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The cheapest order to fly Milan, Venice and Naples from Boston

There are 6 ways to fly these cities, and 4 of them can be priced from fares we have seen. They do not cost the same. The cheapest works out at about $1,273 a person and the most expensive at $1,625, a difference of $352 for visiting exactly the same places.

Fly them in this order

Boston → Naples → Venice → Milan → Boston

About $1,273 per person in flights, based on fares recently seen on these routes, and the cheapest of the 4 ways round we could price.

The 4 we can price

  1. Boston → Naples → Venice → Milan → Boston$1,273
    cheapest order
  2. Boston → Venice → Naples → Milan → Boston$1,318
    $45 more per person
  3. Boston → Venice → Milan → Naples → Boston$1,509
    $236 more per person
  4. Boston → Milan → Venice → Naples → Boston$1,625
    $352 more per person

Why Naples first

  1. Boston to Naples$277
  2. Naples to Venice$21
  3. Venice to Milan$38
  4. Milan to Boston$937
  • Out of Boston, Naples is the cheapest first stop at about $277. Milan would be $463.
  • Going home, Milan is the cheapest city to leave from at about $937, against $1,107 from Naples.
  • The dearest order pays $1,107 for Naples to Boston, a flight the cheapest order never takes.
  • Milan to Boston is 74% of what the cheapest order spends on flights, so it is the leg to watch.

Between the cities

  • Naples to Venice: about 530 km (330 miles) as the crow flies. Also by ground: Frecciarossa / Italo, about 5h 30m, usually $35 to $110.
  • Venice to Milan: about 240 km (150 miles) as the crow flies. Also by ground: Frecciarossa / Italo, about 2h 30m, usually $25 to $60.

Entry rules on a US passport

  • US passport: visa-free in the Schengen area for 90 days in any 180. The Entry/Exit System registers biometrics at the border, and the ETIAS pre-travel authorisation may now be required; check the official site. Official source

Rules change; check the official source for your passport and dates before you book.

What these numbers are

Cached one-way fares, 11 of 12 legs priced from real observations, put together on September 24, 2026, from fares departing September 25, 2026 onwards. Right for comparing one order with another, not a quote for your dates.

A plan prices your own dates and weighs hours as well as fares, so it can pick a different order from this page.

Other trips priced this way

From Boston

Trips through the same cities

Put dates on it

Same cities on real dates, plus what one search cannot show: layovers long enough to count as a free city, two tickets that beat one, and cheaper days either side. No account and no card.

One press starts it on January 2, 2027 to January 16, 2027, 14 days, for 2 travelers. Our dates, not yours, and about two minutes.

Plan Milan, Venice and Naples from Boston nowOpen the form instead and pick your own dates

Signed out, 3 plans a day per address, priced from cached fares and the free sources, so some legs may be estimates and the plan says which. Signed in, legs are checked live, with 2 free trips you can change afterwards.