While I-95 may not be as musically inspiring as other highways (looking at you, Route 66), it connects us to so many major cities in such a direct way. We’ve planned for you the ultimate vacation tool using that homey, if not sometimes frustrating, highway as a guide. Either just off the exit or a little down the beaten path, these properties offer an interlude in places we get to explore with fresh eyes. Road trip (or fly, we don’t judge) to these destinations without the worry of having to reroute — and maybe write a song while you’re at it.
*Westchester Magazine is not responsible for traffic.
The Alida, A Tribute Portfolio Hotel
Savannah, GA; Exit 5
Cozied up to the Savannah River in the Hostess City, The Alida offers a level of Southern hospitality that could soften even the staunchest New Yorker. As storied as the cobblestone streets below, the space was once a thriving bottling plant, the original brick from the building used to build the hotel. With the design striking a balance between mid-century modern and industrial chic, the space’s namesake is Alida Harper Fowlkes, an entrepreneur and preservationist credited with saving several Savannah landmark historical buildings in the mid-1900s. Standing at the crossroads of legacy and the new wave of contemporary, The Alida is your perfect jumping-off point for a full experience in America’s first planned city.
Just like a good glass of sweet tea, The Alida is steeped in tradition and meticulous care. The 173 guest rooms and suites are thoughtfully designed to provide a serene sanctuary, with each room offering plush bedding, contemporary furnishings, and either a pool or river view, complete with a window seat to take in the view. (Or opt for the 2,700-square-foot penthouse with a private wraparound balcony, if you’re feeling fancy.) The boutique hotel threads the needle on its commitment to local, with many of the designs and prints highlighted in each room coming from students at the Savannah College of Art and Design. When every single room has a king-sized bed, you understand that nothing here is just an amenity — it’s an experience.
The art of hospitality is as present in The Alida’s DNA as the custom scent created especially for the hotel that greets you at the door. Upon check-in you’ll receive a refillable water bottle, with taps to fill up (sparkling, cold, or temperate) on each floor. Don’t forget the canapés and snacks every evening in the lobby bar, the freshly baked cookies during the lobby’s “Spritz Hour,” with complimentary Champagne at the reception desk. It is the endless pursuit of perfecting the little things that brings your stay here together with a bow. For a day of laid-back grandeur, lounge by the pool in a private cabana with a bar and Mexican-inspired bites from The Cabana Club a saunter away.
You will smell the sweet and savory cascade of Rhett before you can see it. The hotel’s signature restaurant is an open love letter to the low country — supple dishes like tender shrimp and grits, crunchy fried chicken, and cheddar drop biscuits serve as the exclamation points. Take a seat for brunch (and maybe some recovery from too many pool-side Painkiller cocktails) and swan dive into the expertly seasoned buttermilk biscuits and gravy, fluffy house-made pancakes with blueberry compote, and an audibly crunchy fried green tomato BLT. If you do need some hair of the dog, the bloody mary bar is here for emotional support; and might we suggest the Low Country Bloody: green chili vodka, okra brine, bloody mary mix, andouille, and pickled okra?
Just like a good glass of sweet tea, The Alida is steeped in tradition and meticulous care.
For refined lobby imbibing, The Trade Room (so named because when sailors came from the river’s port they would trade stories) has a dedicated menu of whiskey-based cocktails, along with bites from Rhett’s menu, draft beer, and wine. Take to the skies, or just the rooftop, for some after-dinner alfresco fun at The Lost Square, the crown jewel that sits atop the hotel. Mediterranean-inspired nibbles dance with carefully crafted cocktails as you people-watch the ongoings of River Street’s bustle below. Keep your ears peeled — there’s live music every weekend at The Alida; just follow the sound of the strumming … or the DJ, for that matter.
The city is a turntable of opportunity, and the team members at The Alida are experts at spinning the wheel and offering up a smorgasbord of activities and advice, from ghost tours to speakeasies. A well-rounded jumping-off point is a trolley tour, which The Alida concierge is more than gracious to coordinate. Locally owned and operated, Old Savannah Tours is the longest running trolley tour in the city. Hop-on, hop-off style, zip through the city’s expertly manicured squares and surround yourself with the boundless wellspring of history from your knowledgeable guides.
The Alida is a mirror ball for Savannah, a shimmering statement that the city is yours to see as you want, reflecting the endless opportunities, and there to welcome you as endlessly as your adventure sees fit. —CC
Seasonal rates begin at $275/night.
Inn at Diamond Cove
Portland, ME; Exit 44
After finally getting off the interstate, you can escape the mainland too, by taking a 30-minute ferry ride from downtown Portland to a private island refuge that is all about rest and relaxation.
Opened in 2015, The Inn at Diamond Cove is a 44-room boutique hotel that sits on Great Diamond Island in Casco Bay, with a salty-air boat ride out to the historic inn setting the stage for a picturesque coastal getaway.
Initially a retreat enjoyed by literary icons such as Henry Wadsworth Longfellow and Harriet Beecher Stowe, the island became a military base around the turn of the 20th century. Fort McKinley, with barracks that could house more than 1,000 military personnel, once was a part of the nation’s coastal defense system and protected Portland Harbor during the Spanish-American War.
Today it is a year-round, car-free island of private homes with the inn as its centerpiece. A former army barracks building, the inn has been meticulously restored and refurbished, with high-ceilinged rooms and roomy suites with balconies, plus deluxe condos with kitchens: all elegantly furnished and decorated.
“The island embraces tranquility and quietness — with no cars and small, secluded beaches; it is a true retreat where you can just unplug and recharge,” says Jenn Pendexter, area director of sales and marketing for Colwen Hotels, the inn’s management company.
For solo travelers, couples, families, and groups of friends seeking a place to unwind or a venue for a reunion or a wedding, the inn checks all the boxes with comfortable rooms, delicious food and drink, speckled with impeccable assistance from an attentive staff.
To take in Diamond Cove’s beauty, you can bike or stroll the trails around the 0.3-square-mile island where you’ll pass deer quietly hidden in the greenery. Scenic neighborhoods are dotted with homes that are steps from the small beach enclaves, ideal for picnics and wading. Rent a kayak or paddle board to explore the area; when you return, the heated outdoor pool, hot tub and firepit await you for some more chilling-out time at the inn. Cocktails and dinner can be enjoyed waterside at the nearby Diamond’s Edge Restaurant, which offers local seafood and indoor or outdoor dining and overlooks the marina.
“The island embraces tranquility and quietness — with no cars and small, secluded beaches; it is a true retreat where you can just unplug and recharge.”
—Jenn Pendexter
Rainy days can be spent at the full-size indoor basketball court adjacent to the inn, or trying out kitschy duckpin bowling, along with ping pong, a pool table, and arcade games. Of course, you can just sleep soundly in your room, relishing the calmness and silence of an island that is truly off the beaten path. —JJ
Seasonal rates begin at $464/night.
Portland Harbor Hotel
Portland, ME; Exit 44
Though newly renovated, the Portland Harbor Hotel has been part of the downtown Portland scene since 2002. With a second-level lobby reached via spiral stairs (or an elevator), its stylish charm is part of the fabric of Maine’s largest city; and it is located within walking distance of restaurants, pubs, art galleries, and shops in the Old Port District. Set among cobblestone streets, 19th-century warehouses, funky gelato shops, art galleries, and more, the hotel’s location just one block from the waterfront and its refurbished interior make it a perfect stay when visiting Portland.
A nautical vibe can be felt in its unique 101 rooms and 16 suites — all cozy and comfortable — with plenty of attention to small details, including local artwork and down pillows. The well-designed layout allows guests to grab a snack or fresh coffee anytime at a stocked pantry nook located on each guestroom floor.
What sets the hotel apart in the vibrant, foodie city that is Portland is the ambience of its outdoor restaurant. The Harbor Bistro + Terrace is the only downtown hotel property with outdoor terrace seating, according to the hotel’s sales department, which also proudly notes that the Portland Harbor Hotel is the only AAA Four Diamond-rated hotel in the city, a distinction awarded by the Automobile Association of America for style, décor, and amenities.
Gather around the ample firepit after a meal at the bistro, with menu items that are sourced with ingredients from local farmers and fishermen. The bar boasts several signature cocktails and local beers to accompany shareable small plates to start, like a bone marrow board or waffle fry poutine. The plumply stuffed lobster roll, served with perfectly salted shoestring fries, is a must-have on any trip to Maine. During the colder months, you can even reserve a seasonal igloo on the terrace for an intimate gathering complete with blankets, décor, and speakers for music.
The hotel’s location just one block from the waterfront and its refurbished interior make it a perfect stay when visiting Portland.
Whether you are visiting Portland for a first stop on the way down the coast, or your last stay on a northbound journey, the comfort of this upscale boutique hotel is an ideal respite. To boot, it is a pet-friendly hotel that will accommodate your pup in an equally welcoming way. —JJ
Seasonal rates begin at $593/night.
Hotel Du Pont
Wilmington, DE; Exit 7
A timeless beacon of luxury and sophistication, Hotel Du Pont greets visitors with style and elegance. From its grand facade to its impeccable service, this historic hotel promises an unforgettable experience for discerning travelers.
Guests are transported to an era of opulence and grace from the moment they step onto the lobby’s marble floors. Built in 1913, this Gilded Age marvel is a kaleidoscope of rich detail, from the glimmering terrazzo floors to the handcrafted chandeliers and the sweeping cascade of staircases. Each corner whispers tales of the prominent figures and dignitaries who have graced its halls over the decades.
The hotel boasts 217 rooms, splashed with European flair and contemporary comforts. Deep soaking tubs and mahogany pillars continue the theme of elegance even in your most quiet moments. For those times that a nap is not enough, the Currie Spa boasts a full menu of body treatments and hair services, as well as an infrared sauna.
Culinary enthusiasts will find their personal paradise in The Green Room, recently named one of the top hotel restaurants in the country by USA Today 10 Best Readers’ Choice Travel Awards, and a winner of the Historic Hotels of America Best Historic Restaurant Awards. Shining a spotlight on the concentrated brilliance of Chef Tyler Akin, the French neobrasserie brings the vivacious flavors of North Africa and Provence into innovative iterations of classic cuisine. Food lovers will find themselves zeroing in on the foie gras mousse, steak tartare, scallop amandine, and trofie pasta. For a true gastro journey, pair your plates with natural wines selected by the house sommelier.
For a more casual setting, the Café Du Pont provides a charming atmosphere to enjoy light bites and afternoon tea. Spark*d, the hotel’s well-loved bakery, pops out fresh pastries daily — and we dare you not to take one for the road.
Built in 1913, this Gilded Age marvel is a kaleidoscope of rich detail, from the glimmering terrazzo floors to the handcrafted chandeliers and the sweeping cascade of staircases.
While the hotel itself offers a world of luxury that is tough to tear yourself away from, its location in downtown Wilmington is inviting and in the lap of history. Nearby attractions include the Hagley Museum and Library, Longwood Gardens (which is incomparable around Christmas, if you know… you know), and the Delaware Art Museum, each a different vestige of the region’s splendor.
Hotel Du Pont indulges the senses from start to finish, steeping in timeless luxury and unparalleled service that define tradition and trust. More than 100 years since its doors opened, it is apparent why people from all corners of the world continue to flock here. —CC
Seasonal rates start at $449/night.
Loews Hotel
Philadelphia, PA; Exit 22
If you’re heading south to enjoy some of our nation’s historical sites (or just a cheesesteak), an excellent start is setting up camp in a place that fits the bill itself. Taking residence on Philly’s momentous Market Street, the Loews Hotel is a famed testament of architecture surrounded by the buzz of Center City: the Philadelphia Savings Fund Society building, a 20th-century masterpiece and National Historic Landmark. Gazing upon the 33 stories of Art Deco construction will be one of many “oohs” and “aahs” you’ll utter during your stay (followed by the awe that will strike when you see the original bank-vault doors in the hotel lobby — an homage to its history and a striking art installation).
Don’t let the hotel’s history give you the impression that your amenities will also be a thing of the past. The 581 guest rooms (including 16 suites) are outfitted with modern luxury from the Julien Farel hair and body products to the Chadsworth & Haig Ultimate Doeskin robes. With many of the hotel’s rooms offering sweeping city views, it’s hard not to get caught up in the City of Brotherly Love from the comfort of 100% cotton sheets.
When your muscles are on fire from walking tours and exploring endless city blocks, the Joseph Anthony Retreat Spa & Salon is a double door of relaxation on the fifth floor. Guests are privy to a robust selection of massages and facials, including one-of-a-kind services like the renowned Turkish Bath experience in a tile-embellished, heated room for next-level ambiance. The spa’s unique Soft Pack Float treatments begin with a gentle body scrub, and allow you to float on a pressure-free water cushion.
Heaven forbid the moment comes, but if you find yourself sick of cheesesteaks and crab fries, the hotel is home to Bank & Bourbon, a sleek, modern American restaurant with Chef Craig Meyers at the helm. Using seasonal and creative interpretations of classic American dishes, the menus walk the line between comfortable and unexpected. The bar features a bourbon barrel-aging program for unique house-aged cocktails and liquors, with each sip more special than the last. Bank & Bourbon also showcases local purveyors through its Flavor by Loews Hotels program, highlighting homegrown brands like La Colombe Coffee, Metropolitan Bakery, Conshohocken Brewing Co., and Stoll & Wolfe Distillery. Melt into the tufted leather banquettes and feel at ease with the kitchen’s latest fresh and seasonal samplings.
Gazing upon the 33 stories of Art Deco construction will be one of many “oohs” and “aahs” you’ll utter during your stay.
For a long weekend or holiday away, the Loews Philadelphia gives visitors a welcome to the city that is both warm and lux, cozy and refined, and will have you plotting out just how close Philly is… you know, for next time. —CC
Seasonal rates begin at $279/night.
Delamar Southport
Southport, CT; Exit 19
Sequestered off the beaten path and in a residential part of the quaint town of Southport, a literal stone’s throw from I-95, is the Delamar. If you blink (or break the speed limit), you might miss it, yet it has everything you would need for a peaceful getaway that’s less than hour from Westchester (approx. 40 minutes from White Plains). The rooms in this boutique hotel are individually decorated with hand-crafted, antique furnishings and a style you would find in a well-designed home.
The spa, which was renovated this past January, is serene and peaceful, tucked away off the courtyard of the hotel. Indulge in a deep-cleansing facial, a balancing hot-stone massage, or innovative microneedling. Enjoy the sauna, steam room, and relaxation room before and after your treatment. After the spa, consider enjoying an afternoon tea complete with finger sandwiches, pastries, jams, and teas. (Reservations for tea starting at 2 p.m. Tuesday through Thursday are required at least 48 hours in advance at $50 per person.)
In the evening, make your way to the hotel’s farm-to-table restaurant, Artisan. The chef-driven restaurant not only changes the menu weekly and sources local, in-season ingredients from farms and oyster purveyors, but also grows its own herbs in planters surrounding the patio, picked first thing in the morning for the day’s offerings. Pro Tip: Order from the Market Menu as it is filled with the freshest ingredients and specialties. If you can, try the grilled peaches and buffalo mozzarella to start, and finish with the cheesecake, which is anything but traditional thanks to its interesting toppings, including Harry’s Berries, a bit of citrus, and tiny meringues for crunch. Sit outside for dinner and you won’t regret it; you’ll feel as though you’ve been transported outside of Connecticut.
If you’re looking to go off-property and see downtown Southport or take a drive along the Long Island Sound, the hotel offers a personalized chauffeured picnic with an autumn-inspired menu created by Corporate Chef Frederic Kieffer; it includes an appetizer, main course, dessert, and private-label Champagne. To get there, guests can choose from a 1962 Imperial Crown or a Rolls Royce Phantom Drophead Coupe ($550 for two people and $90 for each additional person; reservations required.)
The rooms in this boutique hotel are individually decorated with hand-crafted, antique furnishings and a style you would find in a well-designed home.
In the fall and winter, curl up with a nightcap by the fire in select rooms and settle down for the night. In the morning you can enjoy a complimentary, gourmet buffet breakfast. —JA
Seasonal rates range from $339–$549/night.
Great Oak Manor
Chesterton, MD; Exit 4A
The bucolic Great Oak Manor has a wondrous history of tradition and change — it shapeshifts into a new form every couple of decades. The walls are painted, furniture rearranged, and function altered, but the rich character remains. From a private country retreat to a wedding venue, to the current intellectuals’ space and intimate retreat, the space adapts and grows with each owner who has stepped through its doors and been inspired. Current owners Werten Bellamy and Kellye Walker embody that love completely, with their unique focus on connection, learning, and wellness. The Georgian-style manor dates to 1938 when Douglas Braik designed the neoclassical building as a private residence styled after an 18th-century English country retreat. The Great Oak Manor is now a boutique luxury hotel with 12 rooms, a private apartment-style carriage house, private beach, and great lawn. Each room and shared space has individualized décor and personality. You won’t be content until you’ve spent time relaxing in every space available to you.
Upon driving up to the manor, you will be awestruck by timelessness. No matter what world you are stepping out of, you enter the gates of the property and are transported to a more sensitive and peaceful realm. The team at the manor seamlessly blends the beauty of history with innovative creation. As you move through the front entrance, to the library, and out to the back lawn, you’ll sense the same creative energy that inspired Hemingway and others who took refuge at this unique manor.
After enjoying one of the carefully curated a la carte breakfast options, grab your coffee and meander onto the back lawn. As the sun starts to rise in the sky, you’ll want to do nothing else but sit with a coffee and a book on the edge of the property that looks out onto the water. Yes, this 15.2-acre property sits between sprawling farmland and the wonderful Chesapeake Bay. With a long stretch of waterside lawn and a private beach, you have endless options for leisure.
Time easily slips away from you at this secret oasis. Don’t forget to take a stroll around the property to find all the historical artifacts that line the walls of the manor. As the evening approaches, you can enjoy a curated menu in the cozy dining room gazing at the sunset over Chesapeake Bay. A good percentage of the food provided at Great Oak Manor comes straight from the farms you pass along the way. In 2023, Executive Chef Mallory Bowen brought his wealth of experience and skills with diverse cuisines to the property, where he fuses the local and the worldly to bring guests a thoughtfully designed dining experience. Each dish is a gift, packaged by a rotating seasonal menu filled with imagination and exceptional standards.
The newly renovated Manor is unlike anything in its genre because Bellamy and Kellye Walker developed this property from their experience of more than 20 years as corporate lawyers. During that time, they identified an unmet need for strong relationships and restorative environments. If you’re coming to the Manor for an educational or professional retreat, the team will work with you to bring in top talent to provide intimate learning opportunities and services. This space is designed to drive creation.
The Great Oak Manor is the adults-only property perfect for your family reunion, executive retreat, and intimate anniversary or birthday. It’s also the perfect place to disconnect from the world while connecting deeply with those who mean the most to you. —MC
Seasonal rates begin at $369/night.
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