Travel Guides for Grandparents
The best places to take grandkids from the Northeast — curated for grandparent pacing, with honest activity ratings, real parking notes, and a printable PDF for every destination.
Drive destinations from Fairfield County, CT and Westchester County, NY — plus island and Caribbean escapes. Full guides with activities, itineraries, and PDFs are available to subscribers.
Unlock every guide + printable PDFs
Full activity lists, where to stay, grandparent tips, and a 2-5 page PDF for every destination.
Quick Trips — Under 2 Hours
Easy day trips from Fairfield County or Westchester
Mystic, CT
Connecticut Coast
World-class aquarium, a living maritime museum, and great pizza — all in one afternoon
Free pick
Olde Mistick Village & Downtown Walk
Newport, RI
Rhode Island
The Cliff Walk, the Breakers, and the best chowder in New England
Free pick
Cliff Walk (First Mile)
Hudson Valley, NY
Hudson Valley
The most underrated family destination in the Northeast — 90 minutes from home
Free pick
Walkway Over the Hudson (Poughkeepsie)
The Berkshires, MA
Western Massachusetts
Norman Rockwell, Tanglewood, and mountain air — the best of New England in one valley
Free pick
Bash Bish Falls
Philadelphia, PA
Mid-Atlantic
The birthplace of the country, a world-class science museum, and the best cheesesteak you've ever had
Free pick
Independence National Historical Park
East End Long Island, NY
Long Island
Beaches, farm stands, a real working aquarium, and the most relaxed harbor town in the Northeast
Free pick
Greenport Village Waterfront
Weekend Destinations — 2 to 3.5 Hours
Best with an overnight stay
Cape Cod, MA
New England
Beaches, bike trails, and lobster rolls — all at grandkid pace
Free pick
Nickerson State Park
Boston, MA
New England
America's most walkable history city — the Freedom Trail, the Aquarium, and cannoli in the North End
Free pick
Freedom Trail (Self-Guided)
Hershey, PA
Pennsylvania
A whole town that smells like chocolate, with a theme park, a zoo, and gardens all in one place
Free pick
Hershey's Chocolate World
Stowe & Burlington, VT
Vermont
Ben & Jerry's, Shelburne Farms, and the most beautiful main street in New England
Free pick
ECHO Lake Aquarium & Science Center (Burlington)
Saratoga Springs, NY
Upstate New York
Thoroughbred racing, natural mineral springs, and performing arts under the stars
Free pick
Saratoga Spa State Park & Mineral Springs
Lake Placid, NY
Adirondacks
Olympic history, a mountain summit with no hiking, and a town built around a perfect lake
Free pick
Mirror Lake Walk
Extended Trips — 4 Hours or More
Plan for 3+ nights to make the drive worth it
Washington D.C., DC
Mid-Atlantic
Free world-class museums, monuments on every block, and the National Zoo — all without spending much
Free pick
National Mall Walking Tour
Acadia & Bar Harbor, ME
Maine Coast
Maine coast at its most dramatic — mountains, tidal pools, and lobster rolls on the dock
Free pick
Jordan Pond Nature Trail & Carriage Roads
Niagara Falls, NY
Western New York
The most powerful waterfall in North America — and you can stand 20 feet from it
Free pick
Niagara Falls State Park & Goat Island
Island & Caribbean Escapes
New England islands, the Caribbean, and Bermuda — flight times from JFK/LGA/EWR
Bermuda, UK Territory
Atlantic Islands
Pink sand beaches, pastel cottages, and 2 hours from New York
Free pick
Horseshoe Bay Beach
Block Island, RI
New England Islands
No cars needed, dramatic cliffs, and the best beach in Rhode Island — 1.5 hours from New Haven
Free pick
Mohegan Bluffs Walk
Nassau & Paradise Island, Bahamas
Caribbean
Atlantis water park, pink colonial streets, and a 30-minute flight from Florida
Free pick
Nassau Colonial Downtown Walk
Martha's Vineyard, MA
New England Islands
Gingerbread cottages, lighthouse cliffs, and the ferry ride is half the fun
Free pick
Oak Bluffs Gingerbread Cottage Walk
Puerto Rico, PR
Caribbean
Old San Juan, bioluminescent bays, and warm Caribbean water — no passport required
Free pick
Old San Juan Walking Tour
St. John, USVI
Caribbean
The most beautiful beach in the Caribbean, and two-thirds of the island is national park
Free pick
Cinnamon Bay Beach
Turks & Caicos, UK Territory
Caribbean
Grace Bay is the best beach in the world — calm, warm, and protected inside a reef
Free pick
Grace Bay Beach
Nantucket, MA
New England Islands
Cobblestone streets, wild cranberry bogs, and the most unspoiled beach town in New England
Free pick
Children's Beach & Brant Point Lighthouse
Cayman Islands, UK Territory
Caribbean
Touch stingrays in the wild, swim with turtles, and walk Seven Mile Beach
Free pick
Seven Mile Beach
Aruba, Dutch Territory
Caribbean
Sunny 365 days a year, outside the hurricane belt, and the best beach bar scene in the Caribbean
Free pick
Eagle Beach
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Parks, beaches, ice cream, museums — curated for grandparents in Fairfield County, CT and Westchester County, NY.