New York City 19-Day Trip Itinerary

Arrive in New York City

Arrive in New York City.

Take public transport (subway or bus) or a shared ride service from the airport (JFK, LGA, or EWR) to your accommodation in Manhattan.

Consider pre-booking an airport shuttle for ease, or use the MTA subway/bus for a budget-friendly option. A 7-day unlimited MetroCard might be a good investment for your time in NYC.

Hotel Check-in & Freshen Up

Check into your hotel and take some time to settle in and freshen up after your journey.

Look for hotels near subway lines for easy access to attractions.

Explore Times Square

Immerse yourselves in the dazzling lights, giant billboards, and bustling energy of Times Square.

It's an iconic, must-see experience, especially as evening approaches.

Be aware of crowds and street performers. Avoid eating at restaurants directly in Times Square for better value.

Dinner in Hell's Kitchen

Enjoy an affordable and delicious dinner in the Hell's Kitchen neighborhood, known for its diverse restaurants just west of the Theater District.

Many cuisines are available, from Thai to Italian. Look for early bird specials or pre-fixe menus for budget options.

Evening Stroll & Broadway Buzz

Take an evening stroll through the Theater District, soaking in the atmosphere even if you're not attending a show.

Enjoy the vibrant nightlife.

Tkts booth in Times Square offers same-day discounted Broadway tickets if you decide to splurge on a show last minute.

Statue of Liberty & Ellis Island

Take the ferry to Liberty Island to see the Statue of Liberty up close, then continue to Ellis Island to explore the museum of immigration.

This is a crucial historical experience.

Book tickets online in advance, especially for Crown/Pedestal access, as they sell out quickly. Arrive early at Battery Park for the ferry.

Lunch near Wall Street

Grab a quick and affordable lunch in the Financial District, perhaps at a deli or food cart.

Wall Street & Charging Bull

Explore the historic Wall Street area, see the New York Stock Exchange, and take photos with the iconic Charging Bull and Fearless Girl statues.

The area can be crowded, especially around the bull. Best to visit slightly off-peak if possible.

9/11 Memorial Pools

Visit the solemn 9/11 Memorial and its twin reflecting pools, a moving tribute to the victims of the 2001 and 1993 attacks.

The museum requires tickets, but the outdoor memorial pools are free to visit.

Walk the Brooklyn Bridge

Stroll across the iconic Brooklyn Bridge from Manhattan into Brooklyn, enjoying breathtaking views of the Manhattan skyline.

Wear comfortable shoes. The pedestrian path is separate from cars but shared with cyclists. Consider walking to DUMBO afterwards.

Dinner in DUMBO

Enjoy dinner in the DUMBO (Down Under the Manhattan Bridge Overpass) neighborhood, known for its scenic views and trendy eateries.

Great photo opportunities with the Manhattan Bridge and Empire State Building in the background.

Central Park Exploration

Enjoy a leisurely morning stroll through Central Park.

Visit iconic spots like Bethesda Terrace, Strawberry Fields, and The Lake.

Rent bicycles for a faster way to see more of the park, or simply enjoy a relaxing walk.

Metropolitan Museum of Art

Immerse yourselves in art and culture at The Met, one of the world's largest and finest art museums.

Choose a few key sections to explore.

It's impossible to see everything; plan ahead which collections you want to prioritize. Free with a NYC cultural pass, otherwise suggested donation.

Late Lunch Upper East Side

Have a late lunch or early dinner in the Upper East Side, near the Met, with options ranging from casual cafes to classic diners.

Grand Central Terminal

Marvel at the architectural beauty of Grand Central Terminal.

Don't miss the main concourse, the zodiac ceiling, and the Whispering Gallery.

Grab a snack or coffee from the lower level food court. It's an active train station, so be mindful of commuters.

Dinner in Midtown East

Find a casual dinner spot in Midtown East, offering various cuisines convenient to Grand Central.

Greenwich Village Stroll

Wander through the charming, tree-lined streets of Greenwich Village, known for its bohemian history, unique boutiques, and historic brownstones.

Explore Washington Square Park, browse independent bookstores, and soak in the artistic ambiance.

Lunch in The Village

Enjoy a casual lunch in Greenwich Village, perhaps at a classic diner or a cozy cafe.

Walk The High Line

Stroll along The High Line, an elevated linear park built on a former railway line, offering unique perspectives of the city and public art installations.

Start at Gansevoort Street and walk north, exiting at 34th Street for easy access to other areas. It can get crowded on weekends.

Chelsea Market

Explore Chelsea Market, a popular indoor food hall and shopping mall with a wide array of culinary delights and unique shops.

Perfect for a snack, coffee, or browsing artisanal goods. Great for unique gifts or souvenirs.

Dinner in Chelsea

Have dinner in the lively Chelsea neighborhood, known for its art galleries and diverse dining scene.

Comedy Club Show

Catch a stand-up comedy show at one of Greenwich Village's famous comedy clubs for a fun evening of entertainment.

Many clubs have early and late shows. Check for student discounts or open mic nights for cheaper options.

Top of the Rock Observation Deck

Ascend to the Top of the Rock for stunning panoramic views of Manhattan, including the Empire State Building and Central Park.

Book timed tickets online in advance to avoid queues. This view offers a great perspective of the Empire State Building.

St. Patrick's Cathedral

Visit the magnificent St.

Patrick's Cathedral, a neo-Gothic Roman Catholic cathedral in the heart of Midtown.

Entry is free, but donations are welcome. Be respectful of ongoing services.

Lunch near Fifth Avenue

Enjoy lunch in the bustling area near Fifth Avenue, with many casual dining options and delis.

Fifth Avenue Window Shopping

Stroll down Fifth Avenue, admiring the iconic luxury storefronts and architecture.

It's an experience in itself, even if you're just window shopping.

Great for people-watching and soaking in the upscale atmosphere.

Explore Rockefeller Center

Spend some time exploring the public spaces of Rockefeller Center, including the plaza and its various shops.

In August, the famous ice rink is not active, but there are often outdoor art installations or events.

Farewell NYC Dinner

Enjoy a last dinner in Manhattan, perhaps trying a cuisine you haven't yet experienced or revisiting a favorite.

Metropolitan Museum of Art

Immerse yourselves in art and history at The Met, one of the world's largest and finest art museums.

Explore its vast collections spanning cultures and millennia. While general admission is suggested donation for NY residents, non-residents often pay a fixed fee.

Allocate ample time; the museum is huge. Check for any special exhibits or free tours. It's best to identify a few key areas or galleries you want to focus on beforehand.

Casual Lunch Near Met

Grab a quick and affordable lunch from a food cart or a casual cafe in the Upper East Side neighborhood after your museum visit.

Central Park Relaxation

Enjoy a leisurely stroll through Central Park, just adjacent to The Met.

Visit iconic spots like Bethesda Terrace, Bow Bridge, and Sheep Meadow. Perfect for people-watching and unwinding.

Wear comfortable shoes. Consider renting bikes if you want to cover more ground, but walking is free and offers great photo opportunities.

Dinner in NYC

Enjoy dinner at a restaurant in a neighborhood of your choice, perhaps exploring more of the Upper East Side or returning to a familiar spot from your earlier NYC days.

Walk Brooklyn Bridge

Start your day by walking across the iconic Brooklyn Bridge from Manhattan to Brooklyn.

Enjoy breathtaking views of the Manhattan skyline, the Statue of Liberty, and the East River.

Wear comfortable shoes. The walk can take about 30-45 minutes one way, plus time for photos. Go early to avoid crowds.

Explore DUMBO & Park

Discover the trendy DUMBO (Down Under the Manhattan Bridge Overpass) neighborhood.

Enjoy the scenic Brooklyn Bridge Park, take photos at Washington Street for the classic bridge view, and perhaps ride Jane's Carousel.

The area is very walkable. Many photo opportunities, especially from Brooklyn Bridge Park. Jane's Carousel is a historic landmark worth seeing, if not riding.

Lunch in DUMBO

Enjoy lunch at one of DUMBO's many eateries, from casual pizza places to diverse cafes, offering options for every taste and budget.

Williamsburg Exploration

Take the subway to Williamsburg, known for its vibrant street art, independent boutiques, vintage shops, and lively atmosphere.

Explore Bedford Avenue and its surrounding streets.

Williamsburg is easily accessible by subway (L train to Bedford Ave). It's a great area for unique finds and soaking in local culture.

Dinner in Williamsburg

Experience the diverse culinary scene of Williamsburg with dinner at one of its many acclaimed restaurants, ranging from trendy bistros to ethnic eateries.

Check Out & Head to Bus Terminal

Check out from your New York City accommodation and make your way to the Port Authority Bus Terminal for your bus to Bangor, Maine.

Bus Journey to Bangor

Embark on a comfortable bus journey from New York City to Bangor, Maine.

This will be a full day of travel, offering scenic views as you head north through New England.

Pack snacks, drinks, and entertainment for the journey. Buses usually make rest stops along the way. Your friends can meet you at the Bangor Transportation Center.

Arrive & Dinner with Friends

Arrive in Bangor, Maine, where your university friends will pick you up.

Settle into your accommodation and enjoy a relaxing dinner catching up with your friends.

Downtown Bangor & Landmarks

Explore downtown Bangor with your friends.

Visit the iconic Paul Bunyan Statue, drive by Stephen King's historic house (from the exterior), and take a stroll along the scenic waterfront park.

This is a great opportunity to catch up with your friends and see the local sights of Bangor.

Lunch with Friends

Enjoy lunch at a local Bangor eatery recommended by your university friends, tasting some local flavors.

Bangor City Forest Walk

If accessible with your friends, visit the Bangor City Forest for a relaxing walk or a short hike on one of its many trails. It's a great way to enjoy Maine's natural beauty.

Confirm transportation with your friends. Wear appropriate footwear for walking trails.

Dinner & Catch Up

Spend the evening having dinner with your friends, whether it's a home-cooked meal together or trying another local restaurant. Enjoy your time reconnecting!

Drive to Acadia National Park

Start your day with a scenic drive from Bangor to Acadia National Park (approximately 1 hour), assuming your friends are driving.

Head towards the main park entrance near Bar Harbor.

Confirm the drive with your friends. Pack water and snacks for the park.

Cadillac Mountain Summit

Visit Cadillac Mountain, the highest point on the U.

S. East Coast, for panoramic views of the park, islands, and coastline. Reservations for vehicle entry may be required during peak season.

Check the National Park Service website for current reservation requirements for Cadillac Mountain summit road.

Lunch in Bar Harbor

Enjoy lunch in the charming seaside town of Bar Harbor, located just outside Acadia National Park.

There are many options from casual seafood shacks to quaint cafes.

Ocean Path & Thunder Hole

Explore the scenic Ocean Path, a relatively easy walk along the coastline, offering views of Sand Beach, Otter Cliff, and the famous Thunder Hole, where waves crash into a small cavern.

Wear layers as it can be breezy by the ocean. Check tide times for the best Thunder Hole experience.

Return to Bangor & Dinner

Drive back to Bangor with your friends after a beautiful day in Acadia.

Enjoy a final dinner together, sharing memories of your park adventure.

Explore Downtown Bangor

Start your day with a stroll through downtown Bangor.

Discover local shops, historic architecture, and get a feel for the city. Don't miss the iconic Paul Bunyan Statue.

The Paul Bunyan Statue is a popular photo op and a symbol of Bangor's logging history, located near the Waterfront Park.

Casual Lunch in Bangor

Grab a budget-friendly lunch at a local cafe or diner in downtown Bangor.

There are many options offering classic American fare.

Visit Stephen King's House (Exterior)

Take a short walk or ride to see the famous (and somewhat spooky) Victorian mansion of author Stephen King.

Please respect the residents' privacy and admire from the street.

This is a private residence, so photos from the street are welcome, but do not trespass. It's a fun spot for fans of his work.

Stroll Through Mount Hope Cemetery

Explore one of the oldest garden cemeteries in the United States, known for its beautiful landscape, historic monuments, and peaceful atmosphere.

It's also mentioned in Stephen King's works.

Free to enter and offers lovely views, especially in the afternoon. A good place for a quiet walk.

Dinner with University Friends

Enjoy a relaxed evening having dinner with your university friends.

They can recommend their favorite local spots or you can cook together at their place.

This is a great opportunity to catch up and experience Bangor through a local's eyes. Consider a potluck or share the cost of a takeout meal to keep it budget-friendly.

Travel to Acadia National Park

Head to Acadia National Park and Bar Harbor, ideally driven by your friends from Bangor.

Enjoy the scenic drive to the coast.

The drive to Acadia is beautiful. If your friends are driving, offer to chip in for gas.

Ocean Path Walk & Thunder Hole

Walk along the scenic Ocean Path, enjoying breathtaking coastal views.

Be sure to stop at Thunder Hole to witness the dramatic spray of waves crashing into a small inlet.

The path is relatively flat and easy. Arrive around mid-tide for the best chance to see Thunder Hole in action. No entrance fee for this specific walk if already in the park.

Lunch at Jordan Pond House

Experience the tradition of popovers and tea (or lunch) at the historic Jordan Pond House, famous for its picturesque setting and delicious baked goods.

Reservations are highly recommended, especially during peak season. It can be a bit pricier, but a memorable experience. There are also walking trails around Jordan Pond if you want to explore more.

Summit Cadillac Mountain

Drive or hike to the summit of Cadillac Mountain, the highest point on the North Atlantic seaboard, for panoramic views of the park, islands, and ocean.

Vehicle reservations are often required to drive to the summit during peak season. Check the NPS website for current regulations. Free if entering the park.

Dinner in Bar Harbor

Enjoy dinner in the charming town of Bar Harbor.

Choose from a variety of restaurants offering fresh seafood and local cuisine before heading back to Bangor.

Bangor Public Library Visit

Spend a relaxed morning at the beautiful Bangor Public Library.

It's a historic building with impressive architecture and a quiet atmosphere, perfect for a peaceful start to the day.

Free to enter and explore. A local gem for history and culture.

Walk at Cascade Park

Enjoy a leisurely walk through Cascade Park, a scenic urban park known for its waterfall and trails, offering a refreshing natural escape within the city.

Free to visit. A great spot for some fresh air and light exercise.

Farewell Lunch with Friends

Share a final lunch with your university friends, reminiscing about your time together and enjoying some local cuisine before you prepare for your journey to Boston.

Last Minute Souvenir Shopping

Pick up some last-minute souvenirs or gifts from local shops in Bangor to remember your visit to Maine.

Look for unique Maine-themed items like maple syrup products or local crafts.

Pack for Boston

Spend the late afternoon packing and getting organized for your travel to Boston tomorrow.

Ensure everything is ready for an early start.

Double-check bus tickets and accommodation details for Boston.

Travel from Bangor to Boston

Take a comfortable bus journey from Bangor, Maine, to Boston, Massachusetts.

This will be the most budget-friendly option without a car.

Check into Boston Hotel

Arrive in Boston and check into your accommodation.

Take some time to settle in and refresh after your journey.

The Cambria Hotel offers good value and amenities, fitting a moderate budget for your stay in Boston.

Stroll the Boston Harborwalk

Enjoy a leisurely walk along the Boston Harborwalk, a public access walkway that stretches for miles along the city's waterfront.

It offers great views of the harbor and city skyline. (TripAdvisor: Boston Harborwalk, Rating: 4.6/5)

This is a free and relaxing way to see the city. You can start near your hotel or head towards the Long Wharf area.

Dinner near the Waterfront

Enjoy dinner at one of the many restaurants near Boston's waterfront.

You'll find options ranging from casual seafood shacks to more upscale dining.

Many places offer fresh seafood, a must-try in Boston. Look for specials to keep within budget.

Explore Boston Common

Begin your exploration of Boston's rich history at Boston Common, America's oldest public park.

(TripAdvisor: Boston Common, Rating: 4.4/5; Google Places: Public Garden, Rating: 4.8/5).

This is the start of the Freedom Trail and a great spot for people-watching. You'll pass by the Boston Common Frog Pond.

Stroll Through Boston Public Garden

Walk through the beautiful Boston Public Garden, America's first public botanical garden.

Enjoy its vibrant flowers, serene pond, and famous Swan Boats (seasonal). (TripAdvisor: Boston Public Garden, Rating: 4.7/5).

A tranquil escape right in the city. The Swan Boats operate seasonally; check their schedule if interested.

Guided Freedom Trail Walking Tour

Join a guided walking tour to immerse yourselves in Boston's revolutionary history.

This tour focuses on the initial sites of the Freedom Trail, bringing stories to life. (Viator: 1 If By Land Walking Tours, Rating: 5/5).

A knowledgeable guide can make history fascinating. Wear comfortable shoes as you'll be walking a lot. Booking required.

Lunch at Faneuil Hall Marketplace

Grab a quick and delicious lunch at Faneuil Hall Marketplace, offering a wide array of food stalls and eateries.

It's a bustling historic site perfect for a midday break.

Lots of diverse and budget-friendly food options in the Quincy Market building. You can also explore the market itself.

Continue Freedom Trail (Self-Guided)

After lunch, continue your self-guided exploration of the Freedom Trail.

Visit the Old State House (Google Places: Rating 4.6/5), Old South Meeting House, and the historic Granary Burying Ground.

The Old State House offers a museum (admission fee) but the exterior is impressive. Granary Burying Ground is free and holds graves of many historical figures like Paul Revere and John Hancock.

Dinner in the North End

Conclude your day with a delicious Italian dinner in Boston's historic North End, known as Little Italy.

There are many fantastic, authentic restaurants to choose from.

Be sure to try some cannolis from Mike's Pastry or Modern Pastry for dessert! It can get busy, so consider making a reservation or be prepared for a short wait.

Boston Common Exploration

Start your day exploring Boston's oldest public park.

Enjoy a leisurely stroll, people-watching, and taking in the city's green heart.

Look out for the Frog Pond, a popular spot.

Boston Public Garden Visit

Adjacent to Boston Common, this beautiful Victorian-era garden features ornate landscaping, famous swan boats, and diverse plant life. It's America's first public garden.

Consider a Swan Boat ride (seasonal) if time and budget allow.

Boston Public Library Tour

Visit the magnificent main branch of the Boston Public Library, a National Register of Historic Places site.

Admire its architecture, art, and grand reading rooms.

Free tours are often available to learn about the building's history and art.

Historic Walking Tour with Photos

Embark on '1 If By Land Walking Tours' to explore Boston's historic streets.

Your guide will show you historical photos of the exact spots you're standing on, bringing the past to life.

Be prepared for walking. Booking in advance is recommended, especially for groups.

Old State House Museum

Visit the Old State House, Boston's oldest public building and a key site of the American Revolution.

Explore its exhibits on colonial history.

Part of the Freedom Trail. Check for entry fees.

Boston Tea Party Ships & Museum

Immerse yourselves in one of America's most famous acts of rebellion with interactive exhibits, replicated 18th-century sailing vessels, and a chance to 'throw tea into the harbor'.

A very engaging and informative experience.

Boston Red Sox vs. Arizona Diamondbacks

Experience America's favorite pastime by catching a Boston Red Sox baseball game at historic Fenway Park.

A classic Boston experience!

Arrive early to soak in the atmosphere and explore the park. Food and drinks inside can be expensive, so consider eating beforehand if on a budget.

Freedom Trail North End Section

Walk a section of the historic Freedom Trail, focusing on sites leading into and within the North End, such as Paul Revere House and Old North Church.

Entry fees may apply for specific sites. Wear comfortable shoes.

North End Neighborhood Food Tour

Savor Boston’s Little Italy on the 'Private North End Neighborhood Tour'.

Sample delicious Italian food while learning about the area's rich history and culture from a local perspective.

Come hungry! This tour is Yelp's 2025 pick for Massachusetts #1 food tour.

Stroll Along Boston Harborwalk

Enjoy a relaxing walk along the Boston Harborwalk, offering beautiful views of the waterfront, historic ships, and city skyline.

A great spot for photos and enjoying the sea breeze.

Long Wharf Visit

Explore Long Wharf, one of Boston's oldest and most historically significant wharves, offering views of the harbor and easy access to ferry services.

Often bustling with activity and a good spot for a quick snack or drink with a view.

Last-Minute Souvenir Shopping

Grab some last-minute souvenirs or gifts for friends and family from Quincy Market or shops around Faneuil Hall.

A lively area with many options, from local crafts to themed gifts.

Travel to Logan Airport (BOS)

Head to Boston Logan International Airport (BOS) for your flight back to New York City.

Public transport (MBTA Silver Line from South Station or Blue Line to Airport station then shuttle) is a budget-friendly option. Taxis/rideshares are faster but more expensive.

Depart Boston for New York City

Board your flight from Boston Logan International Airport (BOS) back to LaGuardia Airport (LGA) in New York City.

Allow ample time for check-in and security at the airport, especially for international flights.