top of page

US Travel: Boston Guide

The USA has it all -- mountains, beaches, islands, big cities, backroads and so much more! It's so important to get out and explore your backyard.

Starlight2Travel loves to help book trips of all kinds, including vacation packages, all-inclusive resorts, cruises, Europe trips and more! We also love to help plan US trips. Often we can only book US trips piece-by-piece. This is no problem; we love to plan and research!

To help you decide where to go, we share vacation inspiration and destination information on our Travel like a Star blog!

In our "US Travel" series, we feature US destinations' history, things to do, places to stay and more! Happy exploring from one adventurer to another!


Welcome to Boston! With Boston’s winding roads, navigating Boston's capital is unlike any other in the United States. It's an incredible mix of history and modern architecture. The seasons bring extreme ranges in weather.

We highly recommend trying to see Boston in the fall, if you can! Summer is the peak season for travelers but in September and October, the trees are bright and beautiful shades of red, orange, gold and green.

Here are some things to keep in mind as you plan your trip to Massachusetts’s capital.

Boston Travel Tips:

The hotels may be historic in many ways! In Boston’s historic hotels and Airbnb rentals, American visitors are sometimes surprised to encounter third-floor walk-ups, steep stairways, creaky floors or smaller rooms than they’re accustomed to. If you need accessible lodging or desire modern comforts, make sure to check whether a place has elevator service, central air conditioning and other amenities, as these features aren’t necessarily a given. Also, many downtown sidewalks are lined with bricks or cobblestones, which makes for some beautiful but treacherous terrain (especially in heels).

Speaking of Airbnbs, take caution. Boston has specific regulations about these rentals. A law passed at the end of 2018 that requires all Massachusetts vacation rental owners to register with the state, carry adequate insurance and pay hotel tax as of July 1, 2019. All of this might explain any extra fees that are included in your rate. Regulations started in January 2019, so you won’t face any surprises.

Special notes from a travel agent about Airbnbs... the problem with them is that the owners can accidentally double book or choose to cancel at any time. Typically, that means cancellation without notice. In the case of any travel protection, it's not a covered reason. That leaves with you vacation time and no where to go. Booking with a travel agent helps ensure there's always a room or cabin with your name on it.

Be ready to walk! Pack comfortable, seasonal-appropriate footwear because you’re going to need it. Downtown Boston is compact, at roughly two square miles (5.1 square kilometers), making it a walkable destination. While subway stations near the city center are often just a couple of blocks apart, it’s faster to walk than wait for a train. Also, the Freedom Trail – a red-brick path connecting many of the city’s most famous historic sites – is 2.5 miles (four kilometers) long, and best explored on foot if possible.

If you're not a walker, we recommend checking out the public transportation system! With big, big cities comes incredible innovation. The public transportation in cities like this go near and far. It's quite affordable and you can easily navigate to all the city's hotspots. The subway system is called the ‘T’, you’ll either want to buy a seven-day unlimited pass or pick up a reloadable plastic CharlieCard. The seven-day pass is a good value if you’re staying longer than a couple of days and includes rides on the Charlestown ferry. If you plan on using the subway sparingly and paying as you go, a CharlieCard offers a 50-cent discount on regular subway fares ($2.25 v $2.75) and allows for free bus transfers. You can order a CharlieCard online or pick one up and add money to it at select stores or subway stations downtown.

Boston has water ferries! In addition to the subway, bus, commuter-rail and ride-share services, you can take ferries and even water taxis to various spots along the Boston Harbor. Charlestown is a quick boat ride from downtown, for instance, and multiple ferries service Hull, Hingham, Quincy, Winthrop and the Boston Harbor Islands. You can even take a 90-minute ferry to Provincetown at the tip of Cape Cod.

Bringing a car might make things a little complicated. Unless you’re staying outside the city center or plan on taking a side trip (say, to Cape Cod, Salem, Portsmouth, New Hampshire, or Newport, Rhode Island), a car is more of a burden than a perk in much of Boston. Most hotels charge upwards of $40 a day to park on-site, and street parking often requires a residential-only neighborhood permit. Even locals have a hard time keeping their cool while navigating the maze of narrow, traffic-clogged roads.

Definitely eat the seafood. Boston is a seafood town, as it's located on the east coast. Whether it’s steamed lobster, fried clams, fish and chips, seared scallops, stuffed quahogs, grilled swordfish, blackened salmon, baked haddock or any other fruit of the ocean, in Boston, you can generally rest assured that it’ll be freshly caught and well prepared. If you see “scrod” on a menu, that’s the catch of the day, usually a whitefish like cod or haddock. You might be able to find $1 oysters in some places from 4-6 pm.

You may be able to find free things to do. Depending on when you visit, you’re likely to find plenty of free events. In summer, look for free concerts at the Hatch Shell along the Charles River Esplanade, or take in one of more than 400 free “Summer in the City” performances presented throughout Boston by Berklee College of Music. Research some free outdoor yoga classes and running clubs to join in on warm and sunny days. During the academic year, check the calendars of Harvard and other universities for free film series, lectures and other events. Many local museums offer admission-free days, too. For example, the Institute of Contemporary Art (ICA) is free to the public on Thursday evenings from 5pm to 9pm.

Boston is full of amazing parks. Boston (as a city) provides 217 City parks, playgrounds and athletic fields, two golf courses, 65 squares, 17 fountains, 75 game courts, 16 historic and three active cemeteries, urban wilds, four High School Athletic Fields, and approximately 125,000 trees, all covering 2,346 acres, 1,000 of which comprise the historic Emerald Necklace. We are also responsible for more than 35,000 street trees. We recommend checking out their natural amusement parks around the country, weather permitting!

Boston is a dog friendly city! If you travel with your pooch, choose to stay near Boston's amazing metroparks and city dog parks. The city may have a lot of hustle-and-bustle happening during the day. If this could cause your dog stress, consider staying on the outside of the city but still near the parks and the metro! Your travel agent can help you plan for the right location.

Don't stay out all night, especially if you're relying on the subway to get home. Apart from a few 24-hour restaurants, supermarkets, a bowling alley and a small handful of late-night clubs, Boston mostly buttons up for the night. Bars close at 2am, and the last subway trains leave the city center at around 12:30am.


Starlight2Travel, Inc. is a Cleveland-based online travel agency. We assist travelers from coast to coast. We specialize in cruises, romance, and family vacations! Our services provide incredible vacation experiences for couples, families, and groups. Please visit our website for travel information and inspiration. Our Star Traveler blog is also an amazing place to find travel tips and resources! Follow us for more travel information!

Recent Posts

See All


bottom of page