Have you ever dreamed of stepping into the lavish world of The Great Gatsby?

This road trip through Maine offers 13 stunning destinations that capture the elegance and sophistication of the Roaring 20s.

1. The Strand Theatre (Rockland)

Lights, camera, action!

The Strand Theatre in Rockland is where Hollywood glamour meets small-town charm.

This Art Deco beauty has been dazzling moviegoers since 1923, and let me tell you, it’s aged better than most Hollywood stars.

With its iconic vertical sign glowing like a beacon of entertainment, you half expect to see Humphrey Bogart strolling up to catch the latest flick.

Inside, it’s a time capsule of cinematic elegance.

The red velvet seats are so plush, you might need a forklift to get out of them after the show.

But don’t worry, the popcorn is worth the struggle.

It’s the kind of place where you can watch both indie films and blockbusters, proving that in Maine, we like our entertainment like we like our lobster rolls – a perfect blend of highbrow and down-home.

2. Victoria Mansion (Portland)

Hold onto your top hats, folks, because we’re about to step into the closest thing Maine has to Versailles.

The Victoria Mansion in Portland is so fancy, it makes Downton Abbey look like a garden shed.

Built in the 1850s, this Italian villa-style home is a monument to the phrase “go big or go home.”

The interiors are a riot of trompe l’oeil walls, gilded everything, and more marble than a Roman emperor’s bathroom.

It’s the kind of place where you feel underdressed in anything less than a ballgown or tuxedo.

But don’t let that stop you from visiting – just remember to pick your jaw up off the ornate floor tiles when you leave.

3. The Colony Hotel (Kennebunkport)

If the Great Gatsby decided to summer in Maine, The Colony Hotel in Kennebunkport is where he’d hang his impeccably tailored hat.

Perched on a bluff overlooking the Atlantic, this grand dame of hotels has been the playground of the well-heeled since 1914.

With its pristine white exterior and emerald lawns, it’s like a wedding cake come to life.

The pool is so blue it makes the ocean jealous, and the wrap-around porch is perfect for sipping gin rickeys and pretending you’re old money.

Just don’t be surprised if you find yourself speaking with a vaguely British accent by the end of your stay – it’s a common side effect of too much elegance.

4. Norumbega Inn (Camden)

Imagine if a fairy tale castle and a Victorian mansion had a baby – that’s the Norumbega Inn in Camden.

This stone château looks like it was plucked from the Loire Valley and plonked down on the Maine coast.

It’s so picturesque, you half expect to see Rapunzel letting down her hair from one of the turrets.

Inside, it’s all old-world charm meets modern luxury.

The rooms are named after famous authors, so you can sleep in Hemingway or lounge in Longfellow.

Just be careful not to get too comfortable – you might start writing the great American novel instead of enjoying your vacation.

5. Portland Observatory (Portland)

Who needs a DeLorean when you can time travel at the Portland Observatory?

This octagonal tower has been keeping watch over Casco Bay since 1807, making it older than most countries’ constitutions.

It’s like a lighthouse that decided to go on a diet and move inland.

Climbing to the top is like ascending through layers of history, with each floor offering a new glimpse into Portland’s past.

And the view from the top?

Let’s just say it’s the kind of panorama that makes even the most jaded Instagrammer reach for their phone.

Just remember to bring your sea legs – after all those spiral stairs, you might feel like you’ve just crossed the Atlantic.

6. Bar Harbor Inn (Bar Harbor)

The Bar Harbor Inn is where “Downeast” meets “upscale.”

Perched on Frenchman Bay like a grand old lady surveying her domain, this inn has been the go-to spot for the upper crust since the Gilded Age.

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It’s the kind of place where you might bump into a Kennedy or a Rockefeller at the breakfast buffet – just try not to spill your mimosa on their yacht shoes.

With its sprawling lawns and ocean views, it’s like someone took the best parts of a country club and a seaside resort and mashed them together.

The result?

A place so posh, even the seagulls wear little cravats.

Okay, maybe not, but after a few days here, you might start to imagine they do.

7. Poland Spring Resort (Poland)

Welcome to Poland Spring Resort, where “taking the waters” is less about hydration and more about living la dolce vita, Maine style.

This place has been a hotspot for the well-to-do since 1794, which is practically prehistoric in resort years.

It’s like the fountain of youth, if the fountain of youth came with golf courses and a museum dedicated to bottled water.

The grounds are so vast and manicured, you might need a golf cart just to get from your room to dinner.

And speaking of dinner, the dining room is the kind of place where you’ll want to sit up straight and remember which fork to use.

Don’t worry if you forget – just watch what the ghosts of presidents past are doing.

They’ve had plenty of practice.

8. Eastland Park Hotel (Portland)

The Eastland Park Hotel in Portland is like the Empire State Building’s cooler, more laid-back cousin.

This brick behemoth has been a landmark since 1927, standing tall and proud like a sentry guarding the city’s skyline.

It’s the kind of place where you half expect to see flappers doing the Charleston in the lobby.

Now known as The Westin Portland Harborview, it’s had a facelift that would make a Hollywood starlet jealous.

But don’t worry, it hasn’t lost its old-school charm.

The Top of the East rooftop bar offers views so spectacular, you’ll forget all about your fear of heights.

Just don’t lean too far over the railing – we’d hate for you to miss the rest of this glamorous tour.

9. Ogunquit Playhouse (Ogunquit)

Darlings, let’s set the stage for some theatrical magic at the Ogunquit Playhouse.

This isn’t just any old barn with delusions of Broadway – it’s been bringing the Great White Way to the Way Up North since 1933.

It’s like someone took a chunk of Times Square and plopped it down in a quaint coastal village.

The marquee lights up the night like a beacon for culture vultures and comedy lovers alike.

Inside, it’s all red velvet and gilt, with enough vintage charm to make you feel like you’ve stepped into a classic Hollywood musical.

Just try not to burst into song in the middle of the performance – unless, of course, it’s a sing-along night.

10. The Abbe Museum (Bar Harbor)

The Abbe Museum in Bar Harbor is where Indiana Jones would go if he traded his fedora for a lobster bib.

This Smithsonian-affiliated gem is dedicated to the Wabanaki Nations, proving that Maine’s history goes way beyond lobster rolls and lighthouses.

It’s like stepping into a time machine, but without the risk of accidentally becoming your own grandfather.

Housed in a building that looks like it could be the summer home of the Addams Family, the museum is a treasure trove of Native American art and artifacts.

It’s the kind of place that makes you say “Wow!” and “I had no idea!” in equal measure.

Just don’t try to take any souvenirs – unlike Indiana Jones, they frown on that sort of thing here.

11. Bowdoin College Museum of Art (Brunswick)

Imagine if the Louvre and a New England prep school had a love child – that’s the Bowdoin College Museum of Art.

This architectural stunner on the Bowdoin campus is like a Greek temple dedicated to the gods of fine art.

It’s so impressive, you might feel the urge to start speaking in iambic pentameter.

Inside, it’s a veritable smorgasbord of artistic delights, from ancient artifacts to contemporary masterpieces.

It’s the kind of place where you can see a Roman sculpture and a Picasso in the same afternoon – talk about a cultural whiplash!

Just remember to use your inside voice and resist the urge to touch the paintings, no matter how lifelike they seem.

12. Merrill Auditorium (Portland)

Merrill Auditorium in Portland is where culture goes to get cultured.

This grand dame of performance spaces has been hitting high notes since 1912, both literally and figuratively.

It’s like Carnegie Hall, if Carnegie Hall wore L.L. Bean and had a thing for lobster.

With its imposing stone facade and art deco touches, it’s the kind of place that makes you want to stand up a little straighter and maybe learn a few words of Italian opera.

Inside, the acoustics are so perfect, you could hear a lobster pick drop.

Whether you’re here for the symphony, a rock concert, or a lecture on the finer points of blueberry farming, Merrill Auditorium delivers the goods with style.

13. Portland Museum of Art (Portland)

Last but not least, we’re rolling out the red carpet for the Portland Museum of Art.

This isn’t just any old art museum – it’s a mash-up of architectural styles that somehow works, kind of like a well-curated cheese board.

From its Federal-style mansion to its postmodern addition, it’s a feast for the eyes before you even step inside.

Once you do enter, prepare for a whirlwind tour of artistic greatness.

From Winslow Homer to Andy Warhol, it’s like Six Degrees of Kevin Bacon, but with famous artists.

The collection is so diverse, you might start the day admiring a moody seascape and end it pondering a piece of contemporary sculpture that looks suspiciously like your grandmother’s coat rack.

There you have it, folks – a whirlwind tour of Maine’s most glamorous spots.

From glittering theaters to majestic mansions, we’ve painted the town red, white, and Vacationland blue.

Let the journey unfold!

This map is your guide to every twist, turn, and unforgettable stop ahead.

Now go forth and get your Gatsby on, Maine style!