Portland, Maine: The Ultimate Foodie-Focused, Walkable Getaway

Portland blends New England tradition with an incredible food scene, so the city is ideal for long weekends, romantic getaways, foodie escapes, or a calm reset by the water. The Old Port district is the heart of the experience—historic brick buildings, cobblestone streets, boutique shops, and some of the most inventive restaurants in the Northeast. Everything is walkable, which makes the trip feel seamless from the moment you check into your hotel.

For dining, my top three recommendations are Twelve, Fore Street, and Scales. Twelve offers an intimate, chef-driven tasting experience with beautiful seasonal dishes—it’s one of those meals that feels like an occasion. Fore Street is Portland’s iconic, wood-fired institution and perfect for clients who want warm, rustic, elevated Maine cuisine in a vibrant setting. Scales sits directly on the harbor with some of the freshest seafood and one of the best raw bars in the city.

For lunch, you truly cannot miss Eventide (famous for their brown-butter lobster roll) or Duckfat (Belgian fries and paninis worth every calorie). These spots are casual but special—ideal for breaking up long walks through Old Port.

Portland shines with its bar scene, too. Blyth & Burrows is the standout—think dimly lit, speakeasy-style cocktails, a chic maritime vibe, and a hidden back room that adds to the adventure. It’s exactly the type of spot I love recommending to clients who want something atmospheric without being over the top.

In terms of hotels, the Press Hotel remains one of my favorites. The entire property is designed around its past life as a historic newspaper building, and the atmosphere is stylish, creative, and warm. It’s perfect for couples or a solo traveler who wants something boutique and design-forward. The Portland Regency Hotel offers the best central location for walking everywhere—ideal for families or anyone who loves being right in the heart of Old Port. Both properties offer two very different experiences, and I love matching clients to the one that suits their travel style.

• Dining reservations are essential, especially for Twelve, Fore Street, Scales, and Eventide. I’m happy to assist with timing and recommendations based on itinerary flow.

• Portland is walkable, but winter visits require good footwear due to icy sidewalks. Summer and fall are peak seasons—book early for the best hotel inventory.

• Parking can be tight in Old Port—many clients appreciate staying central so they can explore on foot.

• Foodies will thrive here. Many restaurants showcase Maine’s farm-and-sea bounty through wood-fired, seasonal menus—it’s truly a culinary destination.

• Great for long weekends. Three nights is the sweet spot for most travelers.

• Easy add-ons: Nearby lighthouses, Casco Bay ferry trips, Kennebunkport or Freeport day trips, brewery tours, and coastal hikes.

For more inspiration and insider recommendations, visit our Portland, Maine page.