Itinerary feedback

Question

My best friend and I will be visiting Boston at the end of March for a week - first time for both of us. Have done a lot of research and have a plan, but interested in feedback. Thanks for any offered. We're staying at The Marriott Custom House, and enjoy walking whenever possible.

Day 1 - Fly in from San Diego, check-in and go to the Museum of Fine Arts Late Nights event in the evening.

Day 2 - Check out Faneuil Hall/Quincy Market in the morning, 1:15 guided Freedom Trail walk, North End for dinner and evening sightseeing.

Day 3 - Self-guided Beacon Hill audio tour in the morning, ending at The Liberty Hotel for brunch. In the afternoon to the SoWa Arts & Design district, and Vintage Market. Dinner in South End.

Day 4 - Plan is to do a day trip - either Providence, Portland, Gloucester, or Cape Cod. It will be a long day, we know, but feedback is especially welcome here.

Day 5 - Cambridge for the day - we want to visit the Cambridge Antiques Market, use the shuttle to visit the different squares, and stay for dinner/music. Have been looking for walking tours but finding only those that concentrate exclusively on Harvard or MIT.

Day 6 - Concentrate on Back Bay sightseeing and exploration. I will confess that, having never been to the city, I'm getting confused by which things are in Back Bay vs. Beacon Hill, but hope we have left enough time to see the Athenaeum, the Public Library, the State House, the Public Gardens and Boston Common between the two days devoted to the areas.

Day 7 - Morning tour at Fenway Park, lunch, and then the Isabella Stewart Gardener, followed by dinner somewhere near.

Day 8 - Opening day at Fenway (we have the tickets). Non-ballpark food recommendations welcome.

Thanks again for any feedback offered.

Answer

Your itinerary for Boston looks well thought-out and offers a great mix of sightseeing, culture, and exploration. Here are some thoughts and suggestions to fine-tune your plans:

Day 1: Starting with the Museum of Fine Arts Late Nights event is a wonderful way to ease into your visit. You'll get to enjoy the museum’s unique exhibits and after-hours vibe. If you’re looking for a quick dinner before the event, there are several good options nearby such as the "New American" restaurant called The Capital Grille or "Oleana" for Mediterranean fare.

Day 2: Faneuil Hall and Quincy Market are popular spots, and your Freedom Trail walk sounds like a perfect way to take in Boston’s history. For North End dining, don’t miss out on a classic Italian spot like "Mamma Maria" or "Giacomo's" (for a more casual, but beloved choice). Be sure to grab a cannoli from Mike's Pastry or Modern Pastry afterward for a sweet treat!

Day 3: Beacon Hill and The Liberty Hotel brunch sound like a great way to start your morning! When in the area, I’d recommend popping into "The Public Garden" for a stroll. If you enjoy antiques, check out "Beacon Hill Antique Gallery" while exploring the neighborhood. The SoWa Arts District is also worth spending more time in. For dinner, the South End is a fantastic choice – try "Toro" for tapas or "B&G Oysters" for a seafood-focused meal.

Day 4: A day trip can be a bit much, but if you’re up for it, all four destinations are great choices. Given the time constraints, Providence or Gloucester might make the most sense, as they are closer to Boston. Providence has an artsy, college-town vibe with great restaurants and shops, while Gloucester offers scenic coastal views and some of the best seafood. Cape Cod might be too far for a day trip, especially in March when some attractions might be closed. If you decide on Providence or Portland, try to leave Boston early to maximize your time there.

Day 5: Cambridge is a wonderful day trip with lots to explore. The Cambridge Antiques Market is great if you're into unique finds. As for walking tours, you might want to check out the "Harvard Square Walking Tour" which focuses on more than just Harvard. It explores the history of the square itself and its local landmarks. For dinner/music, head to "The Sinclair" for live music and tasty food, or "Alden & Harlow" for upscale American cuisine.

Day 6: For Back Bay, be sure to visit the Boston Public Library, the Athenaeum, and the Public Gardens. You may also want to add a walk down Newbury Street for shopping or a quick bite. If you have extra time, head over to Copley Square for the iconic "Trinity Church." Beacon Hill is nearby, and you’ll want to stop by "Louisburg Square" and "Acorn Street," one of the most photographed spots in the city. Consider doing a “Beacon Hill Walking Tour” for historical insights.

Day 7: Fenway Park is iconic, and the Isabella Stewart Gardner Museum is a wonderful complement to your day with its beautiful collections and unique architecture. There are plenty of places to eat around Fenway, including "TITS (The Intercontinental Bar & Grill)" or "Little Donkey" in the Fenway neighborhood for some great food options.

Day 8: For Fenway’s Opening Day, you'll get to experience the excitement of Boston’s baseball culture! Before the game, grab a quick bite at "The Breakfast Club" or "TITS" (The Intercontinental Bar & Grill) which is a local favorite for game days. Afterward, a stroll around the Back Bay area or along the Charles River might be a nice way to finish off your trip. If you have more time in the afternoon, you might want to explore the Seaport District for unique food and fun spots.

Overall, your itinerary looks like it will offer a great mix of history, culture, food, and outdoor activities. Boston is very walkable, so you’ll enjoy getting to explore the different neighborhoods on foot!