Route: Miami, FL → Portland, ME
Total distance: approximately 2,070 miles
Driving days: 5
Best months: May–June or September–October
There are two ways to drive from Florida to Maine. The first is I-95, bumper-to-bumper with freight trucks, all the way up the seaboard. The second is this route — one that trades speed for the Atlantic coastline, the marshes of the Carolinas, a colonial Virginia parkway, Lancaster County farmland, the Berkshire hills, and the lobster-dock harbour towns of southern Maine.
This guide takes the second option. It is built around five named scenic byways and covers 2,070 miles across ten states in five days. Every overnight stop has been chosen so the following morning’s drive opens with something worth an early start.
At a glance
| Day | Start | End | Distance | Highlight |
| 1 | Miami, FL | Daytona Beach, FL | 446 mi | A1A Scenic Byway + Indian River Lagoon |
| 2 | Daytona Beach, FL | Eastover, NC | 495 mi | Savannah, Cape Fear coastline |
| 3 | Eastover, NC | Havre de Grace, MD | 459 mi | Colonial National Historical Parkway |
| 4 | Havre de Grace, MD | East Chatham, NY | 425 mi | Amish Country + Mohawk Trail approach |
| 5 | East Chatham, NY | Portland, ME | 246 mi | Mohawk Trail + Portland Head Light |
Before you leave Miami
Tolls
This route passes through some of the most toll-heavy corridors in the United States. Budget $80–120 for the full journey: the Florida Turnpike, Delaware Memorial Bridge, New Jersey Turnpike, and Maine Turnpike all charge, and the bridges into and around New York City add up quickly. An E-ZPass transponder — accepted in all 19 eastern toll states — saves 20–40% at most plazas and keeps you out of the cash lane.
Best time to drive
May and June offer light traffic before the summer shore rush, and the A1A wildflowers are at their peak. September and October are the other sweet spots: the Mohawk Trail in Massachusetts is one of the most celebrated fall foliage drives in New England, and the New England coast empties after Labor Day. Avoid July and August unless you enjoy standing still on I-95 between Delaware and Connecticut.
What to pack
Sunscreen and a towel for Day 1, a light jacket for Maine evenings year-round, and a small cooler. The seafood you’ll want to eat in Portland is better from the dockside stalls than from a sit-down restaurant, and it travels well for a harbour-side picnic.
Day 1 — Miami to Daytona Beach via A1A (446 miles, ~8 hours driving)
Leave Miami early. The city’s morning rush on I-95 North is avoidable if you are on the road by 7am, and you want the light on the water when you pick up A1A north of the city.
Indian River Lagoon, Space Coast
About 120 miles north of Miami, past Vero Beach, you enter the Indian River Lagoon corridor — a 156-mile estuary system running along the barrier islands of Florida’s Space Coast. Pull off at Riverside Park in Vero Beach or Fort Pierce Inlet State Park to stretch your legs. The lagoon is one of the most biodiverse estuaries in North America, and on a clear morning the still water between the barrier island and the mainland catches the light in a way photographs fail to capture.
From here northward you are on the A1A Scenic and Historic Coastal Byway proper.
A1A Scenic and Historic Coastal Byway
The A1A is Florida’s only All-American Road — the highest designation given to a US driving route by the Federal Highway Administration. Its 72 designated miles trace the Atlantic barrier island chain through Flagler and St. Johns counties, running two lanes between the ocean on one side and the Intracoastal Waterway on the other. Through Flagler Beach, the road sits so close to the water that storm waves occasionally wash across the tarmac.
Don’t miss: St. Augustine — the oldest continuously occupied European settlement in the United States, founded in 1565. Walk Castillo de San Marcos, the 17th-century Spanish stone fort overlooking Matanzas Bay. It takes an hour and earns its place on any East Coast itinerary.
Daytona Beach — overnight
Daytona Beach is a practical overnight, not a destination. The beach itself is wide and firm — historically so, given its century as an automobile speed record venue — and the boardwalk area works for a casual dinner before an early start. Where to stay: The Shores Resort & Spa in Daytona Beach Shores, a few miles south of the main strip, sits directly on the beach and is considerably quieter than the hotels on the commercial drag.
Day 2 — Daytona Beach to Eastover, NC (495 miles, ~8 hours driving)
This is the longest day and the most straightforward section of the route. I-95 North is the spine today, but two stops are worth building in.
Savannah, Georgia
Savannah is 2.5 hours north of Daytona and one of the most walkable cities in the American South. The historic district’s 22 oak-shaded squares are a city planning achievement that still works on foot 200 years later. River Street, one storey below the bluff on the Savannah River, is the right place for lunch. Budget 90 minutes: the Cathedral of St. John the Baptist on Abercorn Street and Forsyth Park are five minutes apart and form a good short loop even if you only have time to stretch your legs.
Myrtle Beach detour — the South Carolina Lowcountry
After crossing into South Carolina, US-17 South offers a quieter coastal alternative to I-95 through the Grand Strand. The drive through Pawleys Island and Murrells Inlet on US-17 Business is flat, green, and easy on the eyes. Murrells Inlet calls itself the Seafood Capital of South Carolina — a fair claim, and good timing for a mid-afternoon stop before pushing north through Wilmington, NC.
Eastover — overnight
Eastover, just east of Fayetteville on I-95, is a positional overnight rather than a destination. Fayetteville, five miles west, has more hotel options; look for properties near the US-401 interchange. Its value is strategic: it sets you up squarely for Day 3’s turn into Virginia.
Day 3 — Eastover, NC to Havre de Grace, MD (459 miles, ~8 hours driving)
The most historically dense day on the route, anchored by the finest short drive on the entire East Coast.
Colonial National Historical Parkway, Virginia
The Colonial National Historical Parkway is a 23-mile National Park Service road connecting three sites foundational to American history: Jamestown (the first permanent English settlement in America, 1607), Colonial Williamsburg (the restored 18th-century colonial capital), and Yorktown (where the American Revolution effectively ended in 1781). The parkway was designed to be driven — no commercial vehicles, no billboards, a canopy of hardwood trees overhead, and the James River visible through the treeline for much of the route.
Allow three hours for the full loop: an hour at Jamestown Settlement and Historic Jamestowne, an hour on Colonial Williamsburg’s Duke of Gloucester Street, and 30 minutes at the Yorktown Victory Monument and bluff overlook. This is the most rewarding stop on the entire five-day route.
From Williamsburg, pick up I-64 East toward Richmond, then I-95 North through the Virginia Tidewater and into Maryland.
Havre de Grace, Maryland — overnight
Havre de Grace sits where the Susquehanna River meets the northern tip of the Chesapeake Bay. The waterfront promenade, Concord Point Lighthouse (1827, one of the oldest continuously operating lighthouses on the East Coast), a decoy duck carving museum, and a grid of Federal-style homes are all within easy walking distance of each other. It has more character — and better food — than the interstate chain strip at Aberdeen ten minutes south.
Where to stay: The Vandiver Inn, a Victorian B&B at the centre of town, puts you within walking distance of the waterfront and the harbour.
Where to eat: MacGregor’s Restaurant on St. John Street for Chesapeake seafood and an outdoor deck facing the water.
Day 4 — Havre de Grace, MD to East Chatham, NY (425 miles, ~8 hours driving)
The two scenic detours today — Amish Country and the Mohawk Trail approach — are the most visually distinct stretches of the entire journey, and they could hardly be more different from each other.
Amish Country Scenic Drive, Lancaster County, PA
From Havre de Grace, head west on US-40 and pick up US-30 into Lancaster County, Pennsylvania. The Amish Country Scenic Drive loops through working farms, roadside produce stands, and the communities of Intercourse, Bird-in-Hand, and Strasburg on country roads where horse-drawn wagons have the same right of way as your car.
A practical note: Route 30 between Lancaster and Paradise is heavily commercialised. The good driving is on the smaller roads — Old Philadelphia Pike (Route 340), Harvest Drive, and Newport Road give you the farmland the tourist brochures photograph, without the outlet malls.
Don’t miss: The Strasburg Rail Road — a steam-powered heritage railway running a 9-mile round trip through farmland. It takes 45 minutes and the antique wooden coaches are the real article, not a replica.
Allow 90 minutes for the scenic loop before heading north on US-222 and picking up I-78 East into New Jersey.
Hudson Valley approach — Taconic State Parkway
Cross into New York via the Tappan Zee Bridge (officially the Governor Mario M. Cuomo Bridge), which gives you a northerly approach and keeps you clear of the city. Follow the Taconic State Parkway north from Westchester County — a graceful, tree-lined parkway with no billboards and no trucks that opens into rolling hills within half an hour. It runs directly to Columbia County and the overnight stop.
East Chatham, New York — overnight
East Chatham is a small hamlet in Columbia County, two hours north of New York City, near the Massachusetts border. Where to stay: The Old Chatham Country Inn, a few miles west, is a well-regarded property with working farmland on site and good evening food.
The Mohawk Trail — evening preview
The Mohawk Trail — Massachusetts Route 2 between Greenfield and North Adams — is technically on Day 5, but if you arrive in East Chatham with daylight to spare, the 20-mile stretch from the Connecticut River crossing to the Hairpin Turn above Charlemont is worth driving before dark. In October, the Berkshire hills on either side of Route 2 turn colour faster than almost anywhere else in New England.
Day 5 — East Chatham, NY to Portland, ME (246 miles, ~4.5 hours driving)
The shortest day, and the one with the best ending.
Mohawk Trail and the Berkshires
Pick up Route 2 East from Greenfield, Massachusetts, and drive it through to the turn. Shelburne Falls — a small town built around a glacial pothole garden in the Deerfield River — is the right spot for coffee and a 20-minute walk before the climb. The Hairpin Turn overlook sits at 1,743 feet and looks west across Vermont and New York on a clear day. It is the best roadside view on this route.
From the Berkshires, take I-91 North to I-89 North into New Hampshire.
New Hampshire and the seacoast
New Hampshire’s coastline — at 18 miles, the shortest of any coastal US state — is worth a brief detour through Portsmouth. Market Square at the centre of the old town and the working tugboat harbour at Strawbery Banke are good for a lunch stop. Portsmouth is also the last chance for a proper sit-down meal before Portland; the Black Trumpet Bistro on Ceres Street is particularly good.
Cross into Maine on I-95 and take the Maine Turnpike north to Portland.
Portland, Maine
Portland is the right place to end this drive. It is a working city — the largest in Maine — with a food reputation well out of proportion to its size and a waterfront that still moves cargo alongside the tourist boats.
Portland Head Light is the first stop. Commissioned by George Washington in 1791, Maine’s oldest lighthouse stands at the entrance to Portland Harbour in Fort Williams Park in Cape Elizabeth, four miles south of downtown. The park is free, open year-round, and takes about 45 minutes to walk fully at a comfortable pace. Arrive at dusk if you can.
The Old Port is Portland’s waterfront neighbourhood — a grid of brick warehouses now occupied by restaurants, fishmongers, and independent shops along cobbled streets. Fore Street restaurant has been listed among the best in the United States for more than two decades; book ahead. For something more casual, the Portland Lobster Company on Commercial Street serves from the dock and the lobster rolls are the honest article.
Eastern Promenade: A mile-long walking path along Casco Bay with views toward the outer islands. The Casco Bay Lines ferry terminal, a 20-minute walk along Commercial Street, runs boats to Peaks Island — a quiet, car-free island with a 4-mile perimeter loop and a pace of life that makes you reluctant to take the ferry back.
Next step: Acadia National Park
If you have one more day — and it is worth planning for — Acadia National Park is 160 miles northeast of Portland on Mount Desert Island. The 27-mile Park Loop Road passes ocean cliffs, pink granite boulder beaches, and the summit of Cadillac Mountain (1,528 feet), the highest point on the US eastern seaboard and the first place in the country to see the sunrise between October and early March. Bar Harbor, on the island’s northeast shore, has accommodation at every price point. For the best lobster stew in the park area, Café This Way on Mount Desert Street in Bar Harbor is the locals’ choice.
Practical notes
Total mileage: 2,071 miles (driving days only; scenic detours add approximately 60–80 miles)
Toll estimate by state:
- Florida Turnpike: $10–20
- Delaware Memorial Bridge: ~$5
- New Jersey Turnpike (full length): ~$17–22
- New York bridges (Tappan Zee): ~$17 for a standard vehicle
- Maine Turnpike: ~$5
- Total estimate: $80–120. An E-ZPass transponder pays for itself within two crossings and is accepted in all 19 eastern toll states.
Fuel: At 30 mpg and $3.50/gallon average, budget approximately $240 in fuel for the journey.
Driving seasons at a glance:
- Spring (May–June): Best A1A conditions; moderate traffic throughout; comfortable temperatures from Florida to Maine
- Summer (July–August): Beach towns are lively but I-95 between Delaware and Connecticut can add two hours on peak weekends; book accommodation 2–3 months ahead
- Autumn (September–October): Best overall; Mohawk Trail and Berkshires peak colour runs late September to mid-October; Acadia in October is exceptional
- Winter: Not recommended; the Mohawk Trail closes in ice conditions and most Maine coastal towns are largely shut between November and April
I-95 vs. the scenic alternatives: This guide uses I-95 as a spine for Days 2 and 3 where the scenic alternatives are slower without being substantially more rewarding. The dedicated scenic mileage — the A1A, Colonial Parkway, Amish Country roads, Taconic Parkway, and Mohawk Trail — is threaded into each day so you are never more than a few miles off the main road to reach something worth the detour.
Route last verified: April 2026. Toll rates, business hours, and seasonal road closures change — check official sources before you travel.