Boston Staycation Guide

Boston, MA — Staycation Inspiration

10 Things To Do In Town

1. Freedom Trail Walk
   • Vibe: Historic and empowering
   • Description: Follow red-brick paths through 16 revolutionary landmarks from Boston Common to Bunker Hill.
   • Special Events: Patriot’s Day reenactments (April)
   • Best Time: Spring and fall
2. Museum of Fine Arts + Isabella Stewart Gardner Museum
   • Vibe: Cultured and inspiring
   • Description: Explore global masterpieces and a Venetian-style mansion filled with dramatic flair.
   • Special Events: MFA First Fridays, Gardner After Hours
   • Best Time: Year-round (especially winter)
3. Fenway Park Tour or Game
   • Vibe: Nostalgic and sporty
   • Description: Visit one of America’s most iconic baseball stadiums — or just grab a Fenway Frank and catch a game.
   • Special Events: Opening Day (April), post-game fireworks
   • Best Time: Baseball season (April–September)
4. Boston Public Garden + Swan Boats
   • Vibe: Romantic and peaceful
   • Description: Ride the iconic boats, see the duckling statues, and enjoy a floral oasis in the city.
   • Special Events: Garden tours, Duckling Day (Mother’s Day)
   • Best Time: Spring and early summer
5. North End Italian Food Crawl
   • Vibe: Flavorful and old-world
   • Description: Savor cannoli, pasta, espresso, and seafood in Boston’s Little Italy.
   • Special Events: Saint Anthony’s Feast (August)
   • Best Time: Summer evenings
6. Boston Tea Party Ships & Museum
   • Vibe: Interactive and theatrical
   • Description: Throw “tea” overboard and experience revolutionary history with a splash of drama.
   • Special Events: Annual reenactment (Dec)
   • Best Time: Year-round
7. Seaport District Sunset Walk + Drinks
   • Vibe: Trendy and modern
   • Description: Stroll the Harborwalk, grab rooftop cocktails, and snap skyline selfies.
   • Special Events: Pop-up art and night markets
   • Best Time: Late spring to early fall
8. Harvard Square + Cambridge Stroll
   • Vibe: Smart and charming
   • Description: Visit bookstores, indie cafés, and historic Harvard Yard.
   • Special Events: MayFair, Harvard Arts First Festival
   • Best Time: Spring and fall
9. New England Aquarium + Whale Watching Tour
   • Vibe: Ocean-focused and family-friendly
   • Description: Meet penguins and turtles, then hop on a catamaran to see whales in the Atlantic.
   • Special Events: Earth Day and science talks
   • Best Time: May to October
10. Boston Harbor Islands Ferry + Hike
    • Vibe: Outdoorsy and quiet
    • Description: Take a ferry to Georges or Spectacle Island for hiking, picnics, or coastal views.
    • Special Events: Sunset concerts and ranger tours
    • Best Time: Summer

10 Things To Do Within 30 Miles

1. Salem Day Trip
   • Vibe: Spooky and historic
   • Description: Visit witch trial landmarks, boutique shops, and maritime museums in this coastal town.
   • Special Events: Haunted Happenings (October)
   • Best Time: October (for vibes) or spring
2. Castle Island + Sullivan’s Snack Shack
   • Vibe: Casual and classic
   • Description: Walk around Fort Independence and grab fried clams or soft serve by the sea.
   • Special Events: Kite festivals and flyovers
   • Best Time: Summer
3. Arnold Arboretum (Jamaica Plain)
   • Vibe: Botanical and peaceful
   • Description: Enjoy tree-lined trails, blooming lilacs, and city views from Peters Hill.
   • Special Events: Lilac Sunday (May)
   • Best Time: Spring
4. Revere Beach
   • Vibe: Old-school and laid-back
   • Description: America’s oldest public beach with summer snacks, sea breeze, and skyline views.
   • Special Events: International Sand Sculpting Festival (July)
   • Best Time: Summer
5. Somerville Assembly Row Shopping + Eats
   • Vibe: Stylish and modern
   • Description: Outlet shopping, riverfront dining, and a seasonal roller rink.
   • Special Events: Fall Fest, summer outdoor movies
   • Best Time: Spring to fall
6. Lexington & Concord Historic Sites
   • Vibe: Revolutionary and serene
   • Description: Walk the Battle Road Trail or visit the Old North Bridge and Minute Man Park.
   • Special Events: Patriot’s Day reenactments (April)
   • Best Time: Fall and spring
7. Blue Hills Reservation Hike
   • Vibe: Rugged and local
   • Description: Get a skyline view from Great Blue Hill — just 20 minutes from the city.
   • Special Events: Guided hikes and snowshoeing
   • Best Time: Fall and spring
8. Charlestown Navy Yard + USS Constitution
   • Vibe: Nautical and patriotic
   • Description: Tour the oldest commissioned warship afloat and explore the naval history museum.
   • Special Events: July 4th ceremonies
   • Best Time: Spring and summer
9. Brookline Coolidge Corner + Cinema
   • Vibe: Indie and nostalgic
   • Description: Browse local bookshops, grab a bagel, and catch a retro or arthouse film.
   • Special Events: Midnite movie series
   • Best Time: Year-round
10. Sam Adams Brewery Tour (Jamaica Plain)
    • Vibe: Chill and hoppy
    • Description: Sample fresh brews and learn about Boston’s beer roots at this local favorite.
    • Special Events: Stein Hoisting Competitions (October)
    • Best Time: Year-round

10 Things To Do Within 60 Miles

1. Rockport + Bearskin Neck
   • Vibe: Coastal and charming
   • Description: Browse art galleries and shops in this fishing village with ocean views and sea air.
   • Special Events: Rockport Music Fest
   • Best Time: Summer and early fall
2. Gloucester Whale Watch + Beaches
   • Vibe: Marine and memorable
   • Description: Head out on a boat tour to see humpbacks or relax on Good Harbor Beach.
   • Special Events: Schooner Festival (Labor Day)
   • Best Time: Summer
3. Plymouth + Plimoth Patuxet Museums
   • Vibe: Pilgrim and educational
   • Description: Visit the Mayflower II, a recreated 1600s village, and beautiful harborside parks.
   • Special Events: Thanksgiving reenactments
   • Best Time: Spring through fall
4. Newburyport Day Trip
   • Vibe: Quaint and historic
   • Description: Explore harborfront shops, cafes, and coastal trails in this elegant seaside town.
   • Special Events: Yankee Homecoming (July/Aug)
   • Best Time: Summer
5. Concord + Walden Pond
   • Vibe: Literary and peaceful
   • Description: Swim or reflect where Henry David Thoreau wrote Walden.
   • Special Events: Poetry walks and Thoreau celebrations
   • Best Time: Summer for swimming, fall for foliage
6. Cape Cod Canal Trail (Bourne/Sandwich)
   • Vibe: Breezy and active
   • Description: Walk or bike the scenic path along this historic shipping route.
   • Special Events: Fishing derbies and art shows
   • Best Time: Spring and early summer
7. Salem Night Tour or Witch Museum
   • Vibe: Spooky and educational
   • Description: Go deeper into Salem’s eerie past with a ghost walk or museum tour.
   • Special Events: Haunted Happenings (October)
   • Best Time: Fall
8. Wachusett Mountain Hike or Ski
   • Vibe: Outdoorsy and seasonal
   • Description: Hike in the fall for foliage or ski in the winter — just over an hour away.
   • Special Events: Applefest (October)
   • Best Time: Fall or winter
9. Nantasket Beach + Paragon Boardwalk
   • Vibe: Retro and beachy
   • Description: Spend the day on the sand, eat saltwater taffy, and play vintage arcade games.
   • Special Events: Summer music series
   • Best Time: Summer
10. Lincoln + deCordova Sculpture Park
    • Vibe: Artsy and open-air
    • Description: Walk among large-scale sculptures set on a hilltop with lake views.
    • Special Events: Outdoor yoga, art workshops
    • Best Time: Spring through fall