Two weeks in Italy is long enough to spend quality time in Rome, rather than zooming past landmarks on a mad dash itinerary.

Rome, Rome to Naples to Amalfi Coast itinerary, includes five days in Rome with an additional four or more, leaving the last days wide open as you head toward other parts of Italy or other countries. For New England-based travellers, Boston to Rome flights make for easy connections to an Istanbul itinerary, as do Chicago departures.

Rome is where the bulk of the museums and historic sites reside. Naples mops up a tough exterior with world-class hospitality and the surprising discovery that Naples is an underappreciated foodie paradise. Rome is your cappuccino. Naples is your espresso.

Here’s a simple, 14-day itinerary:

Days 1–5: Rome

For the first five days, let Rome be Rome, a city travellers have been falling in love with since the day it became the most powerful city-state in the known world.

Day 1: Arrive and see the historic centre. On the first day, you’ll want to take it relatively easy. When you land, check into your accommodation and then head to the Pantheon, Piazza Navona and the streets around them. Walk to the nearby Trevi Fountain, a handy way to see a bit more of the city without over-exerting yourself.

Day 2: Ancient Rome. Spend your morning at the Colosseum, and move on to the Roman Forum and Palatine Hill. These three can be combined into a single day, but it’s worth remembering that this is a lot to see. You’ll need a couple of hours to properly enjoy them rather than snatching a sandwich and hurtling on to your next appointment. Spend the evening in and around Monti; it’s good for a leisurely dinner after the day’s activity.

Day 3: Vatican City. You’ll need the majority of the day to explore St. Peter’s Basilica, the Vatican Museums and the Sistine Chapel. Starting the morning will make the day less hot, and with the afternoon free, you can meander around Prati or the east bank of the river more generally.

Day 4: At the heart of Rome. Visit Campo de’ Fiori, Trastevere and the quiet back streets of the centro storico. This is the day you can visit the smaller churches, browse the one-off shops and possibly spend an entire afternoon sitting in the sun or shade outside a neighbourhood café.

Day 5: Tailored to suit. Return to anywhere you’ve missed in the first four days, visit a museum or make the most of having a free day.

Boston to Rome flights: starting out from New England

If you’re starting from Boston, don’t think of your flight to Rome as a separate step in the process. Consider flying via Istanbul rather than a less graceful way-station on the way to Italy, as Istanbul is roughly a midpoint between North America and the boot.

When working out the best way to plan your Boston to Rome flights, the main consideration is when you’re going to arrive in Rome. If you’re getting there in the morning or early afternoon, you can hit the ground running, check in to your accommodation, and then have at least a couple of hours of daylight to complete day one of your itinerary.

Days 6–9: Naples and an Amalfi Side Trip

This stretch serves as a stylistic counterpoint to the Bay of Naples and includes some of the most famous day tours in southern Italy, without a new hotel every night.

Day 6: Rome to Naples. Take a morning train to Naples to leave the afternoon and evening free for settling into accommodations and more wandering. Do some quality time in the old district after you get into town, and be sure to allow for a proper Neapolitan dinner in the historic centre before wrapping up the evening with another walk.

Day 7: Pompeii. Spend the day at the Pompeii ruins. This one merits a morning and most of the afternoon on its own. A return to Naples in the late afternoon should allow a little extra time on the water’s edge, in the Quartieri Spagnoli, or just off of Piazza Bellini.

Day 8: Amalfi Coast. Head out toward the coast as early as possible: the trip is part of the experience. Pick one or two places to see the best of the road system, make time for viewpoints, maybe split a nice lunch, and get a sense of what the Gulf of Salerno really has going.

Day 9: Naples (or the coast) a little more slowly. Keep the final day open. If you’re still up for history, then Naples is your thing, but if your Amalfi coast visit was the highlight, consider a follow-up.

Chicago to Rome flights: the Midwest alternative

The 14-day concept also helps Americans looking to leave from Chicago. Chicago to Rome flights are the first leg of a trip to Rome and Naples, which more or less replicates the above options.

Do not fall into the trap of booking too many things on the first day of your itinerary. Flying across an ocean and dealing with a time change can only combine with a busy first day to result in no one really having any fun.

This is a great example of how Istanbul as a connection can meaningfully impact the overall hubs strategy. Flights to Rome rely on the concept presented above, and supplement perfectly this example about going beyond Italy, and up into Istanbul and back. Instead of trying to book North America flights, then Europe flights, then flights to India…all as separate tickets! Here you simply pencil in an extra week of travel from the outside, as one seamless experience. The cleanness of the ticketing will depend on where you started and ended, but Rome and Naples work as a core for a nice trip elsewhere!

Days 10–14: Deciding How to End Your Trip

These last five days are left intentionally vague. Do you want to return to Rome for these last five days to do more of what you skipped at the beginning? Do you want to go even deeper into southern Italy? Your 14-day Itinerary is perfect for you now that you’ve made room for slowing down.

Optional Extension: Adding India as a part of the Same Trip

Delhi serves best for the start since it offers top historic attractions in the continent and very strong connections to the next destinations. The next few days can be planned for a visit to Old Delhi, India Gate, Humayun’s tomb and all other places related to heritage and historical remains of the capital of India. If Jaipur were included, it would give an entirely different place on the itinerary to visit.

Spending 3–4 days here in India can give a feel of the place. However, there should ideally be sufficient gaps on the arrival at connecting airports of the hub and the next commitment that span a priority.

Flights to India on the same routing via Istanbul

The wise thing about figuring out an Open-Jaw itinerary: Does the arrival and departure city on the flight booking really have to be the same? The arrival and departure cities do not have to be the same.

Istanbul can also serve as a convenient staging point, not a primary destination, but an airport hub. You can structure the itinerary so that you don’t plan a full add-on trip to Istanbul, but you have the option of breaking up the Europe/India itinerary by using Istanbul as the outlet/entry, if that works with the overall tickets.

Practical Notes: Trains, Timing, and Open-Jaw Routing.

The only way to keep this plan manageable is to break things down into a few large segments: Getting to Rome, getting through Italy, and lining up the most logical place to continue the journey. Don’t complicate the plan with extra hotel stays merely to add another 1-2 nights in another city.

Trains work particularly well between Rome and Naples, for which the urban rail terminuses are downtown, and thus don’t require the airport connections that longer nonstop domestic flights do.

An open-jaw itinerary may save the backtracking, and a gap around long-haul connecting saves you from losing the use of your plan in case of a delay.