It’s a tough pill to swallow, but as the pumpkin flavor begins to roll out and the bags of Halloween candy pepper the supermarket shelves, it’s time to make peace with the fact that summer is coming to a close. Don’t waste your precious few hours of Summer Fridays waiting in traffic for an overcrowded beach or fighting for parking at the shore. These last-minute getaways from the 914 are easy to get to and will guarantee a superb send-off to the season.
Sea Island, Georgia
Fly direct from HPN to Savannah, and drive 1.5 hours
Built on genuine warmth, hospitality, and tradition, it’s no wonder families have been drawn to Sea Island since 1928. Sea Island offers various outdoor activities with endless opportunities for adventure—with or without your family in tow. From horseback riding along the beach to fishing trips on the marsh and thrilling falconry experiences, no two days at Sea Island have to be the same.
The Cloister at Sea Island accommodations include rooms and suites in the Main Building and adjacent wings, suites in the Sea Island Beach Club, and one-, two-, and three-bedroom accommodations in The Cloister Ocean Residences. From a bird’s-eye view, The Cloister encompasses a sprawling range of world-class buildings and amenities, including the Sea Island Yacht Club, The Spa at Sea Island, and the Sea Island Beach Club.
View this post on Instagram
The Hamilton Princess, Bermuda
Fly direct from HPN to Bermuda
The historic Hamilton Princess Hotel & Beach Club in Bermuda is a hop, skip, and jump from our little corner of New York, but will feel like a completely different world (and when you think about it, that flight is shorter than going to the Hamptons…just saying). Dodge the traffic headaches and let loose at the iconic Pink Palace. Melt into your chair at the Princess Beach Club, which offers beachfront privacy across its three beaches that are only accessible to members or guests of Hamilton Princess.
There is an abundance of things to do for solo travelers and families alike, from water hammocks to cabanas, kids’ playgrounds and beach toys, water sports, tennis, pickleball courts, and, of course, the delicious Beach Club Restaurant.
View this post on Instagram
Chatham Bars Inn, Chatham, MA
A 4.5-hour drive from Westchester
Nothing comes close to a quintessential New England summer like Chatham Bars Inn. The beloved Forbes five-star haven and one of Cape Cod’s most beautiful addresses boasts a quarter-mile private beach and individual cottage accommodations, all enhanced with an old-world charm that is rarely seen in today’s modern-tinged world. Visitors can enjoy classic Cape Cod activities such as whale watching, lobstering, and boating.
The inn goes all out this summer with an enticing lineup of exclusive activities that are tough to turn down. A new luxury pontoon boat offers two- to four-hour cruises that explore Chatham, Harwich, and Orleans from the water, with stops for swimming and sunbathing. Charcuterie boards, appetizers, and beverages enhance the experience. Sip for a spell with a glass of grapes — following a year-long search for the perfect rosé, Chatham Bars Inn announced a new private label rosé with Ultimate Provence. What else could you possibly need?
View this post on Instagram
The Boca Raton, Boca Raton
Fly out of HPN to West Palm Beach
The Boca Raton, South Florida’s premier luxury family resort and private club, is as epic as it comes for family vacations that still feel luxe. The 200-acre resort is home to five hotels and Harborside Pool Club, a sparkling, lakefront oasis set among tropical palms featuring three pools, a 450-foot floating river, water slides, luxury cabanas with personalized butler service, a pool bar serving cocktails and light bites, Banyan Bunch kids club, and a FlowRider. In other words, your kids will collapse into bed without a peep.
Stay in the Tower at the Boca Raton, which was fully transformed in 2022 and features 244 spacious rooms and suites with contemporary and flexible configuration, including connecting suites and entire floor takeovers ideal for multi-generational families and groups of friends. The Tower Suite Collection was introduced this year and is made up of a collection of suites including one-bedroom, two-bedroom, townhouse, and penthouse accommodations.
Perks are plentiful for Tower Suite Collection guests, including priority reservations at The Boca Raton’s more than 15 restaurants and lounges, preferred seating at the beach and pools, and priority bookings for activities like water sports and yacht charters. Necessities are tended to by dedicated concierge and butler teams, and individualized service matches each guest’s pace.
View this post on Instagram
Related: 3 Amtrak Day Trips and Weekend Getaways From Westchester
Raffles Boston, Boston, MA
A 3.5-hour drive from Westchester or an Amtrak ride out of New Rochelle
The new Raffles Boston offers an urban oasis in the heart of Boston’s historic Back Bay neighborhood. Good for a road trip stop or a long weekend escape, the 35-story mixed-use hotel features 147 lavish guest rooms with Raffles’ legendary service, including butlers, and exceptional dining venues helmed by Michelin-star chef George Mendes. Signature restaurant Amar by Chef George Mendes serves modern Portuguese cuisine with New England influences. On the other end of the 17th floor is Long Bar & Terrace, a lounge pairing cocktails with sweeping city views.
The hotel also features an exclusive state-of-the-art gym, indoor pool, and a Guerlain Spa. Raffles Boston marks a new era for the 136-year-old hospitality brand, transporting locals, global jetsetters, and East Coasters alike to a tranquil retreat amid Boston’s urban energy and hospitality renaissance.
View this post on Instagram
La Siesta Resort & Villas, Islamorada, Florida Keys
From Westchester, fly direct from HPN to Miami and drive about 1.5 hours to Islamorada
La Siesta Resort & Villas is an idea escape for families and friend groups of all sizes and generations—so no worries about struggling to please everyone. With a variety of accommodations ranging from spacious suites to private villas and multi-bedroom home rentals, there are endless options to fit your group’s needs. There are over 900 private home rentals in Islamorada, and what makes the home rentals at La Siesta unique is that they come with access to full resort amenities such as the pool, a walk in sandy beach, and marina. Guests also have access to the nearby Amara Cay Resort and Three Waters Resort & Marina, Islamorada, A Tribute Portfolio Resort, as all three properties are part of the Islamorada Resort Collection. And who wouldn’t want a butler tending to your whims? That’s right, a butler, who can stock the fridge and pantry for you prior to arrival, arrange fishing charters, off-property excursions, and more. If that doesn’t open up enough time to relax, guests can bring in the resort’s private chef for all cooking needs and no dirty dishes.
View this post on Instagram
BONUS:
While everyone flees the city these next few weeks, hop on a Metro-North train to a staycation when the city that never sleeps is finally a little quiet.
The Shelburne Sonesta New York, Manhattan
From Westchester, hop on the Metro-North to NYC. The hotel is about an eight-minute walk from Grand Central.
Ideally positioned in Midtown Manhattan, The Shelburne Sonesta New York offers 325 very spacious rooms and suites (uncommon in NYC!), including studios and one- and two-bedroom apartments outfitted with kitchenettes and full terraces that provide breathtaking views of the Empire State Building.
The hotel recently debuted two new culinary offerings in collaboration by IGC Hospitality. Take Care, the new ground-floor restaurant concept, is a modern American bistro dedicated to serving both hotel guests and locals with a diverse all-day dining menu featuring fresh, seasonal ingredients. From delightful breakfast favorites to savory dinner dishes, each menu item is thoughtfully crafted with health and wellness in mind.
Vintage Green, the new rooftop experience, brings enticing cuisine to soaring heights. The 11,000-square-foot indoor/outdoor space pays homage to the parks scattered throughout New York City by combining sophisticated metropolitan design elements and a charming garden atmosphere that offers spectacular city skyline views from a wrap-around terrace. This space is a natural extension of the hotel’s artistically designed and residentially inspired accommodations, which encourage visitors to live like a local while exploring some of the city’s top attractions and experiences. A cocktail overlooking the city skyline without mobs of people? Fantastic, we’ll take 13 of them.
View this post on Instagram
The Gardens ES Suites New York, Manhattan
From Westchester, hop on the Metro-North to NYC. The hotel is about a 12-minute drive or subway ride (on the 4 train) from Grand Central.
Located in the prestigious Upper East Side, The Gardens ES Suites is one of the only hotels in NYC offering spacious private patios. Its current Picnic on the Patio Package encourages guests to enjoy the outdoor space and includes a two-night minimum weekend stay in a spacious one-bedroom patio or terrace suite, curated picnic featuring finger sandwiches, wine, seasonal décor and place settings, blankets, speakers, games, and more. Just steps away from luxury designer boutiques, Central Park, and some of the nation’s best hospitals, this charming hotel features spacious suites that provide the ideal retreat for guests looking for a comfortable home-away-from-home experience.
View this post on Instagram
PRO TIP: Take advantage of Sonesta’s Semi Annual sale launching on August 1 for up to 30% off for stays through December 31, 2024. Book by September 6 and use the code SUPERSAVINGS2. Enjoy the best rates at the end of August or get ahead with special rates for the holiday season in NYC.
