The 8 Day Vacay – Boston, Provincetown, Newport

The 8 Day Vacay – Boston, Provincetown, Newport
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What fascinates me the most about the east coast is how small the size of the states are compared to the west.  While it takes more than 10-hours to drive the length of California, you can cross from state to state in a matter of an hour on the east coast.  Which makes traveling to the east coast on your days off, the perfect place for an eight-day vacation.


This is part of my “8 Day Vacay” series!  A travel series aimed at nurses who are looking to take 8 days off from the hospital (with no need to take PTO) and travel to destinations both near and far.  For more information, read A Guide to the “8 Day Vacay” and How to Make the Most Out of Your “8 Day Vacay”


An 8 Day Vacation on the East Coast – Boston, Provincetown, Newport

When I signed my seventh travel nurse contract, I packed up my belongings and moved to Boston with one goal in mind.  To explore as much of the east coast as I could in the short 13-weeks I’d be there.  When I arrived I surveyed others that had lived on the east coast much longer than me.  And what I heard time and time again was, “You must visit Newport!”  “Provincetown is the BEST… you HAVE to go!”  High on my priority list, I made the time to visit both Newport and Provincetown, and what I’m telling you is that the locals weren’t wrong.


WEDNESDAY – Depart from Home, Arrival into Boston, MA

Leave Wednesday for an expected arrival into Boston Wednesday.  I prefer to use Kayak when searching for flights.



Highlights of Boston Day One – The Freedom Trail, Beacon Hill

Transportation:  Upon arrival at Boston Logan International Airport, there are many ways to get into the city.  I would not recommend renting a car at this point, parking is limited and traffic is horrendous.  Everything is accessible by foot, train, or taxi.  From the airport, you can either take an Uber or Lyft to your destination, or the cheaper option ($2.75) would be to use the train – referred to as the “T”.  Upon departing the airport you will catch the shuttle bus, which will drop you off at the blue line – Airport stop.  Once you get to the blue line you can purchase your ticket and get on the train to get to where you need to be.  To figure out where I’m going around Boston, I use the “Transit” app.  It’s a free app that will tell you which train to take and what stop to get off on to get you closest to your destination.


Stay: There are so many great options when finding somewhere to stay in Boston.  The areas that I would suggest to book a place to stay would be Seaport, Downtown, Financial District, Back Bay, or Beacon Hill.  Any of those neighborhoods will put you in the middle of the city.  I recommend using Airbnb or to find accommodations.  (If you’re new to Airbnb, use my referral code for a $55 credit).


Boston is a city unlike any other in the United States.  It’s rich in culture and history, dating back to 1630 when a group of 700 people migrated over from England.  Since then the Boston Tea Party occurred, and the American Revolution, freeing America from the rule of Great Britain and gaining us our independence in 1776.  Boston has managed to merge the “old” with the present times.  And that is why it’s such a uniquely fascinating city.


Freedom Trail

Boston Public Common

To get a feel for how America was founded, and the importance that Boston played in defeating the British army, start by exploring the Freedom Trail.  While you can take a guided tour, I prefer to walk the trail on my own to be able to fully take in the sites.  I found a great resource here if you’re interested in going at it alone.

You’ll begin your 2.5-mile journey at the Boston Common.  America’s oldest public park has been around since 1634.  You’ll weave and wind your way through the city past 16 historic sites before coming to an end at Bunker Hill Monument.  Bunker Hill is where the first major battle of the Revolutionary War took place.


Beacon Hill

Acorn Street - Boston

Continue with learning about Boston’s history by next heading to the historical neighborhood of Beacon Hill.  2.5 miles from your ending point at Bunker Hill, get a taxi, or take the T.  You’ll want to get on the orange line – Community College – heading southbound to Forest Hills.  Get off at Downtown Crossing (three stops) and walk to Beacon Hill.

Once you’ve arrived, walk through the streets lit by gaslight lamps, and take in the classic, brick, federal-style row houses.  Here you’ll find Boston’s most picturesque street – Acorn Street.  If you’re interested in boutique-like shops, spend time on Charles Street.  And weather permitting, walk along the Charles River Esplanade.

• For a tourist stop, make your way to Cheers, as seen on TV •


FRIDAY – Boston

Highlights of Boston Day Two – Seaport District, Fenway


Seaport District

Seaport District - Boston, MA

One of the newer neighborhoods in Boston, the Seaport District sits on the waterfront.  Here you won’t find the classic Boston “look” of the lamps and federal-style row houses.  Instead, you’ll find sleek hotels and restaurants glimmering against the ocean.  A feeling of a “new” Boston with all of the character of “old” Boston.

Seaport houses some of my favorite bars in Boston.  With a mix of both inside and outside, laid back and upscale, there’s a variety of choices to choose from in this small neighborhood.

If you’re looking for upscale… head to Drink.  A cocktail lounge with no cocktail menu.  Just tell your server what you prefer and he/she will make it up for you!

If you’re looking for laid back… head to Trillium.  A brewery with an indoor/outdoor space.

If it’s nice weather… head to Envoy.  Arguably Boston’s best rooftop bar giving you views of the city.



Fenway - Boston, MA

One of Boston’s most famous neighborhoods, thanks to the Boston Redsox, is Fenway.  Here is where the baseball stadium stands, surrounded by loads of bars and restaurants.  With sports bars lining Lansdowne Street, Fenway draws a younger crowd and is always packed.  If you’re in town when the Redsox play tries to catch a game at this iconic field!

• If you’re looking to eat out while exploring Fenway, try Hojoko for an Asian fusion experience •


SATURDAY – Depart Boston, Arrive in Provincetown, MA


Transportation:  There are many options when making the trip from Boston to Provincetown.  You can take the Provincetown fast (or traditional) ferry from May-October, prices vary.  Because Provincetown is a walkable beach town and parking is limited this might be your best option.  However, if you want to get outside of Provincetown and drive the rest of the Cape, renting a car from Boston might be the better choice.

Renting a car is quick and easy in Boston.  I prefer to rent from the airport, having had the best luck with Enterprise Rent-A-Car.  If you reserve a car ahead of time all you need to do is show up at the airport and head to the second floor where Enterprise is located.  Here you’ll find kiosks, where you will enter your information, take your paperwork to the third floor, and pick up your rental.  Without traffic, a drive to the cape will take you about 2.5 hours.  (If you want to compare rental agencies and ensure you’re getting the best price, I like to use QEEQ).


Stay:  The Benchmark Inn – A seven-room bed and breakfast located near the main street in town, Commercial Street.  Owned and operated by two men from Sweden, this cozy B&B has been standing since 1850, but you wouldn’t know it.  With fireplaces in each room, ocean views, and an open dining room welcoming you to breakfast, this is the perfect B&B for one night in Provincetown.  If you find that it doesn’t suit your needs I’d recommend checking out Airbnb or, aiming for a place to stay near Commercial Street.

Visiting Cape Cod - Provincetown, MA

Provincetown is a small coastal town located on the tip of Cape Cod.  As you stare out into the Atlantic, it feels as though you’re on the edge of the world.  A place so small that locals can spot a tourist a mile away, but that doesn’t mean that they aren’t inviting.  Here in Provincetown, you get art culture, killer seafood, a party vibe, and a relaxed atmosphere all at the same time.  I wouldn’t suggest visiting Provincetown before May.  Most bars and restaurants close shop during the winter months, and don’t open again until summer rolls around.

The main attraction in Provincetown is Commercial Street.  Here is where you’ll find most of the bars, restaurants and art shops.  Visit the Squealing Pig for a laid back atmosphere and great seafood, and make sure you don’t miss climbing up the Pilgrim Monument for views over Provincetown.


For more information on visiting Provincetown, read this article


SUNDAY – Depart Provincetown, Arrive in Newport, RI

Highlights of Newport Day One –  Ocean Drive, Thames Street

Transportation:  If you rented a car in Boston, make the 2.5-hour drive west from Provincetown towards Newport.  If you chose to take the ferry to Provincetown, I’d recommend renting a car in Provincetown and make the drive down to Newport.


Stay:  Stay on or near Thames Street.  I use Airbnb or to find accommodations.


Newport is a cozy coastal town located in Rhode Island.  Where the Atlantic meets the east coast, you’ll find killer seafood, the friendliest locals, and old money that has made Newport what it is today.  While you can see all that Newport has to offer in one day, it seems as though you wouldn’t have time to slow down and appreciate Newport for what it is.

Upon arrival to Newport, take the infamous Ocean Drive Historic District.  Ocean Drive is a street that winds through the most historic parts of Newport.  Keep your eyes peeled because you’ll be passing mansions and summer cottages all while driving along the ocean.  If the weather permits, opt to rent a bike and bike this ~2mi drive.

Once you finish with Ocean Drive, spend the rest of the day exploring Thames Street and Bowen’s Wharf.  Full of bars, restaurants, and shops, it’ll be hard to choose where to start!


MONDAY – Newport

Newport, RI

Highlights of Newport Day Two –  The Cliff Walk, Visiting the Mansions

For sunrise, head to the infamous Cliff Walk.  A National Recreation Trail spanning 3.5 miles along the coast of Rhode Island.  If you don’t want to walk the entire 3.5 miles start at “40 Steps” and turn right.  Make sure to bring comfortable shoes, the terrain is rocky.  The Cliff Walk will take you along the Atlantic, where you can view the Newport mansions from the back.  Once you finish the Cliff Walk start your mansion tour.

The Newport Mansions are a glimpse into old money, society, and the Gilded Age.  It’s where the “who’s who” of America came for the summer.  Currently, there are 10 mansions open for viewing.  The most famous being The Breakers, built by the Vanderbilts in 1893.  For information on visiting the famous Newport mansions, click here.


For more information on visiting Newport, read this article


TUESDAY – Depart Newport, Arrive in Boston

Highlights of Boston Day Three – Back Bay, North End


Transportation:  Drive your rental car an hour and a half back to Boston to drop it off at the airport.  If you didn’t end up renting a car, check out Wanderu for different options on taking a bus.


Back Bay

Eight Day Vacation on the East Coast - Boston's Back Bay

Just like Beacon Hill, Back Bay is quintessential Boston.  With bars, restaurants, gas-lit lamps, and federal-style row houses, Back Bay is an affluent neighborhood.  Here you’ll find the most expensive shopping street in Boston, Newbury Street, the Boston Library, and more.  While in Back Bay stop for a bite to eat at The Friendly Toast, Lolita, or Citrus and Salt.


North End

Eight Day Vacation on the East Coast - Boston's North End

Boston’s North End will look familiar to you if you completed the Freedom Trail.  It’s Boston’s “Little Italy” with narrow streets, old buildings, and pastry shops and coffee houses.  A typical stroll through the North End will leave you smelling like marinara sauce or pizza.  With lines out restaurant doors, you’ll have no shortage of restaurants to stop in.

If you’re looking for Italian… head to Pomodoro.  Upon arrival, you won’t notice a sign out front.  Pomodoro is a quaint, hole in the wall with limited seating and a lively atmosphere.

If you’re looking for seafood… head to Neptune Oyster.  A smile, high-end oyster bar dishing out buttered lobster rolls, ceviche, oysters, and more!  With no option to make a reservation, plan to wait in line to get in.

If you’re looking for dessert… head to La Famiglia.  Boston is famous for its cannoli’s, specifically in the North End.  And while you may have heard of Mike’s or Modern, the best cannoli’s are found at La Famiglia.  What appears to be a dumpy restaurant, serves incredible food.


WEDNESDAY – Depart Boston, Fly Home


Depart from Boston on Wednesday just in time to clock in for your shift on Thursday!  And just like that, your eight-day vacation on the East Coast, visiting Massachusetts and Rhode Island is over.


Need more information on Boston?  Check out The Ultimate Guide to Boston for more tips on transportation and where to stay!


What to Pack

Tennis shoes for walking long distances

Swimming suit for the beach

Rain coat/Umbrella

*If you choose to check a bag, don’t forget to pack an extra outfit in your carry on in case your luggage gets lost*


If this is your first time hearing about the Eight Day Vacay and would like some background information, please click here.


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Kylee is a Neonatal Intensive Care (NICU) nurse passionate about making travel affordable and accessible to nurses. Inspiring nurses to travel both near and far, Kylee began Passports and Preemies in 2017 while volunteering in Skopje, North Macedonia as a way to reach nurses and advocate for the prevention of nurse burnout by traveling. Kylee is the original creator of the “8 Day Vacay” – a vacation geared towards nurses who aim to take advantage of the potentially 8 days off between work weeks with no need to use PTO.

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