Portland · For couples
Things to Do in Portland, Maine for Couples
Cobblestones, harbour views, candlelit dining rooms and lighthouses on the rocks: Portland is made for a couple's weekend. Here's how to plan it.
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Dinner for two
Twelve
115 Thames St, Portland Foreside
Modern New England cooking from chef Colin Wyatt (formerly of Daniel and Eleven Madison Park) in a 150-year-old brick building rebuilt brick by brick on the waterfront. Dinner from 5 p.m.; closed Mondays.
Tip: The special-occasion choice in town. Book ahead.
Fore Street
288 Fore St
Portland's landmark since 1996: a big old warehouse room around a wood-fired oven, grill and turnspit, with a menu that changes daily with what farmers and fishermen bring in. Open nightly from 4:30 p.m.; reservations by phone.
Street & Co.
33 Wharf St
A seafood restaurant on a pedestrian cobblestone lane between Commercial and Fore streets. Dinner nightly from 5 p.m.; a few walk-in tables are held each evening, with sign-ups from 4:30 p.m.
Scales
Maine Wharf, 68 Commercial St
A seafood restaurant out on Maine Wharf, with complimentary valet parking and a patio in good weather. Dinner nightly; bar seats can be reserved, and walk-in names are taken from 4 p.m.
A drink somewhere special
Top of the East
Westin Portland Harborview, 157 High St, 15th floor
A 15th-floor lounge with views over the city to Casco Bay, cocktails and small plates. Opens at 4 p.m. daily, until midnight on Fridays and Saturdays; reservations on OpenTable.
Tip: Book a window table for sunset.
Hunt + Alpine Club
75 Market St
A two-time James Beard semi-finalist cocktail bar, opened in 2013 and renovated in 2025, with food to match the drinks. Opens at 3 p.m. Tuesday to Friday and 2 p.m. at weekends; closed Mondays. A few reservations are released, the rest is walk-in.
Eventide Oyster Co.
86 Middle St, Old Port
A James Beard Award-winning raw bar with fresh oysters and shellfish and the famous brown butter lobster roll. Indoor and outdoor seating.
Tip: Go mid-afternoon to skip the queue and share a dozen oysters at the bar.
By day
Portland Head Light & Fort Williams Park
1000 Shore Rd, Cape Elizabeth (15 minutes)
Heads-up: The lighthouse museum closes for the season after Indigenous Peoples Day (October 12, 2026).
The classic Maine lighthouse, on the rocks inside a free public park with old gun batteries, the Goddard Mansion ruin and a small cove beach. The park is open sunrise to sunset year-round; parking is by card meter.
Inn by the Sea Spa
40 Bowery Beach Rd, Cape Elizabeth
The spa at a seaside resort in Cape Elizabeth, with massages, facials, body wraps and packages. Non-guests can book with a card on file.
Casco Bay Lines Mailboat Run
Ferry terminal, 56 Commercial St
Ride along on the working ferry that delivers mail and freight to five Casco Bay islands, including Great Diamond, Long and Chebeague. Two and a half to three and a half hours, year-round, departing 10 a.m., noon and 3:15 p.m.
Ogunquit's Marginal Way
Ogunquit, about 40 miles south
A paved 1.25-mile cliff-top path from Ogunquit to Perkins Cove, lined with more than 30 benches, tide pools and a small lighthouse, ending at a harbour with a pedestrian drawbridge. Free, dawn to dusk, year-round.
Tip: Walk it south to Perkins Cove and have lunch there before driving back.
Our advice
- Book Twelve or Fore Street for your big night and go somewhere casual, like Eventide or Duckfat, for the other.
- Time Top of the East for sunset and ask for a window table.
- Come in September or early October for the best weather and fewer crowds, before the seasonal places close.
Everything here was checked in September 2026. Many places on the Maine coast are seasonal and close or cut their hours from mid-October, so confirm before you go.
Questions people ask
What is the most romantic thing to do in Portland, Maine?
Sunset drinks at Top of the East followed by dinner at Twelve on the waterfront, or a morning at Portland Head Light and an afternoon at the Inn by the Sea Spa.
Where should couples eat in Portland, Maine?
Twelve for a special occasion, Fore Street for wood-fired cooking in a lively room, Street & Co. or Scales for seafood, and Eventide for oysters.
What do couples do in Portland, Maine at night?
A rooftop drink at Top of the East, dinner in the Old Port, then cocktails at Hunt + Alpine Club or a play at Portland Stage.