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Florence 5-Day with Tuscany

Florence 3 nights + Pisa/Siena/San Gimignano day + Chianti wine day

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.

Recommended

Mid-Range

$1,640

Per person, flights excl.

Luxury

$4,000

Per person, flights excl.

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Day-by-Day Detailed Schedule

DAY 1

Duomo + Uffizi + Ponte Vecchio

Renaissance icons + heritage Tuscan

Activities

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.

Transit:

Walking — Old Town is 2km × 1km. Everything within 10 min walk.

DAY 1 Estimated Spend (per person, flights excl.)

Budget $130 Mid $280 Luxury $600
DAY 2

Accademia + Pitti + Piazzale Michelangelo

David + Medici palace + sunset

Activities

  1. 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).
  2. 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.
  3. 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.
  4. 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.
  5. 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.

Transit:

Walking + bus 12/13 (Piazzale Michelangelo). Old Town walkable.

DAY 2 Estimated Spend (per person, flights excl.)

Budget $130 Mid $280 Luxury $600
DAY 3

Oltrarno + Santa Croce + Vivoli + Michelin

Bohemian quarter + leather + Michelin

Activities

  1. 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.
  2. 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.
  3. 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.
  4. 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).
  5. 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.
  6. 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.

Transit:

Walking + Ponte Vecchio/Ponte Santa Trinita to Oltrarno (5 min).

DAY 3 Estimated Spend (per person, flights excl.)

Budget $150 Mid $350 Luxury $1,100
DAY 4

Pisa + Siena + San Gimignano Day Tour

Tuscan medieval cities + Vernaccia wine

Activities

  1. 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.
  2. 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).
  3. 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.
  4. 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).
  5. 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.

Transit:

Full-day guided tour with pickup.

DAY 4 Estimated Spend (per person, flights excl.)

Budget $200 Mid $350 Luxury $700
DAY 5

Chianti Wine Country Day + Michelin Finale

Wineries + Antica Macelleria Cecchini + Michelin

Activities

  1. 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).
  2. 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.
  3. 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.
  4. 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.
  5. 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.

Transit:

Chianti guided tour pickup included.

DAY 5 Estimated Spend (per person, flights excl.)

Budget $200 Mid $380 Luxury $1,000

Book Florence Tours & Tickets

Packing Checklist

Florence 5-Day Itinerary FAQ

Is 5 days enough for Florence + Tuscany?
Yes — Florence 3 days + Pisa/Siena day tour + Chianti day tour = perfect Tuscan introduction. 7+ days unlocks Venice + Rome additions.
Self-drive vs guided tours for Tuscany?
Guided tours easier for first-time + wine days ($80-150 includes everything). Self-drive better for flexibility + 2+ travelers (rental $40-80/day). Cecchini in Panzano specifically requires a driver — wine flows.
5-day budget?
Budget $1,500-2,500. Mid-range $3,500-5,500. Luxury $7,000-12,000+ (includes Pinchiorri 3-Michelin + Cecchini + 5-star hotels). Excludes international flights.

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Why you can trust 5-day itinerary

Jimmy Kong TripPick founder · Travel content creator

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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