Boston is a big city with a lot to see in only five hours.
It’s quite possible to take in the best Boston has to offer in only a handful of hours if you play your cards right. A common cruise port for people sailing along the East Coast out of New York City, Boston has a rich history as one of the primary players in the American Revolution. Follow this packed itinerary to see the major sights in less than a day.
Prepare for Your Visit
For a port like Boston, it’s important to have a good grasp on what you’d like to see once you get there. Spend a few hours surfing the Internet to refresh your memory of all of the events that occurred in Boston on the road to US independence. There’s a lot to take in.
Most cruise ships will offer a variety of excursions, including ones that cover the highlights and even throw in a harbor cruise to boot. But consider taking a hop on hop off tour instead. The HoHo, as they’re called locally, stop at all of the major attractions, and you can pick and choose which ones you want to spend a little extra time at.
Pro Tip: If you book a HoHo online, you’ll receive access to all of the stops. But if you book it onboard the ship, you’ll get a special “express” version that only drops off and picks up at certain HoHo stops. While this makes it easier for you to manage your time, it also limits your options, and you can only get back on specially marked buses. It’s a bit challenging to figure out which stops are the “right” ones for your pass. Ask the driver before hopping off if you’re unsure.
If you buy your HoHo on the ship, you will be designated a boarding time. Buses leave at 15-minute intervals for 1.5 hours after your ship docks. The goal is not to have everyone rush the bus stop all at once. But you can start your tour whenever you want. And many people choose not to start until mid-day.
This means, if you arrive earlier than your designated time, you will be granted access to board the first available bus. For example, the day I took the tour, the first bus was scheduled for 9:15 a.m., and I had a 9:45 a.m. boarding time. I arrived at the stop a half hour early, as was able to board a bus right away.
Boston is a beautiful city. It’s clean, rich with history, and full of diversity. With only five hours to spare, we had to be fast to get a good taste of what the city has to offer. HoHo was the perfect solution. The drivers were friendly and informative, giving the tour a special touch.
While the specially designed cruise tour only takes you to seven stops, you likely still won’t have time to do them all. I’m faster than a speeding bullet (my grandma’s maiden name was Kent, so I figure I get my speed from Superman), yet I only had time to hop off at four stops. Choose wisely, and budget your time well.
Stop 1 – Boston Tea Party
First up, you can take a step back in time to re-enact the events that started America on its path to freedom from British colonial rule. Board replicas of the ships involved in the Boston Tea Party and have a spot of tea at the tea room before picking up a souvenir—like a “tea” shirt—in the shop.
Pro Tip: Check the opening times before your visit to be sure you can enter the site and have a bite to eat. Sometimes, the tea room opens mid-day, so if you hop off your HoHo too early, you won’t get a chance to take it all in. The HoHo swings back around to this stop at the end of the tour before taking you back to your ship, so you could get off here later in the day instead, after you’ve seen the other sites.
Stop 2 – Paul Revere House and the Old North Church
Next, take a walk along the red brick road, known as the Freedom Trail, to Paul Revere’s house. Stroll the same streets he took to reach the Old North Church the night he stalked its towers to watch for the infamous lanterns signalling “one if by land, two if by sea.”
Stop 3 – USS Constitution and Museum
Want to check out “Old Ironsides,” one of the best-known ships of the American Revolution? Here’s your chance. Hop off at this stop to see the infamous wooden ship that’s now a museum.
Stop 4 – Boston Public and Cheers
Drive past TD Gardens and the colonial buildings of downtown Boston on your way to Boston Public. The lush gardens and public park are home to the Swan Boats that will take you on a 20-minute ride through the park. Across the street, have a drink where everybody knows your name, Cheers.
Pro Tip: The good folks at Cheers know you need to get in and out fast. They’ll even ask if you want a pre-packaged mug tacked onto your bill to save you from standing in line in their souvenir shop. Be sure to say, “Bye,” to Tecumseh on your way out!
Stop 5 – Fenway Park
If you’re a Red Sox fan you’ll want to hop off at the big green monster. You can take a tour of the grounds, but be sure to check for availability in advance as the tours don’t run continuously and often fill up. You can also check out the official fan store and have a beer at a local hot spot.
Stop 6 – Prudential Center and Skywalk Observatory
For a 360-degree view of Boston, stop here and ride to the top of the Skywalk Observatory. There are also plenty of great places to shop and have a bite to eat.
Stop 7 – Faneuil Hall and Quincy Market
Whether you’re looking for a handcrafted keepsake, tacky t-shirt, or a seafood snack, you’ll find it at Quincy Market or Faneuil Hall. While there is a good variety of shopping, it’s mainly made up of local artisans rather than chain stores. So if you’re hoping to pop into Anthropologie of J.Crew, you won’t find them here. But you will find a variety of take-out eateries catering to just about every taste imaginable.
Boston is a pretty compact place, and many of the attractions are within walking distance to one another. If you have just missed a HoHo, you may want to consider walking to the next stop instead of waiting 20 minutes for another one to come along. We walked from Stop 2 to Stop 3 to save a bit of time. It only took about 10 to 15 minutes, and we got to see a bit more of the city.
Still think you can’t see Boston in just one day? If you keep a steady pace and don’t dillydally in any one place, you can see the best of Boston in only five hours. Share your Boston pictures using #wanderlustwayfarer on Instagram.Open modal