Sailing in Boston Harbor: The Perfect Beantown Summer Excursion!

I’ve visited my sister in Boston numerous times in the past 7 years, ever since she started school at BU – but only ONCE have I been to Boston in the summer. I attempted to remedy this oversight by booking a megabus ticket for July this year.

Then I thought, SUMMER IN BOSTON! What fun summer things can we do that we haven’t done in Boston before?

As with most every other trip I’ve taken thusfar in 2014, I took to The Google at approximately 11pm the night before and scrambled to make a plan. I happened upon Goldstar, a website with half-off tickets to events in major cities (seriously guys, you’re gonna wanna bookmark that). I parsed through various concerts, plays, and comedy shows to find one of the most PERFECT summer activities in Boston: sailing in Boston Harbor!

Sailing in Boston Harbor 

Now, willingly boarding a boat for an extended period of time is borderline foolish on my end. I’ve been sporadically plagued with motion sickness for most of my life, but these days I keep it under wraps by popping some Bonine or wearing Sea-Band wristbands. I still have PTSD from the time I took a ferry to Block Island for a daytrip and got so seasick on the way there that I couldn’t drag myself on the ferry back to the mainland and had to stay there overnight. It was THE WORST.

I’m basically playing with fire whenever I step onto a boat, but those times I don’t get burned – man, it’s SO worth it.

Spoiler alert: I survived a 2 hour sailing trip around Boston Harbor with Classic Harbor Line and I’ve got the photos to prove it!

solo female travel blog
Sailing in Boston Harbor
Sailing in Boston Harbor 

The Schooner Adirondack III took us straight out into the harbor toward the harbor islands and back. It wasn’t a particularly scenic route, and we didn’t get close enough to have a good look at the islands or the buildings – but that wasn’t really the point of the trip. It was about kicking back on a sunny summer day with a glass (er, plastic cup) of prosecco in hand and wind in your hair, cruising on the water.

My favorite thing was watching the planes take off from and land at Logan International Airport, which is right on the harbor. Anyone else play that game where you guess where planes are heading when they take off? I think I spotted one that must have been heading to Paris.

Sailing in Boston Harbor
Sailing in Boston Harbor 

My sister and I had a blast on our sailing trip! It was such a beautiful, relaxing afternoon exploring a different side of Boston – exactly what I wanted on this visit. Though be warned, even in 85-degree weather you will freeze your tush off when you’re in the shade! Thankfully the crew doled out fleece blankets for those that didn’t bring sweaters (ahem, me).

Sailing in Boston Harbor
solo female travel blog 

Frugal Facts

As of July 2014 —
Classic Harbor Line runs a few different sailing trips on the Schooner Adirondack III:

  • A day sail runs from 3:30-5:30pm daily, plus 1-3pm on weekends, and costs $42 per person.
  • A sunset sail runs from 6:30-8:30pm daily, and costs $52 per person.
  • A city lights sail runs from 9-10:30pm daily, and costs $38 per person.

Note: You may be able to book discounted tickets on Goldstar.

Lindsay Buckley is the photographer and travel blogger behind Frugal Frolicker. She's a New Yorker currently based in Sydney, Australia, documenting outdoor travel experiences Down Under and beyond. Follow along with Lindsay's travel photography on Facebook and Instagram, and be sure to sign up for the monthly Frugal Frolicker newsletter!

Where in the World is This?


  • So glad to hear you kept it all down during your excursion. I need to hit up Boston again—a lot of my family lives close but I hardly ever make it out there, and it’s one of the greatest cities!

    • lindsaypunk

      Boston is AWESOME! I feel ya, I totally don’t take advantage of having my sister there often enough – it’s kinda like, wellllllll I can go anytime, and then I don’t prioritize it and it never happens. WORST!

  • Looks like you had a great time and the day was gorgeous! I think I need to go back to Boston and sail! :D

    • lindsaypunk

      We did indeed! I HIGHLY recommend a summer sail in Boston – definitely try to squeeze one in the next time you’re there! :D

  • Nicki

    You can do this in NYC too! It’s awesome at sunset, and there’s lots of wine involved. :-)

  • lindsaypunk

    YESSSSSS! You read my mind – it’s totally on my NYC bucket list now! The same company actually runs this trip in both Boston and NYC so I’m trying to arrange a trip with them here sometime :) And YAY wine time!!

  • What a great way to spend the day in Boston. I went to school there for a year and still miss it! I’ve done those harbor sails in NYC several times with my old law firm– they are a classic “summer associate” event, but it’s always known as the best one.

    • lindsaypunk

      OOH how are the NYC sailing trips? Been meaning to try one here! I don’t see how it could be anything but awesome if you’re on the water, in the sun, drink in hand, right?

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