RFK Rankings · Portland Me
Best Restaurants for Anniversary in Portland Me (2026)
Anniversary dining · Portland Me · 6 rooms ranked · Updated June 2026
Compiled by the Restaurants for Kings editorial team · Published May 22, 2026 · Updated June 16, 2026 · Reviewed by Fredrik Filipsson, Editor-in-Chief · How we rank · Corrections
Portland, Maine packs more serious cooking into a few waterfront blocks than cities ten times its size, which makes it a quietly great anniversary town. The picks below run from a former Eleven Madison Park chef's tasting room on Thames Street to a wood-fired institution that helped put the city on the map. These six, ranked, are where to mark the year in the Old Port.
1.Twelve
Colin Wyatt's tasting menu in a restored brick foundry is the city's milestone room; book the five-course for the anniversary.
Colin Wyatt cooks at Twelve after twelve years at New York's Daniel and Eleven Madison Park, where his team took the world's best restaurant title in 2017. His modern New England tasting menus run from a three-course at $80 to a five-course at $100, served in a restored 150-year-old brick building at 115 Thames Street, with a Wine Spectator Award of Excellence on the list.
The high-ceilinged foundry room, the open kitchen and the measured pacing make it Portland's most considered occasion table. Book the five-course, ask for a quieter table away from the pass, and let the pairing run the evening.
2.Fore Street
The wood-fired Old Port institution that built Portland's reputation; book a table near the hearth for a warm anniversary.
Fore Street has anchored the Old Port at 288 Fore Street since 1996, the wood-fired room where founding chef Sam Hayward won James Beard Best Chef: Northeast in 2004 and restaurateur Dana Street took Outstanding Restaurateur in 2026. The brick-and-soapstone hearth turns out roast pork, mussels and a daily-changing menu with mains around $30 to $48.
The glow of the open hearth, the copper and the convivial buzz make it warm-romantic rather than hushed. Book one of the tables near the wood oven, order whatever the turnspit is roasting, and settle in for the evening.
3.Scales
A glass-walled seafood room right on the working wharf; book a window table at golden hour for a waterfront anniversary.
Scales sits on Maine Wharf at 68 Commercial Street, a Dana Street and Sam Hayward seafood room with floor-to-ceiling windows over Portland's working waterfront and an open kitchen and raw bar. Whole fish, fried clams and the day's catch run around $28 to $52, with the harbour itself as the view.
The light off the water, the post-industrial space and the easy polish of the service make it the waterfront anniversary table. Reserve a window seat, time it for golden hour over the harbour, and open with a tower from the raw bar.
4.Leeward
Jake and Raquel Stevens' handmade-pasta room is the city's warmest date table; book ahead, the rigatoni sells out fast.
Jake and Raquel Stevens, alumni of Beast in Portland, Oregon and Drifters Wife, run Leeward at 85 Free Street, a celebrated Italian room built on handmade pasta. The bolognese rigatoni, the sheep's-milk gnudi and the crudo lead a menu where most plates land around $18 to $34, in a warm, generous space.
The candle-warm room, the open pasta station and the easy hospitality make it the city's best low-key romantic dinner. Book ahead because it fills fast, sit toward the back, and order across the pastas to share.
5.Street & Co.
A brick-and-candlelight seafood room on cobblestoned Wharf Street since 1989; book a corner for an old-Port anniversary.
Street & Co. has cooked Mediterranean-leaning seafood on cobblestoned Wharf Street in the Old Port since 1989, a small brick room of exposed beams, hanging copper and candlelight. The grilled whole fish, the lobster diavolo and the mussels run around $28 to $46, served from an open kitchen at the back.
The low brick room, the cobblestones outside and the candlelight make it one of Portland's most enduringly romantic tables. Request a corner table, order the lobster diavolo over linguine to share, and let a long dinner unfold.
6.Solo Italiano
Genoa-born Paolo Laboa cooks the city's most authentic Ligurian pasta; book for a warm, wine-led Italian anniversary.
Chef Paolo Laboa, from Genoa, runs Solo Italiano at 100 Commercial Street, cooking simple, authentic Ligurian food: his award-winning pesto, handmade trofie and pansoti, crudo and an all-Italian wine list. Plates land around $22 to $40 in a rustic-chic room with a generous bar.
The warm room, the genuine regional cooking and the all-Italian list make it a relaxed, food-first anniversary. Book ahead, order the pesto trofie that made his name, and let the wine list carry a long Ligurian dinner.
Not for everyone
Romantic-sounding, but wrong for the night
Duckfat. Rob Evans's Belgian-fry and panini counter is one of Portland's best-loved spots, but it is a tiny, counter-service, often-queued room. Save it for lunch, not a quiet anniversary dinner for two.
Eventide Oyster Co.. The James Beard-winning oyster bar is a Portland essential, but it runs loud, communal and walk-in-driven, built for a buzzy raw-bar crawl. For a romantic table, the rooms above are the better book.
DiMillo's on the Water. The floating restaurant on a former car ferry has the harbour novelty, but it trades on the setting more than the kitchen and draws a tour-bus crowd. For a waterfront anniversary instead, Scales earns the night.
How to plan an anniversary dinner in Portland, Maine
Portland's romantic rooms cluster tightly: Fore Street, Scales, Street & Co., Leeward and Solo Italiano all sit within a few Old Port and waterfront blocks, while Twelve is a short ride out to the rebuilt foundry buildings on Thames Street. You can walk between most of them, so picking the room matters more than picking the neighbourhood.
Book one to three weeks ahead for a Friday or Saturday at the top rooms, and use the restaurant's own platform or Resy where you can. Flag the anniversary in the notes, ask for a quiet corner or a window over the water, and at Twelve choose the five-course tasting when you reserve.
Frequently asked
What is the best anniversary restaurant in Portland, Maine?
Twelve on Thames Street is the marquee pick, chef Colin Wyatt's modern New England tasting menu in a restored brick foundry, with a five-course at $100 and a Wine Spectator Award of Excellence. Fore Street, the wood-fired Old Port institution since 1996, is the other default for a warmer, hearth-lit night.
Where can you have a romantic waterfront dinner in Portland, Maine?
Scales on Maine Wharf is the waterfront answer, a glass-walled seafood room with floor-to-ceiling windows over Portland's working harbour and an open raw bar. Book a window table, time it for golden hour over the water, and open with a tower from the raw bar; it sits at 68 Commercial Street.
How far ahead should you book an anniversary dinner in Portland, Maine?
Book one to three weeks ahead for a Friday or Saturday at the top rooms like Twelve, Fore Street and Leeward, which fills fast. Use the restaurant's own platform or Resy, flag the anniversary in the notes, request a quiet corner or window table, and confirm a day or two before.
What is the best Italian restaurant for a special occasion in Portland, Maine?
Leeward on Free Street and Solo Italiano on Commercial Street are the two picks. Jake and Raquel Stevens build Leeward around handmade pasta like the bolognese rigatoni, while Genoa-born Paolo Laboa cooks authentic Ligurian food and award-winning pesto at Solo Italiano; book either ahead for a warm, wine-led night.
Is Twelve good for an anniversary in Portland, Maine?
Yes, it is the city's most considered milestone room. Colin Wyatt cooked at Daniel and Eleven Madison Park before opening Twelve at 115 Thames Street, where the modern New England tasting menus run to a five-course at $100 in a restored brick foundry; book the tasting and ask for a quieter table.
Related rankings
More from RFK
Browse the full Portland, Maine dining guide, read the Twelve profile and the Fore Street profile, plan a night out with the Portland first-date ranking, dine alone with the Portland solo-dining ranking, read the global guide to anniversary dining, compare the calendar with the Portland birthday ranking, or open the full RFK rankings index.
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