10 Awesome Staycation Ideas

Boston Home Management and Errands company

Ah vacation. How many of us want to escape the crazy day-to-day rat race of our normal lives for a week of fun and relaxation somewhere far, far away?

The truth is that for many of us a traditional vacation is not always possible. Between restaurants, hotels, and transportation, travel costs can add up fast especially when you have a family.

But that doesn’t mean summer has to be a total bust! Why not plan a vacation at home? A real Staycation doesn’t have to be a boring week at home, if planned well, it can be a fun and relaxing experience.

So here are some tips that can help.

Set some rules

The point of a Staycation is to break the usual routine and make it feel like a real getaway. Let go of all the to-dos, and since you’re saving on the cost of traveling you can afford to outsource some of the chores, like: cooking, cleaning, laundry. Make sure the entire family is on the same page, it’s important to set some ground rules. Begin by deciding when your vacation begins and ends, then set a few rules for what you and your family may and may not do during this time. For example:

  • No electronics; this includes smartphones, TVs, computers, tablets and yes, video games.
  • No email
  • No working from home

PLAN for fun ONLY!

Just like any vacation, planning fun activities is important, set some money aside for activities, eating out, and perhaps even paying for a splurge or two like treating yourself to a massage or pedicure at a local spa.

If the kids are old enough include them in the planning of the activities. (Below I’ve shared some great ideas) So that everyone feels included, everyone can pick an activity and do one activity each day. If you’re a planner, use your ideas to put together an itinerary.

Here are 10 suggested things to do in Boston:

1. An Abbreviated Freedom Trail
The Freedom Trail is a 2.5-mile-long (4.0 km) path through downtown Boston, Massachusetts that passes by 16 locations significant to the history of the United States. You could take a guided tour or just, download a map and follow your own itinerary. If you have limited time, concentrate on those sites in and immediately around the North End, which is also Boston’s Little Italy.


2. The South End
The South End is a neighborhood of Boston, Massachusetts. It is bordered by Back Bay, Chinatown, and Roxbury. It is distinguished from other neighborhoods by its Victorian style houses and the many parks in and around the area.

the south end

3. The ICA
The Institute of Contemporary Art in South Boston is arguably more interesting for its architecture than its art. Opened in December 2006, designed by Diller Scofidio + Renfro, the museum is all glass and sharp angles, a stark departure from the city’s presiding aesthetic.


4. Back Bay
Back Bay is an officially recognized neighborhood of Boston, Massachusetts. It is most famous for its rows of Victorian brownstone homes — considered one of the best preserved examples of 19th-century urban design in the United States — as well as numerous architecturally significant individual buildings, and cultural institutions such as the Boston Public Library. It is also a fashionable shopping destination (especially Newbury and Boylston Streets, and the adjacent Prudential Center and Copley Place malls) and home to some of Boston’s tallest office buildings, the Hynes Convention Center, and numerous major hotels.

back bay

5. Charles River Esplanade
The Charles River Esplanade of Boston, Massachusetts, is a state-owned park situated in the Back Bay area of the city, on the south bank of the Charles River Basin. To take in its full charm, begin your walk near the Museum of Science (at Monsignor O’Brien Highway and Storrow Drive), which, not incidentally, is a great place to occupy kids for several hours.

charles rive esplanade

6. The Red Sox Fan
Fenway Park is a baseball park located in Boston, Massachusetts, at 4 Yawkey Way near Kenmore Square. Since 1912, it has been the location for the Boston Red Sox, the city’s Major League Baseball (MLB) franchise. It is the oldest ballpark in MLB.

red sox

7. Harvard Yard
Harvard Square is a triangular plaza at the intersection of Massachusetts Avenue, Brattle Street, and John F. Kennedy Street, near the center of Cambridge, Massachusetts, United States. Adjacent to Harvard Yard, the historic heart of Harvard University, the Square functions as a commercial center for Harvard students, as well as residents of western Cambridge and the inner western and northern suburbs of Boston.

harvard yard

8. Jamaica Pond
Jamaica Pond is a kettle pond, part of the Emerald Necklace of parks in Boston designed by Frederick Law Olmsted. Well known to locals but somewhat off the beaten path for visitors is Jamaica Pond which sits at the base of Jamaica Plain (J.P., familiarly), a neighborhood about 5 miles south of Boston that was one of the city’s original “streetcar suburbs.”

jamaica pond

9. The Boston Public Library
The Boston Public Library is a municipal public library system, founded in 1848. Located on one side of the impressively imposing Copley Square (which also houses Trinity Church) the library was designed by the New York firm McKim, Mead, and White and opened in 1895 (a Philip Johnson-designed addition was added in 1972). Remarkable features include several vast murals by popular artists, including a series by John Singer Sargent, and an Italian Renaissance-inspired interior courtyard with bubbling fountains and arched pathways.

boston public library

10. The Black Heritage Trail
The Black Heritage Trail is a path in Boston, Massachusetts, winding through the Beacon Hill neighborhood and sites important in American black history. The Black Heritage Trail links more than 15 pre-Civil War structures and historic sites, including the 1806 African Meeting House, the oldest surviving black church in the United States.

black heritage trail

Be Creative
Let’s be honest, Boston has tons of fun (sometimes free) things to do that you normally never have time for, or don’t even think about because they are so close by.

Just have Fun!
The key to having the best Staycation is to just let go. The best part is you get to do whatever you desire – that’s the point! This is your time…..make the most of it!

Happy Staycation!



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