6 Affordable Summer Adventures to Start Planning Now

Portland, Oregon in the summertime has been described as a hipster playground, and for good reason: Trendy restaurants, food trucks, street musicians, coffee bars, and farmers markets beckon everywhere you turn. It’s a ton of fun if you have the energy to get your hands in everything, as you should. Portland is also oh-so-close to tons of natural splendor: cycling, hiking, and padding are all fair game.

Stay: The Ace Portland.

After a snowy winter, the Catskills Mountains come alive in the summertime. Imagine rolling hills of lush greens, waterfalls, and pleasantly sleepy towns. There’s lots of relaxation and outdoorsy goodness up for grabs, so pack your hiking boots and a good book.

Stay: The Graham & Co. (pictured) or The Arnold House.

The oldest city in South Carolina, Charleston is ripe with Southern charm. Antebellum architecture and surrounding plantation landscapes can make the city seem as though it is suspended in time, but a growing arts scene around Upper High King points to change. Be sure to check out Folly Beach and Cypress Gardens, too.

Stay: Zero George (pictured) or The Elliott House Inn.

Regarded as the gem of Big Sky Country, Bozeman is a charming college town full of tree-lined streets and wild deer as well as museums and galleries. Try white water rafting, exploring the downtown area, or visit the nearby Yellowstone National Park for access to some of the country’s most spectacular nature.

Stay: In a homey, unique AirBnB, of which there are countless options!

Talk to any native Chicagoan about the summertime, and they’ll tell you they’ve earned all of the fun they’re having. And it’s true: After the city’s infamously harsh winters, residents are in a vacation state of mind come warmer months. This makes for a very enjoyable place to visit, with all of the big city culture you expect of the city, plus a certain air of celebration that permeates everything on offer, from outdoor festivals at Grant Park to gatherings at Oak Street Beach.

Stay: The James.

Tucked within the tall redwood forests that pop up along the coast in between Southern and Northern California, Big Sur is in the running for the most magical pocket of nature on the West Coast. Perched high atop the cliffs of Highway 1, Big Sur’s air is crystal clear and the atmosphere is subdued and serene. Hike Pfeiffer State Beach, eat at the Big Sur Bakery, and visit the Henry Miller Memorial Library (where year-round concerts and events are often held beneath the trees and starry night sky).

Stay: Glen Oaks Big Sur.