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Rome, Florence & Positano — Romantic Italy, September 2026
Route sheet · 3 destinations
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On this leg
Rome
flight
New York→Rome
ITA Airways
~$616
/person
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Nonstop and one-stop options available JFK–FCO. ITA Airways operates direct service; Norse Atlantic and Delta also fly this route. Search Ex…
hotel
Via Sistina, 69, 00187 Roma RM, Italy
$800
/night
Check-in
Sat, 12th September 2026
Check-out
Mon, 14th September 2026
Nights
2· $1,600
Rated 4.8 — steps from the Spanish Steps and Trevi Fountain. Elegantly designed Rocco Forte property with a celebrated rooftop pool and spa. Book ahead as suites fill fast in September.
Your day at a glance
You land at Fiumicino and take the flat-rate taxi (~€50) straight to your Rocco Forte suite on Via Sistina — one of Rome's most romantic addresses, perched just above the Spanish Steps. September is Rome at its finest: golden light, warm evenings, and the crowds of August already thinning. After checking in and freshening up, step outside into the living museum of the centro storico.
This afternoon is about unhurried initiation — the Spanish Steps at sunset, the Trevi Fountain at dusk (coins mandatory), and the elegant streets of the Prati/Via Veneto quarter. End the evening with a rooftop dinner at Imàgo, where the entire Roman skyline unfolds below you. Request a window table for two — it is, simply, one of the most romantic dinners in Italy.
5 stops
⭐ attraction
Rome's grandest baroque staircase — 135 steps of travertine linking Piazza di Spagna to the Trinità dei Monti church. Climb to the top at golden hour for sweeping views over the city's rooftops, then linger over a Campari spritz at one of the terrace bars nearby.
Address · Piazza di Spagna, 00187 Roma RM, Italy
Field note
Your hotel is literally steps away — drop bags first, then stroll down at 15:30 before the evening crowds peak.
⭐ attraction
The most famous fountain in the world and Rome's most cinematic spot. Toss two coins — one to return to Rome, two for love. Visit in the soft late-afternoon light before the post-dinner crowd descends.
Address · Piazza di Trevi, 00187 Roma RM, Italy
Field note
The fountain is illuminated beautifully after dark — pop back later in the evening for a completely different atmosphere.
⭐ attraction
The best-preserved building of ancient Rome and a masterpiece of architectural genius — the coffered concrete dome (still the world's largest unreinforced dome) has stood for 1,900 years. The oculus at the top floods the interior with a beam of light that moves across the floor like a sundial.
Address · Piazza della Rotonda, 00186 Roma RM, Italy
Field note
Book timed tickets online at pantheon.roma.it — queues without a booking can be 45+ minutes.
⭐ attraction
Rome's most theatrical piazza — built on the footprint of a 1st-century stadium, now framed by baroque palaces and Bernini's thundering Fontana dei Quattro Fiumi at its center. Street artists and aperitivo bars make it one of the most romantic evening strolls in the city.
Address · Piazza Navona, 00186 Roma RM, Italy
Field note
Order a Negroni at one of the terrace bars facing the fountain — the ultimate Roman aperitivo moment.
🍽️ restaurant
One of Rome's most spectacular rooftop restaurants atop the Hassler hotel, serving refined Italian cuisine with a panoramic view of the entire city — from the Colosseum to St Peter's dome. Signature: spaghetti all'astice (lobster pasta). Ask about dairy-free adjustments — the kitchen is very accommodating.
Address · Piazza della Trinità dei Monti, 6, 00187 Roma RM, Italy
Field note
Reserve weeks ahead and explicitly request the window table for two with city views — it books out for sunset slots.
End of day 1 · until tomorrow
Route map · Day 01
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