From Poughkeepsie: 3 hrs 45 min
Why We Love It: The oldest American seaside resort is making gains in wildlife escapes and historic sites — including its photogenic Victorian painted ladies.
Spend Your Days: You can’t leave the Cape without strolling through its neighborhoods of distinctive, late-Victorian era inns and bed & breakfasts. History and nature buffs can bask in the glory of Cape May Point State Park — brimming with bird sanctuaries, hiking trails, and historic sites like the 1859 lighthouse and Battery 223. After window shopping along Washington Street’s pedestrian mall, stop for a much-needed drink at Cape May Brewing Co. and eat your fill at the famous Mad Batter.
Stay: Drop your long-weekend bags at the Ocean Club Hotel, a five-story resort on the beach, complete with a colorful pool bar and balconies perfect for ocean gazing. From $269/night for June; $599/night for July; $600/night for August.
Catch Some Sun and Sand: Cape May’s beaches are a sophisticated older sibling compared to nearby Wildwood or the heavily stereotyped Jersey Shore. Stroll along scenic, 2.5-mile Beach Avenue to scout the best place to set up camp; the Cove and Broadway beaches are local favorites. After a day of soaking up the quiet, manicured sand, head west toward Sunset Beach for Instagram-worthy — you guessed it — sunset views.
From Poughkeepsie: 5 hrs 15 mins
Why We Love It: Tucked away on the tip of breezy, laidback Cape Cod, this loud and proud beach town is a whole lot of fun.
Spend Your Days: Provincetown is one of America’s best bike towns — and rightfully so. Bring your own wheels or rent from countless shops, and start your day at Beech Forest, Province Lands, or the stunning Dune Shacks trails. Shopaholics and wannabe art historians can find peace at East End and Commercial Street galleries, packed full of local art. Grab a bite to eat at Canteen, The Lobster Pot, or Jimmy’s Hideaway — all iconic, local favorites. And P-town has long been a haven for the LGBTQ+ community, with proud events, like Provincetown PRIDE (June 4–6), Independence Week (July 2–9), and Provincetown Carnival throughout the summer.
Stay: Relish in the rustic, trendy vibes of the up-and-coming Salt House Inn. Their open-concept rooms with wooden beams and rocking chairs are just the thing you need after a long day on the shore. From $170/night for June; $235/night for July and August.
Catch Some Sun and Sand: Past the grass-lined foreground of Cape Cod National Seashore Park, enjoy blue skies and sailboats floating on the horizon at Herring Cove, Race Point, or Long Point beaches. Plus, explore windy sea trails and golden-tipped grasses of hidden gem Hatches Harbor at sunset.
From Poughkeepsie: 4 hrs 45 mins
Why We Love It: Come for the Bushes and stay for the bustling downtown, sunset-soaked beaches, and its up-and-coming foodie explosion.
Spend Your Days: You can’t come all the way to Maine without setting aside time for sealife… and seafood. Book a whale watching tour to Jeffrey’s Ledge, and meander around Cape Porpoise to watch lobstermen reel in cages. Across the Sandy Cove, take in the massive Walker’s Point compound — this peninsula is home to the Bush Family during summer retreats. After some Ocean Avenue summer cottage sight-seeing, dive deep into lobster mania: Devour lobster rolls and chowder at famed The Clam Shack (featured on Diners, Drive-ins and Dives) or visit newcomer Alissons.
Stay: Plopped in the middle of all the Kennebunkport action is the elegant, award-winning White Barn Inn. Antique paintings line the common rooms and barn-style furniture and décor riddle the location. Each room is unique, and has personal touches — almost like you’re staying at a friend’s chic summer home. From $550/night for June; $775/night for July; $790/night for August.
Catch Some Sun and Sand: At this Maine hotspot, there are tons of beaches to kick back and relax (or search for critters like horseshoe crabs). Beach hop around the coast at spots like Goose Rocks, Colony and Arundel Beaches, or the beloved Gooch’s Beach.
From Poughkeepsie: 3 hrs
Why We Love It: Long Island’s North Fork has all the beachy escapism of the Hamptons without the pretense — and with some of the state’s best wineries.
Spend Your Days: A salty former whaling town, Greenport is the best hub from which to explore this northern tip of Long Island. Spend mornings window shopping downtown or traipsing through Provence-esque fields of lavender at Lavender By the Bay, then swing by Little Creek Oyster Farm & Market, housed in a 140-year-old bait-and-tackle shop, to slurp some super-fresh, just-shucked bivalves. Set aside a full day for visiting area wineries. Kontokosta, Lenz, Paumanok, Macari, and bubbly-focused Sparkling Pointe are just a few of our favorites.
Stay: With its bold, black-and-white patterns and prime location downtown, 16-room The Menhaden, opened by a pair of Dobbs Ferry residents in 2018, is a design lovers’ dream. Weekend rates from $609/night.
Catch Some Sun and Sand: The region is dotted with rugged little swaths of sand, many of which offer day permits. At the very tip of the North Fork, Orient Beach State Park boasts 45,000 feet of bay frontage, with stand-up paddleboard rentals, hiking trails, and destination-worthy birding.
From Poughkeepsie: 2 hrs 30 mins
Roll your windows down and put Bruce Springsteen on blast — this iconic beach town is home to tons of fast-paced fun. From miles of family-friendly beaches and entertainment galore to eateries nestled on the boardwalk and throughout town, you’ll always be busy. Parking by the beach is easy with the option to pay-by-app and affordable meters everywhere. For a midday snack, stop by MOGO Korean Fusion Tacos (the fish taco is out of this world) or trendy Playa Bowls for colorful smoothie bowls. On the way home, check out the sauce-swirl pizza at Maruca’s of Asbury, or feast on insanely delicious ice cream from Coney Waffle.
From Poughkeepsie: 2 hrs 45 mins
With smooth tides and manicured beaches, this rocky New England coastline is perfect for slow-moving beachgoers. Visitors can choose between four main beaches: Misquamicut State Beach, Atlantic Beach Park, Westerly Town Beach, and the newly opened Wuskenau Town Beach. Beaches welcome all ages and all types of water activities: Surfing and boogie-boarding, playing catch, and digging for sand crabs are highly recommended. Away from the surf and sand, stop at comfort-food haven B&B Dockside; curb your thirst at the fruity High Tide Juice Co. or caffeine-stocked Junk & Java; and treat yourself to Honey Dew Donuts lemon- or jelly-filled donuts.
From Poughkeepsie: 2 hrs 20 mins
If you’re looking for peace and quiet, Robert Moses State Park is just the place. Stretching across Fire Island — home to some of Long Island’s best sunsets — visitors can enjoy unspoiled oceanfront. The beaches — referred to as “Fields” — are split into five sections, with Fields 2 and 3 being the least crowded, and Fields 4 and 5 having the most attractions and activities. (Surfing and surf-fishing are the most popular pastimes, as is fishing along the piers.) Nearby, beachgoers can play the 18-hole pitch and putt golf course, snack at picnic areas, and visit the iconic Fire Island Lighthouse. Nearby towns, including Kismet and Saltaire, are only accessible by foot (about 45 minutes) or via a 15-minute bike ride from Robert Moses.