Rome in 5 Days for Couples - Guided visits: Florence Duomo, Piazza della Signoria, Doge’s Palace (Venice)
In Collaboration with Eskapas. Updated on January 30, 2026.
A fast‑paced, romantic 5‑day escorted tour that begins and ends in Rome and visits Assisi, Siena, Florence, Bologna, Venice and Montepulciano. Designed for couples who want a curated mix of UNESCO towns, Renaissance art, intimate meals, wine tasting and golden‑hour moments.
This itinerary was created in collaboration with Eskapas, inspired by the tour Veloce Italia. Please check the tour information during your booking process.
Highlights
- Guided visits: Florence Duomo, Piazza della Signoria, Doge’s Palace (Venice)
- Medieval Assisi & Siena’s Piazza del Campo
- Tuscan wine region: Montepulciano lunch + tasting
- Prosecco/Spritz & cicchetti experience in Venice
- Golden‑hour viewpoint at Piazzale Michelangelo (Florence)
Itinerary
Day 1
Depart Rome early for Assisi and Siena; arrive in Florence for dinner and overnight.
Meet at Hotel St. Martin — tour briefing & boarding
Group meet & check‑in with your tour leader; quick welcome briefing and luggage loading onto coach.
Tips from local experts:
- Arrive 15–20 minutes before the meeting time to ensure luggage is loaded and you get a good seat on the coach.
- Store passports and valuables in the hotel safe; keep a day bag with sunscreen and a light jacket for spring breeze.
- Ask the tour leader for a quick map of the coach toilet location and Wi‑Fi instructions if needed.
Coach transfer: Rome → Assisi
Scenic drive north into Umbria. Relax on the coach (onboard toilet & Wi‑Fi).
Tips from local experts:
- Sit on the right side of the coach for the best early views of the Umbrian hills approaching Assisi.
- Use this transfer time to charge devices — many coaches have USB power but bring a charger just in case.
- Keep a small umbrella or light windbreaker handy — spring afternoons can shift from sunny to breezy.
Visit: Basilica of Saint Francis of Assisi (guided/independent time)
Wander Assisi’s medieval lanes and admire the frescoes in the Basilica — a serene spiritual and artistic highlight.
Tips from local experts:
- Dress respectfully for the basilica (shoulders covered) — a light scarf doubles as a cover and a romantic photo prop.
- Head upstairs first to see the Upper Basilica frescoes in cooler light and smaller crowds.
- Pause at a quiet spot outside the basilica for a view across the valley — a lovely couple’s photo opportunity.
Independent lunch in Assisi (leisurely)
Enjoy lunch at a local trattoria — savour Umbrian specialties (olive oil, cured meats, pappardelle).
Tips from local experts:
- Ask your guide for a recommended quiet trattoria away from the main tourist stretch to avoid long waits.
- Try a shared antipasto and a local red wine — perfect for a romantic midday toast.
- If you prefer a shaded terrace, request a table outdoors; spring weather is usually ideal in May.
Coach transfer: Assisi → Siena
Cross into Tuscany and ascend to Siena—time to enjoy hilltop vistas from the coach.
Tips from local experts:
- Sit on the left side this time for sweeping Tuscan valley views as you approach Siena.
- Bring binoculars or use phone zoom for photos of hilltop farmhouses and cypress‑lined roads.
- Stretch your legs right after arrival—Siena’s medieval center is best enjoyed on foot.
Explore: Piazza del Campo & Siena historic center
Guided time in Siena’s UNESCO‑listed shell‑shaped piazza — soak in the atmosphere and views over tiled roofs.
Tips from local experts:
- Walk up to Torre del Mangia for panoramic views (if you both are comfortable with a short climb — great sunset shot).
- Share a gelato and sit on the steps to watch locals — an intimate, low‑effort romantic moment.
- Siena has many narrow alleys; hold hands and wander a little off the main square for hidden photo spots.
Coach transfer: Siena → Florence (hotel check‑in)
Short, late‑afternoon drive to Florence; check in to your 4* hotel and freshen up.
Tips from local experts:
- Ask reception for a map highlighting quieter streets to stroll to dinner — central Florence is walkable but lively.
- Take 30 minutes to freshen up and change for dinner to make the evening feel special.
- Request a room on a higher floor or quieter courtyard side if you want intimacy and less street noise.
Welcome dinner — romantic Tuscan meal
A welcome dinner in Florence with Tuscan specialties — intimate table, candlelight ambiance.
Tips from local experts:
- Reserve a window or corner table when possible for a cozier atmosphere — mention it when seating is assigned.
- Order a bottle of local Chianti Classico to share — the sommelier can suggest a perfect pairing.
- Leave room for a shared dessert (cantucci & Vin Santo) — a classic romantic finish.
Day 2
Full day in Florence: guided morning highlights, lunch at Piazza Santa Croce, afternoon at leisure (optional Uffizi), sunset at Piazzale Michelangelo.
Breakfast at hotel
Buffet breakfast to prepare for a morning of art and walking.
Tips from local experts:
- Have an early breakfast to beat the morning crowds on the Duomo square.
- Grab a takeaway espresso to sip while you walk between sites for an authentic local feel.
- Pack a small day bag with water, a sun hat and comfortable shoes for cobbled streets.
Guided Florence highlights: Duomo, Baptistery, Piazza della Signoria
A guided walking tour visiting the Duomo complex, Piazza della Signoria and the political heart of Florence.
Tips from local experts:
- Stand together at the front of the Duomo square for an iconic couple’s photo with the Dome in the background.
- If you plan to climb Brunelleschi’s dome (optional), book ahead — the climb is steep but rewards you with private skyline views.
- Wear shoes with good grip for marble steps and cobbles; spring mornings can be dewy.
Lunch: Traditional Tuscan restaurant near Piazza Santa Croce
Savor a relaxed lunch by Santa Croce with classic local dishes — included as per itinerary.
Tips from local experts:
- Ask for a terrace or window table facing the square for people‑watching and a romantic atmosphere.
- Share a seasonal antipasto platter to sample local cheeses, cured meats and bruschetta.
- If you prefer a quieter lunch, request a table inside the side room rather than the main bustle near the square.
Afternoon: Free time — optional visit to the Uffizi Gallery
Afternoon at leisure to explore Florence on your own or take the optional Uffizi excursion (bookable extra).
Tips from local experts:
- If you opt for the Uffizi, prebook tickets or the tour to avoid long queues and maximize time with masterpieces.
- For a more intimate experience, stroll the Oltrarno artisan quarter to discover small workshops and jewelry boutiques.
- Take a coffee break in a small cafe away from the tourist routes — the quiet establishments often have the coziest seating.
Golden‑hour: Piazzale Michelangelo viewpoint
Short transfer/climb to the famous panoramic terrace for sunset views over Florence — an unforgettable romantic moment.
Tips from local experts:
- Bring a light wrap — it can get breezy at sunset even in May; plan to arrive 20 minutes early to secure a good viewpoint.
- Share a small picnic or a gelato while you watch the city glow — a more private, memorable moment than crowded terraces.
- If mobility is a concern, drive or take a short taxi up rather than walking the steep steps; there are accessible paths.
Evening: Dinner at leisure in Florence
Choose a cozy osteria or enjoy hotel dining — an unhurried evening after a day of art.
Tips from local experts:
- Ask your guide for a quiet, romantic osteria away from the busiest streets — they often have the best local dishes.
- Reserve ahead if you want a particularly intimate table (corner or candlelit setting).
- Try a dessert wine to end the night softly — a small shared dessert keeps the mood light and romantic.
Day 3
Florence to Bologna for a guided walking and food‑market experience, then continue to Venice Mestre for overnight.
Breakfast and check‑out
Enjoy a relaxed breakfast, then board the coach for Bologna.
Tips from local experts:
- Take time with a cappuccino — Italian breakfasts are a relaxed moment before travel.
- Confirm luggage handling with the driver to ensure smooth transfers between hotels.
- Ask the guide about any specific local specialties to try in Bologna’s markets (e.g., mortadella).
Coach transfer: Florence → Bologna
Short coach drive north to Bologna — enjoy the changing architecture and landscapes.
Tips from local experts:
- Sit on the left for the best approach views of Bologna’s towers coming into the city.
- Charge your camera/phone; the walking tour will offer great photo opportunities.
- Use the transfer to rest your feet — Bologna’s walking route has cobblestones but is layed out for comfortable strolling.
Guided walking tour: Bologna historic centre (Piazza Maggiore & Neptune Fountain)
A guided exploration of Bologna’s porticoes, Piazza Maggiore and the famous Fontana del Nettuno.
Tips from local experts:
- Walk hand‑in‑hand under the porticoes — they offer shade and a classic romantic backdrop for photos.
- Stop for a mid‑tour espresso at a small bar on a side street — locals favour standing at the counter.
- If you’d like a quieter photo, ask the guide to lead you to a less busy vantage point near the Basilica di San Petronio.
Street food experience: Mercato & Quadrilatero
Sample Bolognese specialities at market stalls and small family eateries — a lively culinary interlude.
Tips from local experts:
- Share small plates to try a range of flavors — tagliere, tigelle or fresh tortellini make great tasting options.
- Look for vendors making food to order for the freshest bites and a more intimate experience.
- If you prefer a calmer meal, ask your guide for a quieter trattoria two streets away from the busiest market stalls.
Coach transfer: Bologna → Venice (Mestre) with scenic approach
Afternoon transfer to the Venetian lagoon; arrive into Mestre and check in to your hotel.
Tips from local experts:
- Ahead of arrival, step outside briefly for fresh air and a stretch — a long day on foot follows.
- If you want to visit Venice’s islands tomorrow, ask the front desk for boat times and best arrival piers.
- Request a room with a quiet courtyard view for a more intimate evening in Mestre.
Dinner at hotel or nearby trattoria (leisurely)
Relaxed dinner in Mestre to recharge before the day in Venice.
Tips from local experts:
- Choose a table by a window or terrace if available for a quieter, more intimate setting.
- Order a local seafood starter if you’re curious about Venetian flavours — Mestre kitchens often do well.
- Keep the evening calm to prepare for an early start to Venice tomorrow.
Day 4
Full day in Venice: guided St. Mark’s Square & Doge’s Palace visit, a prosecco/spritz and cicchetti experience, afternoon at leisure (optional Murano & Burano).
Breakfast & transfer to Piazzale Roma (coach/vaporetto transfer)
Breakfast in Mestre and short transfer to Venice’s Piazzale Roma; embark toward St. Mark’s area.
Tips from local experts:
- Bring light layers — morning vaporetto rides can be breezy even in May.
- Keep a small cross‑body bag for valuables while moving through Venice’s busy areas.
- If you prefer less walking, request a vaporetto ticket to the nearest stop to Piazza San Marco (ask the guide).
Guided walking tour: Piazza San Marco & Doge’s Palace (Palazzo Ducale)
Explore St. Mark’s Square and the Doge’s Palace with a specialist guide; cross the Bridge of Sighs.
Tips from local experts:
- Arrive early with the group to enjoy softer morning light for photos in Piazza San Marco.
- Inside the Doge’s Palace, follow your guide’s highlights to save energy and still see the finest rooms.
- Pause at quieter corners near the basilica for a moment together away from the crowds.
Prosecco/Spritz & cicchetti experience (included)
A classic Venetian aperitivo: sip Prosecco or a Spritz and sample cicchetti (Venetian small plates).
Tips from local experts:
- Ask your server to recommend a pair of cicchetti to share — it’s a lovely way to taste many flavors together.
- Sit at a small bacaro counter for an authentic local feel and better people‑watching.
- Toast slowly and enjoy the warm light reflecting on canal waters — a quintessential Venetian couple’s ritual.
Afternoon at leisure — optional Murano & Burano excursion
Free time to wander Venice’s canals, shop for lace and glass, or take the optional boat trip to Murano and Burano (bookable extra).
Tips from local experts:
- If you choose Murano/Burano, book the optional trip early—these islands can get busy in late afternoon.
- For a private moment, lose the main bridges and wander small calle for unexpected canal views.
- Wear comfortable shoes and take water breaks; spring sun + walking can be tiring despite mild temperatures.
Optional romantic gondola (short sunset ride)
Optional short gondola ride at sunset for private canal views and a quiet moment together.
Tips from local experts:
- Book the gondola early in the afternoon if you want a guaranteed sunset time slot.
- Bring a small blanket for cooler breezes and to make photos feel cozier.
- If you prefer privacy, request a route through quieter canals rather than the Grand Canal (some gondoliers oblige).
Return to Mestre hotel; evening at leisure
Transfer back to Mestre for overnight and a restful evening.
Tips from local experts:
- Consider a short freshen‑up before dinner to keep the evening relaxed and romantic.
- If you enjoyed Venetian cicchetti, ask reception for a recommended quiet wine bar in Mestre.
- Plan a calm evening—tomorrow is a longer travel day back toward Rome via Tuscany.
Day 5
Depart Venice early for Tuscany: Montepulciano for lunch, wine tasting and free time; return to Rome and end at Hotel St. Martin.
Breakfast, check‑out and coach boarding
Early breakfast and prepare for the scenic drive through Tuscany to Montepulciano (Val di Chiana).
Tips from local experts:
- Have a slightly earlier breakfast to maximize time in Montepulciano for strolling and tasting.
- Pack a small day bag with sun protection and a jacket for hilltop exposure.
- Keep water on hand — hilltop towns have steps and viewpoints that invite lingering.
Coach transfer: Venice (Mestre) → Montepulciano (Val di Chiana)
Full scenic drive through the Veneto and Umbria into the heart of Tuscany; enjoy rolling hills and vineyard vistas.
Tips from local experts:
- Sit where you can easily access the coach window for photos — rolling Tuscan hills are particularly photogenic in late morning light.
- Stretch legs briefly at scheduled stops — even short breaks help on a longer transfer day.
- Keep your camera ready for postcard vineyard views; spring offers lush green colors in May.
Lunch in Montepulciano — typical Tuscan restaurant near Piazza Grande
Enjoy an included long lunch of Tuscan specialties paired with local wines in Montepulciano’s historic setting.
Tips from local experts:
- Ask for local Vino Nobile by the glass to taste the region’s signature wine — a perfect romantic toast.
- Request a table with a view over the Val di Chiana when possible for an unforgettable meal backdrop.
- Pace your courses and enjoy conversation—Tuscany’s long lunches are made for lingering together.
Wine tasting at a local cantina — Vino Nobile experience
Optional tasting at a historic Montepulciano cantina to sample Vino Nobile and learn about local production.
Tips from local experts:
- Try a guided tasting to learn proper tasting order — sharing notes makes it more intimate and memorable.
- If you prefer a private tasting, ask the guide to arrange a smaller group session in advance.
- Sip slowly and pair tasters with small bites — it stretches the experience into a lovely shared memory.
Free time in Montepulciano — stroll, photos and viewpoints
Time to wander cobbled lanes, enjoy panoramic views and perhaps buy a small local souvenir.
Tips from local experts:
- Wander up to the town walls for sweeping countryside views — a peaceful spot for a private moment.
- Pop into a tiny enoteca for a bottle to bring home — many will ship internationally if you ask.
- Seek out a small cafe with an outdoor terrace for a final coffee before the drive; the light in May is especially flattering.
Coach transfer: Montepulciano → Rome (end of tour at Hotel St. Martin)
Late afternoon drive back to Rome with arrival in the evening; tour concludes in front of Hotel St. Martin.
Tips from local experts:
- Use this final transfer to relax and reflect on highlights — the coach provides onboard facilities for comfort.
- Plan dinner reservations in Rome if you’re staying on — ask the tour leader for recommendations near Hotel St. Martin.
- Collect any souvenirs stored with the coach team and confirm exact drop‑off details for a smooth goodbye.
Itinerary Attributes
| Days | 5 |
| Highlights | 5 |
| Season | - |
| Month | - |
| Persona | Couples |
| Transfers | 9 |
| Restaurants | 10 |
| Total Activities | 23 |
| Total Places | 23 |
| Activities Types | Hotel, Transfer, Attraction, Meal, Neighborhood, Restaurant, Culture, Experience, Outdoor |
