Completed

Boston
Summer
Excursion

Massachusetts · July 2026 · 4 Days

4Days
30+Miles Walked
7Spots Hit
1Seesaw Ridden
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Lane and Aud on Daniel's rooftop with the Zakim Bridge

Day One

Touchdown in Beantown

Friday

Woke up at Lane's place and grabbed an uber around 6:30 in the morning. Got through TSA in no time and sat down to eat our block egg sandwich at 7am. That thing had no business calling itself a sandwich and we absolutely roasted it, but still ate every bite. Hung out at the gate for an hour until boarding at 8. Flew in around 10am, took the bus to the red line station, then hopped on the T toward the hotel. Got on the green line going the wrong way at first and had to hop on the next one back to North Station, but honestly it was all part of the adventure and we were just happy to be there.

Aud with egg sandwich at airport
At the airport
Bus to Boston

We waited a while in the lobby before they let us check in early, which was honestly a win. The CitizenM is this whole vibe. Tiny rooms, floor-to-ceiling windows, mood lighting you control from a tablet, and an elevator mirror situation that was too good not to document. The room was basically a fancy capsule with a king bed crammed into it, but the location was unbeatable and the rooftop views were absurd.

Elevator selfie at CitizenM
Lane at CitizenM

Where We Stayed

CitizenM Boston North Station

Compact but incredibly well-designed rooms with tablet-controlled everything. Lights, blinds, TV, mood colors, you name it. The common areas and rooftop bar made up for the room size. Right next to North Station and walking distance to basically everything.

Dropped our bags, hit the gym downstairs, and then met Aud in the lobby around 1pm. She's been living in and around Boston for a few years now and was going to show us the city. First stop was Mangia Mangia, her uncle's place halfway across the North End. I got the North Ender, Lane got tuna salad. From there we walked the harbor for hours and rode a scooter, which officially sealed our goal to ride as many modes of transportation as possible in one weekend (car, bus, boat, plane, bike, train, and now scooter). The waterfront in this city is something else. Sailboats, skyline, perfect weather. We came all the way back to Langone Park and walked east past the coast guard station and fire station, then past Union Wharf and Lewis Wharf.

Restaurant

Mangia Mangia

Aud's uncle's spot in the North End. Family-run Italian deli with sandwiches that are the real deal. The kind of place you'd never find on your own but you're glad someone who knows the neighborhood brought you to.

Walking the harbor
Harbor waterfront
Boston waterfront
Boston harbor walk
Harbor views
Lane and Aud at Boston harbor

Not a bad first afternoon in town.

We ended the perimeter walk by going into Christopher Columbus Waterfront Park, where we found a photo booth and there were all kinds of festivities going on. We didn't stay, just kept walking. The park has these gorgeous trellis archways covered in wisteria, and the whole North End waterfront area has this mix of old-world charm and modern Boston that just works.

Langone Park
Langone Park waterfront
Columbus Park
Columbus Park trellis

Columbus Park, somewhere between a European courtyard and a New England postcard

Turned a corner in the North End and there it was. The Paul Revere House, just sitting there on a regular street like any other building. Something about stumbling onto a house from the 1680s while looking for a place to grab a drink really puts things in perspective.

Paul Revere House exterior
At the Paul Revere House
Paul Revere House street
A Little History

The Paul Revere House was built around 1680, making it the oldest remaining structure in downtown Boston. Revere owned it from 1770 to 1800, and it's where he left from on the night of his famous midnight ride in April 1775. The building came close to demolition multiple times before being turned into a museum in 1908.

The North End is genuinely one of the best neighborhoods we've ever walked through. Narrow streets, Italian flags hanging from fire escapes, restaurants spilling out onto the sidewalks. We ducked into Florentine Cafe for water and a cold beer since it was absolutely scorching out. The water took about twenty minutes to arrive, which was a whole thing. The people next to us sprayed sunscreen right before leaving, which was a choice. We cooled off and then headed across to Charlestown.

North End streets
Walking the North End
North End neighborhood

Cafe

Florentine Cafe

Outdoor spot on Hanover Street where we stopped to cool down with water and beer on a brutally hot afternoon. Nice location in the heart of the North End, though the service moved at its own pace. We didn't stay long before heading to Charlestown.

From the North End we crossed over into Charlestown, which meant walking across the locks and into a completely different version of Boston. Charlestown has this quiet residential energy mixed with absolutely wild amounts of American history per square foot. The Bunker Hill Monument was looming over everything, and you could see the masts of the USS Constitution poking up from the Navy Yard.

Walking to Charlestown
Charlestown neighborhood

Historic Landmark

Warren Tavern

One of the oldest bars in America, pouring drinks since 1780. We saw it and went in on our way through Charlestown. George Washington and Paul Revere both drank here, and it still has that "founding fathers could walk in and feel at home" energy.

A Little History

Warren Tavern was one of the first buildings erected after the British burned Charlestown during the Battle of Bunker Hill in 1775. Named after Dr. Joseph Warren, a patriot leader killed in that battle, the tavern hosted George Washington during his presidency and counted Paul Revere as a regular. It's been pouring drinks continuously since 1780, making it one of the oldest bars in America.

Golden Hour on the Rooftop

Daniel's place, 48 Harvard Street, Charlestown

We picked up Marc at a Starbucks after grabbing some wine and Sun Cruisers, then headed over to Daniel's place. Getting to the roof deck meant climbing up a ladder, but the second you got up there it all made sense. The North End skyline was right in front of you, and if you turned around, the Bunker Hill Monument was looming right there behind you. You could even look down and see David Pasternak's house below. About twenty people up there, none of whom we knew, but it didn't matter.

Lane and Aud on Daniel's rooftop with Zakim Bridge

The rooftop shot. Zakim Bridge in the background, golden hour doing its thing.

Rooftop views
Charlestown rooftop
Sunset from rooftop

They had two folding tables absolutely loaded with every liquor and mixer you could think of, plus a full drink menu where you could order anything. The drinks were free and they poured them strong. Lane made a Venmo QR code and put out a tip jar for Daniel's friends running the bar, which was the right move. We started with Sun Cruisers, moved on to old fashioneds, and just settled in. It was hot up there, but the views and the company more than made up for it.

David Pasternak's house from the rooftop
Rooftop drink menu
Drinks on the rooftop
Rooftop evening
Bunker Hill Monument
A Little History

The Bunker Hill Monument is a 221-foot granite obelisk commemorating the Battle of Bunker Hill on June 17, 1775, one of the earliest and bloodiest battles of the American Revolution. The battle actually took place on Breed's Hill, but by the time everyone figured that out, the name had already stuck. You can climb all 294 steps to the top for panoramic views of Boston.

After the rooftop we found a playground and got on the seesaw, because when you see a seesaw you get on it. Marc and Aud on one side, us on the other. Lane forgot her hat so we had to run back up to Daniel's, but it was worth the trip.

Seesaw at the playground in Charlestown

Seesaw in Charlestown. Zero regrets.

The walk back toward the waterfront took us right past the Charlestown Navy Yard and the USS Constitution Museum. "Old Ironsides" was right there at the dock. The oldest commissioned warship still afloat in the world. Launched in 1797 and still technically an active U.S. Navy vessel. Just casually parked in Boston like it's no big deal.

USS Constitution Museum

USS Constitution

Launched in 1797, "Old Ironsides" earned her nickname during the War of 1812 when cannonballs were seen bouncing off her thick oak hull. She's the world's oldest commissioned warship still afloat, still crewed by active-duty U.S. Navy sailors, and sails under her own power once a year for a turnaround cruise in Boston Harbor.

On the walk to Pier 6 we stopped to talk with an old couple who had been sailing around on their sailboat all day. They had matching shirts. We got there around 7:45, and Marc and Aud had already secured the best spot in the whole place. Outdoor cushioned furniture with a low table right on the water. Best vibes of any waterfront restaurant we've ever been to, and that's not an exaggeration. We started with drinks and a charcuterie board, then split a margarita pizza while Marc and Aud got fish tacos. The sun was setting over the city, the harbor was glowing, and nobody was in any rush to leave. This was the highlight of Friday, no question.

Restaurant

Pier 6

Waterfront dining in the Charlestown Navy Yard with unreal sunset views of the Boston skyline. Outdoor seating right on the harbor with comfortable lounge furniture. The kind of place where you show up for a drink and end up staying for hours.

Pier 6 views
Sunset selfie at Pier 6
Pier 6 evening
Selfie at Pier 6 with the harbor

Left Pier 6 around 10 and walked back along the harbor to the hotel, getting in around 10:30.

Night walk along Boston waterfront

The walk home. Just the harbor, the city lights, and a really good day behind us.

Found sand in the bed on the 6th floor room at midnight after having issues with the air conditioner. Ended up switching rooms to the 14th floor at 12:15, then noticed water on the floor. We put a towel down and called it a night. Every great trip needs at least one "we will laugh about this later" moment, and Friday night absolutely delivered.

Hotel shenanigans
Hotel situation
CitizenM room adventures
Late night at CitizenM
Hotel night
🎆

Day Two

Fourth of July

Saturday · July 4th

Happy Fourth of July

Spending Independence Day right where it all started

Woke up to puddles on the floor. Luckily nothing got on the bed or our clothes, but we called immediately to get a room switch. They refunded the first night. We had to stash our bags in the lobby storage to pick up later before switching rooms.

Aud picked us up at 8:30, we got to the car at 8:34. Drove to Marc's place first, then from there we hit Whole Foods for breakfast burritos and coffee. I got a turkey chorizo burrito, Lane, Aud, and Marc got bacon egg and cheese burritos, and then a coffee from Starbucks. Picked up some Surfsides from a shop across the parking lot and loaded them into the cooler. Drove about 50 minutes and got to Good Harbor Beach around 10:30.

Whole Foods breakfast run

Breakfast burritos and Surfsides. Fourth of July essentials.

Good Harbor Beach absolutely delivered. You could see the bottom of the water clearly, the sand was perfect, and the coastal towns around us were perched up on the coastline. Really cool spot with an island out there that we unfortunately didn't swim to. We had some great conversations, went in the water a couple times, and got some sun. A lot of other people showed up throughout the day, and by the time we left there were probably 20 people in our group.

Lane and Aud at Good Harbor Beach

Good Harbor Beach, Gloucester. Not a bad Fourth of July setup.

Beach day
Good Harbor Beach
Beach afternoon
Beach vibes
Good Harbor afternoon

Beach

Good Harbor Beach

One of the best beaches on the North Shore. Gorgeous sand, clear water, and a tidal island you can walk to at low tide. About 45 minutes from Boston in Gloucester. Gets packed on holidays but for good reason. It's genuinely stunning.

Left the beach around 2:30 to grab food. Aud came back with me and Lane. I got a chicken wrap, she got a tuna wrap. A storm came out of nowhere while we were eating and talking. Aud headed back to the beach and we tried to call an uber home. Ran into the whole Lyft/Uber situation and ended up waiting about an hour and a half in the parking lot before finally getting one. Lane took a nap in the car on the way back.

Got back to the hotel around 5 and checked into our new room on the 11th floor. Showered, laid in bed, and just chilled for a while.

Got ready and left around 6:30 to go get seafood, but it started raining. We were going to wait it out and just get drinks, but then we found Lo Conte's right near us. Looked at the reviews and people were calling it a hidden gem. Walked into the packed place and asked for a table for two, and they pointed us into a side room that was quieter and honestly perfect. We ate way too much bread and meatballs before the veal parm came out. I got another old fashioned and then we both had wine with our entrees.

Restaurant

Lo Conte's

Hidden gem in the North End. Italian comfort food done right. Packed house with a quieter side room that felt like our own spot. The bread basket and meatballs alone could end you, and then the veal parm shows up.

Lo Conte's dinner
Dinner at Lo Conte's
Lane at Lo Conte's
Lo Conte's food
Lo Conte's veal parm

Walked back to the hotel to drop off food and ran into the bathroom situation. Got a couple drinks at the hotel bar and hung out there for a while.

Hotel bar
CitizenM bar
Drinks at CitizenM

Left the hotel bar around 10:30 to see if we could find fireworks after the rain had cleared. Saw a couple through some buildings and then sat on a park swing in the Rose Kennedy Greenway until about 11:15. Walked downtown to find another bar and walk around more. Saw the State House over in Government Square.

Rose Kennedy Greenway

Rose Kennedy Greenway

A mile-and-a-half ribbon of parks, gardens, and public art in the heart of downtown. Built over the tunnel that replaced the old elevated Central Artery (the Big Dig project), the Greenway transformed the city's waterfront connection. On the Fourth of July, it becomes the center of the celebration.

Rose Kennedy Greenway celebrations

Fourth of July on the Greenway. Exactly as good as it sounds.

Bar

The Point

Ended up finding this spot with live music going. We both got one drink and soaked it in before calling it a night.

Walked back to the hotel around midnight and went to bed.

🍺

Day Three

Beer, Bikes & Carrot Cake

Sunday

Woke up to see my flight was cancelled. The American flight in the evening had doubled in price, and JetBlue ended up rescheduling me for Monday evening, but I wanted to be home Sunday night so I could go to work in the morning. I decided the best choice was to wait until tomorrow morning and booked the same 5:30am flight as Lane. JetBlue gave us a free hotel room because of the cancellation, so that worked out.

Had a very lazy morning and laid in bed until 11:30. Cleaned up, showered, and packed. The vibes were insanely immaculate as we danced around the hotel room and screamed and had so much fun once I was locked in on staying the whole day. Checked out at about 12:45 with a 2pm checkout time, even though it should have been 11 but they accommodated everything for us. We should have left much earlier to be more on time.

Lazy morning at CitizenM

Sunday morning at CitizenM. Flight cancelled, extra day unlocked.

Should have met Aud back in lower downtown around 1 but didn't get there until 1:40. Had to drop off our stuff at the new hotel first. We checked in slightly early and they gave us a nice big room on the 2nd floor with two beds and a nice bathroom. Got downtown and walked down Charles Street and then into the Boston Commons.

Went to the Harpoon Beer Garden where I got an el jefe's burrito bowl and some IPAs. Lane and Aud got Tatte and also some drinks at the beer garden. There was a jazz band up there playing. Vibes were so high.

Beer Garden

Harpoon Beer Garden

Harpoon Brewery's outdoor beer hall in the Seaport. Fresh beer straight from the source, a jazz band, and communal picnic table energy. Burrito bowls, IPAs, and zero reason to leave anytime soon.

Lane and Aud at Harpoon Beer Garden

Harpoon Beer Garden. Jazz band, IPAs, and burrito bowls.

Harpoon Brewery
Beer Garden vibes

Walked down through the Commons and Boston Garden. Saw beautiful weeping willows and me and Lane got an old timey picture that they put in a newspaper. Saw the lagoon and duck island. Then we headed down to the river at Fiedler dock where we stopped and Aud pointed out all the towns and colleges you can see from that view. We saw the T crossing the Longfellow Bridge.

Boston Garden

Boston Garden and the Commons. Weeping willows and duck island.

Walked up the river to the T where we saw it crossing and took it to Harvard station. Stopped at a women's clothing store with insanely high prices, 160 dollars for a pair of jeans. Then we looked at some books. Walked around for a second before stopping into Felipe's to go to the rooftop where I got a strawberry margarita. Said bye to Aud from there.

Took the e-bikes for a spin at about 6:30. Had some issues finding the e-bikes instead of the regular bikes but we managed to get two good ones. Rode those all the way back into the downtown area, all the way back across the bridge and main street, then down Cambridge Street into downtown to get pizza.

Stopped at Ernesto's where there was a perfectly timed table we could get. A couple stood up as we walked in. We each ordered two slices but they give you two per order, so we ended up with four massive slices each. Lane ate two, I had three, and we took the other three to go.

Pizza

Ernesto's Pizza

The slices here are famous for being absolutely massive. They always have a ton of varieties behind the counter and the price-to-size ratio is genuinely hard to beat in Boston. A North End institution for a reason.

Went to Mike's Pastries where we waited in line and talked to an older couple from Mississippi for most of the wait. Got three chocolate chip cannolis and a carrot cake slice. Then we grabbed a bottle of moscato, and while Lane was getting the wine I gave the leftover pizza to two dudes outside.

Mike's Pastries box

Mike's Pastries. Cannolis and carrot cake for the road.

Finished the night with a shower, massages, wine, and amazing carrot cake with How I Met Your Mother on the TV. Went to bed around midnight.

✈️

Day Four

Until Next Time

Monday

Woke up at 4am to get the shuttle to the airport that left at 4:30. Lane and I got row 4 and flew into Philly around 7:45am. Got an uber back to her place to pick up my truck, then drove Lane to the Honda dealer to get her car around 9am. Said bye to my bestie Lane.

🫶

Goodbye, Beantown

Four days, two very tired pairs of legs, one incredible city. Boston gave us harbor sunsets, Revolutionary War history, the best Italian food outside of actual Italy, a seesaw in Charlestown, fireworks on the Fourth, cannolis, carrot cake, and an extra day we weren't planning on. We left sunburned, overfed, and already talking about when we're coming back.


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