WWingAwayWEEKENDSFly to lunchDestination guide 97
Maine · Couples · Two nights

Portland, Maine

Lobster rolls, the Old Port and lighthouses.

Portland is one of the country’s great small food cities. Walk the cobblestones of the Old Port, eat oysters at Eventide and fries at Duckfat, dine at Fore Street, ride a ferry into Casco Bay and drive out to Portland Head Light, one of America’s most photographed lighthouses.

Food cityLighthousesHarbor & islands
See the weekend itineraryFlight & arrival details
Portland Head Light on the rocky shore of Cape Elizabeth, Maine
Portland Head Light, Cape Elizabeth
YOUR ROUTEKMYR to KPWM
STRAIGHT-LINE DISTANCE~721 NM
ILLUSTRATIVE FLIGHT TIME~5 hr 03 min
WEEKEND STYLETwo nights · Walk or rideshare

Time illustration: direct distance at 150 KTAS plus 15 minutes for departure and arrival, matching the discovery page. Use ForeFlight for your actual flight plan.

01 / Aviation & getting around

Land at the Jetport.

KPWM, Portland International Jetport, is a towered airport about 10 minutes from the Old Port.

The FBO

Northeast Air

Portland International Jetport, Portland, ME

207-774-6318

Confirm FBO hours, fees and ground transportation. No live fuel price is shown.

Coastal fog is common in summer. About 720 nm from Myrtle Beach: plan a fuel stop and three nights.

02 / Where to stay

Boutique hotels in the Old Port.

Rates and availability need travel dates.

03 / Where to eat

One of America’s best food towns.

Reserve weekend dinners.

04 / Things to do

Lighthouses, islands and art.

Eat, walk and get on the water.

01

Portland Head Light

An iconic lighthouse in Fort Williams Park.

Lighthouse
02

Casco Bay Lines

Ferries to the islands of Casco Bay.

Ferries
03

Portland Museum of Art

American and European art, including Winslow Homer.

Museum
04

Old Port & Eastern Promenade

Cobblestone streets and a park overlooking the bay.

Visit Portland
05 / What’s happening

Sometimes the season is the reason to fly.

This prototype links to the local visitor site. It does not yet match events to your travel dates.

Summer

Peak season

Long days and busy restaurants.

Fall

Harvest season

Great dining and cooler weather.

Year-round

Food scene

Reserve popular restaurants early.

Concerts, festivals & local happenings

Check the local calendar when choosing a weekend, and confirm dates and tickets with the organizer.

Browse Portland events
06 / Suggested itinerary

Friday in. Sunday home.

A sample long weekend: food, ferries and a lighthouse. Plan three nights for the flight. No bookings or availability confirmed.

DAY 1

Arrive & the Old Port

  1. Arrival

    Land at KPWM, subject to weather, your fuel stop and your actual flight plan.

  2. Afternoon

    Walk the Old Port; lunch at Eventide.

  3. Evening

    Dinner at Central Provisions.

DAY 2

Islands & art

  1. Morning

    A Casco Bay ferry.

  2. Afternoon

    The Portland Museum of Art.

  3. Evening

    Dinner at Fore Street.

DAY 3

Lighthouse & home

  1. Morning

    Portland Head Light.

  2. Before leaving

    Allow time at the FBO.

  3. Fly home

    Watch for coastal fog.

07 / Good to know

Keep the weekend easy to change.

These details make the difference between an appealing list and a usable getaway.

Book in this order

Lodging first, then Fore Street.

Fog

Coastal fog is common; have a plan B.

Long flight

About 720 nm. Plan fuel stops and extra nights.

Best seasons

June to October.

Reviewed · Destination 97

Reviewed November 4, 2026.

Picks and links reviewed by WingAway Weekends. Hours, prices, menus and availability change often, so confirm directly with each place before booking.

WingAway Weekends helps you discover the destination. Use ForeFlight and current official aviation information for route, performance, weather, NOTAMs and preflight decisions. Flight planning and PIC responsibility stay with the pilot.