Portland to Boston 5 day trip

Question

We are planning a road from Portland to Boston in mid November. We are looking at around 5 full days. Would love some suggestions and a sample itinerary!Thank you!

Answer

A 5-day road trip from Portland, Maine to Boston, Massachusetts in mid-November is a wonderful way to explore the New England coast and nearby towns while enjoying crisp fall or early winter scenery. Here’s a suggested itinerary that balances scenic drives, coastal towns, and city exploration.

Day 1: Portland, Maine

Start your day exploring Portland’s Old Port district with its cobblestone streets, boutique shops, and galleries.
Visit the Portland Head Light in Cape Elizabeth for iconic coastal views.
Enjoy lunch at one of Portland’s renowned seafood spots, such as Eventide Oyster Co. or Fore Street.
Optional: Explore the Portland Museum of Art or take a short walk along the Eastern Promenade.

Day 2: Portland to Kennebunkport / Ogunquit

Drive south along Route 1 (about 1–1.5 hours to Kennebunkport).
Explore Dock Square, walk along the scenic coast, and view the historic mansions. Consider a short visit to Goat Island Lighthouse or Cape Porpoise.
Lunch at a local cafe or seafood restaurant in Kennebunkport.
Optional: Continue to Ogunquit (20-minute drive) and stroll Marginal Way for dramatic cliffside views and quaint shops.
Overnight in Kennebunkport or Ogunquit.

Day 3: Kennebunkport/Ogunquit to Portsmouth, NH and Southern New Hampshire

Drive about 1 hour to Portsmouth, NH, a charming coastal town with historic streets and Market Square shopping.
Lunch at a local spot like The Friendly Toast or Row 34.
Explore Prescott Park or take a riverfront walk.
Optional: Drive slightly inland to see New Hampshire’s scenic small towns, especially if leaves are still vibrant.
Overnight in Portsmouth or nearby.

Day 4: Portsmouth to Salem / Marblehead / Gloucester

Drive 1–1.5 hours to Salem, MA. Explore historic sites and museums, even if Halloween season is past; the maritime and witch history is fascinating year-round.
Lunch in Salem at a local café or seafood restaurant.
Optional: Drive a short distance to Marblehead or Gloucester for coastal walks and lighthouse views.
Overnight in the North Shore area or continue toward Boston for a city stay.

Day 5: Boston

Spend your day exploring Boston’s historic Freedom Trail, Boston Common, and Faneuil Hall Marketplace.
Optional: Visit museums such as the Museum of Fine Arts or the Isabella Stewart Gardner Museum.
Enjoy lunch or dinner in the North End for Italian cuisine.
Wrap up your trip with a stroll along the Harborwalk or the Seaport District before departing.

Tips:

Mid-November can be chilly and sometimes rainy, so dress in layers and waterproof footwear if planning outdoor activities.
Booking accommodations in advance is recommended, especially in popular coastal towns.
Take advantage of scenic coastal routes (Route 1A and 1) for beautiful ocean views along the way.
Allow extra travel time as some local attractions may have shorter winter hours.

This itinerary gives a nice mix of coastal charm, small-town exploration, and urban Boston highlights, making for a well-rounded 5-day trip.