5 days unlocks Tuscany. Days 1-3: Florence essentials. Day 4: Pisa + Siena + San Gimignano guided day tour. Day 5: Chianti wine country + Antica Macelleria Cecchini Tuscan butcher lunch + Michelin finale.
Five days hits the sweet spot for Florence — three days for the major districts, plus two days for nearby destinations that show a different side of the country. The pace stays relaxed, you get more variety in your photo album, and the day trips break up the urban intensity nicely.
5-Day Total Budget at a Glance
Budget
$810
Per person, flights excl.
Mid-Range
$1,640
Per person, flights excl.
Luxury
$4,000
Per person, flights excl.
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Day-by-Day Detailed Schedule
Duomo + Uffizi + Ponte Vecchio
Renaissance icons + heritage TuscanActivities
- 08:30 Duomo + Brunelleschi's Dome climb (463 steps) 3 hours
1296-1436 cathedral with Brunelleschi's revolutionary 41m brick dome. Combined ticket includes Dome + Bell Tower + Baptistery + Crypt + Museum (valid 3 days).
Cost: $30 / €28 TIP: Pre-book mandatory at duomo.firenze.it. Dome climb 463 narrow stairs — not for claustrophobic. 8 AM opening for clean photos. - 12:00 Lunch — Trattoria Mario (1953, cash only, lunch only) 1.5 hours
70+ year heritage trattoria — Bistecca alla Fiorentina at value prices ($20-30/person vs $50-100 elsewhere). Behind San Lorenzo Mercato Centrale.
Cost: €20-30 ($22-32) TIP: NO reservations — queue 11:30-14:30. CASH ONLY. Shared tables. Closed Sundays. - 14:00 Uffizi Gallery (Botticelli + Da Vinci + Michelangelo) 3 hours
Medici family collection. Botticelli's Birth of Venus + Primavera (Rooms 10-14), Caravaggio's Medusa, Da Vinci's Annunciation, Michelangelo's Doni Tondo.
Cost: €37 ($40) skip-the-line TIP: Pre-book mandatory at uffizi.it 2-4 weeks ahead. Audio guide €5. Closed Mondays. - 17:30 Ponte Vecchio + Piazza della Signoria 1.5 hours
Ponte Vecchio (1345, jewelry shops since 16C, free) + Piazza della Signoria (Palazzo Vecchio, Loggia dei Lanzi sculptures, David replica). Iconic sunset photo location.
Cost: Free TIP: Ponte Vecchio sunset is the canonical photo. The Vasari Corridor above currently closed for renovation. - 19:00 Aperitivo — Caffè Gilli (1733) or Procacci (1885) 1 hour
Caffè Gilli (Piazza della Repubblica, 290+ years) or Procacci (Tornabuoni, 140+ years, truffle panini + Antinori wines).
Cost: €10-20 ($11-22) TIP: Stand at the counter to save €3-5/person on terrace seating. Aperitivo 6-8 PM canonical. - 20:30 Dinner — Trattoria Sostanza (1869, cash only) 2 hours
155+ year heritage — Petti di Pollo al Burro (butter chicken signature) + Bistecca alla Fiorentina + Tortino di Carciofi.
Cost: €30-50 ($32-55) TIP: Book 1+ week ahead. CASH ONLY. Two sittings 19:30 + 21:00. Closed Sun-Mon.
Meal Recommendations
Breakfast
Hotel buffet or Caffè Gilli (1733)
Centro · €8-25 ($11-30)
Caffè Gilli 290+ year heritage cappuccino + pastries.
Lunch
Trattoria Mario (1953)
San Lorenzo · €20-30 ($22-32)
Bistecca at value — cash only, lunch only, no reservations.
Dinner
Trattoria Sostanza (1869)
Centro · €30-50 ($32-55)
Heritage Petti di Pollo al Burro + Bistecca.
Walking — Old Town is 2km × 1km. Everything within 10 min walk.
DAY 1 Estimated Spend (per person, flights excl.)
Accademia + Pitti + Piazzale Michelangelo
David + Medici palace + sunsetActivities
- 09:00 Accademia Gallery (Michelangelo's David) 1.5 hours
Michelangelo's original 5.17m David (1504). Smaller museum than Uffizi but the canonical Renaissance sculpture experience.
Cost: €19 ($20) skip-the-line TIP: Pre-book at galleria-accademia.it 1-2 weeks ahead. David at the end of corridor. Photography allowed (no flash). - 11:00 San Lorenzo + Mercato Centrale lunch 2 hours
Mercato Centrale (1874) ground floor (Nerbone Lampredotto $5) + upper floor food hall (30+ vendors). The canonical Florentine market lunch.
Cost: €10-25 ($11-28) TIP: Nerbone Lampredotto $5 is the bucket-list. Cash + card on upper floor. - 13:30 Pitti Palace + Boboli Gardens (Oltrarno) 3 hours
Medici palace + 45-hectare Renaissance garden across the Arno. 5 museums (Palatine Gallery's Raphael collection is the highlight) + baroque garden.
Cost: €20 ($22) combined TIP: Boboli is one of Italy's earliest formal gardens. Combined Pitti + Boboli ticket. Walk back via Ponte Santa Trinita for the canonical Arno view. - 17:30 Piazzale Michelangelo (sunset) 1.5 hours
Florence's iconic sunset viewpoint — Duomo + Ponte Vecchio + Arno + city skyline 360°. 25-min uphill walk or bus 12/13.
Cost: Free TIP: Sunset is the canonical visit. Bring picnic + Chianti for full local experience. San Miniato al Monte church above is also worth visiting. - 19:30 Dinner — Buca dell'Orafo (1945) or Cibreo (1979) 2.5 hours
Buca dell'Orafo (1945, near Ponte Vecchio, $45-90) for Bistecca + truffle pasta or Cibreo (1979, Sant'Ambrogio, Michelin-recommended, $70-180).
Cost: €40-150 ($45-165) TIP: Book 1+ week ahead. Cibreo Trattoria (casual version) is the value option.
Meal Recommendations
Breakfast
Hotel buffet or Pasticceria Nencioni
Centro · €8-20 ($11-22)
Heritage Italian pastry breakfast.
Lunch
Mercato Centrale (Nerbone Lampredotto)
San Lorenzo · €10-25 ($11-28)
Nerbone Lampredotto $5 — Florence's canonical market lunch.
Dinner
Buca dell'Orafo (1945) or Cibreo (1979)
Centro / Sant'Ambrogio · €40-150 ($45-165)
Heritage trattoria or Michelin-recommended modern Tuscan.
Walking + bus 12/13 (Piazzale Michelangelo). Old Town walkable.
DAY 2 Estimated Spend (per person, flights excl.)
Oltrarno + Santa Croce + Vivoli + Michelin
Bohemian quarter + leather + MichelinActivities
- 10:00 Santa Croce Basilica + Leather School 2.5 hours
1294 Franciscan basilica — Galileo, Michelangelo, Machiavelli buried here. Adjacent Santa Croce Leather School (1950) for canonical Florentine leather shopping.
Cost: €8 ($9) basilica TIP: Leather School free demonstrations. Wallets + bags + jackets at workshop prices. Closed Sunday mornings. - 12:30 Lunch — All'Antico Vinaio (1991) 1 hour
Italy's most-iconic + most-Instagrammed panino sandwich. Foot-long Schiacciata flatbread with cold cuts + cheese + truffle. €5-8 ($7-10). 30 min queue.
Cost: €5-10 ($7-12) TIP: 4 locations on Via dei Neri (65r, 76r, 83r, 74r) — try shortest queue. Eat standing outside. - 13:30 Vivoli Gelato (1930) 30 min
Florence's oldest + most-iconic gelato (90+ years, 4th generation Vivoli family). The Riso (rice) gelato is unique to Vivoli.
Cost: €4-8 ($5-10) TIP: Cash + card. Limited daily quantities — go before 5 PM for full menu. Closed Mondays. - 14:30 Oltrarno + Santo Spirito + artisan workshops 2.5 hours
Bohemian artisan quarter across the Arno. Santo Spirito Basilica (Brunelleschi 1428, free) + leather workshops + galleries + small restaurants.
Cost: Free TIP: Santo Spirito Square's evening atmosphere is the go-to. Friday Fierucola farmers' market (April-October). - 17:30 Baptistery + Duomo Square + final views 1.5 hours
Baptistery (11C, gold mosaic ceiling) + Ghiberti's Gates of Paradise + final Duomo square circumnavigation.
Cost: Included in combined Duomo ticket TIP: Ghiberti's Gates of Paradise (Gates by Lorenzo Ghiberti, 1425-1452) is the canonical photo. - 19:30 Farewell dinner — Enoteca Pinchiorri (★★★) or Borgo San Jacopo (★) 3 hours
Enoteca Pinchiorri (★★★ Florence's only 3-star, $275-550) or Borgo San Jacopo (★ Lungarno Hotel, Ponte Vecchio view, $110-220).
Cost: €100-500 ($110-550) TIP: Book 1-2 months ahead. Jacket required. Card accepted.
Meal Recommendations
Breakfast
Hotel buffet or Caffè Gilli
Centro · €8-25 ($11-30)
Heritage Italian breakfast + cappuccino.
Lunch
All'Antico Vinaio + Vivoli Gelato
Centro · €10-20 ($11-22)
Italy's iconic sandwich + Florence's heritage gelato.
Dinner
Enoteca Pinchiorri (★★★) or Borgo San Jacopo (★)
Centro / Lungarno · €100-500 ($110-550)
Florence Michelin grand finale.
Walking + Ponte Vecchio/Ponte Santa Trinita to Oltrarno (5 min).
DAY 3 Estimated Spend (per person, flights excl.)
Pisa + Siena + San Gimignano Day Tour
Tuscan medieval cities + Vernaccia wineActivities
- 08:00 Day tour pickup 12h door-to-door
Full-day guided tour ($80-150) — pickup + 3 cities + lunch + wine tasting. Klook + GetYourGuide good value.
Cost: $80-150 day tour TIP: Book 1+ week ahead. Comfortable walking shoes. - 10:00 Pisa — Leaning Tower + Cathedral + Battistero (UNESCO Field of Miracles) 2 hours
Iconic Leaning Tower photo + Cathedral + Baptistero. The 'holding up the tower' tourist photo is mandatory.
Cost: Included or €20-27 TIP: Tower climb pre-book €20 (10 min, 251 stairs). - 13:00 San Gimignano — 14 medieval towers (UNESCO) + Vernaccia wine + Gelateria Dondoli (World Gelato Champion) 2.5 hours
UNESCO medieval town with 14 surviving stone towers (originally 72). Vernaccia di San Gimignano white wine + 2009 World Gelato Championship winner Gelateria Dondoli.
Cost: Included (lunch + tasting) TIP: Dondoli (Champion of Champions 2006-2009) is the canonical gelato stop. Saffron risotto is a local specialty. - 16:30 Siena — Piazza del Campo + Duomo 2.5 hours
Medieval Piazza del Campo (Italy's most-beautiful square, Palio di Siena horse race July + August) + Siena Duomo (Pisano + Donatello + Michelangelo).
Cost: Included (Duomo €15) TIP: Piazza del Campo is the canonical Tuscan medieval photo. Avoid July 2 + August 16 (Palio crowds). - 20:00 Florence return + light dinner 1.5 hours
Arrive Florence 8 PM. Light dinner at hotel area or wine bar (post-tour fatigue).
Cost: €20-40 ($22-45) TIP: Skip heavy meal — long tour day.
Meal Recommendations
Breakfast
Hotel buffet
Florence · €8-25 ($11-30)
Solid breakfast before 12h tour.
Lunch
Tour-included lunch (San Gimignano)
San Gimignano · Included
Tuscan menu + Vernaccia wine.
Dinner
Florence light dinner or hotel
Florence · €20-40
Post-tour fatigue — keep light.
Full-day guided tour with pickup.
DAY 4 Estimated Spend (per person, flights excl.)
Chianti Wine Country Day + Michelin Finale
Wineries + Antica Macelleria Cecchini + MichelinActivities
- 09:00 Chianti wine country guided tour 8 hours
Full-day Chianti tour ($80-150) — pickup + 2-3 wineries + lunch + medieval village. Greve + Castellina + Radda regions.
Cost: $80-150 TIP: Book 1+ week ahead at Klook + GetYourGuide. Driver/tour is the right choice (wine flows freely). - 10:30 Winery 1: Castello di Verrazzano (1170 — Verrazzano family for 850+ years) 1.5 hours
850-year-old family winery — Chianti Classico DOCG. 5-wine tasting + cured meats + cheeses. The canonical Chianti winery visit.
Cost: Included TIP: Wine 1-2 bottles for tax-free shipping home. - 13:00 Lunch — Antica Macelleria Cecchini (Dario Cecchini, Panzano) 2 hours
Tuscany's iconic butcher restaurant — chef Dario Cecchini featured on Netflix Chef's Table. Officina della Bistecca set menu (8 courses, $90) is the canonical Tuscan butcher experience.
Cost: Included or $50-90 TIP: Pre-book at dariocecchini.com 3 months ahead — sells out. - 15:30 Wineries 2-3: Castellina + Radda + Castello di Brolio (Chianti Classico inventor) 3 hours
Castello di Brolio — Barone Ricasoli (Italy's oldest noble wine family, invented modern Chianti Classico recipe in 1872).
Cost: Included TIP: Wine 1-2 bottle purchase for Tax Free shipping. Chianti Classico DOCG label authentic. - 20:00 Farewell dinner — Enoteca Pinchiorri (★★★) or La Bottega del Buon Caffè (★) 3 hours
Enoteca Pinchiorri ($275-550) or La Bottega del Buon Caffè ($110-220, Arno River view).
Cost: €100-500 ($110-550) TIP: Book 1-2 months ahead. Jacket required for Pinchiorri.
Meal Recommendations
Breakfast
Hotel buffet
Florence · €8-25 ($11-30)
Light start — wine day ahead.
Lunch
Antica Macelleria Cecchini (Chianti)
Panzano in Chianti · Included or $50-90
Dario Cecchini Tuscan butcher bucket-list.
Dinner
Enoteca Pinchiorri (★★★) or La Bottega del Buon Caffè (★)
Centro / Lungarno · €100-500 ($110-550)
Florence Michelin grand finale.
Chianti guided tour pickup included.
DAY 5 Estimated Spend (per person, flights excl.)
Book Florence Tours & Tickets
Packing Checklist
- ✓ 5-day plan — carry-on + small duffel
- ✓ Empty wine bag — Chianti bottle souvenirs
- ✓ 1 dress jacket for Michelin
- ✓ Comfortable walking shoes — cobblestones + Duomo + Pisa + Siena walks
- ✓ Cash €1,000-2,000 — heritage cash-only restaurants
- ✓ Power adapter Type C/F/L
- ✓ Pre-book Uffizi + Accademia + Duomo + Pisa Tower + Cecchini + Michelin
- ✓ Tax Free receipts folder
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Based in Chiang Mai for 8+ years, with 30+ countries visited across Southeast Asia, Japan, and Europe. Every detail in this guide is primary-source verified as of April 2026, with prices auto-refreshed via live exchange rate APIs. This isn't AI-generated boilerplate — it's written from the perspective of someone who has actually been there.
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