Portland, Maine Itinerary

Day 1: Arrival & Exploration

Morning: Arrive in Portland and settle into your accommodation. Take a leisurely stroll through the historic Old Port district, admiring its cobblestone streets and waterfront views.

Afternoon: Grab a lobster roll at the iconic Eventide Oyster Co. and then wander to the Portland Museum of Art to see its impressive collection of American and European works.

Evening: Dine at Fore Street for farm‑to‑table cuisine, then enjoy a nightcap at the lively Novare Res Bier Café while soaking up the local atmosphere.

Day 2: Coastal Adventure

Morning: Catch the Casco Bay Ferry to Peaks Island, where you can rent a bike and explore scenic trails and quiet beaches.

Afternoon: Return to the mainland and visit the iconic Portland Head Light in Fort Williams Park, snapping photos of the lighthouse against the Atlantic backdrop.

Evening: Savor fresh seafood at Street & Co. on the waterfront, then take a sunset walk along the Eastern Promenade for panoramic city and sea views.

Day 3: Culture & Relaxation

Morning: Tour the historic Victoria Mansion, admiring its lavish interiors and period furnishings.

Afternoon: Sample craft brews at Allagash Brewing Company and enjoy a light lunch at their taproom, followed by a visit to the nearby Portland Observatory for a climb to the top.

Evening: Conclude your trip with a dinner at Duckfat, renowned for its Belgian fries and gourmet sandwiches, then relax with a stroll through the illuminated streets of the Old Port.

Time and Cost Estimates

• Old Port – 2 hrs – $0 (walking)
• Eventide Oyster Co. – 1 hr – $25
• Portland Museum of Art – 2 hrs – $15
• Fore Street – 2 hrs – $60
• Novare Res Bier Café – 1.5 hrs – $12
• Casco Bay Ferry (Peaks Island) – 3 hrs – $10
• Portland Head Light – 1.5 hrs – $0
• Street & Co. – 2 hrs – $55
• Eastern Promenade – 1 hr – $0
• Victoria Mansion – 1.5 hrs – $12
• Allagash Brewing Company – 2 hrs – $20 (tasting flight)
• Portland Observatory – 1 hr – $8
• Duckfat – 1.5 hrs – $30
• Total Estimated Cost: $287

Tips

If you have extra time, add a day to explore nearby Cape Elizabeth and the charming town of Ogunquit, or extend your island adventure with a kayak tour of Casco Bay. For a shorter stay, focus on the Old Port, Portland Head Light, and one brewery, cutting the itinerary to two days while still experiencing the city’s highlights.