The excitement of visiting New York City begins with the planning stages of creating an itinerary. In a city that never sleeps, and one with five boroughs: The Bronx, Brooklyn, Manhattan, Queens, and Staten Island – the planning possibilities are endless. Where to stay, eat, and play can prove overwhelming to a first-time visitor –even to repeat visitors who crave a new experience. But let’s be honest… most everyone experiencing an inaugural visit wants to begin at the top… of the Empire State Building. While buying a ticket to the top of this landmark tourist attraction is easy, the big question is… what to do next? And most important, how to get to Manhattan in the first place.

How to get there

From Boston Harbor, a Tailwind seaplane ride is an exciting adventure and the absolute easiest commute to Manhattan (or to Provincetown, Montauk, and more stops). During the flight season of spring, summer, and fall, this is a weather-dependent option on an 8-seat… literal puddle jumper. Take friends or family along and you’ll be sure to talk about this adventure for months.

It’s like boarding a boat, except for two factors: 1) you bring luggage on board, such as a VinGardeValise wine luggage if you’re thinking of exploring new wines and want to safely bring back a few bottles, and 2) it’s really fun to takeoff into the sky, hovering just above the clouds – if there are clouds – to keep the ride smooth. The views of Long Island Sound are spectacular, and the water landing and wavy exit from the seaplane will leave you giggling all the way from the dock to the drop-off point at East 23rd Street.

Second to a seaplane, the FlixBus option is the biggest value for your wallet. Expect a cost of at least $28 each way and just under a 5-hour ride to drop you off in midtown Manhattan.

Or you can take the Amtrak train to Grand Central Station, also a fun experience for the entire family. The least exciting and most time-consuming when it comes to pre-boarding and commute to the city is to take a flight on a commercial airline. You can also drive to the city and pay parking fees upwards to $80 per day.

Where to stay

On the Upper East Side of Manhattan, Loews Regency New York Hotel is sited on the same street as Dior, Bergdorf Goodman, Louis Vuitton, and Gucci. Inside, a suite with French doors separates the main bedroom and living room with an undemanding pull-out sofa and two bathrooms that make it easy to bring a friend along for fun. It’s the little rewards that make a stay exciting, and in both bathrooms, televisions are embedded in the mirrors. This is the perfect hotel to stay for luxury amenities and easy lounging. Uncanny is that it feels more like someone’s home than a hotel room.

Best of all, right now and through Labor Day, the hotel is celebrating Summerfest by Loews Hotels, which welcomes family with curated offerings catering to guests of all ages, abilities, and lifestyles. First things first… a toast with a “Summerfest Cocktail” to reflect the hotel’s partnership with Bruno Mars’ award-winning SelvaRey Rum. The inspiration behind this cocktail is based on its location – in proximity to Manhattan’s most iconic park. Yes, the Central Park Coolata includes coconut milk, pineapple juice, lime juice and simple syrup, garnished with sliced pineapple and a cherry on top. Mocktail options for those with wellness in mind include an Upper East Side Breeze made with lime juice, pineapple juice, and simple syrup, garnished with a blood orange wheel and an edible flower.

A fun way to include the whole family is to participate in the hotel’s “Summerfest Cultural Safari,” a self-guided tour with stops at Central Park to catch Shakespeare in the Park, Concerts in the Parks with the New York Philharmonic, and more.

Andaz 5th Avenue is a perfect stop for a stay in a Hyatt property sited in a fantastic location to explore the shopping and dining scene, and to walk (20-minutes) to the Gershwin Theater for a spectacular show in the city. A work-from-hotel area in a standard room offers a view of the city that begs you to go outside and participate in life. Oh, and it’s really close to the Empire State Building.

If you’re able to secure a junior suite with a terrace at the NH Collection on Madison Avenue, do so. What a treat to have a large space to sleep, shower, work, dress, and a separate space to lounge on the brick terrace. In fact, brick is a main design on the interior walls in this culturally-rich designed hotel – the walls almost, but not quite, overshadow the chandelier. In the morning, you can head down to the lobby for pastries and coffee to bring back to your room to chill on the balcony and listen to the New York scenes below. If you’re a serious clean freak, this is the hotel you’ll want to book.

Immaculately designed from top to bottom, inside and out, with sleep features and viewing extraordinaire, Equinox Hotel is located in the trendy Hudson Yards neighborhood, right next to the Edge, New York City’s funky fractal-designed Skydeck -- and the Shops at Hudson Yards with a Ladurée macaron cart, luxury retail shops, and Milos Wine Bar for a glass of Agiorgitiko or another of several Greek wine varietals. Back inside the hotel is the Equinox fitness space spectacular – SoulCycle classes included -- and a spa that offers vitamin IV drips.

What to do

A $10 roundtrip per person ticket out of Grand Central Station will get you to the Bronx to explore the New York Botanical Garden. This is a fun way to take a break – either solo or with friends or family -- from the hustle and bustle of the city when everyone needs to decompress. What’s in bloom depends on the season, but there are 250 acres and a tram to take you throughout the various structures. Plan ahead to book a flower arranging class; take a café break at the on-site eatery, with a stop in the gift shop (yes, you can also buy plants here!).

The Gershwin Theater is one of many options in a city known for its Broadway shows, but the Gershwin is where you can catch a performance of “Wicked,” and you will definitely want to see this show. It’s an extraordinary prelude to the “Wizard of Oz” where you’ll want to shout, ‘Oh, wow. That’s how this came to be!” Questions you hadn’t even realized will be answered. It’s riveting fun for the entire family.

To see and be seen, Electric Lemon inside the Equinox Hotel is the place for dining (polenta fries! and an in-house sommelier to serve the perfect pairings with your meal and dessert) and sunset views of the city. Outside, a walk along the High Line of Hudson Yards is a terrific option to offset those calories. It runs south through Chelsea to the Meatpacking District.

Taxi to Crown Heights in Brooklyn for an Israeli dinner at ALENbi Kitchen. On the menu is Arayes, a grilled pita stuffed with seasoned ground lamb and served with charred veggies, raw tahini, sweet harissa, amba, and cilantro. For dessert, try the Malabi, a coconut rose water custard with pistachio crumble and wild fresh berry sauce. Transformational. And pair the entire dinner with Darom wines by Yatir. For the Arayes dish, a pairing with the 2020 DAROM Red opened up to a dark berry burst of ripened fruit on the palate. The blend is Shiraz, Zinfandel, Marselan, and Grenache Noir grown in the Negev and the southern Judean Hills. If you order the Kruvit, a wood oven roasted cauliflower, green tahini, Arabic salsa, za’atar, sumac – you’ll want to sip on the 2021 DAROM White, a 100% Sauvignon Blanc from the vineyards of the Arad Valley. Look for the wines with the label displaying the Israel National Flower, the beautiful red blossom -- the anemone desert flower.

The Negev (desert) has been the growing region of vineyards in the southern region of Israel by Nabatean tribes as early as the second century BCE. The new Darom wine brand highlights the Israeli desert wine region in all its glory. They said it couldn’t be done, but lo and behold, the vineyards were planted with success! Darom is a new brand from the renowned Yatir Winery, developed by the talented winemaker, Eran Goldwasser, who has been producing award winning and coveted wines for Yatir for more than 20 years.

"The south is an integral part of the history of the Jewish people and their connection to vineyards there have bloomed and flourished in the region since the dawn of history. It is a wonderful natural habitat in terms of climate and soil, and many high-quality local varieties can be cultivated here. We are proud to lead Israel’s southern wine trend with the Yatir, and now with the new Darom brand,” says Yacov Ben Dor, CEO of Yatir Winery.

If you bring your VinGardeValise luggage, you’ll want to save room to bring home a few bottles of Darom wines.

Charlene Peters is a travel and wine writer living in the Boston area. Email siptripper@gmail.com