In just a couple days, we were planning to be heading off to Europe to explore the Balkans! Instead we are staying cozy at home, thankful for the health of ourselves, our family and friends. While the COVID-19 pandemic has altered travel plans around the world, we hope you too are staying safe at home with your loved ones.

And since there is no better time to reflect on past trips and experiences, we thought we would share our favorite daytrips from Boston:

One thing I really appreciated about living in Boston was how many amazing cities and places there were to visit within just a few hours drive. It wasn’t long before the car rental company recognized our faces, showing up first thing every Saturday morning to take our rental car for a weekend road trip. We spent weekends hiking in Acadia National Park, celebrating Christmas in New York City, eating the famous food of Portland, and exploring the fall colors of Vermont.

After taking all these mini-trips, we decided to put together our favorite stops for you here:


Castle Hill on Crane Estate

Distance Traveled: 39 miles (1h) by car.

If you’ve read previous posts, you’ve probably already come to notice that there is no shortage of fancy estate houses in New England. Built by a wealthy Chicago businessman, the Castle Hill mansion was initially erected as a summer retreat in 1928. A few decades later in 1949, it became a museum open to the public.

The mansion is located atop a hill on the 2100 acre Crane Estate, located in Ipswich MA. From the mansion is the famous half-mile “Grand Allee“, a rolling lawn that gives you a view from the residence all the way out to sea.

The grounds and trails of the Crane Estate are open to the public (for a small parking fee if arriving by vehicle). We didn’t end up touring the mansion itself, but walked a series of trails along the beach and through the forests in and around Castle Hill. It’s a great place for a gentle hike.


Portland: Foodie Capital of America

Distance Traveled: 112 miles (1h 53min) by car.

Portland, Maine is a favorite among many Bostonians for its reputation as the foodie capital of the Northeast. Many of my colleagues loved visiting over the weekend to enjoy the city’s best restaurants and new breweries. Portland has no shortage of either of these, and is a great place to spend a weekend or stop over on your way to Maine’s other attractions.

Portland is known for more than just its food and drink, as the city also has a thriving arts scene and many historic sites. The Old Port district is a great place to base yourself and wander for hours, surrounded by brick warehouses and cobblestone streets, all the while enjoying the salty breeze from the ocean nearby.

The city also happens to be nearby America’s most photographed lighthouse, which truly is worth a visit:

Home to over 20 craft breweries, you can easily fill a weekend in Portland just trying to visit them all. Though Allagash Brewing is likely the oldest and most universally known in the city, there are many small breweries to satisfy your palate (and your need to play cornhole – as that appears to be a brewery staple around here).


Kennebunkport: Sweet Little City by the Sea

Distance Traveled: 89 miles (1h 30min) miles by car.

New England is full of charming little towns, and Kennebunkport, Maine is one of them. This cozy little town has no shortage of what coastal New England is known for: weathered red barns, seaside cottages, rocky shores, lighthouses, and a quaint main street filled with local shops and lobster shacks.


Cape Cod: Quintessential New England Getway

Distance Traveled: 70 miles (1h 20min) by car OR 90 minute high speed ferry to Provincetown.

The ultimate Bostonian’s summer getaway is Cape Cod, with its sand dunes, endless beaches, seafood shacks and cozy cottage getaways. See more in our detailed post here.


Newport: Mansions by the Sea

Distance Traveled: 72 miles (1h 30min) by car.

Known for its famous “Newport Mansions”, this vibrant seaside city is where rich and famous metropolitans used to come to relax and spend their money. See our detailed post here.


Nantucket: Our Personal Favorite

Distance Traveled: 2h ferry ride from Hyannis Port.

Our first, and still our favorite, weekend getaway from Boston. A short ferry ride away, this island is so worth a visit. Hydrangea filled streets, beautiful cottages on the ocean, and amazing food. See our detailed post here.


Vermont: Truly the Green State

Distance Traveled: 140 miles (2h 45min) by car to Woodstock.

Vermont is like a breath of fresh air, with it’s lush green forests, small towns with their general stores and farmers markets, and quiet country roads. Though we would visit anytime, autumn is particularly special when the state erupts in brilliant fall colors. See our detailed post here.


Acadia National Park

Distance Traveled: 283 miles (5h) by car.

The only national park in New England, Acadia is a must-see for hiking and nature lovers. Plus who doesn’t love the idea of staying in a quiet bed & breakfast on the ocean? Make the drive worthwhile by stopping overnight in the lively city of Portland, Maine. See our detailed post here.


New York City

Distance Traveled: 215 miles (3h 30min) by Amtrak train.

Who can say no to a weekend in New York City? With so much to see and do, this short weekend trip can be done on repeat. Most recently, we decided to visit NYC over the Christmas season. See our dedicated post here.