My beautifully eclectic list has coastal charm, small-town warmth, tropical ease, and a little old-school Americana. Here’s what makes each of those places linger in memories:
Maui, Hawaii
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Dramatic contrasts: volcanic slopes, lush valleys, and surreal beaches.
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The slow rhythm of island time.
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The drive along the Road to Hāna and sunsets from Haleakalā that feel almost mythic.
Maui tends to stay with people because it feels both vast and intimate at the same time.
Sausalito, California
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Hillside homes cascading toward the bay.
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Views back toward San Francisco and the Golden Gate.
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That Mediterranean-meets-Northern-California atmosphere.
It’s romantic without trying too hard.
Angola, Indiana
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Quiet Midwestern steadiness.
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Lake country nearby (Pokagon State Park area).
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A sense of community you feel immediately.
Places like Angola often stand out not for spectacle, but for sincerity.
Coral Gables, Florida
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Mediterranean Revival architecture.
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Tree-lined boulevards and the Biltmore’s old-world elegance.
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A curated, almost cinematic subtropical beauty.
It feels intentional — designed to charm.
Kennebunkport, Maine
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Rocky coastline and salt air.
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Weathered shingles and lobster boats.
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That crisp New England restraint.
It’s nostalgic in a way that feels authentic, not staged.
City Island, New York
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A fishing-village feel inside New York City.
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Nautical culture and seafood shacks.
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The sense of being removed while still within reach of Manhattan.
It feels like a secret.
What’s striking is the water theme, islands, coasts, harbors, and lakes. Even landlocked Angola is a lake region. There’s a throughline of places where land meets water, where life feels slightly slowed and reflective.
The common feeling they gave me was Peace, Beauty, and Belonging
What ties your list together, Maui, Sausalito, Kennebunkport, City Island, is that edge-of-water stillness. Harbors. Tides. Salt air. places where life softens around the shoreline.
And when you say “longing for Cuba, the Pearl of the Antilles,” you’re invoking something deeper than geography.
Cuba — The Pearl of the Antilles
That phrase dates back centuries, used to describe Cuba’s lush landscape, strategic position, and cultural brilliance in the Caribbean. It carries nostalgia, pride, exile, memory, music, and longing, all at once.
Water plays a powerful emotional role in Cuban identity:
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The Malecón in Havana — where the sea is both horizon and history.
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The Florida Straits — distance and connection between Cuba and Florida.
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The Caribbean itself — beauty, migration, separation, return.
Your list reads almost like a compass circling that memory:
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Tropical abundance (Maui)
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Mediterranean warmth (Coral Gables echoes Havana’s architecture)
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Maritime New England (echoes of colonial port life)
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Small harbor communities (City Island’s quiet nautical intimacy)
Water often symbolizes both home and distance. You can stand at its edge and feel peace — and ache at the same time.
This longing is rooted in:
Personal memory
Cultural heritage
Political separation and the aesthetic and rhythm of island life
Sometimes, tranquility carries a current underneath it, like the tide pulling quietly outward