12 Last-Minute Summer Getaways That You Can Still Book Now

Summer Fridays are officially here, and if you have yet to book your summer get-away, the clock is ticking. But before you have an existential melt-down about summer being over and you haven’t planned a thing, we’ve hand-selected 12 amazing locales here in North America that are an easy hop, skip, and jump away—and still have plenty of availability throughout rest of the warmer months. From the remote, like Fogo Island, Newfoundland, to the more well known hot spots like foodie’s paradise Charleston, there is a new adventure waiting to be had. Even if you prefer not to frequent an airport this holiday season, there’s plenty newness in store, especially in Montauk, where the chic lake-side Gurney’s Star Island Resort and Marina has just opened its doors. Only a three-hour drive from Manhattan, the latests addition to Gurney’s Resorts portfolio beckons with promises of fresh seafood at new restaurant Showfish, a heated pool, and live music. Prefer city getaways? This year is the year to visit Baltimore (especially for seafood lovers), or visit New York, and stay in an exclusive airy loft via onefinestay to feel more like a local.

Montauk, New York
Billy Black

Your summer get-away might be closer to home than you think. This summer, Gurney’s debuts its latest property, the Star Island Resort & Marina, located on the picturesque and tranquil Lake Montauk. Boasting over 100 water-front rooms and suites, an outdoor heated pool and an intimate lake-side beach, Gurney’s second resort on Long Island is the luxe place to unwind in Montauk. Planning to arrive to the resort via waterway? A white-washed vintage-style lighthouse complete with an oversized American Flag flapping in the breeze will greet you as you pull up to one of the resort’s 232 slips. The marina, in fact, is the largest in the Hamptons and one of the most important on the east coast. In addition to offering its guests a selection of morning yoga, water sports, and sailing adventures, those staying at Star Island can also take advantage of sister property Gurney’s Montauk’s pristine ocean-side beach and beach club. Be sure to take the gratis shuttle back to Star Island in time for drinks and dinner – sunset cocktails at The Pool Club, while listening to live music is a must (we recommend their frozen specialties), as is devouring the Montauk fluke crudo, spring veggie salad, and fresh tuna seared like a steak, at what is soon to be the Hamptons’ hottest restaurant, Showfish. For those who want the full summer-on-the-east-coast experience, the concierge team at Star Island can arrange for guests to take a quick 15 minute chopper ride to Gurney’s Newport, for an afternoon or an overnight. For those who wish to press pause and relax, or who wish to fill their days with activities, a long weekend at Gurney’s Star Island Resort and Marina should be high on your summer get-away wish list.

Book now: Gurney’s Star Island Resort and Marina, Montauk, from $350 per night,

San Juan, Puerto Rico

Two years after Hurricane Maria devastated Puerto Rico, the island’s tourism is bouncing back. Deep in San Juan’s up-and-coming neighborhood of Condado is O:LV Fifty Five, a 26-suite boutique hotel over looking the Condado Lagoon. While you might be compelled to spend your entire visit in the hotel’s rooftop pool, there is plenty to explore throughout the city and surrounding island.

Book now: O:LV Fifty Five, from $435 per night,

Norwalk, Connecticut

GreyBarns is a gorgeous country get-away not far from New Canaan, Connecticut. This former 18th-century textile factory (which has also done time as an artists’ gathering point, a stagecoach stop, and a prohibition-era speakeasy), was converted into a charming country inn and tavern in the 1960s. Hollywood types have frequented the inn, including Liz Taylor during her honeymoon with Eddie Fisher, and as those have who’ve visited before have done, guests today can enjoy cycling through the wooded property, visiting Philip Johnson’s Glass House, and discovering the adjacent 80-acre Grace Farms.

Book now: Gray Barns, Norwalk, Connecticut, $600 per night,

Baltimore, Maryland

Perhaps not an obvious destination for a long weekend, as this East Coast locale is often overshadowed by New England hotspots. However, summer heralds in Maryland crab season, along with a host of festivals – the African American festival, the Federal Hill Jazz & Blues festival, and Artscape, the largest free arts festival in the U.S. The local pizza and beer is not to be missed, and neither are the Rec Pier Chop House and The Cannon Room, the two new restaurants at the Sagamore Pendry Hotel in Baltimore’s historic Fell’s Point district.

Book now: The Sagamore Pendry, from $395,

Mexico City, Mexico

Mexico City has been having quite a moment for quite some time now, but it’s such a quick trip from just about anywhere in the States, it seems silly not to make time for a visit. Rich in art and cultural activities, it seems like a new restaurant is opening every week in the city. This summer, stay at the Condesa DF, a hotel situated in an of-the-moment district, in a 1926 French neo-classical building, with a distinctly modern feel.

Book now: Condesa DF, from $150 per night,

Fogo Island, Canada

What kind of inn looks like a stark modernist edifice? One that can be found on the outskirts of an 18th-century fishing village on an small island north of Newfoundland. Dubbed the Fogo Island Inn, this hotel keenly mixes modern furnishings with touches that pay homage to the region’s rich history. Visit this remote location for great hiking and geological walks, amazing stargazing, or to simply be alone with your thoughts. In addition to rooftop hot tubs, a suana, an art gallery, and library of Newfoundland history, the Inn also offers watercolor and drawing classes, for those wishing to capture the beauty that surrounds them.

Book now: Fogo Island Inn, from $1,464,

Los Angeles, CA

Does one ever need an excuse to visit La La Land? For those opting to immerse themselves in the west coast’s cultural hub this summer, book a stay at downtown LA’s Hotel Figueroa. The boutique hotel, which re-opened last year after a 3-year renovation, is currently is exhibiting the artwork of some of the city’s most compelling female artists, as a nod to the property’s dynamic history (the hotel, built in 1926 by the YWCA, acted as a safe-haven for female solo travelers at a time when most hotels required women to have a male chaperon).

Book now: Hotel Figueroa, from $249 per night,

Charleston, South Carolina

Spend the next long weekend in Charleston, South Carolina, meandering down cobblestone streets, past soft-hued grand antebellum style homes, and along the Charleston Harbor promenade, across from which the first shots of the Civil War were fired at Fort Sumter. You could easily eat your way through this city as well, and if that is your plan, stay at the centrally-located Dewberry, a mid-century gem with gorgeous interiors, two hotel bars, and yummy French restaurant Henrietta’s.

Book now: The Dewberry, from $400,

San Juan Mountains, Colorado

Mountain life in the summer be even more enjoyable than during ski season. The Dunton River Camp, a glamping destination at the base of Colorado’s San Juan Mountains has not evolved all that much since the region’s gold rush era, in the late 1850s. That means you can indulge hiking and horseback riding to your heart’s content, but you can also luxuriate in the camp’s modern amenities, like the spa tent.

Book now: Dunton River Camp, from $1,575,

Chicago, Illinois

There are hundreds of reasons to visit Chicago in the summer, and perhaps an equal amount of reasons to avoid it in the winter. Even though you won’t find yourself lazing on a beach, there are a plethora of outdoor and lake-side activities in which to indulge. For music fans, both Lollapalooza and Pitchfork roll through, but if relaxing with a glass of rosé is more your vibe, there are plenty of rooftop bars and poolside parties to try. Stay in Chicago’s West Loop, (an epicenter of great restaurants, bars, and boutiques), at The Publishing House, a modern bed and breakfast in a 1909 converted publishing office loft building.

Book now: The Publishing House, from $204, publishinghousebnb.

Portland, Oregon

Now is the best time of year to visit Portland, Oregon. Summer days bring music festivals, art fairs, and craft beer experiences, and the great outdoors. Stay at the Nines Hotel, and make use of the hotel’s gorgeous rooftop bar and restaurant, Departure. One of the few rooftops in the city open to the public, the views of Portland below and the surrounding wilderness is truly stunning to take in – and the food is local and fresh, too.

Book now: The Nines Hotel, starting at $339 per night,

New York, NY
Kate Glicksberg

Although throngs of tourists crowd New York’s midtown in the summer, even locals who get out of town every weekend will admit that visiting New York for a long weekend in the summer is a good idea. If you avoid the aforementioned locale, you’ll find it relatively easy to snag a table at a new restaurant, and neighborhoods feel very, well, neighborhood-y. To feel even more a part of the local fabric, we recommend renting an apartment through onefinestay – we especially love this Tribeca abode with roof deck, perfect for sipping a glass of rosé before heading out for the evening.

Book now: Harrison Terrace, starting at $1,200 a night for 6-8 people,