Coastal Maine
A week-long romantic road trip down the Maine coast
Overview
This romantic getaway was designed to flow naturally down the Maine coastline — no backtracking, no stress. From the dramatic cliffs of Acadia to the foodie paradise of Portland, every day featured a unique curated experience while leaving room for spontaneous exploration.
The Itinerary
Day by day.
Arrive in Bar Harbor
Portland / Bar HarborFly into Portland, pick up the rental car, and drive up to Bar Harbor. Check into the Bar Harbor Inn — King Harbor View room on the second floor with sweeping views of Frenchman Bay.
Acadia National Park
Acadia National ParkFull day exploring Acadia — drive the Park Loop Road, summit Cadillac Mountain, hike the Gorham Mountain Loop trail, and bike the historic carriage roads.
Whale Watching
Bar Harbor / Gulf of MaineMorning whale watching with Bar Harbor Whale Watch Co (8:30am departure). Spot humpback, finback, and minke whales in the Gulf of Maine. Afternoon at leisure in Bar Harbor.
Stephen King Tour & Boothbay Harbor
Bangor / Boothbay HarborPrivate Stephen King tour of Bangor with SK Tours of Maine — visit the locations that inspired King’s most famous novels. Then drive to Boothbay Harbor for lobster shacks, boutique shops, and salt water taffy. Check into the Leeward Suite at Topside Inn.
Monhegan Island & Drive to Portland
Monhegan Island / PortlandDay trip to Monhegan Island via Balmy Days Cruises ferry. Explore this car-free island with walking trails, dramatic sea cliffs, and a thriving artists’ colony. Drive to Portland and check into the Evangeline Suite at Longfellow Hotel.
Lobstering on Casco Bay
Portland / Casco BayLucky Catch Cruises lobstering excursion on Casco Bay (11am). Haul lobster traps, spot harbor seals, and buy lobster at “boat price.” Afternoon exploring Portland’s Old Port neighborhood.
Lighthouse Bike Tour
Portland / Cape ElizabethGuided lighthouse bike tour — 3 hours, 12 miles. Ride past Bug Light, Spring Point Ledge Light, Portland Head Light, and Two Lights. Explore Fort Williams Park along the way.
Departure
PortlandCheck out of the Longfellow Hotel and head to Portland International Jetport for the flight home.
Exceptional Stays
Hand-picked properties
Bar Harbor Inn
Bar Harbor · 3 nights
A classic waterfront inn on Frenchman Bay with sweeping ocean views. King Harbor View room on the second floor with continental breakfast each morning.
Topside Inn
Boothbay Harbor · 1 night
A hilltop boutique inn in the heart of Boothbay Harbor with panoramic harbor views. The Leeward Suite with breakfast included.
Longfellow Hotel
Portland · 3 nights
A Nordic-inspired boutique hotel in Portland’s West End with a wellness spa. The Evangeline Suite — the perfect home base for exploring Maine’s food capital.
Highlights
What made this
uniquely theirs
Curated Experiences
- Private Stephen King literary tour of Bangor
- Hands-on lobstering cruise on Casco Bay
- Guided lighthouse bike tour — 5 lighthouses in one ride
- Monhegan Island artist colony day trip
VIP Touches
- Harbor-view rooms with breakfast at every property
- Boutique and independent hotels only — no chains
- Scenic route planned to flow south with no backtracking
- Restaurant recommendations for each destination
Seamless Logistics
- Rental car arranged for the full week
- Ferry bookings pre-confirmed
- All excursion reservations made in advance
- Detailed day-by-day schedule provided
Properties
3 boutique hotels
Experiences
7 curated excursions
Route
Bar Harbor → Portland
Total Duration
7 nights, 3 destinations
Ready to plan your
dream trip?
Whether you know exactly where you want to go or need a little inspiration — I’m here to make it happen.