New York

Five Days, Five Boroughs

Program No. 1725RJ
Discover authentic New York on insider-led walks as you learn about architecture, historic monuments and cultural institutions in each of the city’s five boroughs.

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At a Glance

Think you know New York? We invite you to come explore and get to know the whole city. Each day, discover fascinating aspects of each of the five boroughs on educational field trips to meet its people, experience its cultural institutions and explore historic neighborhoods with insider perspectives. Top off your experience with a ride from the inspirational to the sublime, from the rebirth of the Bronx to mansions on the Hudson.
Activity Level
Let's Go!
Walking 5–8 miles per day with lots of stairs. Public transportation used exclusively throughout program.
Small Group
Small Group
Love to learn and explore in a small-group setting? These adventures offer small, personal experiences with groups of 13 to 24 participants.

What You'll Learn

  • Discover the fascinating history and architecture of New York boroughs with narrated walks and illustrated lectures.
  • Walk the magnificent Brooklyn Promenade with its legendary view of the Brooklyn Bridge and Manhattan skyline.
  • Ride the Staten Island ferry past the Statue of Liberty.

General Notes

This is a standard Road Scholar program with a maximum of 38 participants. Select 2022 dates are designated for small groups and are limited to 24 participants or less. All 2023 dates are designated for small groups.
Featured Expert
All trip experts
Profile Image
Karl Baudendistel
A New York City resident for more than 25 years, Karl Baudendistel loves sharing his knowledge of the city with visitors from around the world. Having spent 20 years overseeing ‘the business of show business’ for numerous Broadway and touring productions, chances are he’s been to a city near you. Karl is a member of The Association of Theatrical Press Agents and Managers, is a trained sommelier and was educated at New York University’s Tisch School of the Arts.

Please note: This expert may not be available for every date of this program.

Profile Image of Karl Baudendistel
Karl Baudendistel View biography
A New York City resident for more than 25 years, Karl Baudendistel loves sharing his knowledge of the city with visitors from around the world. Having spent 20 years overseeing ‘the business of show business’ for numerous Broadway and touring productions, chances are he’s been to a city near you. Karl is a member of The Association of Theatrical Press Agents and Managers, is a trained sommelier and was educated at New York University’s Tisch School of the Arts.
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Year
2024
  • 2024
  • 2025
Date
Oct 27 - Nov 01
  • May 12 - May 17
  • May 19 - May 24
  • Jun 09 - Jun 14
  • Jun 23 - Jun 28
  • Sep 01 - Sep 06
  • Sep 15 - Sep 20
  • Sep 29 - Oct 04
  • Oct 13 - Oct 18
  • Oct 27 - Nov 01
Please Note: The program differs on certain dates.
Please Note: The program differs on certain dates.
Select trip year and date
2024
  • 2024
  • 2025
Oct 27 - Nov 01
  • May 12 - May 17
  • May 19 - May 24
  • Jun 09 - Jun 14
  • Jun 23 - Jun 28
  • Sep 01 - Sep 06
  • Sep 15 - Sep 20
  • Sep 29 - Oct 04
  • Oct 13 - Oct 18
  • Oct 27 - Nov 01
While we make every effort to ensure the accuracy of our published materials, programs are typically advertised more than a year prior to their start date. As a result, some program activities, schedules, accommodations, personnel, and other logistics occasionally change due to local conditions or circumstances. Should a major change occur, we will make every effort to alert you. For less significant changes, we will update you during orientation. Thank you for your understanding.
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6 days
5 nights
12 meals
5 B 3 L 4 D
DAY
1
Check-in, Registration, Orientation, Welcome Dinner
New York
D
New Yorker Hotel

Activity note: Hotel check-in from 4:00 p.m. Remember to bring your nametag (sent previously).

Afternoon: Program Registration: 4:00 p.m. Join us in the meeting room to register with the program staff and receive a final itinerary and any updated information. The location of our Road Scholar meeting room will be sent to you the week before in a welcome email from the program provider. Hotel security will also be able to direct you. If you arrive after this evening’s scheduled events, the Group Leader will leave an envelope with the Front Desk; please ask for it when you arrive. Orientation: 4:30 p.m. In the same space, the Group Leader will greet everyone and lead introductions. We will review the up-to-date program schedule, discuss roles and responsibilities, logistics, safety guidelines, emergency procedures, and answer questions. We will learn from local experts who will give lectures and lead field trips. We will be walking a lot and using the New York City subway system which involves going up and down flights of stairs, long corridors, and often crowded conditions. It’s what New Yorkers do every day! Everyone will receive a MetroCard. If you've been with us before and have a Senior MetroCard, please bring it with you. Periods in the daily schedule designated as “Free time” and “At leisure” offer opportunities to do what you like and make your experience even more meaningful and memorable according to your personal preferences. The Group Leader will be happy to offer suggestions. Program activities, schedules, personnel, and indicated distances or times may change due to local circumstances/conditions. In the event of changes, we will alert you as quickly as possible. Thank you for your understanding.

Dinner: In the Tick Tock Diner just off the lobby of our historic hotel. Dinner in the diner is included even if you arrive late. Dinners are early in order to have plenty of time available for engaging in evening activities as a group and individually.

Evening: We’ll wrap up our evening with a short stroll to familiarize ourselves with the neighborhood.

DAY
2
Introduction to NYC, Queens Field Trip
New York
B,L,D
New Yorker Hotel

Activity note: Use of New York City public transportation (subway); extensive stair climbing. Walking up to 8 miles with stops along the way; city streets and sidewalks.

Breakfast: In the Tick Tock Diner.

Morning: Our program is designed to give a broad overview of New York City with a taste of its five boroughs: the Bronx, Brooklyn, Manhattan, Queens, and Staten Island. We’ll spend more time in some and less in others. As part of our exploration of the five boroughs, we’ll experience the wide variety of transportation New York offers its residents. We’ll start the day by registering with the Metropolitan Transportation Authority (MTA) for a senior citizen MetroCard (if you are 65 or over). This cost is included in the program price. A representative from the MTA will take your picture and a copy of your driver’s license to process your permanent MetroCard application. They will give you a temporary card to use for the week, enabling you to ride for half price. A few weeks after you return home, you will receive a permanent card in the mail — your official invitation to come back to New York! If you have been on a previous program and have a Senior MetroCard, please bring it with you. If you’re under 65, you’ll be supplied with a full-fare MetroCard. Next, we’ll meet an expert who will give us an introduction to the boroughs, each with its own history, personality, and appeal. Following our lecture, our expert will lead us over to the #7 Train, often dubbed “The International Express.” Queens is one of the most ethnically and culturally diverse counties in the entire United States. We will set out on a walking field trip through one of the neighborhoods that sprang up in the early 20th century and has seen marked demographic change over the last 100 years.

Lunch: At a neighborhood restaurant in Queens.

Afternoon: We will continue exploring Queens. Before returning to the hotel for a short break, we'll visit The Edge Observatory for a “big picture” look at the city. Just two blocks away from the hotel in the new Hudson Yards complex, The Edge is the highest outdoor sky deck in the Western Hemisphere. It provides an unequaled panoramic vista allowing us to take in the entire skyline from one place.

Dinner: At a restaurant near the hotel.

Evening: Continuing our exploration of the city, we will have a series of elective after-dinner walks with a local expert. Tonight’s walk will visit the outdoor 9/11 Memorial. Note: Our field trip does not include the 9/11 Museum or the 1 World Observatory that are separate from the Memorial. If you wish to visit them during your time in New York, we recommend making reservations online before leaving home for a date and time convenient for you.

DAY
3
Brownstone Brooklyn
New York
B,L,D
New Yorker Hotel

Activity note: Use of New York City public transportation (subway); extensive stair climbing. Walking up to 8 miles with stops along the way; city streets and sidewalks.

Breakfast: At the hotel.

Morning: Today it’s “Brownstone Brooklyn.” A subway ride will take us back in time as we go with our architectural historian to a few Brooklyn neighborhoods where we’ll learn about the development of this borough throughout the 19th century. Until it was consolidated into the City of New York in 1898, Brooklyn was an independent city. It was founded by the Dutch in 1646 as the village of Breukelen. Today it is one of the most densely populated of all the boroughs, and if it were its own city, it would be the fourth largest in the United States, rivaling Philadelphia and Houston.

Lunch: At a restaurant in Brooklyn.

Afternoon: We’ll continue our exploration of Brooklyn with a stroll along the renowned Brooklyn Promenade and view the Brooklyn Bridge, one of America’s most significant engineering achievements in the 19th century. Designed by a German immigrant, John A. Roebling, this magnificent suspension bridge of granite and steel took 14 years to complete (1869-1883), spanning the East River to connect Brooklyn and Manhattan. Sadly, Roebling didn’t survive to its completion. His son Washington Roebling took over supervision of the construction until his health took a turn for the worse and was replaced in turn by his wife, Emily — an incredibly rare position of power for a woman in the 19th century. We’ll return to the hotel via the East River Ferry.

Dinner: At a restaurant near the hotel.

Evening: Tonight’s elective walk will be to Times Square to learn some of the history and see this storied crossroads lit up at night. It is actually brighter at night with the lights on than it is in full daylight. If you’re interested in seeing a Broadway matinee on Wednesday, a local expert will explain how to use the TKTS booth to secure an advance ticket this evening.

DAY
4
Lower Manhattan & Staten Island
New York
B,L
New Yorker Hotel

Activity note: Use of New York City public transportation (subway); stair climbing. Getting on/off a ferry. Walking 5-8 miles with stops along the way; city streets and sidewalks.

Breakfast: At the hotel.

Morning: With the Group Leader, we will travel via subway to the very bottom of Manhattan Island, where we’ll then board the Staten Island Ferry for a ride across bustling New York Harbor to the city’s smallest borough (population less than 500,000). On our way, we’ll have a fantastic close-up view of the Statue of Liberty. We’ll focus our short visit to Staten Island on the historic Fort George neighborhood.

Lunch: At a restaurant on Staten Island.

Afternoon: Returning to Manhattan, our Group Leader will lead us on a walking field trip through the oldest continually occupied section of Manhattan. Today, it’s the financial district.

Dinner: This meal has been excluded from the program cost and is on your own to enjoy what you like. The Group Leader will be happy to offer suggestions.

Evening: At leisure. This is an excellent opportunity to take in a Broadway show. If you wish to attend a performance, you may want to order tickets in advance. The app TODAYTIX may be helpful in this regard. The fees are modest and significantly below those paid on Ticketmaster or Telecharge. And don't forget the TKTS Discount Booth in Times Square for day-of tickets which you'll see and learn about during the elective Times Square field trip earlier in the week. Many performances are available at 20-50 percent off regular prices.

DAY
5
The Bronx, Upper Manhattan
New York
B,D
New Yorker Hotel

Activity note: Getting on/off a motorcoach; city driving, several hours riding time throughout the day. Use of New York City public transportation (subway); extensive stair climbing. Walking 3-5 miles with stops along the way; city streets and sidewalks.

Breakfast: At the hotel.

Morning: Today we will explore aboard a private motorcoach. With our local expert, we’ll ride through Upper Manhattan and Harlem, arriving in The Bronx where we’ll see a variety of neighborhoods representative of the vast changes that impacted this borough over the course of the 20th century. We’ll discuss some of the factors and results of these changes.

Lunch: On your own to enjoy what you like along Arthur Avenue in the Little Italy section of the Bronx. The Group Leader will be happy to offer suggestions.

Afternoon: Our exploration will continue through The Bronx to Wave Hill where we’ll have some time to explore its beautiful gardens overlooking the Hudson River independently. We’ll then return to the hotel for a short break.

Dinner: At a neighborhood restaurant near the hotel. Share favorite experiences with new Road Scholar friends during our farewell dinner.

Evening: We’ll hop on the subway one last time and head downtown for an elective stroll over the iconic Brooklyn Bridge. Returning to the hotel, the remainder of the evening is at leisure. Prepare for check-out and departure after our closing session in the morning.

DAY
6
Living in New York City, Program Concludes
New York
B

Activity note: Hotel check-out by 12:00 Noon.

Breakfast: At the hotel.

Morning: As a final highlight, we’ll be joined by a New Yorker for a closing discussion about living in the city: how current New Yorkers manage it, how celebrated writers have portrayed it, and how we have experienced it during our program. We expect the session to end by 10:30 a.m. This concludes our program. If you are returning home, safe travels. If you are staying on independently, have a wonderful time. If you are transferring to another Road Scholar program, detailed instructions are included in your Information Packet for that program. We hope you enjoy Road Scholar learning adventures and look forward to having you on rewarding programs in the future. Don’t forget to join our Facebook page and follow us on Instagram. Best wishes for all your journeys!






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