Welcome to Level 2 of our vacation vision quest. Last time, we master-planned three trips for under $500 (with no sketchy hostel compromises). But this time, we’ve got even more beans for the bartering with a max budget of $800, and the same task of finding three places for some R&R (rest and Robocop viewing) after a long day at the beach—or whatever quaint, cobblestone-y town becomes the canvas for our projected main character complex. 

Naturally, the options widen considerably with our extra couple of hundos. (You can eat not one, but several, overstuffed lobster rolls.) We’re still planning trips for just a handful of days at a time, as well as booking those last-minute, really affordable flights on airlines with names that sound like breath mint companies (sup, Spirit). However, this time around, we’ll be balling out a bit harder on the Airbnbs, which means no more bookings with names like, “Private Well-Lit Room,” or “Tent in Jan’s Yard Oasis” (no shade to Jan, get that money). No, we’re talking about the Airbnbs of our lockdown-era dreams that are [gasp] close to the city centers, and strike the right balance between location, privacy, and still having a generous food per diem.

The following three vacations fly out of Los Angeles, New York, and Atlanta, and by the time you slap on the SuperGoop (not sponsored; just slaps) you’ll respectively land in Savannah, Georgia; Big Sky, Montana; and Portland, Maine. 

Bon voyage!

You’re leaving New York

Where to go? Go to Savannah, Georgia. There are round trip flights on Expedia for around $130-150 (for four-day trips in July). 

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Photo: Getty Images

What to do? Relaaaaaax, sugar. Savannah runs on molasses time. You’re here to stroll around the historic downtown in your finest suspenders, floss your teeth with Spanish moss, drink whiskey on storybook porches in the state’s oldest city, shop Picker Joe’s Antique Mall, and re-read Midnight in the Garden of Good and Evil (still slaps). Then, go to the Olde Pink House for a swank dinner or cocktail hour of shrimp and scallops ($22.95) with a bottle of wine (starting at $33), or get chummy with all the otherworldly beings on one of the many Savannah vampire and ghost tours ($5-$45). 

Where to stay?

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Perfectly Renovated Historic Downtown Home; sleeps up to 4, $213/night at Airbnb

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Perfectly Renovated Historic Downtown Home. Photo: Airbnb

Elegant Victorian Restoration Steps from Forsyth Park; sleeps up to 4, $198/night a Airbnb

Carriage House on Historic Chatham Square; sleeps up to 2, $120/night at Airbnb

You’re leaving Atlanta 

Where to go? Go to Portland, Maine, and its surrounding area, because round-trip tickets on Expedia from August 21-24 are running around $180

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Photo: Getty Images

What to do? Portland is Vacationland’s biggest city, and a great launching point into the rest of the East Coast. Explore the Casco Bay Islands and the heritage downtown area; and pop the question at the International Cryptozoology Museum (basically an homage to Bigfoot); and get loose on some of the country’s best beer brewery tours. Blast the yacht-rock jams and eat lobster rolls ($18) for breakfast from J’s Oyster. Renting a car and running on Jerry Time? Visit the Dead Zone in South Yarmouth for a new tie-dye hacky sack to kick into the tide, then go to a drag show in. There’s just so much to sea (sorry) on the Northern East Coast.

Where to stay?

Fresh East End Apartment Walkable to Downtown Portland; sleeps up to 4, $275/night at Airbnb

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Fresh East End Apartment Walkable to Downtown Portland. Photo: Airbnb

A private, pet friendly townhouse by the beach; sleeps up to 4, $150/night at Airbnb

Bright 1 Bedroom in the Arts District with Parking; sleeps up to 2, $133/night at Airbnb

You’re Leaving Los Angeles

Where to go? Go to Montana. Round-trip flights on Expedia to Big Sky from July 16-20 are going for around $185

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Photo: Getty Images

What to do? Montana is quickly becoming Hollywood’s favorite backyard. Not in a gross and overwhelming way; just in an effortlessly hip pied-à-terre way for the likes of Kanye West, Bennifer, and anyone hankering for some cowboy catharsis. Where else can you blow kisses to wild pronghorns, make detours to Yellowstone National Park or Glacier National Park, and soak in the hot springs? Give in to the romance of wide open spaces and embrace the room to make the Big Mistakes. Make it a full road trip and visit Bale of Hay Saloon, the oldest bar in Montana (which also holds a ghost tour every night at 10 PM), or a 1960s tiki bar called the Sip ‘n Dip Great Falls (complete with Montana Mermaids). There’s an entire VICE guide to Montana Airbnbs that are elbow-deep in nature, but here’s a handful more places near Big Sky to sweep you off your keister…    

Where to stay?

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Old Karst Cabin; sleeps up to 2, $95/night at Airbnb

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Charming Riverside Cabin near Big Sky/Bozeman; sleeps up to 6, $164/night at Airbnb

FX Ranch Rustic Pioneer Cabin; sleeps up to 4, $76/night at Airbnb

See you in the hot springs. 


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