The Ultimate 9-Day Southern New England Road Trip
New England is perfect for a road trip thanks to picturesque towns, dramatic landscapes, and more attractions than you could possibly dream up.
The region is one of the United States’ most culturally rich in terms of US history, and has everything from mountains to sandy shoreline.
I spent a year in New York and one of my goals was to spend at least one night in each of the northeastern states (update: I did it!).
During this 9 day trip we explored New England’s southern states: Connecticut, Rhode Island, and Massachusetts.
This itinerary outlines exactly what we did during our southern New England road trip.



9 Day Southern New England Road Trip
Mystic, Connecticut
Mystic is a seaport town known for constructing ships throughout the late 1700’s and into the 1800’s.
Today it makes a great Connecticut destination thanks to its charming downtown area and ample entertainment options.
Fun Fact: The name Mystic came from the Native American Pequot’s term “missi-tuk.” Meaning “great tidal river” in reference to the Mystic’s tidal waters.

Things To Do In Mystic, Connecticut
Below is everything we did during our day and a half in Mystic.
Maritime Seaport Museum
You’ll find this museum on most “Things To Do In Mystic” lists, and for good reason!
It’s an outdoor museum with sailing ships and wooden boats, an active shipyard, and a huge 19th century seafaring village replica.
They also have a full exhibit hall, classes, boat tours, and games for children… Phew, got that all?
We spent a few hours here, but you could easily spend days trying to see everything in this very comprehensive museum.
You can book tickets in advance here: Mystic Seaport Museum.

Walk Through Downtown Mystic
Restaurants, boutiques, and ice cream shops line Mystic’s Main Street.
We browsed the many local businesses and grabbed a slice of their famous pizza, followed by a scoop of delicious ice cream.
When you’re finished shopping and dining, walk across the draw bridge and explore the cute nearby homes and riverfront.
The downtown area is small and can easily be explored in just an hour or two.


Noank
Just a short 2.5 miles from Mystic is the charming village of Noank.
The village has gorgeous seafront views and a handful of cute shops and restaurants. This is definitely worth a quick stop on your way in or out of Mystic.
You May Also Like: How To Spend One Day In Mystic, CT & The Top Things To Do In Mystic, CT

Where We Ate In Mystic
I eat primarily vegan and my husband eats a meat-based diet, so we try to find options which accommodate both.
This is everywhere we ate during our stop in Mystic, Connecticut:
- Karma Kitchen & Juicery Mystic – vegan & meat-based options.
- Pizzetta – we opted to eat here instead of the famous Mystic Pizza, simply because they offer vegan options in addition to meat-based. (Unfortunately, Pizzetta is now closed.)
- Mystic Drawbridge Ice Cream – vegan & dairy options.
Where To Stay In Mystic
We stayed at the Hyatt Place Mystic, which is just a short drive from downtown.
I really enjoyed this hotel and would recommend staying here.
Watch Hill, Rhode Island
Distance from Mystic, CT to Watch Hill, RI – 25 minutes (14 miles)
On day two of our trip, we headed to Newport, Rhode Island with a stop in Watch Hill.
Watch Hill sits just outside Connecticut on a peninsula jutting into the Block Island Sound.
It’s a charming small town, with the main draw being the beach and its subsequent water activities.

Things To Do In Watch Hill
Below is everything we did in Watch Hill. We did all of this in just a few hours, the town is very compact.
Lounge Out At East Beach
East Beach is the town’s public, white sand beach with sweeping views of the ocean.
This is a great spot to lounge out and enjoy activities such as swimming, sunbathing, and beach games.
Sneak A Peak At Taylor Swift’s House
Watch Hill’s most famous resident is one we know all too well, 14-time Grammy winning pop star, Taylor Swift.
Her 11,000(ish) square foot mansion overlooks the west end of East Beach and is clearly visible to beach-goers.
If you wish to see the house, doing so from East Beach is your best option.

Walk The Shops
Watch Hill has a very small downtown area right on a harbor, it’s loaded with fun boutique shops and delicious restaurants.
Most shops are located along Bay Street, but it’s worth also exploring the surrounding streets, especially towards Ocean House Hotel.
Napatree Point Conservation Area
Just a short walk from Bay Street is the Napatree Point Conservation Area. The 86 acre preserve is known for its beautiful beach and impressive bird watching.
You can follow the full 3.2 mile loop through the park, or simply go for a short stroll as we did.
You May Also Like: The Best Things To Do In Watch Hill, Rhode Island

Where To Stay In Watch Hill
We did not stay in Watch Hill, instead visited for a few hours while traveling between Mystic, CT and Newport, RI.
If you’d like to spend the night here, check out the gorgeous Ocean House.
Newport, Rhode Island
Distance from Watch Hill to Newport – 50 minutes (40 miles)
The next two nights of our trip were spent in Newport, RI.
Newport is one of the most beloved Rhode Island towns, and a very popular stopping point on any New England road trip itinerary.
This harborside city is overflowing with beauty, history, and old money.

Things To Do In Newport, Rhode Island
Day 1 In Newport
Walk Bowen’s Wharf
Newport’s ample waterfront is lined with wharfs, the most famous of which is Bowen’s Wharf.
This popular tourist attraction is full of shops, outdoor restaurants and bars, and boats ready to take eager tourists out on the water.
It’s touristy, yes, but I’d still say it’s a must-see while you’re road tripping through New England.
Walk Thames Street
Thames Street is the main hub running through Newport. It’s lined on either side with various shops, restaurants, and bars. All of which continue for blocks on end.
While in Newport, plan to walk Thames Street at least once.
Don’t forget to leave plenty of time to explore the surrounding side streets and quiet marinas, these are lesser known than aforementioned Bowen’s Wharf, but definitely worth checking out.

Go For A Hike
Newport has ample state parks and open areas, perfect for getting away from the bustle of downtown.
We chose to take a quiet hike in the Albro Woods of Middletown, near our vacation rental.
The hike was flat, easy and a perfect way to wind down after a busy day.

Sunset At Second Beach
To conclude our first day here we watched the sunset from Second Beach.
This is one of the most popular beaches for sunbathing and surfing, and an excellent spot to catch a quiet sunset.
The beach doesn’t face west, however the sun does set right atop a rather picturesque boarding school which makes for pretty photos.
If you want the best possible sunset spot, check out Brenton Point State Park or Castle Hill.

Day 2 In Newport
Tour Breakers Mansion
Our second day in Newport began with a tour of the gorgeous Breakers Mansion.
This Vanderbilt summer “cottage” was built in 1893 and is jaw-dropping in its grandeur. Built right on the ocean, with no detail too small, the historic home is absolutely incredible to witness.
You’ll get to see portions of the home via self-guided tour, it’s best to book your tickets in advance.
The number of Gilded Age mansions in Newport is seriously impressive. If mansions and American history are your thing, consider doing additional tours. The Breakers Mansion is most famous, but Marble House is very popular as well.


Stroll The Newport Cliff Walk
Following a tour of The Breakers, access the Cliff Walk via Ruggles Avenue, right next to the mansion.
This oceanside walk is one of Newport’s most famous attractions and a must-see during your New England road trip.
The 3.5 mile trail provides excellent views of the rugged Rhode Island coastline and the grand mansions lining it.
Treat the Cliff Walk as if you were going on a hike.
Wear proper attire, including good footwear, and bring sun protection and water. The trail is much more rugged in areas than I had anticipated.


Ocean Drive
If you’d rather not do the Cliff Walk, or if you have time to do both as we did, I highly recommend exploring Ocean Drive.
The famous roadway meanders through a picturesque neighborhood dotted with mansions perched on hills, with ocean views in the distance.
We really enjoyed driving aimlessly through the incredible neighborhoods in this area.
Tip: If time permits, stop at Castle Hill for a drink or bite to eat on their famous lawn overlooking the Atlantic.
Brenton Point State Park
Ocean Drive’s southernmost point is encompassed by Brenton Point State Park.
The park features wide vistas over the Atlantic Ocean and plenty of open space. All in addition to hiking trails and rocky coastline for the public’s enjoyment.
We happily spent about an hour here and encountered few other people.

Sunset Sailing Tour
After enjoying Newport’s epic mansions and never-ending ocean views all day, we were excited to get out on the water.
Many tour companies offer sunset cruises out of Bowen’s Wharf, we chose to tour with Sailing Excursions, Inc Schooner Adirondack II.
The 1.5 hour sail provides great views of bayside mansions, a 19th-century military fort, Newport Bridge, and beautiful old lighthouses all from the calm waters of the Narragansett Bay.
Cozy up with a blanket and cocktail while enjoying the magic of being out on the water.
You May Also Like: Newport, Rhode Island Weekend Itinerary & The Best Things To Do In Newport, RI

Where We Ate In Newport
Below is everywhere we ate in Newport, Rhode Island:
- Brick Alley Pub – vegan & meat-based options.
- Shaw’s Supermarket – Lots of pre-prepared options from their deli, in addition to frozen goods and fresh produce.
There’s tons of good restaurants here. If you’re a foodie, plan to hit a few of Newport’s famous dining establishments during your visit.
Where To Stay In Newport
We stayed at a vacation rental in Middletown. We booked an Airbnb outside of Newport for budget reasons and it ended up being perfect for us.
This was the Airbnb we booked: Vacation Rental In Middletown, RI.
The rental was right by a winery, only 15 minutes from the heart of Newport, 10 minutes from Second Beach, and it was much quieter than Newport.
Having said that, there are definitely benefits to staying closer to Newport’s core. Most notably is not having to deal with parking.
For those who’d rather stay closer to the tourist hub, check out the following hotels in Newport:
Boston, Massachusetts
Distance from Newport, RI to Boston, MA – 1 hour, 40 minutes (71 miles)
For our 4th and 5th day of the trip we stayed in Boston.
Boston has some of the deepest history of any American city, thanks to its central role in founding the United States.
In addition to its rich history, the city is known for its entertainment, passionate sports fans, and a truly unique accent.
We spent two days here visiting family and seeing all the sights.

Things To Do In Boston, MA
Below is everything we did during our two days in Boston.
Day 1 In Boston
Salem
Before heading into Boston we went about 20 minutes north to Salem, Massachusetts.
This is a town famous thanks to a weird stretch from 1692 to 1693. This is when Salem successfully tried and hanged 19 citizens for practicing witchcraft. Proof of said witchcraft is shaky, to say the least.
The whole thing sounds like a bad case of hearsay at the expense of a few unlucky souls.
During our day here we viewed famous sites such as the home of the infamous Judge Jonathan Corwin, a vocal leader during the trials. As well as The House of the Seven Gables and Salem Witch Trials Memorial.
We also thoroughly enjoyed the many kitschy, but fun, witch-themed shops throughout town.
And of course, as a 90’s kid, I had to see the filming sites of Hocus Pocus!
For the full itinerary, check out my Salem day trip guide: Day Trip To Salem, MA.
This was one of my favorite stops along our 9 day New England road trip.


Baseball Game At Fenway Park
Upon arriving in Boston we handed off our car to the hotel’s valet as quickly as possible (driving in Boston isn’t my idea of fun, and I couldn’t wait to be out of the car).
After some brief downtime at the hotel we excitedly headed over to Fenway to catch a Red Sox game!
I’m a huge baseball fan and love the stories and nostalgia which accompany a historic stadium such as Fenway.
We sat in the rowdy bleachers (which I highly recommend), saw four homers fly over the Green Monster, drank a few beers, and watched the Sox win.
It was a perfect evening!
If you’re up for pre or post-game libations, there are tons of bars in the area. We went to Bullpen Kitchen + Tap before the game and had a great time.

Day 2 In Boston
Our second day in Boston was absolutely jam-packed with sightseeing.
I’m still baffled as to how we were able to see so much in just one day.
Our family who lives here showed us around, below is the route we followed. Be warned, it was a lot of walking!
Harvard & Cambridge
The original founders of Boston placed high value on education, a sentiment which is still prominent in the area today.
There are so many impressive universities in the area, and one of the most famous is Harvard.
We took a stroll through Harvard Yard, which is the central point of the main campus.
After our quick tour of Harvard, we followed the Charles River for a nice walk.
From the river we eventually wandered into Mid-Cambridge which is a popular neighborhood with picturesque homes, as well as quality dining and shopping.
We spent about 2 hours exploring the area before hopping on the subway back towards downtown Boston.


Charles River Esplanade
Upon arrival downtown we took a walk through Charles River Esplanade.
I loved this park and think it’s absolutely worth a stroll if you’re in Boston on a nice, sunny day.
Here you can kayak, sunbathe on the docks, or simply find a shady spot on a bench to enjoy some people watching.

Beacon Hill, Public Garden, & Boston Common
From the park we followed Charles Street through Beacon Hill. This is a posh neighborhood known for great shopping and dining.
Beacon Hill is one of the most popular neighborhoods in Boston for good reason. It’s certainly worth spending some time exploring the beautiful homes throughout the area.
Tip: Be sure to check out Acorn Street which is a charming cobblestone alley known as the most photographed street in the US.
Public Garden and Boston Common are large parks flanking Charles Street, on the edge of Beacon Hill.
Both parks are characterized by beautiful mature trees, thoughtful gardens, and of course, swan boats.
We enjoyed about an hour walking between the two parks.



Quincy Market
Following our time in the park, we made our way through City Hall Plaza and over to Quincy Market, a historic building and marketplace.
Built in the 1820’s its been one of the city’s focal points for almost 200 years.
The market is lined with dining options, ranging from quick bites to savory sweets.
Outside the market are additional food and craft stalls, as well as popular shopping retailers and street entertainers.
This is a popular spot to grab a snack or meal if you’re hungry. However, the area does get very crowded.

North End
The North End is a hodgepodge of narrow streets with some of the city’s oldest buildings.
The area, also referred to as Little Italy, was once physically divided from the rest of Boston due to the construction of I-93.
The physical rift left the North End behind, with residents continuing on without disturbances from the growing and modernizing downtown area.
The obstructing portion of the highway was moved underground in the early 2000’s, reconnecting again the North End to the rest of Boston.
Traveling between the two is almost like traversing into a new city — with stark contrasts still easily noticeable.
When I pictured Boston, North End is what I had in mind.
Imagine narrow sidewalks with outdoor cafe seating, bakeries and delis that have been around for generations. It’s incredibly charming.
While exploring the neighborhood, be sure to check out the Paul Revere Mall and Old North Church.


Christopher Columbus Waterfront Park
We made a brief stop in this waterfront park on our way to the Seaport District.
It’s just a short walk from the North End and a fun spot to watch the boats dotting the harbor.
The area was a former shipping port and still holds onto that industrial vibe even today.

Seaport District
Our final stop of the day was the Seaport District.
This is one of Boston’s most modern sections thanks to recent redevelopment.
It also offers excellent views of the Boston skyline, so I highly recommend at least taking the short walk across Evelyn Moakley Bridge for a photo or two.
We spent our time here enjoying food and drinks in addition to the great views.
For more information and tips, be sure to check out my Weekend in Boston Guide.


Where We Ate (& drank!) In Boston
Below is everywhere we ate and drank during our two days in Boston:
- Clover Food Lab in Cambridge – quick breakfast and lunch options, vegan and meat-based options
- The Paramount in Beacon Hill – vegan and meat-based options
- The Barking Crab in Boston Harbor – meat-based options
- Lolita – drinks at a cute Mexican restaurant
- Cisco Brewers Seaport – beer garden
Where To Stay In Boston
We stayed at the Courtyard Boston Downtown, which had an excellent central location.
Be aware, though, the hotel sits between two nightclubs so if you’re sensitive to noise, I’d avoid this location.
Additional places to stay in Boston include:
- Harborside Inn Of Boston
- The Bostonian Boston
- Boston Harbor Hotel
- Moxy Boston Downtown
- Revere Hotel Boston Common
Plymouth, MA
Distance from Boston to Plymouth – 50 minutes (40 miles)
For the final leg of our road trip, we headed to Cape Cod, with a quick stop in Plymouth.
Plymouth, Massachusetts is the site of the first Pilgrim settlement in 1620. It’s now a tourist destination for those interested in the early history of the United States.
This was a perfect half day stop as we traveled from Boston to Cape Cod.
Did You Know? Plymouth is named after Plymouth, England where the Mayflower set sail for America.

Things To Do In Plymouth
Below is everything we did during our half day in Plymouth.
Walk The Shops & Restaurants
Upon arriving in Plymouth we wanted to grab a bite and explore the town a bit.
Water Street, which overlooks Pilgrim Memorial State Park and Cape Cod Harbor, is lined with restaurants and shops as well as Court Street, which runs parallel.
I enjoyed Court Street the most, it’s a little less crowded than Water.
Learn About The Pilgrims
We visited the Jabez Howland House, which is the only remaining house in Plymouth where pilgrims actually spent time.
We then passed through Pilgrim Memorial Park, which is a waterfront park housing both Plymouth Rock and Mayflower II.
Plymouth Rock is believed to be the rock the pilgrims first set foot on when arriving to America (moved to this location from Provincetown, Massachusetts).
Mayflower II is a full scale replica pilgrim ship gifted to the United States from England following WWII.
Tip: While walking from Jabez Howland House to Pilgrim Memorial Park, be sure to pass through the Brewster Gardens.
Again, Plymouth is small so we were able to see all of this in just a few hours.
Additional Things To Do In Plymouth
If you have more time here or are interested in learning more about the history, check out Pilgrim Hall Museum or Plimoth Patuxet Museum.
For more ideas, check out The Best Things To Do In Plymouth, MA & Plymouth, MA: Day Trip Itinerary.

Where We Ate In Plymouth
We had breakfast Will & Co. Cafe in Plymouth, they offered vegan and meat-based options.
Where To Stay In Plymouth
We did not stay here, but if you wish to, check out:
Cape Cod
Distance from Plymouth, MA to Cape Cod (Hyannis) – 40 minutes (33 miles)
The final days of our trip were spent in Cape Cod.
Cape Cod is a popular summer destination distinguished by white sand beaches, seafood shacks, and nature preserves.
The Cape refers to a hook-shaped peninsula cutting into the Atlantic, which stretches 65 miles from end to end.
Note: The below itinerary is a bit jumbled, we made decisions based off weather and didn’t exactly follow the most logical route. Be sure to also check out my 4 Day Cape Cod Vacation Itinerary. This lays out exactly how I should have structured our trip to Cape Cod.

Things To Do In Cape Cod
Below is everything we did during our 4 days in Cape Cod.
Day 1 In Cape Cod
Stop In Hyannis
Following our quick trip to Plymouth, we arrived in Hyannis.
Hyannis is the first city you’ll reach in Cape Cod and is by far the largest.
The town has a wide selection of retailers and is a great spot to stock up on goods before heading further down the Cape.
Visit The Beach In Hyannis
We spent our afternoon relaxing at Kalmus Beach, which overlooks the harbor.
The water here is calm thanks to the Nantucket Sound and the beach is sandy with small pebbles and shells mixed in.
This is a fun beach if you enjoy watching boats and kite surfers pass by.
Honestly, we could’ve skipped this. I think it’s worth it to head further down the Cape, to Cape Cod National Seashore, this is where we ended up on day two, where the beaches are nicer.

Day 2 In Cape Cod
Cape Cod National Seashore
During our second day on the Cape we were blessed with absolutely perfect weather.
Our entire day was spent enjoying the sunny weather and gentle breeze at Cahoon Hollow Beach on Cape Cod’s National Seashore.
The National Seashore has perfect, fine sand set against the Atlantic Ocean.
It’s superb for sunbathing, beach games, playing on the sandbar, and if you’re able to bear the cold, swimming.
Any beach along the National Seashore is excellent, check out these additional options:
- Nauset Light Beach
- Coast Guard Beach
- Race Point Beach
- Head Of The Meadow Beach
- Herring Cove Beach
- Marconi Beach

Nauset Lighthouse
Nauset is one of the most famous of the Cape’s many lighthouses.
It’s an iconic, red and white striped structure so loved it’s even on the Cape Cod Chips bag.
It’s right off the National Seashore and definitely worth a quick visit.
We stopped here in the late evening before sunset.

Sunset Over Cape Cod Bay
After visiting the lighthouse we enjoyed a quiet sunset over Cape Cod Bay.
The bay sits west of the peninsula, making it a prime spot for watching the sun dip into the horizon.
First Encounter Beach is where we watched the sunset, but any spot along the ample shoreline will do.
Tip: Brewster Flats is a great place to watch the sunset if low tide and sunset coincide.


Day 3 In Cape Cod
Chatham
During our third day we spent the morning exploring Chatham.
The town is located at the southeastern tip of Cape Cod and has a lovely Main Street full of popular boutique shops and picturesque homes.
There’s also a sandy beach, the Chatham Lighthouse, and Monomoy National Wildlife Refuge. All of which are worth checking out while you’re in the area.

Walk Bass Hole Boardwalk At Gray’s Beach
While visiting Cape Cod I highly recommend making a quick stop at Gray’s Beach in Yarmouth.
This is one of the most unique beaches in the area featuring a bog, sand dunes, and views of the ocean.
The area is always changing, so whether you plan to visit at high or low tide, you’re sure to witness something incredible.


Provincetown
For the afternoon we headed to Provincetown, located at the furthest tip of Cape Cod.
This is the Cape’s most lively town which centers around Commercial Street, lined with shops, restaurants, nightclubs, and cabarets.
The eclectic town is known as a haven for artists and the LGBTQ+ community, which you’ll immediately notice upon seeing the colorful buildings draped in rainbows and American flags.
You could easily spend a whole day exploring this adorable and very lively town.


Whale Watching
From Provincetown we did a whale watching tour.
Provincetown is in a prime location for whale watching, and is therefore one of the best spots on Cape Cod to book a tour.
We booked our tour through Dolphin Whale Watch and would definitely recommend it.
Expect to see humpback, fin, minke, and pilot whales, in addition to dolphins and seals from about April through October.
During our 3.5 hour tour in mid-May we saw 4 fin whales and one minke, in addition to a few seals.
This was definitely one of the highlights of our southern New England road trip.

Day 4 In Cape Cod
Day Trip To Nantucket
For the final day of our trip, we took the fast ferry out to Nantucket, and what an incredible day trip it was!
Nantucket managed to capture our hearts in the few short hours we spent there.
I’ll be honest, with such little time to spend in Nantucket, I was unsure this excursion would be worth the ferry fees. However, my fears immediately vanished upon arrival.
Stepping onto Nantucket is like stepping back in time.
This former whaling town has an incredible amount of charm, from the cobblestoned streets and brick sidewalks, to the steepled churches and historic homes.
It’s hard to put into words just how gorgeous Nantucket is.
During our few short hours here we relaxed at Jetties Beach and browsed the shops along Easton Street, the town’s main drag. We then wandered the surrounding neighborhoods, adorned with seemingly endless rows of picture-perfect homes.
You May Also Like: Everything To Know About A Day Trip To Nantucket



Where We Ate In Cape Cod
Below is everywhere we ate in Cape Cod:
- Trader Joe’s Grocery Store in Hyannis- Lots of pre-prepared options from their deli, in addition to frozen goods and fresh produce. It’s especially great for those with dietary restrictions.
- Stop & Shop Supermarket in Orleans – Again, a wide variety of pre-prepared options from their deli, as well as frozen goods and fresh produce.
- Ice Cream Cafe in Orleans – vegan and dairy options
Where To Stay In Cape Cod
We spent our first night at the DoubleTree Cape Cod – Hyannis, which is located at the base of the Cape.
Following this, we spent two nights in a tiny cottage vacation rental in Eastham, very similar to this one: Cape Cod Vacation Rental.
I recommend staying in a central location along the Cape such as Eastham, Orleans, Yarmouth, Harwich, Dennis, or Chatham.

When To Visit New England
Late spring through fall is the best time to visit New England.
Spring can be rainy, but otherwise, mild and pleasant weather.
Summer can be very warm and humid, but is the best time if you want to enjoy outdoor activities.
Fall offers incredible foliage and mild weather.
Winter can be very cold and snowy, but is a great time to visit with less crowds.

How Long Do You Need For A New England Road Trip?
New England is a very large region with six diverse states.
To see the highlights, you need at least 3 to 4 weeks.
We planned for two 9 day road trips. We saw the lower half in this trip, followed by the upper half a few months later — Maine, Vermont, New Hampshire.
Is New England Worth Visiting?
New England offers beautiful and diverse landscapes as well as lively, historical cities and quiet villages.
There is truly something for everyone here.

As you can see, there is so much to see during your southern New England road trip. I hope this itinerary is helpful in your trip planning. Happy travels!
Any questions? Please leave a comment below or reach out on social media.
Looking for more ideas? Check out my additional New England guides below.
More Information For Your New England Vacation:

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