From hidden beaches and jaw-dropping views of the Boston skyline,
to family-run eateries that have been pleasing hungry masses for decades,
Eastie + Winthrop are all about the authentic, local experience
East Boston (aka “Eastie”) is a neighborhood most known for housing Boston Logan Airport. However, the area is also home to some of the most eclectic restaurants in the entire city. Travelers to this region of Boston witness the most stunning views of the Boston Harbor and city skyline. Eastie’s history, sights, and food artfully interlace to provide visitors and locals with one of the region’s most culturally rich experiences. And when you’re ready to head into downtown Boston, you’re just a short drive or speedy water taxi away!
Winthrop, an oceanside town located at the North entrance of the Boston Harbor, is one of the oldest communities in the United States. The peninsular city boasts scenic seaside views from almost any vantage point and has a decidedly quaint, fisherman’s village feel. Visitors can stroll through the winding roads, sunbathe on quiet beaches, engage a local in conversation, and immerse themselves in Winthrop’s charming, laid-back atmosphere.
Spend 36 hours in Eastie + Winthrop, and you’ll see there’s more to the area than meets the eye.
– SEE & DO –
Piers Park is a popular spot to escape the hustle and bustle of Boston and simply appreciate the city life from a distance. The park is an ideal destination to see breathtaking skyline views and enjoy being near the harbor in a peaceful, laid-back setting.
Piers Park Sailing Center
95 Marginal Street, Boston, MA 02128
Want to get a bit more adventurous? Take a sailing lesson at the Piers Park Sailing Center! If you’re particularly dedicated, you can take the non-profit’s 21-hour sailing course. However, if you just want to enjoy the waves while someone else does the work, you can also rent both a sailboat and staff member to sail it for two hours.
While everyone escapes to the Cape this summer, make your way over to one of Boston’s gems: Constitution Beach. What better way to wake up from a pleasant beach nap than to open your eyes, look across the water, and see the beautiful Boston skyline. You’ll even get to see planes taking off and landing at Boston Logan in the distance! And when you get tired of sunbathing, try your hand at more recreational activities at the beach’s tennis, handball, and basketball courts.
111 Orient Avenue, Boston, MA 02128
One of the most famous sights in Eastie is the impressive Madonna Shrine. This 35-foot statue was built in 1956 at the top of Orient Heights. Take in the beautiful mosaics and experience yet another area where you can view the Boston Harbor and skyline.
290 Tafts Avenue, Winthrop, MA 02152
Deer Island, one of Boston’s Harbor Islands, symbolizes the importance of natural resource preservation for the City of Boston. The island boasts 60-acres of parkland and hills where visitors can jog, hike, bike, sightsee, picnic, and fish. It is accessible by car and bus.
Winthrop Shore Drive
Winthrop Beach is the go-to beach for many of the locals during the summertime. The beach is small but has a unique charm and relaxed vibe. Water shoes are recommended for swimmers as there are quite a few rocky areas. Great spot to escape from the touristy crowds!
Jazz At the Firehouse, Frank Vignola & Raniolo
260 Sumner Street, Boston, MA 02128
June 12th – Starts at 5 pm and doors open at 4:30 pm, $15 per ticket
Frank Vignola is one of the world’s most admired guitarists. He has played for some of the industry’s biggest musicians like Ringo Starr, Madonna, Donald Fagen, Wynton Marsalls, Tommy Emmanuel, the Boston Pops, the New York Pops, and Les Paul.
Irish Music Concert
365 Bremen Street, Boston, MA 02128
June 18th – Starts at 3 pm, FREE
Enjoy an hour of lively Irish folk music hosted by Boston Public Library!
Matt Heaton Concert
365 Bremen Street, Boston, MA 02128
June 22nd – Starts at 10:30 am – 11 am, FREE
Looking for something to take the kids to? Matt Heaton is an artist who caters his performances toward families and children. He uniquely combines surf, American roots, and Irish traditional in all the music he performs. His shows are family-friendly and comedic.
La Hacienda Restaurant & Bar
150 Meridian St, Boston, MA 02128
If freshly made Mexican, Salvadorian, and a touch of American fare strikes your fancy, La Hacienda Restaurant & Bar is sure to satisfy your palate. Start the weekend with a breakfast buffet, or fill up on carne asada and mango margaritas just about anytime at this international, culinary heavy hitter.
111 Chelsea St, Boston, MA 02128
First established as a bakery in 1903, this pizzeria is now a landmark eatery for both tourists and locals alike. Considered by many to be the best pizza in Boston, Santarpio’s offers both pizza pies and barbecue skewers to hungry lunch-goers. Don’t miss an opportunity to visit one of East Boston’s most treasured restaurants while you’re visiting the area. But please remember, Santarpio’s is cash only!
Maverick Marketplace Café
154 Maverick St, Boston, MA 02128
The Maverick Marketplace Café is a hot lunch spot for anyone craving fresh burgers, sandwiches, and salads. Visitors can accompany their meal with refreshing, local craft beer. The restaurant prides itself on its selection of beverages sourced only by Boston-area distilleries. The Maverick Marketplace Café is an excellent pick for anyone craving a light meal and good drink in a relaxed setting.
Gigu Café & Lounge
102 Meridian Street, Boston, MA 02128
Feeling that mid-afternoon slump? Head over to Gigu Café for a quick caffeine fix! The restaurant has an artistic flair and the walls are decked with pieces by local artists. If you’re feeling extra tired and need a sugar rush, try something from Gigu’s scrumptious dessert menu.
KO at the Shipyard
256 Marginal Street, Boston, MA 02128
It’s time to whip out that culinary passport again and travel to Australia! KO at the Shipyard offers a variety of authentic vegetarian and meat pies. Each pie at KO is carefully crafted so that you’ll enjoy each bite until the end. And on Friday nights, KO does a “pie and a pint” for $10! This joint is an excellent stop to take a short break from your day of exploring and re-fuel on a savory Aussie pastry.
1012 Bennington St., Boston, MA 02128
If you’re in the mood for Mexican food, try out Angela’s Café. This quaint restaurant’s menu focuses on food from the Puebla region of Mexico. The ingredients are known for being incredibly fresh, and you’ll receive only the most traditional and exquisite culinary experience from any dish you order. Start your meal with the freshly made, tableside guacamole!
Belle Isle Seafood
1 Main Street, Winthrop, MA 02152
For a true, local, straight-from-the-sea goodness, head to Belle Isle Seafood. Dubbed “Boston’s Best Lobster Roll” by Improper Bostonian, you can bet it delivers. With no shortage of cooked to order seafood, the hardest part will be deciding if you want it fried, broiled, baked, grilled, or blackened to perfection.
258 Saratoga Street, Boston, MA 02128
Grab an early Italian dinner Rino’s Place (the earlier the better since the wait at this popular restaurant can get long!) at this small but mighty-tasty eatery. Rino’s was featured on Food Network’s Diners, Drive-Ins, & Drives and is famous for its hearty, mouth-watering Italian food. Opened 24 years ago by Rino and Anna DiCensio, the restaurant is now run by son, Chef Anthony.
107 Porter Street, Boston, MA 02128
If you’re craving some late-night snacks and a few well-crafted cocktails, try out Ecco Boston. This vibrant lounge has a late bar menu with tapas and a large assortment of interesting cocktails and craft beers. Close out your day at this elegant hotspot in Eastie!
Eddie C’s Bar
34 Maverick Square, Boston, MA 02128
Want to grab drinks somewhere a bit more casual and divey? This popular Eastie sports bar is visited by both locals and tourists alike. Grab a handful of free pretzels at the bar, line up your favorite song on the jukebox queue, and throw back an ice-cold beer to finish up a day well spent!
Hyatt Regency Boston Harbor
101 Harborside Drive, Boston, MA 02128
This waterfront hotel is located very close to the airport and is right on the Boston Harbor. In addition to traditional hotel amenities, the Hyatt Regency offers water taxi transportation to downtown Boston.
The Winthrop Arms Hotel & Restaurant
130 Grovers Avenue, Winthrop, MA 02152
This charming hotel is located a block away from the beach and has an old-fashioned, homey atmosphere. Frequented by locals for cocktails and mac & cheese, it’s a hidden gem you’ll want to have on your radar.
Rooms range from $155-185 a night.
Harrington House Bed & Breakfast
2 Terrace Avenue, Winthrop, MA 02152
Located in a 19th century Victorian home, this beautiful bed and breakfast overlooks the harbor and allows guests to immerse themselves in a classic New England-feel. This B&B has three rooms for rent, so be sure to book enough in advance!
MBTA: East Boston and Winthrop stops are on the Blue line train – get off at Maverick, Airport, Wood Island, Orient Heights, and Suffolk Downs stops.
Parking: Parking at the MBTA stops is $5 per 24 hours.