3 Days in Plymouth, Massachusetts
Disclaimer: We are not paid to promote any restaurant, hotel, activity, product, or attraction. All opinions are subjective and based on our personal experience. Your experience may be different.
Plymouth, Massachusetts is a wonderful coastal city, well-known for its’ many historical, cultural, and entertainment offerings. The picturesque New England waterfront city is one of the most visited East coast cities. It is on my list of recommended daytrips from Boston. While I recommend a full weekend to explore, at least consider a daytrip here from the city if you are limited on time.
I had the privilege of living just a half hour from this city for many years. I really loved the mix of nature and historical attractions you could enjoy year-round. The city is most notably famous for being home to Pilgrim Memorial State Park, one of the most visited parks in the US. It is home to Plymouth Rock and the Mayflower II replica, plus the views are gorgeous.
Historical sites aside, I love the vibrant downtown and waterfront district. There are so many interesting shops, scenic dining choices, and great tourist attractions to explore.
Below is a sample 3 day itinerary that I have devised after many trips to the city. I have tried to incorporate a mix of historical, natural, and fun attractions into the schedule so there is something for everyone.
Day 1
4:00pm – Check into your Plymouth hotel. You will find an assortment of options in town, including: cozy bed and breakfasts, historic inns, and standard chains. To get the most out of your visit, including convenient access to most attractions, consider booking a stay with the John Carver Inn The inn is conveniently located within walking distance to most great attractions and home to many great amenities, including: an indoor pool, on-site restaurants, and a full service spa.
6:00pm – Enjoy an excellent, authentic Italian dinner at Mamma Mia’s, a fantastic local Italian chain with several locations throughout the Southeast Massachusetts region. I love this waterfront location (if your visit happens to fall during the warmer spring or summer months, definitely sit outside).
Aside from the views, the food is always excellent. Plenty of traditional favorites and specialties can be enjoyed (and gluten-free choices too!). This cozy, local Italian restaurant is one of my favorites in Massachusetts.
8:00pm – Take a historic haunted ghost tour with Plymouth Night Tour. A fun time for history buffs, those interested in the paranormal, and anyone looking for something fun to do during the Halloween season. Don’t worry if your visit doesn’t fall during October: the tours run year-round! If you have ever wanted to try out real ghost hunting equipment, here’s your chance. I really loved this tour. Our guide was so entertaining and we learned a lot about local haunting legends.
Each guest gets their own EMF meter to use while exploring the city’s oldest and most haunted sites. My favorite part of the tour is walking through creepy Burial Hill Cemetery, believed to be one of the most haunted places in the US. Note: You will want to meet up for the tour about a half hour in advance.
Day 2
7:00am – Enjoy breakfast at Persy’s Place, a rustic American diner with the coziest dining room. The food is great here and the ambiance is so comfortable. This is by far my favorite breakfast place in the state. There are several cafes throughout the region. The Kingston cafe is about a 10 minute drive from the city.
8:00am – Explore Plymouth’s small, yet attractive collection, at Plymouth Center for the Arts. It’s a small museum, yet a great way to experience some local culture.
9:00am – Take a stroll along the beautiful waterfront before the afternoons crowds start arriving. If your visit falls during the colder winter months, you should have no problem with any crowds. There are beautiful beaches to explore and historical sights to photograph (Plymouth Rock and the Mayflower). If you are into photography, this is a great place to capture a few nice waterfront landscapes.
10:00am – Enjoy an early lunch at Wood’s Seafood, an excellent local seafood restaurant with an attractive location on the waterfront. Fresh local lobster, beautiful waterfront views, and a casual setting make it the perfect pre-cruise option. No visit to Massachusetts would be complete without enjoying some lobster and this great local gem provides a gorgeous setting for doing so.
Noon– Take a morning whale watching cruise with Captain John’s, one of the best places in the state for seeing these beautiful creatures up close. Not only are the views fantastic, but they also guarantee sightings, meaning if you do not see a whale, your next visit is complimentary. Everything about this cruise is fantastic. The tour guides are both interesting and entertaining: you will not fall asleep as is the case in many tours. You will likely see several whales (we saw a lot), and possibly some dolphins too. The views as you arrive back into Plymouth Harbor are simply stunning – I love the view of Plymouth Rock. Check out my whale watching tips for a great experience.
Winter alternative: If your visit falls outside of whale watching season, you can visit an indoor attraction like the Pilgrim Hall Museum, the oldest operating museum in the country. You will be able to learn more about the Pilgrim’s journey via informative exhibits and videos.
4:00pm – Head over to your hotel for a bit of rest and relaxation before heading out to dinner. Your whale watching adventure is a fun, yet long and often cold journey (I was absolutely freezing even though we booked a summer cruise). Take some time to rejuvenate and warm up in your hotel hot tub.
6:00pm – Enjoy a great dinner at Carmen’s Cafe Nicole, an eclectic restaurant serving an interesting array of American, Mexican, and Seafood dishes. They offer a lot of healthy and vegetarian options which is a bonus for me. If the weather is nice enough, be sure to enjoy the cozy outdoor patio, which features relaxing views of the waterfront.
8:00pm – Take a relaxing stroll around downtown Plymouth. You will find various events going on throughout the year. A nice selection of pubs and wine bars to choose from (check out New World Brewery) will keep you busy all night.
Day 3
7:00am – Get up early and enjoy a self guided historical tour of Plymouth (if you prefer, you can sign up for a tour through local businesses such as The Jenney Museum). There are many interesting and magnificent sights to take in, including: Burial Hill, Old Parish Church (one of the country’s oldest), and the National Monument to our Forefathers.
11:00am – Enjoy another healthy, home cooked brunch at Persy’s Place. This diner features New England’s largest breakfast menu. I recommend treating yourself to the Dapper Dans special, a hefty plate which includes eggs, potatoes, a muffin or toast, and 2 pancakes. It’s one of the better breakfast plates I’ve enjoyed in a long time.
1:00pm – Head over to Myles Standish State Forest, the largest recreation area in Southeast Massachusetts, for a fun afternoon of hiking or biking the park’s massive trail system. This gorgeous, quiet, underrated park provides a spectacular setting for photography, particularly during the beautiful fall season. The park is just as stunning during the winter when covered with fluffy white snow. During this time of the year, snowshoeing and cross country skiing is a scenic and intense! way to explore the trails. A great pick anytime of the year. For first time visitors, I recommend an easy loop around the 2.5 mile Reservoir trail.
5:00pm – Head back into town for some souvenir shopping and a treat! I love all the little shops here which specialize in either souvenirs or handcrafted creations. Since moving to the region, I really enjoyed exploring all these little Main Streets which feel like a step back in time. No chains, just local small business. Consider stopping for an extravagant treat at Cupcake Charlies. Dessert lovers will have a field day choosing amongst the enticing display of specialty cupcakes, available in an assortment of tempting flavors.
7:00pm – Choose another waterfront restaurant for dinner – you won’t ever get sick of the tremendous views! Plymouth is home to so many great waterfront dining options. Anna’s Harborside Grill is one fantastic choice. At Anna’s, Greek and American favorites are served in a casual, waterfront setting. Enjoy your last night with some great food and great views!
9:00pm – Head back to your hotel and pack up everything so you are ready to go in the morning. This will give you time to enjoy a final breakfast and walk around the waterfront before checking out of your hotel the next morning. No need to waste time in the morning organizing. Spend your last few hours enjoying the gorgeous New England setting!
Addresses & Attraction Information
- John Carver Inn – 25 Summer St. Visit the inn website to make your reservations.
- Mamma Mia’s – 122 Water St.
- Plymouth Night Tour – 120 Water St. Tours are $25 per person.
- Persy’s Place – 117 Main Street
- Plymouth Center for the Arts – 11 North St. Open Wed-Sat from 11am-4pm except Sunday (1-4pm).
- Pilgrim Memorial State Park/waterfront area – Water Street
- Wood’s Seafood – 15 Town Wharf
- Captain John’s Whale Watching – 10 Town Wharf. The season usually runs from the beginning of May until the end of September. 9am, Noon, and 2pm tours are available, depending upon the month. Prices (as of 2025) are $74 per adult, and $54 for children (4-12).
- Pilgrim Hall Museum – 75 Court St. Open daily from 9:30am-5:00pm (closed Christmas, New Year’s, and the month of January).
- Carmen’s Cafe Nicole – 114 Water St.
- Downtown Plymouth – Main St.
- Jenney Museum historical walking tours – 48 Summer St. Call 508-747-4544 to make a tour reservation. Times vary based on type of tour/time of year.
- Myles Standish State Forest – 194 Cranberry Rd.
- Charlie’s Cupcakes – 6 Town Wharf
- Anna’s Harborside Grille – 145 Water St.
