2-Day Florence & Tuscany Overnight from Rome: Duomo, David & Wine

2 days
Max 10 people
Rome, Italy

About this activity

A 2-day overnight trip from Rome to Florence and Tuscany, with Siena, San Gimignano, a Tuscan winery, skip-the-line access to Michelangelo's David and Florence Duomo.

Full description

Florence and Tuscany deserve more than a rushed day trip. On this curated overnight 2-day journey from Rome, you’ll do more than check boxes, you’ll go deeper. Travel by private minivan, stay overnight in a 4-star hotel, and get insider access to the region’s most storied sites. A walk through Siena, lunch at a family-run winery, a wine window tasting and Florentine steak dinner in Florence, then skip-the-line entry to a world-famous statue and a landmark cathedral before a final stop in a medieval hill town. Every moment is designed to unlock Italy’s art, flavors, and landscapes.

A local tour leader accompanies you every step of the way, and this tour is limited to 10 people maximum for an intimate and personal experience. Let us handle the logistics so you can lose yourself in Renaissance masterpieces, medieval towns, and vineyard vistas. 

Day 1: Rome - Florence


Stop At: Siena

Description: Travel from Rome by minivan, and arrive in Siena where a local guide meets you for a walking tour across the shell-shaped Piazza del Campo, home to the world-famous Palio horse race, then inside the Siena Cathedral, one of Italy's great Gothic interiors, striped marble and floor mosaics included.

Admission: Included

Duration: 2 hours

Stop At: Tuscan Winery

Description: Continue into the Tuscan countryside to a family-run winery for a tour of the cellars and a tasting of the estate's wines. Sit down to a homemade lunch made with local ingredients, paired with the wines you've just tasted, with the rolling hills spread out in front of you.

Admission: Included

Duration: 2 hours 30 minutes

Stop At: Oltrarno, Florence

Description: Arrive in Florence and settle into your hotel before heading into Oltrarno, the neighborhood locals consider the real heart of the city. Taste wine poured through a centuries-old wine window, then sit down to a Florentine steak dinner at a family-run trattoria.

Admission: Included

Duration: 3 hours

Day 2: Florence — Rome

Stop At: Accademia Gallery & Florence Duomo

Description: Skip the line into the Accademia Gallery to see Michelangelo's David, then continue to the Duomo for a skip-the-line visit. It's a paced, unhurried look at two of Florence's most recognized sights, without the wait most visitors face.

Admission: Included

Duration: 2 hours

Stop At: San Gimignano

Description: Cross the Ponte Vecchio and head to San Gimignano, the medieval hill town known as the city of towers. Explore at your own pace before the drive back to Rome, arriving in the evening.

Admission: Free (self-guided time)

Duration: 2 hours

Included / Excluded

  • 1 night in a carefully selected 4-star hotel
  • Roundtrip transport by minivan from Rome
  • Skip-the-line ticket to see Michelangelo's David
  • Skip-the-line ticket to the Duomo
  • Lunch and wine at a Tuscan winery
  • Traditional Florentine steak dinner at a family-run trattoria
  • Expertly guided walking tour of Florence
  • Expertly guided walking tour of Siena
  • Free time in San Gimignano
  • English-speaking tour leader
  • Headsets (when needed)
  • Gratuities

Cancellation policy

Free cancellation up to 30 days before the activity starts

Up to 24 hours before the beginning of the activity: full refund Less than 24 hours before the beginning of the activity or no-show: no refund

Reviews

⁨Kiara M.⁩
Aug 2026
5.0

Amazing Tour!!

Jolynn
Jul 2026
5.0

A highly recommended experience.

Lisa
Jun 2026
5.0

The tour was great and having priority on the boat was excellent

Additional information

Ticket age ranges:
- Adult (15+)
- Child (7-14)