Take advantage of Boston’s lovely (well, sometimes) shoulder season to get out on the water! Avoid the crowds by taking these three popular Boston boat rides on a warm day in September.

There’s something here for every schedule and budget, and they all leave from Boston’s Long Wharf. If you have time, the whale watch is an absolute showstopper! Be sure to pack a sweater!

Shoulder season in Boston

Ah, September in Boston. The students are back (normally that’s a lament, but honestly, I had really missed them), but the tourists are gone. The days have grown shorter, but not always colder, and the shoulder season still offers plenty of opportunities to enjoy what warm-weather Boston has to offer.

Usually shoulder season finds me packing my bags for a grand adventure; my Facebook memories this month are filled with memories of trips to Hungary, France, Spain, and the UK. Alas, as with last year, I’m enjoying shoulder season at home.

Boston Harbor, Boston, Massachusetts, USA

Three Boston boat rides

Getting out on the water from Boston’s Long Wharf is a ton of fun, and, especially with the whale watch, will give you a huge dose of wonder. You have plenty of options from here, and I’m going to tell you about three:

  • Charlestown Ferry
  • Historic Harbor Cruise
  • New England Aquarium Whale Watch Cruise
Boat ride on Boston Harbor
Old Ironsides (USS Constitution), with the Bunker Hill Monument in the background. Boston Harbor, Boston, Massachusetts, USA

Fast and cheap: The Charlestown Ferry

I haven’t done this one for a few years, but it’s a lot of fun and requires no advanced planning. Friends and I used to hop on for a short trip to the USS Constitution on the Charlestown Ferry, a ten-minute or so boat ride over to Charlestown operated by the MBTA that will run you $3.70 one-way.

We’d stand on the deck, take in the views, and then wander around the USS Constitution Museum. If we were feeling adventurous, we’d head up to the Bunker Hill Monument. Then we’d grab a drink at Tavern on the Waterfront (sadly departed; Pier 6 has taken its place—it’s a little pricier) before hopping back on the boat back to town.

Get on the Ferry!

Info and Schedules: Charlestown Ferry

Location: Catch the ferry on Long Wharf South in Boston. Directions

Cost: $3.70USD, one way; $7.40 round trip

Duration: ~10 minutes per leg


  • Masks are required on all public transportation.
  • This is a short ride not far out on the water, making it a good option even as we get into autumn
Castle Island. Poe took inspiration for a very creepy short story from a legend about Castle Island. Even creepier, the story is likely true! Boston Harbor, Boston, Massachusetts, USA

A lovely, informative 90 minutes: Historic Harbor Cruise

If you have a little more time, consider the 90-minute Historic Harbor Cruise around Boston Harbor offered by City Cruises. You’ll get a picture-perfect view of Boston’s skyline, views of Boston’s Harbor Islands, along with a lovely little ride around the harbor, all whilst learning a little something.

I’ve visited Castle Island for years, but I had forgotten that Poe had taken inspiration from a legend (later proven to be true) of an officer chained up and sealed in the fort to write the “Cask of the Amontillado.” The legend of the Lady in Red speaks of a woman who haunts Long Island (the one in Boston, not the other one). I’ll leave the other stories, including ones about pirates, to the narrator.

You’ll also get a killer view of planes taking off from Logan.

Cruise Boston Harbor!

Info and Schedule: Historic Harbor Cruise by City Cruises

Location: Leaves from 1 Long Wharf, Boston

Cost:  $34.95USD

Duration: ~90 minutes


  • Masks required to board and in enclosed spaces.
  • Book your ticket online. Same day should work just fine this time of year, but on a nice weekend day, some times could still sell out.
  • While you don’t get out on the open water with this cruise, I’d still try to pick a calmer day to cut down on motion.
Whale Watch
Whale fluke. Not the best shot, as I was too busy whooping. Stellwagen Bank Marine Sanctuary

Four hours of magic: New England Aquarium Whale Watch Cruise

This tour is awesome, as in knock your socks off with wonder. If you’ve never seen a whale up close before, get ready to whoop. The New England Aquarium teamed up with Boston City Cruises to offer the New England Aquarium Whale Watch Cruise. This is a Whale Sense cruise that respects the animals. Boat strike is one of the most frequent causes of whale injury/death, along with fishing, and it’s important to take care with the tour outfit you choose.

On this whale watch, you’ll ride out on a catamaran to Stellwagen Bank Marine Sanctuary, one of the most active marine sanctuaries in the world and the only one in New England. You’ll see Boston Light, considered the oldest lighthouse in the Americas on your way out, along with other Harbor Islands. Birds dart this way and that, and you’ll lose sight of land completely. 

A Humpback whale! Stellwagen Bank Marine Sanctuary

And then … you start to see water spraying, and then you SEE WHALES! We saw fourteen whales, mostly humpbacks, including three mother/calf pairs! I’m normally able to keep it together on the outside, but I could not stop whooping as I saw flukes rise out of the water and seeing these truly majestic creatures in their habitats. I was hardly alone.


Our guide Sydney, thrilled by how many whales we saw, pointed out different whales like Nile, Dross, and Dyad, the latter two who had calves with them. Humpback whales can be recognized by their flukes. We also caught a glimpse of a fin whale. In the far distance, we saw splashes as whales leapt from the water; alas, I’ll have to see that up close another time.

Cruising back into Boston, it’s magical to see land come into view, the lighthouse and islands, and then the Boston skyline.


Info and schedules:  New England Aquarium Whale Watch Cruise

Location: Leaves from 1 Long Wharf, Boston

Cost: $63USD

Duration: ~3.5-4 hours


  • Masks are required to board and in enclosed areas.
  • Buy your tickets online ahead of time, and get there early. I arrived 30 minutes early, and I still stood on the railing the entire time. I didn’t mind, but it’s something to consider.
  • If you want to hear the guide clearly, get up to the top deck.
  • If you by some chance do not see any whales, you get a voucher good for another cruise. They honor this promise.
  • Make sure to pack something warm, even if it’s hot out. Especially on the trip back, it’s going to be chilly out there. This cruise runs until November, but I wouldn’t go much past the end of this month. It starts up again in May.
  • If you think you might be seasick, I’d consider some Dramamine. Better safe than sorry.

There’s still time this shoulder season

Summer is not over just yet. Take advantage of the shoulder season and enjoy getting out on the water. Just make sure to cover those shoulders! Have you ever been on a whale watch? Let me know in the comments!

Know before you go on any of these cruises

  • Masks are required for these trips, as of this writing. Details in the considerations.
  • Bring something warm. It’s cooler out on the water. I went on my whale watch on one of the hottest days of the year, and I needed a light sweater out on the water.
  • Sunscreen! On a sunny day, the water makes the sun more intense, and it’s really easy to get a sunburn.
  • Wear shoes with a decent sole. It can get slippery and the boat can rock with the waves, even on the Charlestown Ferry.
  • Snacks and drinks (nothing special) are available for purchase on board for all three cruises. Cash only.
  • You can find discounts for the harbor cruise and whale watch on various discount sites. 
  • For the harbor cruise and whale watch, plan ahead, but not too far ahead. Keeping an eye on the weather will be helpful.


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