Trip no. 3: 160 miles
Day 1: Branford, Conn., to Madison, Conn.
Distance: 15 miles
Do. Start your morning on the Long Island Sound. The Sea Mist, which sails hourly (starting at 10:15), winds through the Thimble Islands while its captain spins local yarns -- including the tale of pirate Captain Kidd, who is said to have buried treasure nearby ($12 per adult).
Eat. Crustacean time! Locals like the Lobster Shack, where a roll is $15. Not cheap, but the outdoor tables are BYOB. Jenn McCulloch, editor of Branford Patch, suggests picking up dessert at Bishop's Orchard Farm Market in Guilford. "We go every year," she says. August is blueberry time, while September brings pears and more.
Stay. Tuck in at the Scranton Sea Horse Inn in nearby Madison. Rooms start at $140, about 25% less than similar B&Bs in better-known Branford. Midweek, rates on pricier rooms drop by $30 a night.
Day 2: Madison, Conn. to Wallingford, Conn.
Distance: 42 miles
Do. Thirty minutes at the wheel and you'll reach Hamden, Conn. There New England guidebook author Kim Knox Beckius recommends Sleeping Giant State Park for its range of hiking options. Take the Tower Path (three miles) for panoramic views of the sound, or choose the Blue Trail (5.1 miles) to traverse the "giant" -- the hill that gives the park its name.
Eat. Drive to Wallingford's Gouveia Vineyards, where you can taste five vintages for $8. The winery doesn't have a restaurant, but the owners encourage picnics on the grounds and provide delivery menus from local cafés. (Stay until 8 p.m. weekdays, 9 p.m.Friday and Saturday.)
Stay. History buffs will like the High Meadow Bed and Breakfast, which dates from 1742. Rooms start at $110 -- or about half the price of more central lodging like the Wallingford Meriden Hotel.
Day 3: Wallingford, Conn. to Cornwall Bridge, Conn.
Distance: 71 miles
Do. Head to Cheshire for a classic road trip stop: the quirky museum. At the Barker Character Comic and Cartoon Museum you'll see many of your childhood favorites in toy or action-figure form ($5, Wednesday through Saturday).
As you head north on Route 7, suggests Boston Globe travel writer Steve Jermanok, stop at Kent Falls State Park to check out the falls. "It's a gem," he says. Entry is $7 on weekends, but weekdays are free. Later, drive on to West Cornwall, where you can cross the Housatonic River via covered bridge.
Eat. West Cornwall restaurant RSVP offers an impressive prix fixe for $80. For a more budget-friendly dinner, get a patio seat at the Wandering Moose Café ($20 or so).
Stay. Bunk at the Cornwall Inn, starting at $169. Too pricey? The owner accepts best offers Sunday through Thursday.
Day 4: Cornwall Bridge, Conn., to Great Barrington, Mass.
Distance: 32 miles
Do. Stop at Bartholomew's Cobble to spot some of the preserve's 200-plus bird species before heading into Great Barrington. In town, Lindsey Schmid of Berkshire Visitors Bureau recommends grabbing tickets to a show at the Mahaiwe Performing Arts Center.
Eat. Multitask at the Gypsy Joynt Café, an eclectic café/bar/music venue/clothing shop. Bonus: Most of the food -- including a spread of drool-worthy desserts -- is locally sourced.
Stay. Finish the day at Acorn's Hope Bed and Breakfast. It's just three minutes from downtown, but surrounded by grazing horses and llamas (yes, llamas). Rates can hit $220 in summer, but the owner encourages a New England tradition: haggling before you book.
They soar above ordinary trips and perform feats of vacation derring-do, all while nailing their budget. Here are their travel tips.