Curator’s statement
Florence is where I studied abroad and discovered my love for travel that feels both intentional and free. It’s a city best experienced on foot, wandering, pausing, returning to the same café more than once. The Renaissance masterpieces are unforgettable, but so are the quiet rituals: espresso at the bar, Chianti at sunset, markets tucked into neighborhood streets. This itinerary honors both: the icons and the in-between.
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Day 1: Arrive in Florence
View of Giotto’s Bell Tower from the dome of Cathedral of Santa Maria del Fiore
Arrive in Florence and start by heading into the historic center to orient yourself. Begin at the Cathedral of Santa Maria del Fiore—seeing the cathedral in person sets the tone for the city. If you’ve booked tickets in advance, climb Giotto’s Bell Tower or the dome for panoramic views over Florence’s rooftops. It’s the best way to understand the layout of the city on your first day.
From there, stop for a quick espresso at a nearby bar before walking through Piazza della Signoria and continuing toward Ponte Vecchio, letting yourself explore.
As golden hour approaches, pick up a bottle of Chianti from a neighborhood wine shop or small grocery and head to Piazzale Michelangelo for sunset.
Finish the evening with a relaxed dinner—you’ve officially settled into Florence.
A note from Alyssa
Insider tip: There are several reservation options for exploring the Duomo complex and nearby museums. Tickets should be booked well in advance, especially from late spring through early fall.
Day 2: Michelangelo’s David, Sant’Ambrogio & Oltrarno finds
Mercato di Sant'Ambrogio
Start your morning at the Accademia Gallery to see Michelangelo’s David. Book the earliest timed entry available to avoid long lines and crowds. It’s worth seeing before the city fully wakes up.
Head toward Sant’Ambrogio Market, stopping for a quick espresso on the way. Inside, you’ll find produce vendors, cheese counters, and small cafés filled with locals. Outside, the clothing and goods market offers scarves, leather accessories, vintage pieces, and everyday Italian staples. It’s an easy place to browse and exactly where you might justify that extra suitcase.
In the afternoon, cross into Oltrarno, Florence’s artisan neighborhood. Wander through leather workshops, independent boutiques, and specialty paper shops before settling into aperitivo at Il Santino, a small wine bar known for excellent regional pours and simple plates
A note from Alyssa
Insider tip: Sant’Ambrogio’s outdoor clothing market runs in the mornings and is best earlier in the day. Bring cash!
Day 3: Chianti wine country escape
Lunch in Tuscany
Dedicate your third day to getting out of the city and into the Tuscan countryside. The Chianti region is less than an hour from Florence and offers rolling hills, olive groves, and small family-run wineries. Booking a private driver or small-group wine tour makes the day seamless and allows you to fully enjoy the tastings without worrying about logistics.
Plan to visit two wineries with guided tastings and a relaxed lunch featuring seasonal Tuscan dishes. Many estates include vineyard walks or cellar tours, which add context to what you’re drinking.
Return to Florence in the late afternoon.
A note from Alyssa
Insider tip: Reserve wine tours at least a week or two in advance, especially from May through October. If you prefer flexibility, I can arrange private drivers and customized vineyard visits based on your wine preferences.
Need to know
The best times to visit Florence are late April through June and September through October, when the weather is mild and the city feels lively but manageable. Harvest season in Tuscany typically runs from mid-September through October, which is an especially beautiful time to visit wine country. Vineyards are active, olive groves are being prepared for pressing, and many wineries offer special tastings.
July and August can be very hot, and some smaller shops and restaurants close in August as locals take their holiday.
Plan major museum reservations well in advance during peak months, especially for the Accademia and Duomo complex.
Markets like Sant’Ambrogio operate in the mornings, and many independent shops close for riposo (midday break), typically reopening around 3:30–4 p.m.
Florence is extremely walkable, so comfortable shoes are essential—cobblestones are charming but unforgiving.
If you’re visiting in late June, you may catch Calcio Storico, Florence’s historic football tournament held in Piazza Santa Croce, a uniquely local event worth researching in advance.
Travel Advisor
Alyssa Juris
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For more inspiration and insider recommendations, visit our Florence page.