Maine & New England trip planning

We plan the whole trip.
You just go.

A day trip, a long weekend or the two-week bucket list — answer a few questions and a local's knowledge builds your day-by-day plan: real drive times, seasonal warnings, where to eat, what to skip. Ready in about five minutes, from $19.

Ready in ~5 minReal drive timesLive-checked before deliveryWe make it right
Signature specials

Preset tours, personalized to you

One trip type, done right — pick a corridor, tell us your dates and start point, and a local builds the drive.

In season now

The Leaf Peeper's Special

A custom peak-color driving tour of Maine & New Hampshire — built around your dates, your starting point and how far you want to roam.

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The Waterfall Run

Falls, gorges and swimming holes strung into a drive that actually makes sense — with honest notes on what's roaring and what's a trickle.

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The Lighthouse Trail

Maine's lights, ordered so the driving makes sense — with the photo hours, the fog truth and the lobster stop between them.

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Sled season is coming

The Snow Season Special

Snowmobile country, ski mountains and ice fishing — a Maine winter planned around real trail logic, groomed miles and warm places to land.

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How it works

Three steps to a plan you can drive

1

Describe the trip

Dates, where you're starting, who's coming, what you love — about four minutes of questions.

2

Pick a tier

$19 The Plan — the full day-by-day itinerary. $29 Perfected — adds a complete rewrite from your notes + printable dashboard cue cards. $39 Full Kit — adds tap-to-navigate map links, the stay & eat shortlist, a dated reservation checklist and the pre-trip re-check. Compare tiers →

3

Read, revise, go

Days appear as they're written, on a permanent link that's emailed too. Print it, load a day's route in Google Maps, and drive.

Real sample

Three days, a couple, midcoast + Acadia

Exactly as delivered. Yours is written for your answers.

Midcoast & Acadia in September — Couple, 3 days, Balanced paceMid-September

Base: Road trip: 1 night Camden, 1 night Bar Harbor  ·  Interests: lobster & food, lighthouses, easy hikes, art

Day 1 — Portland to Camden: lighthouses, Route 1 and the Farnsworth

TonightCamden — an in-town inn within walking distance of the harbor
On the roadPortland → Cape Elizabeth 20 minCape Elizabeth → Bath 50 minBath → Rockland 1 hrRockland → Camden 15 min

Morning

Roll out between 8 and 9 — earlier buys you the lighthouse nearly alone — and start where Maine starts for most people: at the water's edge in Cape Elizabeth, before Route 1 pulls you north at its own two-lane pace.

  • Portland Head Light (Fort Williams Park, Cape Elizabeth · grounds free to walk) — the most photographed lighthouse in America, and it earns it: the 1791 tower on its headland, surf breaking below, Ram Island Ledge Light out in the channel. Give it 45 minutes — the low morning light is the photo, and the tour buses arrive by mid-morning. From the park it's a 20-minute drive back into downtown Portland.
  • The Old Port, Portland (coffee before the drive) — a coffee on the cobblestones, a last taste of city before two days of harbor towns. To stay on schedule, be back in the car within 45 minutes: it's about 50 minutes up I-295 to Brunswick and Route 1 at Bath — where the midcoast properly begins — then 15 more to the Wiscasset bridge.
  • The Wiscasset lobster-roll question (Route 1 · lunch) — aim for Wiscasset around midday, when the bridge bottleneck arrives with a decision: Red's Eats is the famous line, and Sprague's Lobster across the street serves a comparable roll in half the time. Locals will tell you the line is the attraction, not the roll (verify current hours — both are seasonal). Rockland is 40 minutes on from here.

Afternoon

Route 1 rolls on into the working midcoast, where the galleries share Main Street with the fish piers — Rockland is your afternoon.

  • Farnsworth Art Museum (Rockland · give it 90 minutes, no more) — three generations of Wyeths painted this exact coast, and seeing their world a few miles from where it was painted changes how the rest of the drive looks. Louise Nevelson, a Rockland kid who conquered New York, gets her due here too. The breakwater is a five-minute drive across town.
  • Rockland Breakwater (seven-eighths of a mile of granite · about 45 min round trip) — shake off the museum with a walk on the great granite blocks, harbor on one side, open bay on the other, a lighthouse waiting at the end. Flat but uneven — watch your footing — and skip it outright in fog or big swell. Start the walk by mid-afternoon and you're back at the car with the day's best light still ahead — leaving Rockland then means you're right on pace.

Evening

Fifteen minutes more up the coast and you're in Camden — the harbor town all the others get compared to. Arrive with an hour of daylight in hand, so check-in doesn't eat the golden hour.

  • Camden Harbor at golden hour — check in, drop the bags, and walk straight down to the water: the schooner fleet is still rigged in September, and the light on Penobscot Bay does its best work around 6 pm. This is the postcard you get to stand inside of.
  • Dinner in town (reserve earlier in the day) — September evenings fill Camden's dining rooms, so call ahead at lunch. Afterward, the local move is the stroll down Bay View Street past the yacht club, harbor lights on your left, tomorrow's mountains dead ahead.

If it rains

  • Owls Head Transportation Museum (20 min from Rockland) — antique planes and cars they actually fly and drive, in a hangar you could spend half a day in. Swap it for the breakwater and the day loses nothing.

Locals' note

In-town Camden inns put you within walking distance of everything; the Route 1 motels just north are quieter and cheaper. And don't burn the evening driving up Mount Battie — that view is tomorrow morning's first stop, when the light comes from the right side.

🔒 Day 2 — Camden to Acadia — Mount Battie, the Penobscot Narrows and the Park Loop Road
🔒 Day 3 — Cadillac sunrise, the quiet side and a lobster pound on the way out
…each written to the same depth, plus the full "Before You Go" section — seasonal warnings, packing list, rainy-day alternates and locals' notes. On The Full Trip Kit, add the stay & eat shortlist, the dated reservation checklist, printable dashboard cue cards and the pre-trip re-check. Yours is written for your trip →
Signature trips

Or build the trip around any idea

These are just answers in the planner — name the trip you're imagining and a local builds it.

Island Hopping

Peaks, Monhegan, Vinalhaven, Swans Island — days built around real ferry logic, so you're never watching the last boat leave without you.

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The Lobster Trail

Eat your way up the coast — the famous shacks, the working pounds locals actually use, and the roll-vs-line truths, in driving order.

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Moose & the North Woods

Moosehead, the Golden Road, dawn on a logging-pond flowage — the wild Maine most visitors never see, planned so you actually see a moose.

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Beach Days

The famous sand plus the local gems — parking truths, tide timing, and the warm freshwater swims for when the ocean says no.

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The Family Week

Kid-proofed days: short walks with big payoffs, beach afternoons, rainy-day escape hatches, and ice cream placed exactly where the whining starts.

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The One Free Day

In town for a single day? Tell us where you're standing and what you love — we'll make it the day they talk about at dinner for years.

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Chasing leaf season, lighthouses, waterfalls or sled season? Those four get the one-click treatment — see the Signature Specials ↑

Where we plan

Maine first, then the rest of northern New England

Portland & Casco BayFood, breweries, Old Port, ferries to the islands
Southern Maine beachesKittery, Ogunquit, Kennebunkport, Old Orchard Beach
MidcoastBath, Boothbay, Damariscotta, Rockland, Camden, Belfast
Acadia & Mount Desert IslandBar Harbor, Park Loop Road, the quiet side, Schoodic
Downeast & Bold CoastMachias, Cutler, Lubec, Eastport, Campobello
Lakes regionSebago, Belgrade Lakes, Rangeley, Moosehead
Western mountainsBethel, Sugarloaf, Rangeley, Grafton Notch
Katahdin & Baxter State ParkMillinocket, Katahdin Woods & Waters, the Golden Road
NH White MountainsNorth Conway, Franconia Notch, Kancamagus Highway
VermontStowe, Woodstock, Burlington, Northeast Kingdom
Cape Cod & the islandsOuter Cape, Provincetown, Nantucket, Martha's Vineyard
Pricing

One payment. No subscription.

A human planner charges hundreds and takes a week. Northbound is written for you, tonight.

The Plan

$19
one trip, one-time
  • Up to 14 days, morning / afternoon / evening
  • Real driving times between stops
  • Seasonal warnings for your dates
  • Rainy-day alternates & locals' notes
  • Live web check before delivery
  • Word download, print-to-PDF, email
Get The Plan

The Plan, Perfected

$29
everything in The Plan, plus
  • One full rewrite — read the draft, send notes, the whole plan is rewritten around them
  • Dashboard cue cards — a printable one-page-per-day set in big type: just the drive legs and stop names, made to sit on the dash. Print, fold, go.
  • Previous draft kept for comparison
Get The Plan, Perfected

Custom digital product — all sales final. Something genuinely wrong? Contact us and we’ll make it right. Secure checkout by Stripe.

Free guide: how to plan a Maine trip that doesn't spend itself in the car

Most people planning a first trip to Maine make the same mistake: they open a map, see that Portland, Acadia and the lighthouses are all "on the coast", and try to do all of it in four days. Then they discover that Route 1 is a two-lane road through every town center between Bath and Ellsworth, that Bar Harbor is three hours from Portland before the first stop, and that Downeast is a different trip entirely. A good Maine itinerary is mostly about choosing what to leave out.

Pick a shape: one base or a road trip

With three or four days, a single base wins. Camden or Rockland puts the whole midcoast — Boothbay, Damariscotta, the Farnsworth, the breakwater, the schooners — within an hour. Bar Harbor or the quiet side of Mount Desert Island gives you Acadia without a daily drive. Portland alone is a genuinely good long weekend of food, breweries, Casco Bay islands and Portland Head Light. With five days or more, a road trip makes sense: south to north up the coast, or coast plus one inland leg into the lakes, the western mountains or the White Mountains.

Let the season set the plan

September is the local favorite — warm days, cool nights, thin crowds after Labor Day, everything still open. July and August are the warmest and the busiest; book lodging months out and expect lines at the famous lobster shacks. Late May and June are lovely on the coast and buggy inland. Foliage peaks in the mountains and the far north around the turn of October, then works its way to the coast by mid-to-late October, and many seasonal businesses close between Columbus Day and Halloween. Mud season (late March into April) is the one time we tell people to wait.

Acadia needs a plan of its own

Acadia is one of the most visited national parks in the country. Driving to the Cadillac Mountain summit requires a timed vehicle reservation through the reservation season, and the sunrise slots go first. The Park Loop Road lots at Sand Beach, Thunder Hole and Jordan Pond fill by mid-morning in summer; the free Island Explorer shuttle solves that. Thunder Hole only thunders in the couple of hours before high tide. The Beehive and Precipice trails have iron rungs and real exposure — spectacular for the sure-footed, wrong for small kids and anyone nervous about heights, which is why every Northbound plan asks about your party before naming a trail. The quiet side (Southwest Harbor, Bass Harbor) and the Schoodic Peninsula are the same park with a fraction of the people.

Lobster: pound versus restaurant

A lobster pound is a working dock with picnic tables: pick your lobster, pay by weight, crack it yourself, bring your own drinks. A lobster restaurant is table service with a bigger menu. They are different experiences and worth doing both. The famous roll with the hour-long line is rarely better than the less famous one across the street; a good itinerary tells you which is which.

Beyond Maine

The White Mountains are two-plus hours from Portland and combine well with the western Maine lakes; the Kancamagus is gorgeous and gridlocked on foliage weekends, so we send you on a weekday or early. Vermont's color runs a week or two ahead of the coast. Cape Cod is its own trip — the bridges are the whole story on summer weekends — and we plan it the same way: real drive times, real seasonal warnings, and a short list of what to verify before you go.

FAQ

Questions travelers ask before ordering

Is this a real itinerary or a generic list of attractions?

It is a day-by-day plan written for your dates, your party and your interests, built around real driving times and the practical local knowledge we feed into every plan: where Route 1 backs up, when Acadia's summit road needs a reservation, which trails have ladders, when the lobster shacks close for the season. Every place named is a real town, trailhead, park, museum or long-established business — and every plan is checked against the live web before delivery.

Who actually writes it?

Every plan starts from a detailed local-knowledge brief written by a Mainer who has driven every one of these roads. An AI writer drafts your itinerary from that brief and your answers, under strict rules: name real places, never invent hours or prices, prefer well-established spots so nobody gets sent to a business that has closed — then the named places are verified against the live web before delivery. Local judgment, delivered in minutes instead of a week.

How fast do I get it?

Writing starts the moment your payment clears and typically takes five to ten minutes. Your itinerary lives on a permanent private link — emailed to you and shown right after checkout — where you can read it, print it to PDF, or download it for Word. It stays available for the life of your trip and after.

How do you handle hours, prices and schedules?

We do not state them. Restaurant hours, park fees, ferry times and reservation windows change every season, so the itinerary tells you exactly what to verify and when ("seasonal — check current hours", "book the Cadillac Summit Road reservation before you arrive"). The plan is the route and the reasoning; a two-minute check before each stop keeps it current.

Do you book anything for me?

No — we plan, you book. The itinerary tells you which towns to sleep in and for how many nights, the shortlist gives you specific places to consider, and on The Full Trip Kit the dated reservation checklist tells you exactly what to book and by when. Your money stays in your hands and you book directly with the ferry, park or inn.

What is a revision?

After you read the first draft you can send notes — "swap the hike for a boat trip", "we're staying in Rockland not Camden", "less driving on day 3" — and the whole itinerary is rewritten with your original answers, your notes and the previous draft in hand. The $29 and $39 tiers include one revision (plus the printable dashboard cue cards); the $19 itinerary does not.

What is in The Full Trip Kit?

Everything in the $29 tier plus four things: tap-to-navigate map links — every day of your itinerary ends with one Google Maps link that loads that whole day's route, stop by stop; a restaurant and lodging shortlist organized by the towns you will actually be in, with $ / $$ / $$$ tiers and booking notes; a dated reservation checklist — the timed entries, ferries and tours that book out for your specific dates, each with a concrete book-by date; and the free pre-trip re-check.

What is the pre-trip re-check?

A few days before your first trip day, we automatically take your finished itinerary back to the live web and re-verify every named place in it — seasonal closings, businesses that have shut their doors since your plan was written, road and trail closures. If everything checks out you get an all-clear email. If something changed, we rewrite the affected days around it automatically and email you what changed — your link always has the current copy. Included with The Full Trip Kit.

How far ahead should I order?

Any time, but the plan is most useful before you book lodging, because it tells you which towns to sleep in and for how many nights. For summer and foliage trips, that means months ahead — coastal inns fill early and Acadia's summit reservations open on a rolling window.

Do you cover places outside Maine?

Yes: the New Hampshire White Mountains, Vermont, and Cape Cod and the islands, on their own or combined with Maine. Maine is the deepest coverage — coast, Acadia, Portland, midcoast, lakes, western mountains, Downeast, and Katahdin/Baxter.

Can I get a refund?

Itineraries are custom digital products written on demand for your specific trip, so all sales are final. That said, we stand behind the work: if something is genuinely wrong — the plan ignores your must-avoid list, routes your party somewhere it cannot go, or writing failed — contact support and we will make it right, starting with a free rewrite of anything broken. Legitimate problems we cannot fix are reviewed for refund case by case.

Is my information used for anything else?

No. Your answers are used to write your itinerary and stored with your order so you can reopen the link. We do not sell data and the AI providers we use do not train on it.

How do I reach a human?

Email us or use the contact form — both land in the same inbox and we answer within a business day. See the Contact page linked in the footer.

Have your Maine trip planned tonight

Four minutes of questions, one payment, a plan you can actually drive.

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