Quick Trips from NYC with SmartFlyer's Michelle Jackson

It is that time of year when we are all restless after our January hibernations and ready to travel. As a busy mom I know that planning a trip is a significant amount of work and sometimes we want options that we can easily drive to.

With this in mind I asked MerriMama Michelle Jackson, Travel Advisor with SmartFlyer – a Manhattan-based luxury travel agency – to share her top recommendations for weekend family getaways, as well as quick trips to take with that special someone.


1 Hotel Brooklyn Bridge

Designed with the nature enthusiast in mind, 1 Hotel Brooklyn Bridge incorporates greenery and reclaimed materials in their lobby and entrances, making for a warm welcome. What I love about this hotel is its location in DUMBO, just south of the Brooklyn Bridge; meaning, the property offers expansive views of the East River and Manhattan skyline from several room categories. With endless museums, shops, eateries and parks just walking distance (or a complimentary Tesla ride away), families can enjoy all that DUMBO has to offer.

Jane’s Carousel is one popular local spot where you can create beautiful – and conveniently, Instagramable – moments with your children riding the glass-housed carousel, all with the Manhattan skyline as a backdrop. Plus, each weekend, 1 Hotel Brooklyn Bridge offers three separate family movie viewings in their screening room, a complimentary amenity for all hotel guests! And no need to worry about who’s going to watch your dog for the weekend; furry family members are also welcome at this pet-friendly property.


Winvian Farms

One visit to Winvian Farms and you’ll quickly see why guests return time and time again. With 18 unique cottages, each experience is unlike the last. Located in Litchfield Hills, the property offers a tranquil setting steeped in rich history; guests are warmly welcomed upon arrival and ushered into the beautifully resorted manor home that dates back to 1775.

The Restaurant at Winvian Farms, like the overnight accommodations, is a special experience all on its own, offering a fresh and seasonal farm-to-table menu.

Winvian Farm is the perfect destination to bring that special someone for a romantic weekend. Their Beaver Creek cottage incorporates cozy outdoor elements indoors with an inviting wood burning fireplace and second story reading nook. Traveling with kids? Winvian Farm’s Helicopter Cottage is fit for the ultimate sleepover party! Your little loves can set up camp inside the restored 1968 Sikorsky Sea King Pelican Helicopter, a focal point of the cottage.


Gurney’s Newport

One property that I was most excited to see open its doors last year was Gurney’s Newport. Having visited their Montauk outpost many times, having the same brand of hospitality brought to New England was the perfect fit. Located minutes away from bustling downtown Newport, there is never a shortage of things to do for visitors, no matter the time of year. 

During the winter months, Gurney’s offers a seaside ice skating rink where guests can skate while taking in views of Newport Bridge and Newport Harbor Lighthouse. Kicking off Memorial Day through Labor Day, Gurney’s Newport offers a Kids Club program that runs seven days per week from 10AM-4PM, giving parents time to go enjoy the hotels Seawater Spa. Plus, in the summer, the property is the only in the area with an outdoor pool.



Nestled away in Upstate New York, Troutbeck is a hidden gem for couples seeking an escape from life’s daily stresses. A little over an hour away from Southern Connecticut, Troutbeck’s convenient location makes this country house estate one you’ll love sneaking away to time and time again. Situated on over 45 acres of land, guests can embrace the beauty of the Hudson Valley region participating in outdoor activities such as fly fishing, hiking, horseback riding and skiing.

What I really love about Troutbeck is that the entire 34-room property can be rented for intimate group celebration. So, whether you’re looking for an intimate couples getaway or the opportunity to commemorate a special occasion with your crew, Troutbeck is a top pick. Not to mention, the ideal spot to get away from it all.




As a Virtuoso Travel Advisor and SmartFlyer affiliate, Michelle is able to ensure her clients receive added amenities such as complimentary breakfast, resort credits and upgrades, making any getaway a VIP experience. SmartFlyer is a full-service travel agency that caters to high-end corporate and leisure travel worldwide. With an extensive industry network and expert knowledge, clients benefit from a customized approach when booking their travel.


With a background in hospitality, Michelle joined the SmartFlyer team last year. The bustling nature of the role perfectly aligned with her on-the-go lifestyle as a New Caanan mom. Being a luxury travel advisor affords her the opportunities to fulfill her own jet-setting desires, too, constantly on the hunt for the next great spot for her clients. To plan your next trip email Michelle directly at: Michelle.Jackson@smartflyer.com or  learn more here: SmartFlyer


 Photos courtesy of each property