Beyond New England, the rest of the country is fair game: national parks, Southern cities, and West Coast escapes. Find ideas for your next domestic trip here.
Key West trades the polished-resort version of Florida for something looser and more relaxed, where porches, bicycles, and sunset celebrations are part of daily life. The slower pace is what keeps people coming back.
A sailing holiday gives couples uninterrupted time together in a setting that naturally slows the pace. Sharing the experience often becomes just as memorable as the destinations themselves.
New England is made for road trips because so much changes within a few hours’ drive, from rocky coastline to mountain passes to historic villages. Here, the drive is often as memorable as the destination.
Cape Cod’s breweries have quietly become the answer to a gray afternoon or an evening off the beach, taprooms scattered through towns you’d otherwise only drive past. Working through a few is a low-key way to see the inland Cape between the sand and the sunset.
Chicago packs its whole personality into summer, which is both the reason to go then and the trap. The lakefront, the festivals, the rooftops all come alive, and so do the crowds. Knowing which sights are worth the queue and which neighborhoods reward wandering is what turns a packed few days into a great one.
On Cape Cod the honeymoon problem isn’t finding a romantic hotel; it’s choosing among dozens. The right one depends on the honeymoon you picture, a quiet inn or a lively harbor town, oceanfront grandeur or tucked-away charm. Decide the mood you want first, and the shortlist writes itself.
Pennsylvania hides plenty of quiet romance within an easy drive of its cities: covered bridges in Bucks County, wineries in the hills, a small mountain town for the weekend. The appeal is how little planning a spontaneous getaway here actually takes.
Boston and New York invite constant comparison, and their boutique hotels say a lot about each city’s character. One leans historic and understated, the other bold and buzzing, and the better stay depends on which mood you’re traveling for. The rivalry is half the fun; the hotels are where you actually feel the difference.
New England isn’t the first place that comes to mind for wine, and that’s precisely its charm. The region’s vineyards trade California’s polish for a low-key, personal kind of tasting, often with the winemaker pouring. Come without the Napa expectations, and the surprise of good wine in unexpected country is half the pleasure.
A good novel can keep a favorite destination close between trips. Stories set on Martha’s Vineyard capture the island’s character in ways that make returning, even on the page, part of the experience.
Cape Cod has inspired plenty of novels, but the best ones capture more than the scenery. Set among the island’s summer light and family secrets, this is the kind of story that keeps the Cape close between visits.
Boston’s ghost stories tend to cling to its oldest places: Revolutionary taverns, colonial burying grounds, the crooked lanes downtown. A haunted tour doubles as a walk through the city’s history, told after dark with the lights turned low.
A bed and breakfast offers the opposite of a resort romance: a handful of rooms in a historic captain’s house, a breakfast cooked for you, and an innkeeper who knows the quiet corners of the Cape. For couples, the appeal is the intimacy, not the amenities.
Islands, cut off and evolving on their own terms, are among the best places on earth to see animals you’ll find nowhere else. A wildlife-focused island trip trades the beach lounger for early mornings and a good guide, and pays you back in creatures found only there. The isolation that shaped them is exactly why they’re worth the trip.
New England hides an unusual amount of world-class art in small places: a Berkshires hill town with a Renoir collection, a Boston mansion frozen as its owner left it, Yale’s free galleries. You can see serious paintings without the big-city crowds that usually come with them.
A riverboat trades speed for a different view of New Orleans, the city and the old plantation coast seen from the water at the river’s own unhurried pace. The choice is really how much of that pace you want: a couple of hours or a couple of days.
Los Angeles has a reputation for being expensive, but many of its best experiences are free. Beaches, hiking trails, public art, and iconic neighborhoods make it easy to explore the city without spending much at all.
New England winter rewards the prepared and punishes everyone else, which makes the packing list the difference between a magical getaway and a cold, miserable one. Layers, real boots, and respect for how fast the weather turns are non-negotiable. Pack like a local who knows what’s coming, and the season’s beauty is yours to enjoy.
Some of Boston’s best meals hide on the North End’s narrow streets. Restaurants that celebrate the Feast of the Seven Fishes keep an Italian-American holiday tradition alive through seafood served with a sense of occasion.
Dennis, near the middle of Cape Cod, makes an easy home base: calm bay beaches on one side, the open Atlantic a short drive on the other, and much of the Cape within easy reach. Staying here gives every generation something to do without spending half the vacation in the car.
The holidays give Boston’s grand hotels a different atmosphere. Seasonal menus and festive events at Bar Boulud make it easy to turn an evening in the city into part of the celebration.
On the Maine coast, the seafood worth seeking out is rarely the fanciest place in town. In Brunswick it’s the unpretentious spot where the fish is fresh, the prices are fair, and the locals actually eat.
Layers do the real work on a New England fall trip, where a single day can start crisp and end mild. Pack pieces you can add and shed, and no hour catches you underdressed.
Where you stay shapes a city trip as much as what you see. The Mandarin Oriental pairs a central Boston location with the kind of service and calm that make returning at the end of the day part of the experience.
Cape Cod is often best experienced from a small waterfront inn rather than a large hotel. Falmouth’s Upper Cape location keeps the beaches, harbor, and village close at hand while encouraging a slower pace.
Fine dining in the Berkshires tends toward warmth rather than formality, and the Red Lion Inn reflects that tradition well. Historic surroundings and thoughtful food make the meal feel like part of the getaway.
Rockwell is easy to dismiss as greeting-card Americana until you stand in front of the originals, where the craft and the quiet social commentary come through. The Berkshires setting, and his relocated studio on the grounds, make it more than a picture gallery.
The Huntington is known for its rare books and paintings, but its gardens are the real reason to give it a full day: a serene Japanese garden, a surreal desert garden, and a classical Chinese garden, each a world of its own. The art almost becomes the side trip.
From Orleans, both calm bay beaches and the Atlantic side of the National Seashore are only minutes away. It’s a convenient base for exploring the quieter Lower Cape.
A Berkshires getaway is shaped as much by where you stay as what you see. A country inn known for comfort food and relaxed hospitality makes an easy base for exploring the region.
Some memorable travel meals come from a gourmet market instead of a restaurant. The Brown Jug makes it easy to assemble a picnic that fits the day instead of planning the day around a reservation.
The Bradbury Building looks unremarkable from the street, which is why most visitors walk right past one of Los Angeles’s great interiors: a sunlit Victorian atrium of wrought iron and open-cage elevators that has appeared in everything from Blade Runner to Chinatown. Stepping inside costs nothing and takes ten minutes.
Decked for the holidays, Newport’s Gilded Age mansions come closest to feeling lived-in: candlelight, towering trees, and rooms staged the way a Vanderbilt Christmas might have looked. It’s the season the grandeur turns warm instead of museum-cold.
Los Angeles rewards travelers who spend time getting to know one neighborhood instead of chasing landmarks across the city. Some of its most memorable places are the ones locals return to, and staying put means spending less time in traffic and more time exploring.
A historic bed and breakfast offers something a chain hotel can’t: a genuine sense of place. The Deacon Timothy Pratt B&B pairs New England history with personal hospitality in the heart of Old Saybrook.
The Newport Mansions take on a different character during the holidays. Seasonal decorations add another layer to homes that were already designed to impress.
Bethel is the rare ski town that’s still a real village, with a Main Street and covered bridges just a few miles from Sunday River. It offers mountain scenery without feeling dominated by the resort.
The Last Bookstore has become a downtown Los Angeles landmark less for what it sells than for how it feels: a cavernous former bank filled with book tunnels, arches made of paperbacks, and quiet corners to get lost in. People come to wander as much as to buy.
Not every Cape Cod stay needs a lobby, concierge, or resort activities. Sometimes a private beach, a kitchen, and a quiet stretch of shoreline are exactly the point.
An observation deck sells one thing that’s genuinely worth the ticket: the moment a sprawling, confusing city suddenly makes sense from above. High over downtown Los Angeles, the grid, the freeways, and the distant ocean fall into place at once. It’s the fastest way to understand a city that otherwise refuses to hold still.
Manchester is well suited to the kind of weekend that moves at an unhurried pace. A historic inn becomes part of the experience, giving you a comfortable base for exploring southern Vermont.
Sandwich is the oldest town on Cape Cod and the first you reach over the bridge, which makes it an easy off-season weekend when the summer crowds are gone. A boardwalk, a historic village, and empty beaches are the whole appeal in the quiet months.
Some places continue to shape people long after they leave. This memoir explores Martha’s Vineyard through the memories and experiences that keep drawing people back to the island.