Boston to Naples is one of our busiest winter routes. You leave Hanscom Field in Bedford and land at Naples Airport about three and a half hours later, a few minutes from downtown Naples, Old Naples and the beaches.
Aircraft we fly to Naples
On a flight this long, range and cabin comfort both matter. Flights to South Florida are typically nonstop. A full aircraft combined with winter headwinds sometimes requires a short fuel stop, which typically adds 45 minutes to an hour. This is most likely in the Phenom 300 or Citation XL; the Challenger 604 flies the route nonstop with a full cabin. We'll tell you which applies when we quote your trip.
| Aircraft | Passengers | Typical flight time | Nonstop | Best for |
|---|---|---|---|---|
| Challenger 604 | 8 to 12 | About 3 hr 15 min | Yes, including a full cabin | Larger families, seasonal luggage, stand-up cabin, cabin attendant |
| Phenom 300 | Up to 7 | About 3 hr 30 min | Typically | Couples and small families |
| Citation XL | Up to 8 | About 3 hr 40 min | Typically | Small groups who want a larger cabin than a light jet |
Times are typical airborne estimates and vary with winds, routing and traffic; your quote includes an exact schedule. Southbound flights can run a little longer than northbound because of prevailing winds. See full specifications on our fleet page.
Choosing your Southwest Florida airport
Naples Airport (APF)
The closest airport to downtown Naples and the usual choice for private flights. The airport runs its own FBO, and Naples Jet Center opened a new executive terminal on the field in 2026.
Southwest Florida International (RSW)
In Fort Myers, about 30 miles north of Naples. A good fit for Bonita Springs, Estero and Fort Myers, and the airport to use if you need to clear customs on an international trip.
Marco Island Executive (MKY)
Just south of Naples and the most convenient option for Marco Island. Its runway is shorter than Naples Airport's, so we'll confirm which aircraft fit your trip.
One-way flights and the winter season
Many Naples trips are one-way: south in the late fall or around the holidays, north again in the spring. One-way pricing reflects the aircraft returning to Boston, so tell us if your dates are flexible or you are open to sharing a positioning leg. The seasonal flow of aircraft between New England and Florida also creates empty-leg opportunities, and we're happy to let you know when one lines up with your plans. You can also check our current empty legs.
Peak dates such as Thanksgiving, Christmas week and Presidents' Day book early. If you know your winter plans, reserving ahead gives you the widest choice of aircraft and departure times.
Other Florida routes
We fly from Hanscom to South Florida all winter. See also Boston to Palm Beach, Boston to Fort Lauderdale and Boston to Miami.
Departing from Hanscom Field
Hanscom Field (BED) in Bedford is about 20 minutes from downtown Boston and has none of the terminal lines or ground congestion of Logan. Arrive at the FBO shortly before departure, walk to the aircraft, and leave on your schedule. We keep offices at both Atlantic Aviation and Signature at Hanscom, along with our own hangar and in-house maintenance team, so the people preparing your aircraft work on the same field you depart from.
Booking with the operator, not a middleman
Many charter websites are brokers: they take your request and resell a flight operated by another company. When we fly your trip on one of our aircraft, the certificate, crews, maintenance and dispatch are all ours, and you deal with the same team from quote to landing. If you do book through a broker, it is worth asking who the operating carrier is.
Waltzing Matilda Aviation has flown from Hanscom Field since 2008 and has held its FAA Part 135 air-carrier certificate (No. 6WZA614N) since April 2015. Our operation is ARGUS Gold rated and IS-BAO Stage 2 registered, and we are members of NBAA.
Frequently asked questions
How long is the flight from Boston to Naples, Florida?
About 3 hours 15 minutes to 3 hours 45 minutes nonstop from Hanscom Field (BED) to Naples Airport (APF), depending on aircraft and winds. Southbound flights can run longer than northbound, and a fuel stop adds roughly 45 minutes to an hour.
Can I fly nonstop from Boston to Naples?
Typically, yes. Most Boston to Naples flights are nonstop, but a full aircraft combined with winter headwinds sometimes requires a short fuel stop, most often in the Phenom 300 or Citation XL. The Challenger 604 flies it nonstop with a full cabin.
Should I fly into Naples (APF), Fort Myers (RSW) or Marco Island (MKY)?
Naples Airport is closest to downtown Naples. RSW in Fort Myers suits Bonita Springs and Estero, and Marco Island Executive is best for Marco Island. We can quote more than one option.
Can I book a one-way charter to Naples?
Yes. One-way trips are common on this route. Pricing reflects the aircraft's return to Boston, and flexible dates or empty legs can reduce the cost.
Is Waltzing Matilda Aviation the operator or a broker?
We are the operator. Waltzing Matilda Aviation holds FAA Part 135 certificate No. 6WZA614N and flies its own aircraft from Hanscom Field.
Request a Boston to Naples quote
Tell us your dates, passengers and preferred airports and we'll build a tailored quote, typically within the hour during business hours.