Visiting New York in October: Our 5-Day Adventure

If you are dreaming of your own autumn escape to New York, this is exactly what you can expect.

The Journey: Aer Lingus from Shannon to JFK

Flying from Shannon makes the whole experience feel that bit more relaxed, especially with pre‑clearance making your arrival in the US so much smoother.

Outbound: Economy Class Comfort

On the way out, we flew economy from Shannon to JFK with Aer Lingus. It was a great balance of comfort and value:

• Relaxed check‑in and friendly crew that immediately set the holiday tone
• Seat‑back entertainment with plenty of films and TV for the flight
• A hot meal and drinks service, ideal to help you settle into “holiday mode”
• The convenience of flying directly to JFK, which is particularly handy when you want to get straight into Manhattan

By the time we landed, we were refreshed enough to navigate immigration, collect our bags, and head into the city without feeling too drained.

Our Base: The Westin New York at Times Square

Staying at The Westin New York at Times Square put us right in the middle of Manhattan’s Theatre District, just steps from the bright lights and Broadway buzz of Times Square.

What we loved about the hotel:

• Location: You can walk to Times Square in minutes, and it is also well placed for Broadway shows, Fifth Avenue, Bryant Park and even the Hudson River. Several subway lines are nearby, so it is incredibly easy to get around.
• Rooms: Spacious by New York standards, with comfy Westin beds, modern bathrooms and those all‑important city views that remind you exactly where you are.
• Facilities: A well‑equipped gym, on‑site dining and bars, 24‑hour reception and room service, plus easy access to shops and cafés all around the hotel and if you are watching the budget you are just minutes walk for Hell Kitchen for an array of restaurants that won’t break the bank.
• Atmosphere: A polished, contemporary feel, but still relaxed. Ideal for couples, friends and families who want a quality base with everything on the doorstep.

For a short New York break, it is a fantastic “home in the city”: you can head out early, come back to freshen up before a show, and never feel far from the action.

Our 5‑Day Itinerary:

This is a great structure for a five‑day October trip, especially if it is your first time in New York.

Day 1: Arrival & Times Square

• Check in to the hotel and freshen up after arriving via Private transfers from JFK Airport.
• After freshening up we took a gentle stroll around Times Square to get our bearings and soak up the atmosphere: the billboards, street performers, and that electric New York energy.
• We enjoyed an early dinner near the hotel and aim for an early night to reset after the flight.

Day 2: Midtown Highlights & Top of the Rock

• We started our day with Bryant Park and the New York Public Library. In October, Bryant Park feels particularly pretty, and it is a lovely place for a coffee.
• We walk up Fifth Avenue for some window shopping and to see famous stores and landmarks along the way.
• We visited St. Patrick’s Cathedral and then head to Top of the Rock for breath-taking views of the skyline and Central Park.
• In the evening we took in a Broadway show – Fathom of the Opera; A Broadway show it is an absolute must for a first visit and so convenient from Times Square as there are so many to choose from.

Day 3: Statue of Liberty, Ellis Island & Downtown

• We took an early ferry to Statue of Liberty and Ellis Island. It is an iconic part of any first‑timer’s trip and a powerful insight into New York’s immigrant history.  We even found the names and details of our ancestors who emigrated to New York so many years ago and created a life for themselves in the USA.
• We spent the afternoon around Lower Manhattan:
• 9/11 Memorial & Museum for a moving and beautifully designed tribute
• Wall Street, the Charging Bull and New York Stock Exchange
• A walk across Brooklyn Bridge for those picture‑perfect skyline views
• In the evening we had drinks & dinner in Brooklyn before heading back to Midtown.

Day 4: Shopping at Woodbury Common

We dedicated a day to shopping which we felt was a brilliant use of time, especially in October as you start thinking about Christmas gifts or updating your wardrobe.

• We headed out to Woodbury Common Premium Outlets, one of the most popular outlet malls for visitors on a coach from the Port Authority which was walking distance from our hotel which was ideal.
• You will find a large range of designer and high‑street brands, often with excellent savings compared with home.
• There are plenty of cafés and eateries to break up your shopping.
• We return to the city in the late afternoon and had a relaxed dinner near the hotel to rest our feet after all the shopping.

Day 5: Central Park, Neighbourhood Wandering & Last‑Minute Sights

• We spent the morning in Central Park, which is beautiful in October with its autumn colours. You can stroll, hire bikes, or simply find a bench and people‑watch.
• We then explored nearby areas such as the Upper West Side / Upper East Side for a more local New York feel.

There is so much to see and do and depending on your interests, you might fit in:

• The Metropolitan Museum of Art (The Met)
• The Museum of Modern Art (MoMA)
• Last‑minute shopping on Fifth Avenue or around Herald Square
• Later in the afternoon we collected our bags and took a private transfer to JFK for our business‑class flight home, ready to relax after a jam‑packed trip.
  
  

Homeward: A Taste of Luxury in Business Class

For the return leg, we upgraded to business class, which turned the journey home into part of the treat rather than the end of the holiday.

Our experience included:

• Priority check‑in and fast‑track through the airport
• Lounge access, where we could relax, have a bite to eat and unwind before boarding
• Spacious lie‑flat seats, ideal for getting proper rest after a busy few days walking the city
• Elevated dining, with a more refined menu and drinks service
• A quieter, more private cabin atmosphere that felt like a gentle transition back to reality

If budget allows, combining economy on the way out with business on the way home is a lovely way to keep costs balanced while still enjoying that premium travel experience and get a few winks on the way home which may help with the jetlag.

Some Hints and Tips!

Great Value Places to Eat near Times Square:

Times Square is not always known for value, but there are some good options if you know where to look. A few styles of places we found handy and good value for the area:

• Pizza by the slice spots: Ideal for a quick, inexpensive bite between sightseeing, and very “New York”.
• Diners and casual grills: Great for hearty breakfasts, burgers, salads and sandwiches at more reasonable prices than some of the tourist traps.
• Delis and salad bars: Perfect for grabbing a made‑to‑order sandwich, soup or salad if you want a lighter or quicker option.
• Pre‑theatre menus: Many restaurants in and around the Theatre District offer set menus before shows, which can be excellent value compared with à la carte.

When I plan your trip, I can recommend specific restaurants that match your tastes, whether you prefer classic American diners, Italian, steak, or something lighter.

Getting Around New York: Public Transport Tips

New York’s public transport network is extensive and, once you get the hang of it, very straightforward. It is also the best way to keep costs down and avoid traffic.

Here are some practical tips:

1. Use the Subway for Speed and Value
• The subway is usually the fastest and most cost‑effective way to move around Manhattan and between boroughs.
• Trains run frequently and cover most major areas you are likely to visit as a first‑timer.
2. Tap to Pay or Use a MetroCard
• You can tap in with a contactless bank card or phone, which is very handy for visitors.
• If you prefer, you can buy a MetroCard and load it with pay‑as‑you‑go credit or an unlimited travel option, depending on how intensively you plan to travel.
3. Buses for Shorter Hops and Scenic Routes
• Buses are great when you do not want to navigate steps or when you prefer to see the city as you move around.
• They are especially handy for cross‑town routes, such as getting from west to east in Midtown.
4. Plan for Walking
• Manhattan is very walkable in blocks, and you will often find you cover far more on foot than you might expect. Comfortable shoes are essential, particularly for a busy 5‑day itinerary.
5. Taxis and Rideshares
• Yellow cabs and rideshare services are plentiful and useful late at night or when you are tired, but they can be slower and more expensive due to traffic. They work best for airport transfers or shorter hops when you have luggage.

When I put together your holiday, I can also include guidance on the easiest subway routes for your hotel and attractions, so you arrive confident and ready to go.

Why October Is a Brilliant Time to Visit

October is one of my favourite months for New York:

• Comfortable temperatures for walking and sightseeing
• Autumn colours in Central Park and the city’s tree‑lined streets
• A subtle Halloween atmosphere, with decorations, pumpkins and themed events starting to appear
• Often less intense humidity than the summer months, yet still long enough days to see plenty

Combine that with a balanced flight experience, a well‑located hotel like The Westin New York at Times Square, and a focused 5‑day itinerary that covers the must‑see highlights plus shopping at Woodbury Common, and you have a fantastic first‑timer’s trip.
If this itinerary appeals to you or if you would like a more tailored itinerary to your wishes, why not get in contact and I will take the stress out of organising your amazing trip to the Big Apple for you.