where to stay · Welcome dinner
Valle d'Itria, Ostuni & Polignano · best May to June, September to October
Whitewashed hill towns, trulli houses, olive groves and masseria farm estates where many weddings take place.
- Getting there: Bari (BRI) and Brindisi (BDS) are each about 1 hour from the Valle d'Itria.
- Car needed: Mostly yes, or book drivers
- Activity prices: Budget-friendly
- Group favorites: alberobello trulli walking tour; orecchiette pasta class in a masseria; olive oil tasting at a historic masseria
Things to do · Weekend itinerary · Where to stay · Welcome dinner
Sirmione, Gardone & Riva del Garda · best May to June, September
Italy's largest lake, with castle towns in the south, mountains in the north and vineyards on the shores. Easier to reach and often better value than Lake Como, with plenty for guests to do.
- Getting there: Verona (VRN) is 30 to 45 minutes from the south of the lake. Milan Bergamo (BGY) is about 1 hour, and Milan Malpensa (MXP) about 2 hours.
- Car needed: Not usually
- Activity prices: Mid-range
- Group favorites: boat tour around the Sirmione peninsula; bardolino wine tasting at a family winery; valpolicella and Amarone wine day
Things to do · Weekend itinerary · Where to stay · Welcome dinner
Rome · best April to June, September to October
Ancient ruins, Baroque piazzas and long dinners in Trastevere. The historic center is compact and best explored on foot.
- Getting there: Rome Fiumicino (FCO) is 45 minutes by car or 32 minutes on the Leonardo Express train to Termini.
- Car needed: Not usually
- Activity prices: Mid-range
- Group favorites: colosseum, Roman Forum and Palatine Hill tour; vatican Museums and Sistine Chapel tour; trastevere food tour
Things to do · Weekend itinerary · Where to stay · Welcome dinner
Taormina & Mount Etna · best May to June, September to October
A clifftop town with a Greek theater, an active volcano covered in vineyards, granita for breakfast and the bay of Isola Bella below.
- Getting there: Catania (CTA) is about 1 hour by car or bus from Taormina.
- Car needed: Mostly yes, or book drivers
- Activity prices: Budget-friendly
- Group favorites: mount Etna jeep tour with lava caves; etna wine tasting at a volcanic vineyard; isola Bella and Blue Grotto boat tour
Things to do · Weekend itinerary · Where to stay · Welcome dinner