A Weekend in New England

Spend a long weekend exploring the gorgeous Maine coast and historic sights of Boston. You’ll be planning your next trip before you even leave!

Note: This post contains affiliate links. For more details visit my disclosure page.


For this trip we flew into Boston on JetBlue, one of our favorite airlines. We love the leg room, complimentary drinks and snacks, and free entertainment that most other airlines skip these days. We also had an empty seat in our row, so we had plenty of room during our trip. Well, I should say I had a lot of room - Ryan had the window and I sat in the middle because I wanted to be by him. :)

Once we arrived, we snagged our (included - yay!) carry-on, picked up our rental car, and headed north. Have you scored a rental car at Boston before? You’ll want to grab one of the complimentary buses over to the rental counters once you have your bags - car rentals are in a totally separate building. It’s easy, I promise!

We hit zero traffic on the way up, so we decided to make a stop in Portland on the way. More specifically, a stop at Allagash Brewing! It was only about 10 minutes off the highway, so it was totally worth the quick detour.

LSS Allagash Cold Beer Section

We didn’t have time to hang out for a full brewery tour, but we did have time to sample a few beers! They have different sized pours available, so we opted to do half pours of a few different varieties. My favorite will always be the Allagash White, but I also really liked the Brett IPA and a sour they had (but can’t remember the name of). They had a large, dog-friendly outdoor space we opted to hang out at because duh - DOGS! The covered portion of the exterior was crafted with wood beams and picnic tables, and the completely open areas had bar-height tables to stand at and fresh picked flowers in mason jars. Totally rustic and cozy!

We snagged a seat at a picnic table under the covered portion, right near the Mr. Tuna Food Truck that was on-site. It only took a few minutes before I caved and made a sushi order. Their rolls were delicious! I was a little nervous to order sushi from a food truck because let’s be honest, not all sushi is super fresh. But, I had no reason to worry. The California and Spicy Tuna were SO fresh and I loved their unique take on what a “roll” was. It kind of looked like a stuffed seaweed ice cream cone!

LSS Allagash Beer
LSS Mr Tuna Sushi

We made a quick pit stop at Trader Joe’s in downtown Portland next for some wine, snacks, and flowers to bring family, and then continued the rest of our drive. If you have time on the way up or on the way back, you HAVE to stop in Wiscasset for a Sprague’s Lobster Roll. A lot of people wait in the hours-long line at Red’s Eats, but Sprague’s is right across the street, has better seating/view, and is insanely delicious. You can expect to pay around $20 for one lobster roll (depending on current market prices), but since they are so big, splitting it with someone will still leave you feeling pretty full. These are fresh, butter-lovers rolls - not the soggy, soaked in mayo kind!

LSS Sprague's Lobster

Soon we arrived in Rockland, and spent the rest of the evening reconnecting with family at my Aunt and Uncle’s House. We filled the next few hours with lots of laughter, wine, appetizers, and homemade pizza (you should be a chef Uncle Kyle!).

It was a long day of travel and fun, so we hit the hay early and got a full night’s sleep. The next morning, we celebrated my grandmother’s amazing life at the prettiest little church in Cushing, Maine and reminisced on so many wonderful memories. We miss you, Gramma!

LSS Rhumb Line Cocktail

Later in the afternoon we all reconnected at the Rhumb Line in Camden. This spot had a great outdoor space on the edge of the harbor, including a massive outdoor bar. We hung here for a couple of drinks and chatted. I ordered a spicy cocktail with extra jalapeños and finished every drop! Afterwards we switched things up and headed over to the 16 Bay View Hotel. They have a great first-floor lounge bar, as well as a rooftop bar with spectacular views of the harbor. So great, in fact, that the bar is actually named The View! I stayed with the spicy theme and ordered The Sunfire, with Tanteo jalapeño tequila, watermelon, lime, cilantro, and simple syrup. We all sat around a warm fire pit, enjoying the boats and talking. It was a great evening! We usually stay with family during our visits to the Maine coast, but this hotel looked really nice and would would probably be great to stay at during your trip! There are a ton of other home rentals, bed and breakfasts, and hotels in the area, too.

LSS Laura and Ryan
LSS Laura and Craig

After drinks my other Aunt and Uncle had us over to their mountainside home for a full, buffet-style spread for dinner. My Aunt Cindy made a ton of delicious food. We watched football and hung out here for awhile, then Ryan, my cousin, and I hit up a dive-bar in Rockland for a little whiskey and music before calling it a night. 

The next morning we said our goodbyes and hit the road back to Boston, where we planned to spend the evening. The drive went smoothly, and we dropped off our rental car at the airport. Since Boston Logan is so close to the downtown, we just snagged a quick UBER over to the Hyatt Regency. We’ve stayed here a few times and love the hotel and location. It’s right off the Common in the Theatre District and is central to all the sights! We can walk pretty much anywhere from this spot and there’s plenty of breakfast and coffee spots nearby in the mornings, or shopping in case you forget to pack something.

LSS Downtown Boston

We dropped off our bags, freshened up, and walked over to my favorite part of Boston - the North End! The brick streets, historical vibes, and Italian food and wine make it a magical little neighborhood. We had an amazing dinner at Ristorante Euno and the service was incredible! They even brought us complimentary ‘creamy’ Limoncello at the end of our meal. I guess I’ve never had the creamy variety before, but I definitely prefer this style now! It’s a little smoother and less sweet. We split a bottle of wine, and ordered the Caprese Salad, Caesar Salad, Rigatoni, and Half Chicken. In warmer weather, request a table near the front windows - they open up to the street and you can enjoy the breeze and ambiance of the North End. 

LSS Yvonnes Boston

After dinner we snagged a seat at Bacco and watched some football before heading over to a spot near our hotel that I had looked up before our visit - Yvonne’s. We would have normally missed spotting this, because it’s tucked down an alley. You guys - you HAVE to go here when you are in Boston! Not only is the decor insanely cool, but the drinks and staff are awesome! It’s surprisingly massive inside, and they have multiple bars, dining areas, and lounges. Even the bathrooms are fucking cool. Do yourself a favor, order the Grande Dame, and take a picture with Christopher Walken. You’ll see what I mean when you go. We are going here for dinner next time for sure, because the menu looks amazing.

The next morning we slept in, got ready, and had the hotel hold our bags while we ventured out. Our flight was delayed, so we had some extra time to wander. We snagged a Starbuck’s drink and then walked among the cool cemeteries and historic sights to Faneuil Hall and Quincy Market. Here we split some incredible New England Clam Chowder and a California Roll at the indoor market, then grabbed a couple of Margaritas at MIJA Cantina.

LSS Faneuil Hall Boston
LSS Boston Quincy Market

Afterwards, we popped into nearby Central Wharf for a drink and some Oysters, and I couldn’t stop taking pics of the interior! I loved the mix of old-time brick and modern, nautical pieces. Definitely worth visiting! Then, we picked up our bags at the hotel and headed to the airport to catch our flight back. I didn’t mind the slight delay because it meant a few extra hours in one of my favorite cities.

LSS Central Wharf Co

We had a super quick weekend because we had to get back to our pups, and I didn’t want to leave! I love the east coast so much, and can’t wait to get back there. I hope you have a chance to visit sometime, too! If you have more time in Maine, be sure to visit the Owl’s Head Museum, spend a day in Bar Harbor, and climb the Beehive. Or, in Boston, definitely do The Freedom Trail and stop at Fenway. Don’t hesitate to message me if you have any questions. Now, onto the next adventure!