Anniversary Weekend in Boston

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Advisor - Amy Hansen
Curated By

Amy Hansen

  • Boston

  • City Travel

  • Weekend Getaways

  • Couples Travel

  • Arts & Culture

  • Romantic

Advisor - Anniversary Weekend in Boston
Curator’s statement

A fun anniversary getaway with our friends! My husband, Kurt, lived near Boston during his childhood (Franklin, Mass. to be exact). The last time he visited, he was about 12, so he was excited to experience the area again. Our friends also relocated to the area, so it was a perfect reason to visit! What a beautiful city!

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Day 1: Beacon Hill

Lunch in the Public Garden

We stayed in the Beacon Hill area of Boston for the coffee shops, cobblestone streets, and local feel. In a big city, I usually choose to stay in a place where we will feel like we live there, and where locals will be around for advice on where to eat! It’s also a short walk to Boston Common and Public Garden, and what’s better than staying near a park where you can hang out during a busy visit?

We decided the size and service at the Beacon Hill Hotel was perfect for us. The small, boutique hotel has 14 rooms and is a 19th century pair of townhomes-turned-hotel. Lovely! We requested an early check-in and told them it was our anniversary, and they graciously gave us an early check-in and a corner king room for our stay. The rooftop here is a great place for breakfast or getting a drink from the bar and watching the sun set.

It’s a couple blocks to the Public Garden, so we grabbed lunch from Tatte Bakery (wonderful homemade sandwiches, salads, and pastries!) on Charles Street and enjoyed relaxing on a bench watching the ducks. The bartender at the hotel recommended the “Lobstah” at Legal Seafoods and it was indeed delicious, and we also tried out Sweet Cheeks Q (thanks Tiffani of Top Chef) before rooting on the Red Sox at Fenway! Sadly, the Astros were hot that night, but the biscuits and brisket from our dinner got us through the night.

Day 2: Explore like a local

Beacon Hill Books and Cafe

We started this day with coffee (do the words Lavender Latte mean anything to you?!) and treats from our across-the-street neighbor of Tatte Bakery. This morning was perfect for walking the Beacon Hill streets. Robert Frost lived here and wrote poetry after his wife died, so we had a look (outside) at his apartment. This was also near the most “beautiful street in America,” (aka Acorn Street) which is a gorgeous little street. Do remember that actual people live here… we took a picture at the end of the block.

Beacon Hill Books and Cafe lured us in for lunch (make reservations) and has a precious outdoor eating area that feels just like Europe. Serving soups, quiche, and salads, it’s a perfect spot to pop into while walking or shopping in the area. We also went upstairs to the bookstore (beautiful) and walked the four floors looking through the nearest releases.

Cross the street for Flat of the Hill for any shirts, sweatshirts, or bags you’d like to take home. This is not a touristy shop, but a mix of home necessities and decorative goods. My favorite BOS sweatshirt was purchased here. The softest!

We bought tickets to View Boston, the city’s only observation deck, to enjoy the sunset. After toasting to a great day, we ended our day of exploring with The Salty Pig, featuring charcuterie, pizzas, and salads. Molto Bene!

Day 3: Historical Boston

Sunset on the Charles River

Boston, of course, is teeming with history and we were here for it! Walking on the same soil as our country’s founders and acknowledging both the victories and losses was meaningful. Our favorite historical outings were walking on the Freedom Trail, the Granary Graveyard (graves from the 1600s), climbing the Bunker Hill monument (295 steps!), and seeing the USS Constitution.

We actually met the crew of the Constitution at Warren Tavern for lunch… what a treat to see them all come in and eat! Warren Tavern is the oldest tavern in Massachusetts (George Washington ate here) and has the best clam chowder we’ve ever had. It was a perfect, warm, and satisfying lunch during a rainstorm, plus we got to check clam chowder off the list of must-do’s!

We also loved our visit to Paul Revere’s house and the Old North Church (sans Nicholas Cage) with a stop at Modern Pastry for goodies on the way home. No guilt though, since we hiked the monument, ha! They will box up your orders to take with you, or you can sit in the cafe.

Our last night in the city, we met our friends at Nightshift Brewing on the Esplanade. The beautiful setting on the Charles River gave us the chance to experience not one, but TWO marriage proposals. We ordered wood-fired pizza from the food truck (they have a food vendor each night they are open) and settled down with our friends to enjoy the breeze and the Saturday night vibe of Boston.

Sailboats in the river, friends meeting at tables and catching up at the end of the week, and a classical concert at the edge of the park… could I live here? I think yes. What a wonderful weekend. Thank you Boston!

Need to know

Stop at Modern Pastry for goodies on the way home. This is cash only! We were able to snag our favorites… eclair for me and pistachio creme for him. There is always a line for this place, and once you try the food you know why.

Advisor - Amy Hansen

Travel Advisor

Amy Hansen

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