Morning
Land at Logan (BOS)
Skip the rental counter today. Boston garage rates are brutal and you do not need a car until day 3.
Afternoon / Day
Check in: The Lenox
61 Exeter Street at Boylston. Back Bay corner hotel open since 1900, two blocks from the library and Newbury Street.
Lunch at Saltie Girl
279 Dartmouth St. Tinned fish, oysters and caviar in a room the size of a galley. Book on OpenTable.
Boston Public Library, McKim Building
700 Boylston St. The McKim building is free to walk into, and the library runs its own art and architecture tours of the murals and reading rooms.
Newbury Street
Eight blocks of brownstone storefronts running from the Public Garden to Massachusetts Ave. Best browsed downhill.
Public Garden and Acorn Street
Cross the Public Garden, then climb Beacon Hill to Acorn Street. Cobbles are ankle-turning; wear real shoes.
Evening
Dinner at Neptune Oyster
63 Salem St in the North End. Walk-ins only, no reservations ever. Put your name down, then get the hot buttered lobster roll.
Cannoli at Modern Pastry
257 Hanover St, open to 11 PM Sunday to Thursday and midnight on Friday and Saturday. Cannoli are filled to order; the tiramisu is their best-known cake.
Morning
Isabella Stewart Gardner Museum
25 Evans Way. A Venetian palazzo courtyard hung exactly as she left it in 1924. Closed Tuesdays; anyone named Isabella gets in free.
MFA Boston (optional)
465 Huntington Ave, a five-minute walk from the Gardner. Also closed Tuesdays; open late Thursday and Friday if you would rather swap.
Afternoon / Day
Red Line to Harvard Square
Green Line to Park Street, change to the Red Line outbound. About 25 minutes door to door.
Brunch at Alden & Harlow
40 Brattle St. Brunch runs Saturday and Sunday only, 10:30 to 2:30 — the rest of the week it opens at 5 for dinner.
Harvard Art Museums
32 Quincy St. Free admission every day, over 50 galleries on three floors around the glass-roofed Calderwood Courtyard. Closed Mondays.
Mount Auburn Cemetery
580 Mount Auburn St. A landscaped garden cemetery and the best colour in Cambridge. Open 8 to 8; Washington Tower shuts at 6.
Evening
Dinner at Oleana
134 Hampshire St. Turkish and Middle Eastern small plates, much of the produce from their own farm. Opens 5 daily; books 30 days out.
Morning
Pick up the rental car
An in-town office beats Logan for both price and time. Everything from here north is easier with your own wheels.
I-95 north to Portsmouth
About an hour from Back Bay outside rush hour. There is a toll on the Hampton stretch of the NH turnpike.
Afternoon / Day
Lunch at Popovers on the Square
8 Congress St, right on Market Square. Popovers, salads and sandwiches; a fast stop before the museum.
Strawbery Banke Museum
14 Hancock St. Nearly ten acres of houses on their original foundations, furnished across 350 years. Closed Tuesdays; tickets are good two days.
Ceres Street waterfront
Cobbled lane of brick warehouse buildings running down from Market Square to the Piscataqua River. Ten minutes, and the best light in town.
Evening
On to Portland
Another hour up I-95 and the Maine Turnpike. Aim to be parked in the Old Port before dark.
Check in: The Press Hotel
119 Exchange St, the old Portland Press Herald building. Valet parking, which is the easy answer in the Old Port.
Dinner at Eventide Oyster Co.
86 Middle St. Order the brown butter lobster roll they are known for; the raw list is the other half of the reason to come.
Start from this itinerary.
Copy all 7 days into your account, then change whatever you like.
Already have an account?
Morning
Breakfast at Standard Baking Co.
75 Commercial St, 7:30 to 5 every day. Croissants and morning buns from a wood-and-flour operation that has been at it since 1995.
Portland Head Light, Fort Williams
1000 Shore Road, Cape Elizabeth. Park is sunrise to sunset; meters take cards only, $6 for two hours. Keeper's house museum shuts in mid-October.
Afternoon / Day
Lunch at Duckfat
43 Middle St. Belgian frites twice-fried in duck fat, served in a cone. No reservations, first come first served.
Portland Museum of Art
7 Congress Square. Strong Winslow Homer holdings, and the museum also runs tours of his studio at Prouts Neck. Check hours and admission before you go.
Allagash Brewing tasting room
50 Industrial Way, ten minutes out of downtown. Allagash White is the one that started it; check tour times before driving out.
Evening
Old Port at dusk
Cobbled blocks around Exchange and Fore Street, with the working wharves a block below. Twenty minutes before your table is ready.
Dinner at Fore Street
288 Fore St, open daily from 4:30. Everything comes off the brick and soapstone hearth; the menu is rewritten each afternoon.
Morning
Check the state foliage report
Maine Forest Service publishes zone-by-zone colour reports through the season. Coastal and Downeast turn later than the mountains.
US-1 north up the midcoast
Two hours to Camden on Route 1 through Bath, Wiscasset and Rockland. Slower than the interstate and the entire point.
Mount Battie Auto Road
280 Belfast Road, Camden Hills State Park. Paved road to the summit, gate open 8 to 4, day-use fee at the booth. Penobscot Bay below.
Afternoon / Day
Lunch at Long Grain
20 Washington St, Camden. Southeast Asian cooking on Maine produce. Lunch 11:30 to 2:30, closed Sunday and Monday. Reserve for dine-in.
On to Mount Desert Island
Two more hours via Belfast, Ellsworth and the Route 3 bridge onto the island. Fill the tank in Ellsworth.
Evening
Check in: Bar Harbor Grand Hotel
269 Main Street, a reproduction of the 1895 Rodick House. Walking distance to everything in town, which matters here.
Book the Cadillac Summit Road slot
Vehicle reservations are required to drive the summit road from 20 May to 25 October, $6 per vehicle, booked on recreation.gov in advance. Check the park fee page while you are there — a per-person surcharge now applies to non-US residents on top of the entrance pass.
Dinner at Side Street Cafe
49 Rodick St. Open from 11 daily, with an online waitlist you can join before you walk over. Lobster mac and a table on the porch.
Morning
Sunrise on Cadillac Mountain
Highest point on the eastern seaboard, and from 7 October to 6 March the first place in the country to see the sun rise. Bring the booked reservation and gloves.
Breakfast at Cafe This Way
14 1/2 Mt. Desert St. Serves 6:30 AM to 1 PM daily, so it is open before you come down off the mountain.
Afternoon / Day
Park Loop Road: Sand Beach
Much of the 27-mile loop is one way, so drive it round rather than back. The Sand Beach lot fills first; head straight there.
Thunder Hole and Otter Cliff
Walk the Ocean Path south from Sand Beach. Thunder Hole only booms near high tide with a swell running; check the tide chart.
Popovers at Jordan Pond House
2928 Park Loop Rd, Seal Harbor. Tea and popovers on the lawn since 1893. Most tables are held for walk-ins; expect a wait.
Evening
Bar Harbor Shore Path
Gravel path along the front from Agamont Park past the old summer cottages. The sandbar to Bar Island opens either side of low tide.
Dinner at Havana
318 Main St, 4 to 10 daily. Latin-leaning Maine seafood and one of only two Wine Spectator award lists in the state. Reserve ahead.
Bass Harbor Light, then south
Morning
Bass Harbor Head Light
Tremont, on the quiet southwest corner of the island. One small lot and no roadside parking, so arrive early or skip it.
Route 3 off the island, then I-95
Roughly five hours back to Boston. Break it at Portland, which sits almost exactly halfway.
Afternoon / Day
Lunch at The Holy Donut
The Commercial Street shop in Portland. Donuts made with Maine potato, which is why they are heavy and stay soft.
I-95 south to Boston
Two hours to Logan if you clear Portsmouth before the afternoon build-up. Southbound is the easy direction on a Friday.
Evening
Return the car at Logan
Rental returns sit in the consolidated centre; the shuttle to the terminals adds 15 minutes on top of the drop-off.
Fly out of BOS
Evening departure. About a thousand kilometres behind you and not one of them a single long push.
Explore other trips
Patagonia on Foot: Fitz Roy and Paine
Solo Adventure·Jan 7 – Jan 17·11 days
Pacific Coast Highway Solo Run
Solo Adventure·Sep 5 – Sep 12·8 days
Canadian Rockies Road Trip
Road Trip·Jul 9 – Jul 17·9 days