Portland, Maine

Here's a fun and diverse itinerary for your 4 days in Portland, Maine:

Day 1:

• Morning: Start your day with a delicious breakfast at The Holy Donut, known for their unique potato-based donuts.
• Mid-Morning: Head to Fort Williams Park to explore the iconic Portland Head Light and enjoy a scenic coastal hike along the Cliff Walk Trail.
• Lunch: Grab a lobster roll at Bite Into Maine food truck located in the park.
• Afternoon: Visit the Portland Museum of Art to admire its impressive collection of American and European art.
• Dinner: Enjoy a seafood dinner at Eventide Oyster Co., known for their fresh oysters and innovative small plates.

Day 2:

• Morning: Have breakfast at Standard Baking Co. for some freshly baked pastries and bread.
• Mid-Morning: Drive to Bradbury Mountain State Park for a morning hike with beautiful views of the surrounding area.
• Lunch: Stop by The Farmer's Table for a farm-to-table lunch experience.
• Afternoon: Explore the Old Port district for some shopping and sightseeing.
• Dinner: Indulge in a farm-to-table dinner at Fore Street, known for its locally sourced ingredients and cozy atmosphere.

Day 3:

• Morning: Start your day with a hearty breakfast at Becky's Diner, a local favorite for classic American breakfast dishes.
• Mid-Morning: Drive to Wolfe's Neck Woods State Park for a scenic hike through the forest and along the coastline.
• Lunch: Enjoy a picnic lunch at the park or head to The Lobster Shack at Two Lights for a traditional Maine lobster meal.
• Afternoon: Visit the Portland Observatory for panoramic views of the city and harbor.
• Dinner: Treat yourself to a fine dining experience at Street and Co., known for its Mediterranean-inspired seafood dishes.

Day 4:

• Morning: Have breakfast at Tandem Coffee + Bakery for some artisanal coffee and pastries.
• Mid-Morning: Explore the Eastern Promenade Trail for a leisurely walk with stunning views of Casco Bay.
• Lunch: Head to Duckfat for their famous Belgian fries and gourmet sandwiches.
• Afternoon: Visit the Portland Head Light again for a different perspective during the day.
• Dinner: End your trip with a memorable dinner at Central Provisions, a trendy spot offering creative small plates and craft cocktails.

I hope this itinerary gives you a good mix of outdoor activities, cultural experiences, and delicious dining options during your stay in Portland, Maine! Let me know if you need any more recommendations or adjustments.