The 13 Best Places to Drink and Stay in Portland

A cocktail bar on Portland's tourist-heavy Wharf Street that opened with a stated mission to make the block worth visiting. The drinks lean on reworked classics, with hot dogs and bar snacks to keep things honest. The $28 Flaming Scorpion Bowl arrives in a blaze of mild chaos, which tells you the room doesn't take itself too seriously. Punch named it one of the best new bars in the country, and Esquire flagged its espresso martini among the best in America.

1. Esquire Espresso Martini · The Best Martinis in America
2. Punch Best New Bars
3. Portland Press Herald Best 75 places to eat and drink in Greater Portland

1. Esquire 50/50/50 · The Best Martinis in America

1. Wildsam The 50 Most Essential Bars in America

Six rooms in a residential house a few blocks from the Danforth Street sibling, this Lark Hotels guest house holds a Michelin Key and wears its size lightly. Vintage furnishings and local artwork give it the feel of staying with someone who has better taste than you do. The neighborhood is quiet, walkable, and genuinely residential, which means you'll pass actual Portlanders on the way to breakfast.

1. Michelin Guide 1 Key

The name nods to the Prohibition speakeasy that once operated in the basement, which is a better origin story than most boutique hotels can manage. Lark Hotels gave the old house a full renovation, and their signature formula is intact: photogenic rooms, genuinely comfortable beds, and a walkable neighborhood that makes you feel like a local who somehow has nicer lodgings than anyone else on the block. The Michelin Guide awarded it one Key.

1. Michelin Guide 1 Key

Sitting on the cobblestone end of Fore Street in Portland's Old Port, this boutique hotel leans into a nautical theme without going full lighthouse gift shop. Rooms run contemporary-classic, with large soaking tubs in many bathrooms and fireplaces in some suites. BlueFin handles fresh North Atlantic seafood on-site, though the Old Port's bar and restaurant scene starts essentially at the front door.

1. Michelin Guide Selected Hotels

The former home of the Portland Press Herald spent nearly a century printing the news; now it's a 110-room boutique hotel in the Old Port where the newspaper theme is more than wallpaper. The building itself does the heavy lifting, so the vintage journalist decor reads like atmosphere rather than concept. Selected by the Michelin Guide, it's a Marriott Autograph Collection property, which means independent spirit with loyalty points attached.

1. Michelin Guide Selected Hotels

1. Michelin Guide Selected Hotels

A six-room B&B tucked into a stately red-brick Georgian house in Portland's quieter, more residential West End. The rooms are handsome and distinct, the décor classic without feeling like a period piece, and the cooked-to-order breakfast is a proper morning. An automated wine bar is an odd and welcome touch, and afternoon cheese boards keep things civilized. Downtown is a short walk northeast when you need it.

1. Michelin Guide Selected Hotels

1. Punch Salad Bar Martini · Our Favorite Cocktails

1. James Beard Awards 2023 · Semifinalist · Outstanding Bar
2. Portland Press Herald Best 75 places to eat and drink in Greater Portland
3. James Beard Awards 2025 · Semifinalist · Outstanding Professional in Cocktail Service · Nathaniel Meiklejohn

Mahogany double doors shipped from Puerto Rico anchor the entrance to this Puerto Rican cocktail bar in the Old Port, where salsa and merengue fill the room and the tiled bar is the obvious place to sit. The drinks lean inventive, the food is serious enough to linger over, and the whole thing has a regional Spirited Award to its name. Portland has seafood shacks covered; this is doing something else entirely.

1. Condé Nast Traveler 15 Best Restaurants in Portland, Maine
2. Portland Press Herald Best 75 places to eat and drink in Greater Portland
3. Spirited Awards 2024 · Regional Honoree · Best New U.S. Cocktail Bar – U.S. East

1. Portland Press Herald Best 75 places to eat and drink in Greater Portland
2. Spirited Awards 2023 · Regional Honoree · Best U.S. Cocktail Bar – U.S. East