Photo: King of Hearts · CC BY-SA 4.0Boston & New York in 5 Days: The Amtrak First-Timer's Classic
Five days on the classic Northeast corridor by Amtrak: three days in Boston on the Freedom Trail, Beacon Hill and the North End, then two days in New York for Midtown icons, Central Park and downtown Manhattan. The plan re-plans itself around how you travel — swap museums for ballgames, or fine dining for slice shops, without breaking the day.
Pick a style, a budget and a pace — the route and days below re-plan themselves.
14 stops · 10 meals · 2 hotels · 1 transferThis is the editor’s pick.
5 days, 2 cities
From Boston to New York City, with 1 move between cities. The map shows the whole route — pick a day to zoom in.
Boston
Beacon Hill · Downtown · North End
- Day 1Beacon Hill: Boston Common & the State House
- Day 2Downtown: Faneuil Hall & the Old State House
- Day 3North End: The Freedom Trail & the Paul Revere House
- Coach to New York City · 5h
New York City
Midtown Manhattan · Lower Manhattan
- Day 4Midtown Manhattan: The Empire State Building & Times Square
- Day 5Lower Manhattan: The Statue of Liberty & the 9/11 Memorial
Charles Bulfinch's 1798 capitol crowning Beacon Hill, topped by the famous gold dome. Free guided tours visit the House and Senate chambers — about 45 minutes, starting in Doric Hall.
- Free guided tours run weekdays 10am-3:30pm; the public can enter 8:45am-5pm.
Founded in 1634, the oldest public park in the US. Fifty acres of lawns, the Frog Pond (skating in winter, spray pool in summer) and the start of the Freedom Trail.
- Start the Freedom Trail on the Common, then climb Beacon Hill to the gold-domed State House.
The Bull & Finch pub that inspired the TV show Cheers. Burgers, beers and TV memorabilia in a cozy Beacon Hill landmark; open daily 11am-10pm.
A narrow cobblestone lane of 1820s brick rowhouses, often called the most photographed street in the US. Walk it between Willow and Mt Vernon streets — the homes date to about 1825.
A stretch
The fine-dining room inside the Omni Parker House (1855), the longest continuously operating hotel in the US. This is the birthplace of Boston cream pie and the Parker House roll.
Classic Beacon Hill dive bar and sports pub: 8 beers on tap, darts, and regulars' favorites like the French dip and reuben. Weekday happy hour is half off appetizers until 6pm.
61-room Beaux-Arts luxury boutique on Beacon Hill: gas fireplaces, marble bathrooms, the Mooo.... steakhouse, and a rooftop deck with Charles River views. Named the #1 Hotel in Boston in the 2026 Travel + Leisure World's Best Awards.
Boston's oldest public building (1713), now a Revolutionary museum. The balcony where the Declaration of Independence was first read to Bostonians; the Boston Massacre site is marked outside.
- Open daily 10am-6pm; the $15 combo ticket with Old South Meeting House is the best deal.
The 1743 'Cradle of Liberty' plus Quincy Market's food hall: dozens of New England stalls (lobster rolls, clam chowder), 80+ shops and daily street performers. Free to wander — and the Great Hall is free to enter.
- Open Mon-Sat 10am-9pm, Sun 11am-7pm; the Great Hall itself is free.
- Three minutes apart: pair the Old State House museum with Quincy Market's food hall.
America's oldest restaurant, serving since 1826 in a pre-Revolutionary building on the Freedom Trail. The original oyster stalls still stand where Daniel Webster sat; come for the award-winning clam chowder and raw oysters.
- America's oldest restaurant sits on the Freedom Trail by Faneuil Hall — chowder after the market stalls.
Waterfront aquarium centered on the four-story Giant Ocean Tank with its Caribbean coral reef. Penguins, seals, sea turtles and a shark-and-ray touch tank.
- Timed-entry slots; adult tickets run about $32-33.
The waterfront flagship of Boston's beloved seafood chain, steps from the Freedom Trail and the Aquarium. Famous clam chowder and lobster rolls, plus a seasonal patio.
- Aquarium morning, then chowder and lobster rolls on the patio at the waterfront flagship.
America's oldest continuously operating tavern, opened in 1795 by Boston's last town crier. Pints, pub fare and live music in a multi-room historic spot near Faneuil Hall.
Stay put: 17 min walk back from the Aquarium tonight, 15 min walk to the Paul Revere House in the morning.
Downtown Boston's oldest building (c. 1680) and Paul Revere's home from 1770 to 1800. The self-guided tour covers four period rooms with Revere-family furnishings and midnight-ride exhibits.
Cash-only, lunch-only North End institution since 1974, named a James Beard America's Classic in 2018. Join the line for crisp-edged Sicilian pizza slices, arancini and calzones — most items under $5, and they close when they sell out.
Boston's 2.5-mile red-brick walking route linking 16 historic sites from Boston Common to the Bunker Hill Monument. Self-guided and free — allow half a day to go inside the buildings.
- Foundation guided 90-minute tours with costumed 18th-century guides cost $14 for adults.
- Lunch-window fuel: the cash-only Sicilian slice line sits right on the Freedom Trail.
Boston's original pizzeria, serving thin-crust brick-oven pizza in the North End since 1926. The timeworn Thacher Street original draws a steady line for classic cheese and pepperoni by the slice.
Boston's oldest standing church (1723), where two lanterns hung on April 18, 1775 launched Paul Revere's ride. Tour the sanctuary, the crypt and the Clough House.
- The $10 Discovery Pass covers the sanctuary tour, history exhibit and crypt.
- Two lanterns, one famous ride: the North End Freedom Trail stop lands you right at Old North Church.
Boston's fourth-oldest restaurant (1885): a romantic former speakeasy doing French-Italian classics and old-school cocktails near Downtown Crossing.
- Dollar oysters run daily 4-6pm and 9-10pm.
Stay put: 17 min walk back from Old North Church tonight, 15 min walk to the Paul Revere House in the morning.
Boston to New York City
301 km, rated for speed and cost. For a first-timer trip on a comfortable budget at a balanced pace, take the FlixBus / Greyhound express bus. It's only 30 min slower than the quickest option, at $ instead of $$$.
The Art Deco icon: open-air 86th-floor and glass 102nd-floor observatories with 360-degree city views. On clear days you can see six states. Book tickets online in advance.
- Open 365 days, typically 9am-midnight; tickets from $44.
Classic New York slice joint — the Times Square location of the 1975 original. Cash and card; slices are big enough to fold.
The 'Crossroads of the World': towering neon billboards, Broadway theaters and round-the-clock crowds in the heart of Midtown. Come after dark, when the billboards are brightest — it's free.
- The TKTS booth at 47th & Broadway sells same-day discounted Broadway tickets.
Italian food hall at the World Trade Center with restaurants, markets and a rooftop. Multiple counters; the rooftop has harbor views.
Business hotel by the World Trade Center, steps from the 9/11 Memorial.
Twin reflecting pools set in the tower footprints, and a museum chronicling September 11. The Memorial is free; the Museum requires timed tickets.
Observation decks on the 100th-102nd floors of One World Trade Center with panoramic harbor views. The Sky Pod elevators climb 102 floors in 47 seconds; timed tickets required.
- A natural downtown pairing: the reflecting pools, then 102 floors up in the Sky Pod.
Historic 1762 tavern where Washington bid farewell to his officers; now a restaurant and museum. The museum upstairs covers Revolutionary War history.
The ferry from Battery Park to Liberty Island and Ellis Island, with crown and museum access.
- Crown tickets sell out months ahead — book the moment you know your dates; go in the morning to beat the crowds.
A stretch
60th-floor New American restaurant with sweeping skyline views. Book for sunset; the dining room faces the harbor.
Stay put: 13 min walk back from the Statue of Liberty tonight, 3 min walk to the 9/11 Memorial in the morning.
Where to stay in Boston & New York City
Ranked for first-timer travelers on a comfortable budget. The places this plan sleeps in come first.
Boston
XV Beacon
61-room Beaux-Arts luxury boutique on Beacon Hill: gas fireplaces, marble bathrooms, the Mooo.... steakhouse, and a rooftop deck with Charles River views. Named the #1 Hotel in Boston in the 2026 Travel + Leisure World's Best Awards.
Hotel Ivy Boston Common
Budget stay by Boston Common in a historic 1877 brownstone: compact rooms at a price nothing else nearby can touch.
YOTEL Boston
Playful tech-forward Seaport hotel: 326 cabins with adjustable SmartBeds, airline-style self check-in, and the Deck 12 rooftop bar 12 stories above the harbor.
New York City
Club Quarters Hotel World Trade Center
Business hotel by the World Trade Center, steps from the 9/11 Memorial.
The Jane Hotel
1908 sailors' hotel with tiny cabin rooms in the West Village. Verify current operating status for 2026 before booking.
The Lucerne
Upper West Side boutique hotel near the Museum of Natural History. Steps from the 79th St subway and the park.
Flights to Boston & New York City
Fly into BOS (BOS)
Flight results via Travelpayouts — we may earn a commission on bookings.
Getting around Boston & New York City
How to actually move around each city — transit, rideshare, bikes, and taxis.
Boston
Public transit
The MBTA ('the T') runs the subway, buses, commuter rail and ferries. Visitors mostly need the four subway lines (Red, Orange, Blue, Green) plus the Silver Line bus rapid transit.
- MBTA subway, buses & Silver Line
Subway and Silver Line rides cost $2.40, local buses $1.70 — the same price whether you tap a CharlieCard, a paper CharlieTicket, a contactless bank card, or pay cash. Subway fares include free transfers within 2 hours.
Tip: The 7-day LinkPass ($22.50) pays off after about 9 rides; the 1-day LinkPass is $11, monthly $90. Buy passes at station vending machines.
- MBTA Commuter Rail
Purple-line trains reach Salem, Concord, Providence and other day-trip towns; Zone 1A (e.g. South Station area) rides are $2.40, same as the subway. Tickets via the mTicket app or station machines.
Tip: Weekend $10 unlimited Commuter Rail passes make out-of-town day trips cheap.
Rideshare
Uber and Lyft both operate across Greater Boston, including Logan Airport pickups. Expect surge pricing on weekend nights and during bad weather.
- Uber
Full Uber coverage in Boston and Cambridge, including UberX, XL and scheduled rides; pickups at Logan's designated rideshare areas.
Tip: From Logan, the Silver Line bus to South Station is free and often faster than a rideshare at rush hour.
- Lyft
Lyft operates citywide with standard, XL and scheduled options; it also runs the Bluebikes bikeshare system under contract.
Tip: Compare Uber and Lyft prices before booking late at night — surge differs between the two.
Bikes
Bluebikes is the metro-wide docked bikeshare, with stations across Boston, Cambridge, Somerville and Brookline — ideal for the Esplanade and the Harborwalk.
- Bluebikes
Single trip $3.00 (up to 30 minutes on a classic bike); Day Pass $11.99 for 24 hours of unlimited 2-hour rides. Ebikes cost $0.33/min for pass holders. Thousands of bikes across 13 municipalities.
Tip: Buy the Day Pass in the Bluebikes app rather than at a kiosk — kiosk purchases carry a $25 security hold.
Taxis
Boston's licensed taxis run on meters set by the city. Street hails work downtown and around hotels; everywhere else, e-hail is easier.
- Curb (official Boston taxi app)
Curb is the City of Boston's official taxi app: it hails licensed cabs (Boston Cab, Metro Cab and other fleets) with upfront pricing, live tracking and in-app payment. You can also street-hail and 'Pair & Pay' from the app.
Tip: Tip 15–20% on metered fares. A city pilot also lets licensed taxis accept Uber and Lyft trip requests, so a cab may show up for either app.
New York City
Public transit
The subway runs 24/7 and is the fastest way across town; buses fill the gaps. Tap to pay with OMNY.
- OMNY tap-to-go on the subway
Subway and local buses cost $3.00 per ride; tap a contactless card, phone, or OMNY card at the turnstile. Transfers between subway and bus are free. After 12 paid rides within 7 days using the same payment method, the rest of the week's rides are free (7-day fare cap, $35).
Tip: Use the same card or phone every tap so the 12-ride fare cap tracks you; single-ride tickets cost $3.50 and don't count.
- JFK AirTrain
From JFK, the AirTrain ($8.75) connects all terminals to Jamaica station (E/J/Z trains and LIRR to Penn Station or Grand Central) and to Howard Beach (A train). Pay with any contactless card, phone, or OMNY card; the subway leg onward costs $3.00.
Tip: For the fastest airport-to-Manhattan trip, take the AirTrain to Jamaica and switch to the LIRR (about 20 minutes to Grand Central).
- LaGuardia via the free Q70 bus
LaGuardia has no rail link; the Q70 LaGuardia Link bus runs free between all LGA terminals and the Jackson Heights-Roosevelt Av subway station (7/E/F/M/R), about 30-45 minutes to Midtown for one $3.00 subway fare.
Tip: The planned AirTrain to LaGuardia was cancelled, so plan on the Q70 + subway; it's luggage-rack equipped.
Rideshare
App-based cars are everywhere and usually faster than a cab outside Manhattan. Expect surge pricing at rush hour and late nights.
- Uber
Uber operates citywide across all five boroughs with upfront pricing shown before you book. Expect surge pricing at rush hour and late nights, when the subway is usually cheaper for short hops.
Tip: Tipping 15-20% in the app is the expected norm; drivers rate riders, and cash isn't needed.
- Lyft
Lyft operates citywide across all five boroughs with upfront pricing, and its app can also hail yellow taxis through the Curb partnership. Like Uber, prices rise at peak times.
Tip: You can hail a yellow cab inside the Lyft app via its Curb partnership and still get Lyft's upfront pricing and in-app tipping.
Bikes
The city is flat and the densest sights sit within a few miles; bikeshare beats a cab for short hops below Central Park.
- Citi Bike
Lyft-operated bikeshare with stations across all five boroughs, 24/7. A day pass ($25) buys unlimited 30-minute classic-bike rides for 24 hours; e-bikes cost extra per minute (27 cents/min for members, more for pass holders). Get the pass in the Citi Bike or Lyft app.
Tip: E-bike overage racks up fast: dock within 30 minutes or grab another bike.
Taxis
Iconic and plentiful in Manhattan; elsewhere you'll usually wait less for an app car.
- Yellow cabs and the Curb app
Yellow cabs are the only cars allowed to pick up street hails anywhere in the city; hail by raising a hand or book through the Curb app for upfront pricing. Street hails run on the meter. Green boro taxis serve northern Manhattan and the outer boroughs at the same metered fares.
Tip: Tip 15-20% on the metered fare at the back-seat touchscreen; cards are accepted in every cab.
Keep exploring
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