Photo: King of Hearts · CC BY-SA 4.02 Days in Boston: Freedom Trail, Harbor & Back Bay
Two unrushed days in Boston: walk the Freedom Trail's historic core on day one, then do Back Bay and the working harbor on day two. Answer a few questions about how you travel and the plan re-plans itself around you — your pace, your budget, your stops.
Pick a style, a budget and a pace — the route and days below re-plan themselves.
6 stops · 4 meals · 1 hotelThis is the editor’s pick.
2 days
Each day takes one part of Boston, kept close so you walk more than you ride. The map shows the whole route — pick a day to zoom in.
Start here if you want the civic postcard: Bulfinch's 1798 capitol under the gold dome. Free 45-minute guided tours run 10am to 3:30pm on weekdays, starting in Doric Hall.
America's oldest public park, and the Freedom Trail's official start. The visitor center at 139 Tremont Street runs the guided tours.
- Start at the Common — the trail's official guided tours leave from the visitor center at 139 Tremont — then climb Beacon Hill to the State House's gold dome.
America's oldest restaurant, serving since 1826 in a pre-Revolutionary building. Sit at the oyster bar where Daniel Webster sat; the chowder is the award-winner.
The 1713 building where independence was first read to Boston, with the Massacre site marked outside. The $15 combo with Old South Meeting House is good value.
A stretch
Fine dining in the 1855 Omni Parker House — the longest continuously operating hotel in the US. Dress it up.
- Parker's is the birthplace of Boston cream pie and the Parker House roll — save dessert.
America's oldest continuously operating tavern, opened in 1795 by Boston's last town crier. Pints, pub fare and live music near Faneuil Hall.
Sixty-one rooms in a Beaux-Arts pile on Beacon Hill — gas fireplaces, marble showers, the Mooo steakhouse, and a rooftop deck with Charles River views. 2026 Travel + Leisure's #1 hotel in Boston.
Downtown's oldest building, and Revere's home from 1770 to 1800. The self-guided walk through four period rooms is quick — thirty minutes is plenty.
- Plan around it: closed Mondays January through March.
Cash-only, lunch-only Sicilian slices for under $5 — a James Beard America's Classic since 2018. The line moves fast.
- Cash only and lunch only — stop at an ATM before you join the line.
- Two minutes from the Revere House, this cash-only lunch counter does crisp Sicilian slices for under $5.
The 2.5-mile red-brick line from Boston Common to the Bunker Hill Monument, linking 16 sites. Free and self-guided — a couple of hours for the walk, half a day if you go inside.
Boston's original pizzeria, serving thin-crust brick-oven pies since 1926. Cheese or pepperoni by the slice at the timeworn Thacher Street shop.
Where two lanterns launched the midnight ride. The sanctuary is small and atmospheric; the crypt tour is the part people remember.
- The $10 Discovery Pass covers the sanctuary tour, exhibit and crypt.
- Follow the red-brick line to the North End: Old North is the trail's 'one if by land' stop, where two lanterns launched the midnight ride.
Boston's fourth-oldest restaurant, opened in 1885 — a romantic former speakeasy doing French-Italian classics and old-school cocktails.
Stay put: 17 min walk back from Old North Church tonight, 15 min walk to the Paul Revere House in the morning.
Where to stay in Boston
Ranked for first-timer travelers on a comfortable budget. The places this plan sleeps in come first.
XV Beacon
Sixty-one rooms in a Beaux-Arts pile on Beacon Hill — gas fireplaces, marble showers, the Mooo steakhouse, and a rooftop deck with Charles River views. 2026 Travel + Leisure's #1 hotel in Boston.
Hotel Ivy Boston Common
Budget stay by Boston Common in a historic 1877 brownstone — now operating as the Hotel Ivy. 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 above the harbor.
Flights to Boston
Fly into BOS (BOS)
Flight results via Travelpayouts — we may earn a commission on bookings.
Getting around Boston
How to actually move around the city — transit, rideshare, bikes, and taxis.
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.
Keep exploring
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- Photo: King of Hearts · CC BY-SA 4.05 days
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