Experience · Portland

Sunset Lighthouse & Old Port Dinner

Begin your evening with a breathtaking view of the Portland Head Light as dusk settles, offering stunning photo opportunities of Maine's iconic coastline. Then, head back to Portland's vibrant Old Port for a memorable local seafood dinner. Conclude your night with an optional rooftop cocktail, taking in the city lights and harbor views.

A 3.5-hour Old Port evening plan for couples — Portland Head Light, Street & Co, Luna Rooftop Bar.

Duration
3h 30m
Cost
$60–$150
Stops
3 stops
Area
Old Port
Walking
Light walking · Total 3.4-mile driving route
Best time
5:00 – 10:00 PM
Ideal for
Couples · Friends · Solo
Start Plan
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Sunset Lighthouse & Old Port Dinner

The plan

The plan

  1. 1Portland Head Light(1 hr)→
  2. 2Street & Co(1 hr 30 min)→
  3. 3Luna Rooftop Bar(1 hr)

Why this plan works

Every stop sits in Old Port, so the whole plan happens inside one neighborhood. Street & Co is the main event and takes the biggest block of time; the other stops are built around it. It finishes at Luna Rooftop Bar — a short, low-effort stop you can skip if you're ready to call it. Best suited to couples, friends, and solo who want a planned Portland outing without improvising between stops.

The story

Overview

Begin your evening with a breathtaking view of the Portland Head Light as dusk settles, offering stunning photo opportunities of Maine's iconic coastline. Then, head back to Portland's vibrant Old Port for a memorable local seafood dinner. Conclude your night with an optional rooftop cocktail, taking in the city lights and harbor views.

The itinerary

3 stops, one great day

  1. Portland Head Light1
    1 hr
    Portland Head Light

    Arts & Culture

    Still operative 1791 lighthouse & navigation museum on rocky, scenic coastline in Ft. Williams Park.

    What to do — Explore the grounds of Fort Williams Park, walk along the rocky coastline to view the lighthouse, and capture photos of the sunset.

    Scout Side Quest

    Pick your favorite vantage point along the path to watch the light fade over the water.

    Book it · Portland Head Light

    3.2 mi · 10 min drive

    Then Drive back towards Portland's Old Port, about 15-20 minutes away.

  2. Street & Co2
    1h 30m
    Street & Co

    Food & Drink · Old Port

    Simple, upscale preparations of local fish in a rustic & snug bistro on a cobblestone alley.

    What to do — Dine on simple, upscale preparations of local fish and seafood in a rustic, intimate bistro setting on a cobblestone alley.

    Scout Side Quest

    Before opening the menu, guess what dish the other person will be most tempted by tonight.

    0.2 mi · 4 min walk or 3 min drive

    Then Walk a short distance within Old Port to find a rooftop bar.

  3. Luna Rooftop Bar3
    Optional 1 hr
    Luna Rooftop Bar

    Nightlife · Old Port

    Elevated bar bites & cocktails in a sleek rooftop mainstay featuring a terrace with harbor views.

    What to do — Optional nightcap for those who drink—skip it and the plan still works. Enjoy craft cocktails and elevated bar bites with sleek harbor views.

Scout Stories

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The route

On the map

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Common questions

Planning this outing

Is this a good Portland itinerary for couples?
Yes. It's built for couples, friends, and solo and runs about 3 hr 30 min across 3 stops, starting at Portland Head Light.
How long does this outing take?
Plan on 3 hr 30 min door to door, including time between stops.
How much does this Portland itinerary cost?
Roughly $60–$150 per person, before parking and tips. Free and low-cost stops are marked on each card.
Is this itinerary walkable?
Not entirely. The stops cover about 3.4 miles, so you'll drive or rideshare between at least one pair.
Do I need reservations?
No. Every stop on this plan takes walk-ins, though weekends move faster if you arrive early.

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