itinerary suggestions from Boston to Bar Harbor

Question

My husband and I will be taking our 30th anniversary trip this early September from Boston to BH. We fly into Boston and will stay for 2 nights before renting a car and heading up the coast. We will have 6/7 nights outside of Boston to wander our way up. My thought was to end in Bar Harbor for a 4 night stay leaving us 2/3 days to stay between Boston and BH. I know its late for reservations but I already have them made in Boston and BH (which can still be modified). We want to explore the best of the coast, eating and shopping our way up to BH. We love history and aren't looking for the super touristy things, unless they are a 'can't miss' situations. My questions are these: where do you recommend we stop and stay for a night or 2 that is central enough for some 'must see' places before arriving in BH? I was hoping if we leave Boston early enough we can spend a few hours in Ogunquit & Kennebunkport. I was told to stop in Portland for lunch. Then we continue heading up north? Stay in Cambden, Rockport or Boothbay? We aren't looking for luxurious lodging , just something clean and close to the ocean. Suggestions? Best places to eat on our way up? Any activities you recommend (short hikes, boat rides, lighthouse visits)? Thank you in advance!!

Answer

For a 30th anniversary road trip from Boston to Bar Harbor in early September, you have a fantastic opportunity to explore the Maine coast at a relaxed pace, with plenty of charming towns, lighthouses, and seafood stops along the way. Since you have 6–7 nights to travel north, here’s a detailed itinerary suggestion that balances sightseeing, dining, and accommodations.

Day 1–2: Boston

Spend two nights in Boston exploring historic sites, such as the Freedom Trail, Boston Common, and the North End for Italian cuisine. Consider a harbor cruise or a walk along the Charles River if you enjoy water views. Your lodging in Boston can stay as planned since you’ll be leaving early on your departure day north.

Day 3: Boston → Ogunquit → Kennebunkport → Portland

Depart Boston in the morning and head up the coast. Ogunquit is roughly 1.5 hours from Boston.

Ogunquit: Walk the Marginal Way coastal trail (about 1.5 miles each way), enjoy ocean views, and explore local art galleries and boutique shops.
Kennebunkport: Another 15–20 minutes north. Stroll Dock Square for quaint shops, visit the Seashore Trolley Museum if interested in history, and grab a quick coffee or snack.
Portland: Stop for lunch in the Old Port district. Recommended seafood spots include Eventide Oyster Co. for fresh oysters and lobster rolls, or Portland Lobster Co. for classic lobster dishes.

After lunch, continue north and stay overnight in the Camden or Rockport area, about 1.5 hours from Portland.

Camden/Rockport: Both are charming coastal towns with easy access to the harbor, local shops, and walking trails. Accommodations can range from inns to bed-and-breakfasts. Look for places with waterfront views for that Maine charm.
Evening activity: Short hike at Camden Hills State Park for sunset views over Penobscot Bay.

Day 4: Camden/Rockport → Boothbay Harbor → Midcoast Maine

Boothbay Harbor: About 1 hour from Camden. Visit the coastal walkways, the harbor, and consider a boat tour for wildlife or lighthouse views. Lunch can be at The Lobster Dock or Boothbay Craft Brewery for local fare.
Afternoon: Drive further north to Lincolnville or Belfast for overnight. Both towns have clean, comfortable accommodations and are centrally located for exploring midcoast Maine.

Day 5: Midcoast Maine → Acadia/Bar Harbor

Spend the morning exploring local lighthouses and short hikes along the coast. Popular options include:

Pemaquid Point Lighthouse
Fort Knox Historic Site near Bucksport
Walking along scenic coastal trails or small harbor towns

Arrive in Bar Harbor in the late afternoon or early evening. Check into your hotel for a 4-night stay.

Days 6–9: Bar Harbor & Acadia National Park

Spend the next several days enjoying Acadia National Park and Bar Harbor:

Drive the Park Loop Road, stopping at Sand Beach, Thunder Hole, and Otter Cliffs
Short hikes suitable for views: Jordan Pond Path, Ocean Path, or Cadillac Mountain summit for sunrise
Kayaking or boat tours for wildlife and coastal scenery
Explore Bar Harbor shops, galleries, and restaurants, including seafood and local specialties like lobster rolls

Food suggestions along the way:

Eventide Oyster Co. (Portland)
Portland Lobster Co. (Portland)
The Lobster Dock (Boothbay Harbor)
Thompson’s Point Lobster Shack (midcoast Maine)
Galyn’s or Stewman’s Lobster Pound (Bar Harbor)

This itinerary allows for relaxed travel with plenty of sightseeing, local shopping, and coastal charm. It avoids overly touristy stops while still hitting the highlights of Maine’s coast, ensuring a memorable anniversary trip.