When I'm showing visitors around Boston or giving suggestions on what to see, I try to consider their interests, the weather, if they have kids, and their familiarity with the city. Below are some of my go-tos, with a mix of traditional tourist sites and some lesser known gems. Enjoy, and if you have any suggestions, please let me know!

All
Rainy day
Kid friendly
Arts
Science/Tech
Museums

Day 1-2: Orientation

1. Prudential Skywalk Observatory

Basics
Rainy day
Kid-friendly
History
$13-18
From one of the top levels of the soaring Prudential Tower, this gives you a 360 degree view of Boston. I like to start here because it includes an audio guide that orients you to the landmarks and provides history of the city. Budget at least an hour so you can absorb the tour.

2. Newbury Street

Basics
Shopping
Outdoor
After leaving the Prudential Building, walk along Newbury Street toward downtown (against traffic). This street is known for its fancy shops and restaurants, and it's fun to window shop and people watch. If it's not too early, you can get a cupcake at Georgetown Cupcake.

3. Public Garden

Basics
Kid-friendly
Outdoor
Newbury Street ends at the Boston Public Garden, the first botanical garden in America. Stroll through, and if you have time, take a ride on the Swan Boats with your kids. Then pose for pictures with the Make Way For Ducklings statues.

Cheers Boston

Rainy day
Drinks
If you get thirsty and want to go where everyone knows your name, or just for a photo op, cross Beacon Street and pop into the Cheers Bar.

4. Boston Common

Basics
Kid-friendly
Outdoor
Continue into the Boston Common. Founded in 1634, it was the first public park in America. Read the panels at the entrance for some history.

5. The Freedom Trail

Basics
Older-Kid
Outdoor
History
Be prepared, this is a long walk, and depending on how many stops you'll make, you should budget the whole afternoon. Start from the Visitor Center in the eastern section of Boston Common, by the Park Street T stop, and then follow the red line on the ground. You'll pass a number of historical sites. I usually stop to watch the street performers and then eat something in Quincy Market, which is on the trail. Most of the time we finish in the North End with a cannoli from Parziale's Bakery, where they fill it in front of you, or at the landmark Mike's Pastry with all the tourists. If you really have stamina, continue to the end of the trail in Charlestown for the USS Constitution and the Bunker Hill monument.

Day 2-3: Cambridge

Harvard

6. Harvard University

Older-Kid
Outdoor
History
Harvard offers a number of free, high-quality, historical tours of the campus. They also have a tour for prospective college students, but the one you want is the Guided Historical Tour.

7. Glass Flower Collection

Science/Tech
Rainy day
Museums
Art
Older-Kid
$8-12
While you're in Harvard Square, visit the Harvard Museum of Natural History for the glass flower collection. These remarkable glass models of botany are sure to impress. (Closed for restoration until Saturday, May 21, 2016)

8. Harvard Square

Outdoor
Shopping
Explore the vibe of Harvard Square and check out some of the shops. Follow the Honey sells only honey. The Curious George Store is dedicated to its namesake, and has other children's items as well. The Coop (pronounced coop, not co-op), is the Harvard and MIT campus store and a great place to get memorabilia.

MIT

9. MIT tour

Science/Tech
History
Older-Kid
Join a walking tour of MIT, or download the map and take a self-guided tour.

10. MIT Museum

Science/Tech
Museums
Older-Kid
Rainy day
$5-10
Cool museum, filled with MIT artifacts and science and technology exhibits from slide rules to computers.

Day 3+: Exploring further

Factory Tours

Taza Chocolate Factory Tour

Rainy day
Older-Kid
$8
On this 1-hour tour you'll learn how they make stone ground chocolate, and taste the results. Online reservations required. Located in Somerville.

Harpoon Brewery

Rainy day
Drinks
$5
You will learn how they make beer and sample the results. In addition to beer, they sell fresh-baked pretzels, which really are delicious. These tours fill up early, especially on weekends, and you can only buy tickets on the day of the tour, and in person, so plan accordingly. In the Seaport District.

Sam Adams Brewery Tour

Rainy day
Drinks
$2
Tickets handed out on a first-come, first-serve basis. In Jamaica Plain.

Sports

Fenway Park Tour

Rainy day
Sports
Kid-friendly
$18
Even if you can't catch a game, you can take a guided tour of this historic ball park.

Arts

Events at the Berklee College of Music

Rainy day
Art
Varies, many free
Berklee is the "Harvard of music." Check out their upcoming events for a real treat.

SoWa Artists Guild

Rainy day
Art
This is one of the country's most famous art districts. Check out the critically-acclaimed art galleries. While you're in the area, enjoy the eclectic architecture of the booming South End.

Museum of Fine Arts

Rainy day
Art
Museums
$10-25
Extensive galleries and exhibits. There are various discounts and free days, and if you have a library card and plan ahead, you can usually check out a discounted pass from the library.

Isabella Stewart Gardner Museum

Rainy day
Art
Museums
$5-15
In addition to the art collection, this museum is also famous for its exterior gardens, and the famous art heist that occurred here.

The Institute of Contemporary Art (ICA)

Rainy day
Museums
Art
$0-15
The museum itself is a work of art. It's a contemporary building in the Seaport District overlooking the water.

Other Gems

Castle Island

Outdoor
History
Kid-friendly
A fantastic park in South Boston. There's a boardwalk, a beach, and a castle.

Haymarket

Outdoor
Shopping
As one of America’s oldest open air markets, it's basically a giant farmer's market, with incredibly low prices for fresh produce. Fridays and Saturdays only.

Boston Public Library

History
Art
Rainy day
The main branch of the Boston Public Library is a beautiful building adorned with significant art. There are free public tours, or you can just pop in.

JFK Presidential Museum & Library

History
Rainy day
Museums
Older kids
$0-14
John F. Kennedy's presidential museum.

Edward M. Kennedy Institute for the US Senate

Older kids
History
Rainy day
Museums
$0-16
This is a very interactive museum, meant to engage you through its use of technology. Next door to the JFK Presidential Library.

Museum of Science

Kid-friendly
Science/Tech
Rainy day
Museums
$8-23
Very interactive, and a perpetual favorite of kids and adults who love science and just cool stuff in general.