Hollyday Planner

Check out my itinerary for the quick reference.

Day 1 – Fly in

Late flight out to Boston. We wanted to go the night before so we had all of our first full day to explore. We flew in as late as we could and stayed out by the airport.

Day 2 – Boston

UBER / SUBWAY: To hotel (Blue line to State). – All subway references are close to our hotel. I highly recommend staying downtown. It’s close to a lot of the sites & centrally located for subway access. Get a 7 day MBTA Charlieticket at a kiosk from any station.

SITES. Freedom Trail. Walking distance. Tickets at the door. 

• Old State House (opens 10a)
• Boston Massacre Memorial – a plaque in the sidewalk outside the Old State House.
• Faneuil Hall – This one is a market downstairs & historic upstairs.

Lunch: Bell in hand Tavern – a favorite every time I go to Boston. A common theme among our restaurant choices is they are very old. This tavern has been around since 1795.

SITES. Freedom Trail. Walking distance. Tickets at the door. 

• Old Corner Bookstore – Exterior is historic. Walk by.
• Old South Meeting House – I like this one
• Granary Burying Ground (closes @ 4p) – Probably my favorite of the freedom site Cemeteries. Lots of famous figured buried here.
• King’s Chapel & Burying Ground (walk by)
• Park Street Church (walk by)
• Massachusetts State House (walk by)
• Boston Common (walk through) – This is a large park. Stroll through for some great photo ops. It’ll be close to Cheers.

Walk down Acorn Street – We wanted to see the architecture. It was a block off the main road, but we loved seeing the buildings.

BREAK: Cheers – They had a replica of the set upstairs. We walked around and took pictures. I’ve eaten here before and do recommend it.

UBER to hotel

BAR: Sam Adams Taproom – We didn’t have time on this trip for the brewery. So, we checked out the taproom instead.

SUBWAY: State station. Orange line to community college. 

DINNER: Warren Tavern – My first time here. I loved it!! Built in 1780. Bunker Hill Monument is also fairly close by.

SUBWAY: Orange line to State Station

Day 3 – Boston

SUBWAY: Blue line. State Station to Aquarium. 

COFFEE: The Pink Carrot – To be honest, we wanted to go to Polcari’s but it wasn’t open. Super glad we found this place instead. It’s adorable and had what we needed (good coffee!).

SITES: Freedom Trail Sites. Walking distance. Tickets at the door. 

• Copp’s Hill Burying Ground – we skipped this one.
• Old North Church (opens 10a) – Always a favorite for me. Do the underground crypt tour if it’s open!
• Paul Revere’s House – Also a favorite of mine.

UBER: to USS Constitution – I love this boat. Be sure to check the website for ticket requirements. They’ve been different just about every time I’ve been.

LUNCH: Uber to Russell House Tavern – Great lunch spot.

CAMBRIDGE: Walking distance 

• Walk around Harvard
• Harvard Art Museum – Tickets at the door. This is where our plan fell apart. We LOVED this museum and wasn’t expecting it. We spent a lot more time here than expected. We were going to go down past MIT. We also planned to see Fenway Park on our way to Stewart Gardner. However, we enjoyed the Art Museum too much.

STOP: Isabella Stewart Gardner Museum (Bag restriction 12” x 12”) – Our plan continued to fall apart. This place was amazing and crazy at the same time. We loved it. We had seen the Netflix documentary about this museum and wanted to go. Very glad we did. Don’t skip this one. I would suggest planning this on a day with Fenway rather than Cambridge.

SUNSET CRUISE: Uber to Classic Harbor line  – Our previous two stops took longer than expected. We waited until the last second to get an Uber. Plus, it was heavy traffic time. This was the most intense Uber ride I’ve ever had. The cruise itself was a highlight. It was a casual boat ride through the harbor. The best part is getting to watch the USS Constitution fire the cannon to signal sunset.

DINNER: Uber to Lolita Fort Point – This restaurant was awesome. It was a later dinner and we did family style small bites. Loved the atmosphere!

UBER: to hotel

Day 4 – Salem 

SUBWAY: State Station Orange to North Station. Transfer to purple train (Newburyport/Rockport) to Salem. Get the MBTA app and pre-buy tickets for the round trip to Salem.

SITES: (walk around)

• Howard Street Cemetery (where Giles Corey was pressed to death)
• Downtown – Downtown Salem is adorable. It’s a great place to take a casual stroll and do some shopping.

LUNCH: Rockafellas – Love this restaurant. Order the Crab Cake BLT and thank me later.

• The Witch house (12p-3:30p; $9 at door) – The only remaining historical building from the times of the trials. This house belonged to the judge.
• Charter Street Cemetery / The burying site Cemetery & memorial – They have a memorial for the witch trials at the entrance. But there are some interesting and old graves to see. Including a Mayflower passenger.  

BAR: Village Tavern – It started raining on us at the cemetery. So, we ducked into this nearby tavern for a break.

Witch Pix – yes, we did and we loved it! While sitting in the Tavern, we saw this was nearby. And our group of 40-somethings thought this would be fun. We had a blast! Our husbands thought we were crazy but we stand by our choice.

7:30 SUBWAY: Purple line to Swamscott. Transfer to North State

Dinner – Union Oyster House / Green Dragon Tavern – The group split up for this dinner. Not everybody wanted Oysters. I would highly recommend the Oyster House. It has a wider menu than expected,. Those of us who went did want the oysters and they were fabulous. This is the oldest restaurant in Boston (est 1826). The group at Green Dragon didn’t have a good experience.

Day 5 – Newport, RI

WALK/SUBWAY (State to Downtown to South Station)

AMTRAK: South Station to Kingston.

CAR: Limousines of Newport & Providence to Newport – best decision to hire a driver. We had the car and driver for the whole day. Split between the group this was the most effective & affordable way to get around. And this company was great.

LUNCH: The Mooring Seafood & Kitchen Bar – In the Bowen’s Wharf area. We loved this restaurant.

SITES: 

• Newport Mansions – Buy tickets at the door. We bought a pass for multiple mansions. As many as were open the day we were there.
• Cliff walk – This spans most of the coast. Great views.
• Southern Coastal Drive – Our driver took us down this highway. He pointed out some homes owned by famous people and we stopped where we wanted for pictures.
• Castle hill lighthouse – We stopped and took the short walk to this lighthouse. This was the only stop we got out of the car. The weather was cold and rainy.
• Bowen’s wharf – We rounded the day with time back at Bowen’s Wharf. Great area to walk around for shopping or sit at a bar for a drink.

DINNER: White Horse Tavern – Another very old restaurant. Oldest in the US, 10th oldest in the world (serving since 1673). This was our one “nice” restaurant for the trip. It’s fabulous. The dress is business casual attire, which includes slacks, denim trousers, blazers, button down shirts, sweaters, dresses. No athletic wear.

AMTRAK: Our car took us back to Kingston station for the ride to South Station.