Planning a Northeast getaway? This 5-day itinerary from New York City to Boston is the perfect blend of iconic landmarks, rich history, and vibrant cultural experiences-ideal for travelers seeking both structure and spontaneity. Whether you’re a first-time visitor or a frequent road tripper, this route along the I-95 corridor is packed with must-see stops and local gems that you can fully customize using TripPilot’s AI trip planner.
Let’s break down the itinerary of New York & Boston so you can make the most of your journey-and then personalize it to match your pace, interests, and travel style.
Day 1: Explore the Icons of New York City
Kick off your adventure in one of the most dynamic cities in the world-New York City. From towering landmarks to cultural hot spots, Day 1 is all about embracing the city’s signature energy.
Morning:
- Start with a ferry ride to the Statue of Liberty and Ellis Island. Learn about America’s immigration history while soaking in skyline views.
Afternoon:
- Stroll through Central Park, one of the city’s most beloved green spaces. Whether you rent a bike, visit the Central Park Zoo, or relax by Bethesda Terrace, you’ll feel a world away from the city's bustle.
Evening:
- Catch a Broadway show or simply take in the electric vibe of Times Square.
- Wrap up your night with dinner at a Midtown rooftop restaurant, offering delicious food with unforgettable skyline views.
Day 2: NYC to New Haven, CT – History and Ivy League Charm
Approximate drive: 2 hours
Say goodbye to the skyscrapers and begin your scenic journey northeast. Your first stop: New Haven, Connecticut, home to Yale University and coastal charm.
Morning:
- Head north through the Bronx, taking in views of the Harlem River and stopping for a quick bite or photo op in Pelham Bay Park, NYC’s largest green space.
Midday & Afternoon:
- Arrive in New Haven and explore the prestigious Yale University campus. Visit the Yale University Art Gallery or tour the gothic-style architecture.
- Grab a slice at Frank Pepe Pizzeria Napoletana, one of the country’s most famous pizzerias.
Evening:
- End the day with a sunset stroll at Lighthouse Point Park, where you’ll catch ocean breezes and views of the historic lighthouse.
Add personal interests, more museums, or foodie stops by building this route with TripPilot’s custom travel itinerary planner.
Day 3: New Haven to Providence, RI – Seaport Culture & Creative Vibes
Approximate drive: 2.5 hours
Continue your adventure through coastal New England with a mix of maritime history and artful living.
Morning Stop – Mystic, CT:
- Take a short detour to the Mystic Seaport Museum, the nation's leading maritime museum. You can climb aboard historic ships and explore the recreated 19th-century seafaring village.
Afternoon:
- Arrive in Providence, Rhode Island, a city known for its art scene and creative culinary culture.
- Have lunch by the marina or explore Federal Hill, Providence’s Little Italy.
Evening:
- Dive into the local art world at the RISD Museum or catch an event at WaterFire (seasonal). Finish your day with craft cocktails at a local speakeasy.
Day 4: Providence to Boston – Colonial Roots & Modern Energy
Approximate drive: 1.5 hours
Your final destination is Boston, one of America’s oldest cities, rich with Revolutionary War landmarks, elite universities, and modern neighborhoods.
Morning:
- Drive into Boston and head straight to the Freedom Trail-a 2.5-mile walk that connects 16 historical sites including Paul Revere’s House and Old North Church.
Afternoon:
- Shop, snack, and people-watch at Faneuil Hall Marketplace. The cobblestone streets are filled with performers, vendors, and food from around the world.
Evening:
- End your day with an Italian dinner in Boston’s North End, where you’ll find family-owned trattorias and authentic pastries from Mike’s Pastry.
Day 5: Discover More of Boston or Extend Your Adventure
Use your last day to slow things down-or dive deeper into Boston's world-class institutions.
Morning Options:
- Tour the Museum of Fine Arts or head across the river for a guided visit of Harvard University in Cambridge.
Afternoon:
- Take a Charles River cruise or stroll along the Esplanade, where locals bike, kayak, and picnic by the water.
Evening or Departure:
- Choose to extend your itinerary with nearby escapes like Cape Cod, Salem, or even Portland, Maine.
TripPilot’s dynamic itinerary planner makes it easy to add extra days or change direction on the fly.
Ready to Travel Your Way?
Whether you’re traveling solo, with friends, or planning a family getaway, this 5-day itinerary from NYC to Boston offers the perfect foundation-and TripPilot helps you personalize every mile.
Customize a 5-day itinerary from NYC to Boston - Our AI trip planner builds a personalized itinerary in minutes, tailored to your pace, preferences, and travel goals.
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