New York City 16-Day Trip Itinerary

Arrive in NYC & Hotel Check-in

Arrive at your New York City accommodation, settle in, and prepare for your first explorations.

Take a moment to refresh after your journey.

After checking in, you can take the subway or a taxi to your first activity. Purchase a MetroCard for easy public transport access.

NYC Private Walking Tour

Enjoy a private, customized walking tour of New York City with a local guide, gaining an insider's perspective on iconic sights and hidden gems.

Your guide will customize the tour based on your interests. Wear comfortable shoes as this is a walking tour.

New York Public Library Visit

Visit the monumental main branch of the New York Public Library, known for its stunning architecture and historical collections, including the impressive Rose Main Reading Room.

Free admission. Check for any special exhibitions or events. Respectful quiet is appreciated in reading areas.

Dinner in Midtown

Enjoy a delicious dinner in Midtown Manhattan, with various options ranging from classic American to international cuisine.

Consider making reservations, especially if dining alone or at a popular spot. Many restaurants offer pre-theater menus.

Hamilton & Washington Revolutionary Walking Tour

Embark on a captivating journey through history in Lower Manhattan, visiting sites significant to Alexander Hamilton and George Washington with an expert guide.

A fantastic tour for history buffs. Book in advance. Comfortable shoes are essential for walking.

One World Observatory Visit

Experience breathtaking panoramic views of New York City, its iconic landmarks, and surrounding waters from the One World Observatory, located atop the One World Trade Center.

Book tickets online in advance to secure your preferred time slot and avoid long queues. Allow time for security checks.

Stroll The Battery

Enjoy a leisurely walk through The Battery park, offering beautiful waterfront views of the Statue of Liberty, Ellis Island, and the New York Harbor.

A great spot for photos.

Ferries to the Statue of Liberty and Ellis Island depart from here if you wish to extend your visit.

Dinner at The Seaport

Dine at The Seaport, a lively area with diverse culinary options and a vibrant atmosphere, perfect for an evening meal after exploring downtown.

The Seaport offers a variety of restaurants, from casual to more upscale. Enjoy the historic waterfront setting.

#1 Rated NYC Chinatown Food and History Walking Tour with FNYT

Explore the vibrant and historic Chinatown, enjoying three sit-down indoor tastings while learning about the neighborhood's rich culture and hidden gems with Foods of NY Tours.

Come hungry! This tour includes plenty of food. Wear comfortable shoes for walking through the bustling streets.

Museum at Eldridge Street

Visit the stunning Museum at Eldridge Street, housed in a magnificent, restored 1887 synagogue, offering a glimpse into Jewish American history and architectural beauty.

Check for tour times or self-guided options. The architecture alone is worth the visit.

Walk the Brooklyn Bridge

Enjoy an iconic walk across the Brooklyn Bridge, offering spectacular views of the Manhattan skyline, the Statue of Liberty, and the East River.

Connects Manhattan to Brooklyn.

Start from the Manhattan side for the best views towards the city. Beware of cyclists; stay in the pedestrian lane. Wear comfortable shoes.

Dinner in DUMBO, Brooklyn

Experience the vibrant dining scene in DUMBO (Down Under the Manhattan Bridge Overpass) in Brooklyn, offering a range of casual eateries with waterfront views.

Consider dining at one of the many pizza places or waterfront restaurants. It's a great spot for evening photos of the Manhattan skyline.

Central Park Pedicab Tour– Top Highlights

Discover the magic of Central Park on a private pedicab tour with a friendly local guide.

See iconic spots like Bethesda Terrace, Strawberry Fields, and Literary Walk.

Pedicabs are a relaxing and efficient way to cover a lot of ground in the park. Perfect for photos.

Central Park Photography Tour

Capture the beauty of Central Park with a local photographer who will guide you to the best spots and offer tips on scouting for images and visual editing.

Bring your camera or smartphone. This tour is great for improving your photography skills while enjoying the park.

Pre-Show Dinner

Enjoy an early dinner in the Theater District, with many restaurants offering convenient pre-show menus perfect for catching a Broadway production.

Reservations are highly recommended for pre-theater dining. Inform the restaurant if you have a show to catch.

Experience a Broadway Show

Immerse yourself in the magic of live theater with an evening Broadway performance.

Choose from a variety of musicals and plays showing in the iconic Theater District.

Book tickets well in advance, especially for popular shows. Check discount ticket vendors like TKTS for same-day deals if you're flexible.

NYC Secrets of Grand Central Private Walking Tour

Discover the hidden tennis court, the backwards ceiling, and many other secrets and surprising history of Grand Central Terminal on this private guided walking tour.

An fascinating look into one of NYC's most iconic buildings. Your guide will share unique insights.

Fifth Avenue Shopping

Explore the legendary Fifth Avenue, renowned for its luxury boutiques, flagship stores, and iconic department stores.

Ideal for unique shopping experiences.

Even if just window shopping, Fifth Avenue offers a quintessential NYC experience. Popular stores include Saks Fifth Avenue, Tiffany & Co., and Bergdorf Goodman.

Color Factory New York

Immerse yourself in a vibrant world of color at the Color Factory, an interactive art experience voted the #1 Immersive Art Experience in America.

Book tickets in advance as time slots can fill up quickly. A fun and visually stimulating experience, great for photos.

Fine Dining Experience

Indulge in a fine dining experience, choosing from New York City's world-renowned culinary scene, offering exquisite cuisine and impeccable service.

Reservations are essential, often weeks in advance for top establishments. Dress code may apply.

Chinatown Food & History Tour

Embark on the #1 Rated NYC Chinatown Food and History Walking Tour with FNYT.

Enjoy 3 sit-down indoor tastings while exploring historic landmarks and hidden side streets.

Meet your guide at a designated spot in Chinatown. Come hungry!

Central Park Pedicab Tour

Discover the magic of Central Park on a private pedicab tour, seeing top highlights like Bethesda Terrace, Strawberry Fields, and the Cherry Hill Fountain with a friendly local guide.

Pedicabs are efficient for seeing a lot of the park in a short time. Your guide can customize the route.

Dinner in Greenwich Village

Enjoy a casual dinner in the charming and historic Greenwich Village, known for its diverse culinary scene and bohemian atmosphere.

Explore quaint streets after your meal.

Many cozy cafes and restaurants, perfect for a relaxed evening. Consider 'Minetta Tavern' for classic American or 'Joe Allen' for a Broadway-adjacent experience.

Grand Central Secrets Tour

Embark on the NYC Secrets of Grand Central Private Walking Tour to uncover hidden gems, surprising history, and fascinating facts about this iconic New York City landmark.

Learn about the Whispering Gallery, the hidden tennis court, and other architectural marvels.

New York Public Library Visit

Visit the monumental main branch of the New York Public Library, known for its stunning Beaux-Arts architecture and the magnificent Rose Main Reading Room.

Take a moment to appreciate its grandeur.

Check for any free guided tours offered upon arrival. It's a peaceful escape from the city bustle. Booking: https://www.tripadvisor.com/Attraction_Review-g60763-d116236-Reviews-New_York_Public_Library-New_York_City_New_York.html?m=66827

Times Square Exploration & Shopping

Immerse yourself in the dazzling lights and vibrant energy of Times Square.

Explore the surrounding shops, grab a snack, and soak in the iconic atmosphere.

Beware of crowds, especially in the afternoon. Perfect for people-watching and souvenir shopping.

Broadway Show

Experience the magic of a live Broadway performance.

Choose from a variety of award-winning musicals or captivating plays for a quintessential New York cultural experience.

Book tickets in advance for best seats and prices. Consider a pre-theater dinner near your chosen venue.

Late Fine Dining

Indulge in a fine dining experience to cap off your evening.

New York offers an array of Michelin-starred restaurants and upscale eateries.

Consider a restaurant near the Theater District like 'Per Se' (if you're feeling extravagant) or 'Blue Hill' for farm-to-table cuisine. Reservations are highly recommended.

Last NYC Breakfast

Enjoy a final New York breakfast at a local diner or cafe near your hotel before heading to the airport.

Grab a classic bagel with cream cheese or a hearty diner meal.

Transfer to NYC Airport

Travel from your hotel to one of New York City's major airports (JFK, LGA, or EWR) for your flight to Orlando.

Allow ample time for traffic, especially if traveling to JFK or EWR. Consider public transport, ride-share, or a pre-booked car service.

Flight to Orlando

Fly from New York City to Orlando International Airport (MCO).

Enjoy in-flight entertainment or catch up on some reading during your journey south.

Orlando Hotel Check-in

Arrive in Orlando, transfer to your hotel, and check in.

Settle into your new surroundings before dinner.

Pre-arrange airport transfer or use a ride-share service. Many hotels offer shuttle services to theme parks.

Casual Dinner in Orlando

Enjoy a relaxed dinner near your hotel in Orlando.

There are many family-friendly and casual dining options available.

Depending on your hotel location, explore options along International Drive or in the Disney Springs area for a wide variety.

Walt Disney World: Magic Kingdom

Spend a full magical day exploring the iconic Magic Kingdom park.

Enjoy classic rides, character encounters, and the famous Cinderella Castle.

Arrive early to maximize your time. Consider using the My Disney Experience app for wait times, mobile ordering, and Genie+ planning. Booking required for park entry.

Dinner & Fireworks

Enjoy dinner at a casual restaurant within or near Magic Kingdom, followed by the enchanting evening fireworks display over Cinderella Castle.

Book dining reservations in advance if you prefer a table-service restaurant. Check showtimes for the fireworks display.

Private Day Sailing Experience

Experience the joy of sailing on the beautiful Central Florida lakes with a private 2-hour day sailing tour, offering scenic views and a relaxing escape.

Confirm exact meeting location and wear comfortable clothing. Enjoy the tranquility of the water.

Lunch at Universal CityWalk

Grab a casual lunch at Universal CityWalk, a vibrant entertainment complex offering a variety of dining options, from quick bites to sit-down restaurants.

A great spot to fuel up before heading into the theme parks, with choices like burgers, pizza, or Mexican cuisine.

Universal Studios Florida

Spend the afternoon at Universal Studios Florida, enjoying thrilling rides, immersive worlds like The Wizarding World of Harry Potter - Diagon Alley, and exciting shows.

Consider purchasing the Universal Express Pass if you want to skip lines. Download the Universal Orlando Resort app for park maps and wait times. Booking required for park entry.

Dinner near Universal

Enjoy a mid-range dinner at one of the many restaurants located around the Universal Orlando Resort area or along International Drive.

CityWalk has many options, or venture to nearby International Drive for a wider selection of cuisines and price points.

Walt Disney World's Magic Kingdom

Spend a full day immersed in the magic of Cinderella Castle, classic rides, and enchanting parades.

Enjoy the various lands like Fantasyland, Adventureland, and Tomorrowland.

Arrive early to maximize your time. Consider using Disney Genie+ for quicker access to attractions. Wear comfortable shoes!

Dinner at Liberty Tree Tavern

Enjoy a patriotic, all-you-care-to-enjoy meal in a colonial-style inn located in Liberty Square.

Reservations are highly recommended, especially for dinner. Offers traditional American fare.

Disney Fireworks & Projections

Conclude your day with a spectacular fireworks and projection show over Cinderella Castle.

Find a good viewing spot in Liberty Square or Main Street U.S.A. early.

Explore Lake Eola Park

Enjoy a leisurely walk around the iconic Lake Eola Park in downtown Orlando.

You can rent swan-shaped paddle boats and admire the Orlando skyline.

A beautiful urban park perfect for relaxation and light activity. Check for local farmers' markets or events on Saturdays.

Lunch in Downtown Orlando

Grab a casual lunch at a local eatery in the vibrant downtown Orlando area, near Lake Eola.

Many cafes and restaurants are available, from casual delis to diverse cuisines.

Private 2-Hour Sailing Experience

Experience the tranquility of Central Florida's lakes on a private sailing tour.

Relax and enjoy the scenic views from the water.

Book in advance for this private experience. This is based on Viator's 'Private 2-Hour Day Sailing Experience'. Confirm meeting point and what to bring.

Dinner at Kres Chophouse

Indulge in a fine dining experience at Kres Chophouse, known for its elegant ambiance and excellent steaks and seafood.

Reservations highly recommended. Dress code is smart casual. Located in a historic building downtown.

Epcot: World Showcase & Future World

Explore the wonders of Epcot, from the cultural pavilions of World Showcase, where you can 'travel the world,' to the innovations of Future World.

Try snacks and drinks from different countries in World Showcase. Enjoy rides like Test Track and Spaceship Earth. Check for festival schedules.

Dinner in Morocco Pavilion

Dine at one of the authentic restaurants within Epcot's Morocco Pavilion, offering unique Moroccan cuisine and cultural ambiance.

Spice Road Table offers small plates with waterfront views, while Restaurant Marrakesh provides a more traditional setting with entertainment. Reservations are recommended.

Epcot Nighttime Spectacular

Witness Epcot's breathtaking nighttime show, a harmonious blend of fireworks, water, and light over World Showcase Lagoon.

Popular viewing spots fill up quickly; arrive early for a good vantage point.

Introductory Indoor Tactical Experience

Engage in an immersive indoor tactical theme park experience, offering various scenarios for training and competition in a safe and controlled environment.

Perfect for those seeking a unique, active, and mentally stimulating challenge. Check age and height restrictions. This is based on Viator's 'Basic Drill: Introductory Indoor Tactical Experience'.

Shopping at Orlando Premium Outlets

Enjoy an afternoon of retail therapy at one of Orlando's large premium outlet centers, offering a wide array of brands and discounts.

Bring comfortable walking shoes. Consider visiting early afternoon to avoid larger crowds.

Event at Kia Center

Attend a live event, concert, or sports game at the state-of-the-art Kia Center in downtown Orlando.

Check the Kia Center's official schedule for May 10th for available events and book tickets in advance. Based on TripAdvisor's 'Kia Center'.

Morning Leisure at Resort

Enjoy a relaxed morning at your hotel.

Take a dip in the pool, use the fitness center, or simply enjoy a slow breakfast.

Visit Orlando Museum of Art (Optional)

Explore the Orlando Museum of Art, featuring a diverse collection of American, African, and ancient American art.

A good cultural 'hidden gem' away from the parks.

Check current exhibitions and opening hours. Admission fees apply. This provides an alternative cultural experience.

Casual Lunch at Tin & Taco

Enjoy a delicious and creative casual lunch at Tin & Taco, known for its unique taco combinations and relaxed atmosphere.

Multiple locations throughout Orlando, offering a lively and affordable dining option.

Packing and Departure Preparation

Use the afternoon to pack your belongings, check out from the hotel, and prepare for your onward journey to New York City tomorrow.

Ensure all bookings for your next travel segment are confirmed.

Hotel Checkout & Transfer

Enjoy a final breakfast in Orlando, complete any last-minute packing, and check out from your accommodation.

Arrange for a taxi, ride-share, or shuttle service to Orlando International Airport (MCO).

Ensure you have all your belongings and any souvenirs purchased during your trip. Plan to arrive at the airport at least 2 hours before your domestic flight to New York.

Check-in for NY Flight

Proceed to your airline's counter or self-service kiosk at Orlando International Airport (MCO) for check-in and baggage drop-off for your flight to New York.

Have your ID and flight confirmation ready. Security lines can be unpredictable, so allow ample time.

Flight to New York

Board your flight from Orlando International Airport (MCO) to a New York area airport (e.

g., JFK). Enjoy the flight and relax before your international connection.

Grab a snack or light meal during your flight if available, as there will be limited time during transit in New York.

New York Airport Transit

Upon arrival at your New York airport (e.

g., JFK), proceed to your connecting terminal for your flight to Calgary. Use this time to stretch your legs, grab a quick meal or coffee, and prepare for your next flight.

Check your departure gate and terminal for the Calgary flight. Depending on the airline, you might need to re-check baggage if changing terminals or airlines, or pass through security again.

Check-in for Calgary Flight

Head to your airline's gate for your international flight from New York to Calgary.

Complete any final check-in procedures if necessary.

Ensure your passport and any required travel documents for Canada are readily accessible.

Flight to Calgary

Depart New York for your final journey back home to Calgary.

Reflect on the wonderful memories made during your New York and Orlando adventure.

Adjust your watch to Mountain Time (MDT) during the flight. Enjoy your final leg home!