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Italy Deep Dive: Rome to Southern Villages, Puglia Masseria & Northern Cities — 17 Jan to 4 Feb 2026

Viewed by 145 travelers

Day 1: Arrival & Settling

Rome, Italy on January 17, 2026

3:00pm

Hotel check-in & orientation walk

Arrive, check into central Rome accommodation, then take an easy orientation walk to get your bearings and local essentials (ATM, pharmacy, grocery). Good for group acclimation.
EUR0, 1h30m

5:00pm

Piazza Navona & evening stroll

See the Baroque fountains and street artists; outdoor cafés are open in the early evening — seasonal hours vary, but piazza is public and open year‑round.
EUR0, 1h0m

7:30pm

Dinner — Trattoria For Local Roman Fare

Classic Roman dishes (cacio e pepe, carbonara) in a nearby trattoria ideal for groups; reserve ahead for 8. Most traditional trattorie open 7pm–11pm.
EUR30, 1h30m

Day 2: Ancient Rome

Rome, Italy on January 18, 2026

8:30am

Colosseum, Roman Forum & Palatine Hill

Full morning exploring Rome's principal ancient sites; book a guided timed entry (Colosseum typically opens ~8:30, winter closing ~16:30 — confirm exact times & prebook skip‑the‑line tickets).
EUR18, 3h0m

12:00pm

Lunch — Trattoria or Enoteca near Monti

Relaxed lunch in Monti neighbourhood — seasonal openings generally 12:00–15:00; try local antipasti and porchetta sandwiches for quick energy.
EUR25, 1h0m

2:00pm

Capitoline Museums or Basilica of San Clemente

Choose Capitoline Museums for artifacts and city views (usually open ~9:30–19:30) or San Clemente to see layered Rome (open mornings and late afternoons); both deepen context after the Forum.
EUR12, 2h0m

6:30pm

Dinner — Jewish Ghetto/Carciofi alla Giudia

Sample Roman Jewish cuisine (fried artichokes) in the Ghetto; restaurants are typically open evenings from 7pm.
EUR35, 1h30m

Day 3: Vatican & Centro

Rome, Italy on January 19, 2026

8:30am

Vatican Museums & Sistine Chapel

Book early timed tickets (Museums generally open ~9:00; arrive early). A guided visit avoids long lines and explains masterpieces including the Sistine Chapel.
EUR20, 3h0m

12:30pm

Lunch — Borgo Pio

Light lunch near Vatican with salads and Roman pizzas; small restaurants open 12:00–15:00.
EUR20, 1h0m

2:00pm

St. Peter's Basilica & Dome (cupola)

Visit St. Peter's Basilica (open early to early evening; free entry), and optionally climb the dome for panoramic city views (dome access closes earlier in winter — check in advance).
EUR10, 1h30m

4:30pm

Leisure time & shopping

Explore Via Cola di Rienzo or Via del Corso for shopping and cafés; many shops stay open until early evening.
EUR0, 1h30m

7:30pm

Dinner — Modern Roman Cuisine

Treat the group to a contemporary Roman dinner (reserve for 8), good for sampling evolved regional cuisine.
EUR40, 1h30m

Day 4: Historic Center

Rome, Italy on January 20, 2026

9:00am

Pantheon, Piazza Navona & Campo de' Fiori

Walk the historic center: Pantheon (generally open 9:00–19:00), Piazza Navona and the lively market at Campo de' Fiori; short stops show Roman urban life and baroque art.
EUR0, 2h0m

11:30am

Lunch — Tasting Menu in Centro Storico

Longer lunch to savour Roman seasonal produce; many central restaurants open 12:00–15:00 and offer set menus for groups.
EUR35, 1h30m

2:00pm

Trastevere & Gianicolo viewpoint

Cross the Tiber to Trastevere for cobbled lanes and artisan shops, then walk/up to Gianicolo for skyline views; Trastevere is open as a neighborhood all day.
EUR0, 2h30m

6:30pm

Evening at Leisure & Dinner

Choose a relaxed restaurant in Trastevere or near the hotel; book for the group to ensure seating.
EUR30, 1h30m

Day 5: Naples & Pompeii

Pompeii / Naples, Italy on January 21, 2026

8:00am

Train Rome → Naples, transfer to Pompeii

High‑speed train Rome Termini → Napoli Centrale (1h10m), then Circumvesuviana or private transfer to Pompeii; book tickets in advance for 8. Trains run frequently early morning.
EUR30, 3h0m

11:30am

Pompeii Archaeological Park

Explore the extensive ruins (site open ~9:00–16:30 in winter); a guided tour gives the best insight into daily Roman life preserved by Vesuvius.
EUR18, 2h30m

2:00pm

Lunch — Pizzeria in Naples

Travel back to Naples for authentic Neapolitan pizza (many pizzerias open midday and evenings; try a classic Margherita).
EUR15, 1h0m

4:30pm

Naples brief walk & return to base or continue to Amalfi next day

Short walk along the Lungomare or a view of Castel dell'Ovo; keep schedule flexible to collect rental car in Naples if planning to drive to the Amalfi Coast the next morning.
EUR0, 1h0m

7:30pm

Dinner — Seafood in Sorrento/Naples

If based in Sorrento or Naples, choose fresh seafood or local dishes; reserve a table for 8.
EUR35, 1h30m

Day 6: Amalfi Coast

Amalfi / Ravello / Positano, Italy on January 22, 2026

9:00am

Drive or private transfer to Positano/Amalfi

Collect hire car (group minivan recommended) or take private transfer from Naples/Sorrento to the Amalfi Coast; roads are winding so plan comfortable drivers and allow 1–2 hours travel time depending on start point.
EUR0, 2h0m

11:30am

Positano walk & viewpoints

Stroll Positano's steep lanes for ceramics, boutiques and sea views; open-air village, accessible year‑round though some shops close in low season.
EUR0, 1h30m

1:30pm

Lunch — Amalfi Coast Restaurant

Coastal dining with seafood and limoncello specialties; restaurants generally open 12:00–15:00 and 19:00–23:00, but check reservations during winter.
EUR35, 1h30m

3:00pm

Ravello gardens — Villa Rufolo or Villa Cimbrone

Visit stunning cliffside gardens with panoramic views (gardens usually open 9:00–17:00 in winter); Ravello is quieter in January but beautiful, ideal for photos and calm walks.
EUR7, 1h30m

6:00pm

Check-in & dinner at coastal hotel

Relax at your hotel and have a reserved dinner for the group overlooking the sea.
EUR40, 1h30m

Day 7: Coast to Matera

Amalfi Coast → Matera, Italy on January 23, 2026

8:30am

Morning seaside relaxation

Enjoy a slow morning in Amalfi/Positano — short walks and photos, cafés open early though some winter services may be limited.
EUR0, 2h0m

11:00am

Drive to Matera (approx. 3.0–3.5h)

Scenic drive east into Basilicata towards Matera; plan rest stops and an early arrival to explore the Sassi at dusk. Roads are good but allow time for winter conditions.
EUR0, 3h30m

3:00pm

Check-in & short rest

Arrive in Matera and check into a cave hotel if possible for the authentic experience; cave hotels are open year‑round but book early for a group.
EUR0, 1h0m

4:30pm

Sassi di Matera at sunset

Walk the UNESCO Sassi and laneways as evening lights come on — Sassi are open to visitors anytime, but museums have set hours (check Casa Grotta opening around 9:00–19:00).
EUR0, 1h30m

8:00pm

Dinner — Cave restaurant tasting local Lucanian cuisine

Dine in a restaurant carved into the rock featuring regional specialties; reserve for the group.
EUR40, 1h30m

Day 8: Matera Exploration

Matera, Italy on January 24, 2026

9:00am

Guided Sassi walking tour & Casa Grotta

Guided tour through the Sassi's cave dwellings and churches; many sites open from morning to late afternoon — guided tours are highly recommended to understand the unique history.
EUR15, 2h0m

11:30am

Museo Nazionale Ridola or rupestrian churches

Visit archaeological exhibits or rock churches with frescoes; check museum opening times (usually 9:00–19:00 in winter but confirm closures).
EUR6, 1h30m

1:30pm

Lunch — Local trattoria

Savour Lucanian specialties such as peperoni cruschi and orecchiette; many restaurants open midday and in the evening.
EUR25, 1h0m

3:30pm

Leisure & optional visit to Matera viewpoints

Relax, shop for local ceramics or take panoramic photos from viewpoints over the Sassi.
EUR0, 1h30m

7:30pm

Dinner & early rest

Enjoy another evening meal in town; group rest recommended—next day is a transfer into Puglia.
EUR35, 1h30m

Day 9: Alberobello & Masseria

Alberobello / Puglia, Italy on January 25, 2026

9:00am

Drive Matera → Alberobello (approx. 1h45m)

Short scenic drive into the heart of Puglia; roads are straightforward and drive time is manageable for the group with stops as needed.
EUR0, 1h45m

11:00am

Explore Alberobello Trulli

Wander the UNESCO trulli district (open year‑round) and visit the Trullo Sovrano museum (check opening times, usually morning to early evening).
EUR6, 1h30m

1:00pm

Lunch — Local trattoria

Lunch featuring focaccia, orecchiette and local cheeses; many Puglian restaurants open 12:00–15:00.
EUR25, 1h0m

3:00pm

Check-in at a masseria & olive grove walk

Settle into a traditional masseria (farmhouse) to experience rural life; many masserie welcome guests year‑round and offer olive grove walks and oil tastings.
EUR0, 1h30m

5:00pm

Cooking class at the masseria (hands-on)

Afternoon cooking class focused on Puglian dishes (orecchiette, focaccia, desserts) followed by a group dinner. Classes typically run 3–4 hours — book a private session for 8 adults; this satisfies your cooking class requirement.
EUR80, 3h0m

Day 10: Puglia Villages

Ostuni / Polignano a Mare / Bari, Italy on January 26, 2026

9:30am

Drive to Ostuni & explore

Visit the white hill town of Ostuni with narrow lanes and sea views; town is pedestrian-friendly and open year-round.
EUR0, 1h30m

11:30am

Polignano a Mare visit

Seaside cliff town famous for dramatic views and seaside cafés; great for photographs and a short coastal walk (public access always available).
EUR0, 1h30m

1:00pm

Lunch — Seafood cliffside restaurant

Lunch with fresh seafood and local pasta near the sea; restaurants usually open midday and require reservations for a group.
EUR30, 1h30m

3:30pm

Drive to Bari and check-in

Head to Bari for an overnight stay; Barivecchia (old town) is pleasant to walk in the evening.
EUR0, 1h0m

7:30pm

Dinner in Bari — Local cuisine

Group dinner in Bari’s old town sampling focaccia Barese and seafood; reserve a larger table.
EUR30, 1h30m

Day 11: Bari to Bologna

Bari → Bologna, Italy on January 27, 2026

8:30am

Morning in Bari (Basilica di San Nicola)

Visit the Basilica of Saint Nicholas and Bari's old town for a morning stroll; basilica generally open mornings and afternoons, check winter hours.
EUR0, 1h0m

11:00am

Train Bari → Bologna (high-speed)

Frecciargento/Frecciarossa train north to Bologna (~3.5–4h). Book seats for a comfortable group journey and allow transfer time at stations.
EUR45, 4h0m

4:30pm

Check-in & short city walk

Arrive in Bologna, check into hotel and walk to Piazza Maggiore and the Two Towers area; many sites accessible in late afternoon.
EUR0, 1h0m

7:30pm

Dinner — Bolognese cuisine (tagliatelle al ragù)

Enjoy Emilia-Romagna specialties at a recommended osteria; book a table for 8 in advance.
EUR35, 1h30m

Day 12: Bologna Food & Culture

Bologna, Italy on January 28, 2026

9:30am

Guided food market & tasting tour

Walk through Quadrilatero market and sample mortadella, Parmigiano Reggiano, cured meats; morning markets generally active 8:00–13:00.
EUR45, 2h0m

12:00pm

Lunch — Local osteria

Relax over fresh pasta or cured meats from the market; many lunch places open 12:00–15:00.
EUR30, 1h0m

2:00pm

Walking tour: Two Towers & Santo Stefano

Climb (optional) one of the towers for views and visit the complex of Santo Stefano churches; towers and sites usually open with winter hours—check access times.
EUR8, 2h0m

6:30pm

Dinner & evening at leisure

Evening to enjoy a leisurely meal and local wine; reserve for groups at popular spots.
EUR35, 1h30m

Day 13: Florence Arrival

Florence, Italy on January 29, 2026

9:30am

Train Bologna → Florence (40m)

Short high-speed transfer to Florence; trains run frequently and are comfortable for groups.
EUR20, 1h0m

11:00am

Duomo & Baptistery (exterior and optional climb)

Visit Florence Cathedral and Baptistery; Duomo access hours vary but typically 10:00–16:00 in winter — reserve tickets if you want to climb Brunelleschi's dome (limited slots).
EUR20, 1h30m

1:00pm

Lunch — Florentine cuisine

Try bistecca alla Fiorentina or lampredotto at a local trattoria; many restaurants open mid‑day and evenings.
EUR30, 1h0m

3:00pm

Uffizi Gallery (booked timed entry)

Afternoon visit to the Uffizi to see Renaissance masterpieces — book timed tickets in advance (winter opening often 8:15–18:50 but confirm dates).
EUR20, 2h0m

7:30pm

Dinner — River‑side restaurant

Evening meal near the Arno; make reservations for a group seating.
EUR40, 1h30m

Day 14: Chianti Countryside

Chianti / Tuscany, Italy on January 30, 2026

9:00am

Drive or minivan to Chianti wine region

Rent a small coach or minivan for a comfortable countryside day visiting vineyards and hill towns; scenic drives and short walks show rural Tuscan life.
EUR0, 1h30m

10:30am

Winery visit & tasting

Tour a Chianti Classico estate with cellar tour and tasting; book a private tasting for the group (estates usually open 10:00–17:00).
EUR35, 2h0m

1:30pm

Lunch at agriturismo

Farm-to-table lunch showcasing seasonal Tuscan produce and rural life; agriturismi usually require advance reservation for groups.
EUR45, 1h30m

3:30pm

Visit Greve or Castellina for small town charm

Wander the main squares and small markets to sample local olive oil and cured meats; towns are open year-round with shops closing in late afternoon on some weekdays.
EUR0, 1h30m

6:30pm

Return to Florence & dinner

Return to Florence for an evening meal and overnight rest.
EUR40, 1h30m

Day 15: Siena Day Trip

Siena, Italy on January 31, 2026

9:00am

Drive or train to Siena

Short journey to medieval Siena to explore Piazza del Campo and the Duomo; Siena's main attractions are open during winter but museum hours vary — check specific sites.
EUR15, 1h30m

11:00am

Piazza del Campo & City Museum

See the famous shell-shaped piazza and climb Torre del Mangia if open (tower hours seasonal), for panoramic views of the Tuscan hills.
EUR10, 1h30m

1:00pm

Lunch — Local osteria

Try pici pasta and Tuscan specialties in a local osteria; many are open midday and in the evening.
EUR30, 1h0m

3:00pm

Return to Florence & evening at leisure

Return trip to Florence for a relaxed dinner and packing for the next day's travel to Parma/Modena region.
EUR0, 1h30m

Day 16: Parma & Modena Food Day

Parma / Modena, Italy on February 1, 2026

8:30am

Train/drive Florence → Parma (approx. 2h)

Travel to Emilia food heartland; hire vehicle or train for convenience with luggage and group sizes.
EUR30, 2h0m

11:00am

Parmigiano Reggiano dairy visit

Visit a local dairy for a Parmigiano Reggiano tasting and cellaring explanation; dairies generally host tours by appointment and are open mid‑morning to mid‑afternoon.
EUR25, 1h30m

1:00pm

Lunch — Prosciutto di Parma tasting

Combined tasting of Parma ham, local bread and wine at a family producer or traditional osteria; reserve ahead for a group.
EUR35, 1h30m

3:30pm

Modena balsamic vinegar visit (acetaia)

Guided tasting of aged traditional balsamic at an acetaia (book in advance; many open afternoons), learning about production and countryside traditions.
EUR30, 1h30m

7:00pm

Overnight in Parma/Modena & dinner

Group dinner sampling regional fine dining or a convivial trattoria; reserve for 8.
EUR40, 1h30m

Day 17: Travel to Milan Area

Parma → Milan area (Lake Como/Bergamo option), Italy on February 2, 2026

9:00am

Drive or train Parma → Milan (1h)

Short travel to Milan region; if desired, stop en route at Cremona (violin-making) or continue straight to Milan for logistics and sightseeing.
EUR15, 1h0m

11:00am

Optional Lake Como day trip (drive/train ~1h)

If the group prefers scenic lakes, head to Como for a boat or lakeside walk; note winter boat schedules are reduced, so check timings for Jan/Feb.
EUR20, 4h0m

4:30pm

Check-in Milan suburb / hotel outside city if preferred

Settle into your final region base near Milan to prepare for the final days; central Milan hotels are convenient but book early for group rooms.
EUR0, 1h0m

7:30pm

Dinner — Milanese cuisine

Try risotto alla Milanese or ossobuco in Milan; reserve for groups at a recommended restaurant.
EUR45, 1h30m

Day 18: Bergamo or Lake Como

Bergamo / Lake Como → Milan, Italy on February 3, 2026

9:00am

Optional Bergamo Alta visit

Explore medieval Bergamo Alta with its Venetian walls (open outdoor spaces year‑round, museums vary by season); easily accessible from Milan by train (~50m).
EUR0, 3h0m

1:00pm

Lunch — Bergamo polenta or lakeside trattoria

Traditional lunch sampling local polenta or fresh lake fish; restaurants open midday and evening.
EUR30, 1h0m

3:30pm

Return to Milan & early evening shopping / aperitivo

Enjoy Milan’s aperitivo culture (typically 6–9pm) for a relaxed group experience before the final full day in the city.
EUR15, 2h0m

8:00pm

Dinner near Navigli

Canal‑side dinner in the Navigli district — lively evening atmosphere with many group-friendly restaurants.
EUR40, 1h30m

Day 19: Milan Highlights — Arrival Deadline

Milan, Italy on February 4, 2026

9:00am

Duomo di Milano & terraces

Visit the iconic Duomo and terraces for panoramic city views (Duomo open from ~9:00, terrace hours vary by season—prebook tickets to avoid queues).
EUR15, 1h30m

11:00am

Santa Maria delle Grazie — The Last Supper (book ahead)

If possible, secure advance tickets for Leonardo's Last Supper (strict timed entries) — book well in advance as slots are limited, especially for groups.
EUR15, 1h0m

1:00pm

Lunch — Milanese trattoria

Enjoy a leisurely lunch and Milanese specialties; many restaurants open 12:00–15:00.
EUR35, 1h0m

3:00pm

Galleria Vittorio Emanuele II & shopping area

Stroll the galleries and elegant streets, ideal for last-minute shopping and photos; galleries are open to the public year‑round.
EUR0, 1h0m

5:30pm

Final group dinner / aperitivo & ensure presence in Milan evening

Gather the group for a final celebratory meal or aperitivo near the center — by evening you will be in Milan as required. Confirm transport to airports or onward travel plans from here.
EUR45, 2h0m
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