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BOSTON

Neighborhoods
  • Back Bay – Classic Boston with beautiful brownstones, Newbury Street shopping, the Public Garden, and plenty of cafés and restaurants.

  • Beacon Hill – One of Boston's most charming neighborhoods, known for its brick sidewalks, historic homes, and Acorn Street.

  • North End – Boston's Little Italy, packed with Italian restaurants, bakeries, and historic sites.

  • Seaport District – Modern waterfront neighborhood with rooftop bars, seafood, Harborwalk views, and newer restaurants.

  • Fenway – Baseball, museums, and a growing food scene centered around Fenway Park.

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Restaurants & Coffee
  • Tatte Bakery & Café – My favorite coffee stop in Boston. Great coffee, breakfast, pastries, and beautiful spaces to work or relax.

  • Neptune Oyster – Famous for lobster rolls and fresh oysters. Expect a wait, but it's worth it.

  • Saltie Girl – Excellent seafood with one of the city's best lobster rolls.

  • Mamma Maria – Upscale Italian tucked into the North End.

  • Giacomo's Ristorante – Cozy, no-frills North End Italian that's consistently worth the line.

  • Contessa - An elegant rooftop Italian restaurant overlooking the Public Garden. The brunch is excellent, and the views are even better.

  • Beacon Hill Books & Cafe - A charming bookstore café that's perfect for browsing, grabbing coffee, or enjoying a light breakfast or lunch.

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Things to Do​
  • Wander Newbury Street for shopping, cafés, and people watching.

  • Stroll through the Boston Public Garden and Boston Common.

  • Walk or Run the Charles River Esplanade, especially around sunset.

  • Browse Quincy Market and Faneuil Hall.

  • Explore the Museum of Fine Arts if you enjoy art.

  • Catch a Red Sox game at Fenway Park or simply tour the stadium.

  • Explore the Prudential Center - A shopping and dining hub that's perfect for rainy days. You can easily spend a few hours wandering through the stores, restaurants, and cafés.

  • Walk Commonwealth Avenue -A gorgeous boulevard lined with historic brownstones and towering trees. One of the prettiest walks in the city.

  • Explore Beacon Hill - Take your time wandering the side streets—you'll find some of the city's most photogenic corners.

  • Visit Boston College - A stunning campus in Chestnut Hill with beautiful Gothic architecture.

  • Tour Harvard and Harvard Square - Walk through Harvard Yard, then spend some time exploring the shops, cafés, and street performers around Harvard Square.

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Don't Miss
  • Grab a coffee from Tatte before wandering Back Bay.

  • Spend an afternoon walking Beacon Hill → Boston Common → Public Garden → Newbury Street—it's one of the best routes for first-time visitors.

  • Eat at least one dinner in the North End, then finish with a cannoli from either Mike's or Modern.

  • If you're visiting in the fall, Boston is especially beautiful from late September through early November, when the weather is crisp and the foliage is at its peak.

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Travel Tips

Best Time to Visit: May–June and October–November.

Avoid: Marathon Monday in April unless you're visiting specifically for the race.

Airport: Boston Logan is one of the easiest major airports to navigate and is only about 15 minutes from downtown.

NYC RECOMMENDATIONS

West Village Restaurants

Waverly Inn – Classic, iconic American restaurant with timeless comfort dishes and a cozy ambiance for brunch or dinner.
L’Artusi – Italian favorite with excellent pastas, thoughtful wine list, and stylish vibe.
I Sodi – Tuscan Italian gem known for authentic pasta and cozy atmosphere. Lemon pasta!
Don Angie – Modern Italian American with standout pasta and creative flavors. Lasagna!
American Bar – Classic NYC bar with steakhouse-style food and drinks. Martinis!
Little Ruby’s – Casual spot great with kids (4 yo niece-approved).

Pastis – Beloved French bistro with classic bistro fare and a lively mood in Meatpacking District. 

Bus Stop Cafe - Love the vibe in here for lunch, or favorite place for a Sunday breakfast. 

La Bonbonniere - dive breakfast perfect after a long night out 

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West Village Coffee Shops

Hungry Llama – Relaxed coffee vibe perfect for working, lots of space. Great breakfast.
The Elk – Quaint coffee shop with bites, coffee, and little trinkets you didn't know you needed. 
Buvette – Charming French-style cafe and wine bar ideal for brunch or small plates.

11th Street Cafe - quick coffee stop with amazing gluten free blueberry scones. 

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Midtown

Hatsuhana – Not a trendy vibe, almost feels like a hole in the wall, but it's well-known and loved sushi spot. 
Estiatorio Milos – Elegant Greek seafood and Mediterranean dishes with fresh fish. There is also a Hudson Yards location which has a gorgeous sunset view over the Hudson. 

Quality Bistro – Lively vibe with an especially spicy Caesar salad and "bread service".

​Liberty Bagels - home of the rainbow bagel but also lots of other great bagels​

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Favorite Workout Spots

BodyRok – Pilates reformer class that feels classic but is really hard. 
Fuze House – Sculpt style classes in a heated room. 
Solidcore – Intense ab burn, you can find them within a half mile in any neighborhood.
Barry’s – Classic high-intensity interval workout (multiple NYC locations).

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Tuscany, Italy 

Chianti 

Borgo Vescine 

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- Castello di Brolio

- truffle hunting 

- cooking class 

- wine tastings 

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Capri, Italy 

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​Places: 

  • Caesar Augustus 

  • Le Grotelle

  • Il Riccio

  • La Fontelina

  • Villa Margherita

  • Quisiana

  • Anema e Core

  • Monte Salaro hiking trail

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Tip: Taking the cable car to the port was very easy and quicker than waiting for a cab when trying to catch the ferry. 

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Positano, Italy ​​​​​

Places: 

Rada Beach Bistrot

Da Adolfo

Da Vincenzo

Don't Worry Bar

Hotel Sirenuse,

La Sponda 

La Tagliata 

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Other: hiking, boat day, custom sandal making, shopping, ceramics shopping. ​​​

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Sally Rychlak

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