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16 Mar 2025Updated last time
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Coastal Maine 5 days Itinerary

Coastal Maine 5-Day Itinerary Overview

Embark on a scenic adventure along the beautiful coast of Maine with this comprehensive 5-day itinerary. Start your journey at the iconic Portland Head Light, a historic lighthouse offering breathtaking views of the rugged coastline. Continue your exploration at Acadia National Park, one of America's most picturesque national parks, known for its extensive trails, diverse wildlife, and stunning landscapes. Nearby, Bar Harbor awaits with its charming seaside atmosphere, bustling with shops, restaurants, and a vibrant waterfront.

Next, make your way to the serene Camden Hills State Park, where you can enjoy panoramic views of Penobscot Bay and discover numerous hiking opportunities. In Boothbay Harbor, immerse yourself in the picturesque surroundings and maritime activities of this quaint harbor town. Your journey continues with stops at other captivating destinations such as Old Orchard Beach for a classic New England beach experience, and the historic charm of Kennebunkport.

Explore the vibrant arts scene in Rockland and take in the panoramic ocean views at Pemaquid Point Lighthouse. Finally, visit the idyllic village of Wiscasset, often touted as the prettiest village in Maine. This itinerary ensures a well-rounded experience of Maine's coastal treasures, blending natural beauty with cultural charm.


Recommended Activities

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    Kennebunkport

    Charming coastal town with historic sites.
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    Old Orchard Beach

    For its classic New England beach experience.
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    Portland Head Light

    One of the most iconic and historic lighthouses in Maine, offering breathtaking views of the rugged coastline.
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    Boothbay Harbor

    A picturesque harbor town known for its scenic beauty, maritime activities, and vibrant local culture.
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    Pemaquid Point Lighthouse

    Stunning lighthouse with panoramic ocean views.
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  • Quaint village known as 'the prettiest village in Maine.'
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    Camden Hills State Park

    Offers panoramic views of Penobscot Bay and surrounding mountains, making it a popular spot for hiking and nature lovers.
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  • Known for its vibrant arts scene and historic lighthouse.
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  • A charming seaside town that serves as the gateway to Acadia National Park, known for its shops, restaurants, and beautiful waterfront.
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    Acadia National Park

    One of America's most beautiful national parks, offering stunning natural landscapes, hiking trails, and diverse wildlife.
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Restaurants

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    Eventide Oyster Co.

    9.2
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    Eventide Oyster Co.

    Known for its innovative take on classic New England seafood, especially fresh oysters.
    9.2
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    Duckfat, Portland, ME

    Duckfat, Portland, ME

    Famous for its Belgian-style fries cooked in duck fat and delicious panini sandwiches.
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    The Lost Kitchen, Freedom, Maine

    4.8
    $$$$

    The Lost Kitchen, Freedom, Maine

    A unique dining experience located in a historic mill, offering a farm-to-table menu that changes daily.
    4.8
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    McLoons Lobster Shack

    4.7
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    McLoons Lobster Shack

    Offers the quintessential Maine lobster experience with stunning views by the water.
    4.7
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    The Lobster Shack at Two Lights - Cape Elizabeth, Maine

    4.3
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    The Lobster Shack at Two Lights - Cape Elizabeth, Maine

    Iconic spot for enjoying fresh lobster with panoramic ocean views.
    4.3
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Hotels

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    The Press Hotel, Maine

    4.7

    The Press Hotel, Maine

    A unique boutique hotel in a former newspaper building, with literary-themed rooms.
    4.7
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    Inn by the Sea, Cape Elizabeth, ME

    4.7

    Inn by the Sea, Cape Elizabeth, ME

    An eco-luxury beach resort known for its beautiful seaside setting and sustainable practices.
    4.7
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    Cliff House Maine

    4.6

    Cliff House Maine

    Dramatically perched on the cliffs of Cape Neddick, offering stunning ocean views and luxurious amenities.
    4.6
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    The Inn at Ocean's Edge

    4.7

    The Inn at Ocean's Edge

    A tranquil retreat with gorgeous views of Penobscot Bay and an infinity pool.
    4.7
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    Chebeague Island Inn

    4.3

    Chebeague Island Inn

    An idyllic island escape offering historic charm and breathtaking views of Casco Bay.
    4.3
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Local Events & Happenings


Travel Gems from Reddit


Music for Your Journey

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    Incubus - Drive

    Incubus - Drive

    A song about embracing adventure and the open road, perfect for a scenic drive.
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    Billie Eilish - ocean eyes

    Billie Eilish - ocean eyes

    A dreamy and soothing tune that complements the serenity of coastal views.
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    Rascal Flatts - Life is a Highway

    Rascal Flatts - Life is a Highway

    An energetic road trip anthem that motivates you to keep exploring.
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    Simon & Garfunkel - Scarborough Fair / Canticle

    Simon & Garfunkel - Scarborough Fair / Canticle

    A folk classic that evokes the rustic charm of New England.
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    Eagles - Take It Easy - 2013 Remaster

    Eagles - Take It Easy - 2013 Remaster

    A laid-back song perfect for enjoying the relaxed vibes of the coastal towns.
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    Katrina & The Waves - Walking On Sunshine

    Katrina & The Waves - Walking On Sunshine

    A feel-good track to match the sunny and upbeat atmosphere of your trip.
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    Van Morrison - Into the Mystic - 2013 Remaster

    Van Morrison - Into the Mystic - 2013 Remaster

    A soulful and reflective song that pairs well with the mystical landscapes of Maine.
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    Matt Simons - Catch & Release - Deepend Remix

    Matt Simons - Catch & Release - Deepend Remix

    A soothing melody that evokes the sense of escape and connection with nature.
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    The Temper Trap - Sweet Disposition

    The Temper Trap - Sweet Disposition

    An uplifting and anthemic track that complements the scenic beauty of the coast.
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    Bobby Darin - Beyond the Sea

    Bobby Darin - Beyond the Sea

    A timeless classic that captures the essence of seaside adventures.
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