Coastal Escape: Plymouth & Cape Cod Road Trip from Boston

Trip Snapshot:

• Distance & Driving Time: ~200 miles round-trip (5–6 hours total drive time).
• Best Time of Year to Visit: Late spring through fall. Summer offers beach weather (but heavy traffic on peak weekends), while September brings milder crowds and early fall foliage.
• Ideal For: History buffs, beach lovers, families, and anyone craving a mix of American heritage and classic New England seaside charm.
• Quick Route Summary: Boston ➔ Plymouth (via Route 3 south, 40 minutes) ➔ cross Sagamore Bridge onto Cape Cod ➔ Sandwich ➔ Hyannis ➔ Chatham (optional extension to Provincetown) ➔ return to Boston (optionally via I-495 to avoid congestion).
• Top Highlights: Seeing Plymouth Rock and the Mayflower II, strolling the Sandwich boardwalk and Heritage Museums & Gardens, visiting the JFK Memorial in Hyannis, boutique shopping on Chatham Main Street, and beach-hopping along the Cape Cod National Seashore.

Route Overview

Head south from Boston on Route 3. In about 40 minutes, you’ll reach Plymouth, known as “America’s Hometown.” After exploring Plymouth, continue south and cross the Sagamore Bridge onto Cape Cod. You’re now on the Upper Cape follow signs for Route 6A, the Old King’s Highway, for a scenic drive through quaint villages and salt marshes (this historic road is often dubbed one of the world’s most scenic drives). Your first Cape stop is Sandwich, about 60 miles from Boston. From Sandwich, drive east along either Route 6 (the highway) or the more meandering Route 6A toward Hyannis on the Mid-Cape. In Hyannis, you might detour to the harbor or beaches, then continue on Route 28 or 6 toward the Lower Cape town of Chatham at Cape Cod’s “elbow.” Chatham is roughly 85 miles from Boston (without traffic, about 1.5–2 hours). If time allows and you’re ambitious, you could drive further up Cape Cod to Provincetown at the very tip (about 115 miles from Boston, 2.5–3 hours one-way). Otherwise, from Chatham you’ll loop back. For the return, consider taking Route 6 to the Bourne Bridge and I-495 north, which bypasses some of the Cape bridge traffic and brings you back toward Boston via the outer loop. This entire loop can be done in one long day, but it truly shines as a relaxed 2–3 day excursion with an overnight on the Cape to soak in the seaside atmosphere.

Top Stops & Experiences

• Plymouth: Park near the waterfront to see the legendary Plymouth Rock (ensconced under a granite canopy at Pilgrim Memorial State Park) and the Mayflower II, a full-scale replica of the Pilgrims’ ship. These iconic sites draw over a million visitors each year. Stroll the historic downtown streets, lined with colonial-era buildings, and consider visiting the Plimoth Patuxet Museums (a living history museum just outside town). Don’t leave without grabbing a cup of New England clam chowder or local seafood Plymouth’s harbor has plenty of eateries where you can dine with a view of the Mayflower II.
• Sandwich (Upper Cape): The Cape’s oldest town exudes charm. Stop by Heritage Museums & Gardens in Sandwich, a 100-acre complex featuring beautifully manicured gardens and unique exhibits like classic American automobiles and a working 1908 carousel. It’s a peaceful spot to stretch your legs among flowers and art. Afterwards, visit downtown Sandwich for its quaint shops and the famed Sandwich Boardwalk a wooden footbridge stretching over marshes to the beach, offering a picture-perfect Cape Cod vista.
• Hyannis: As a bustling hub of the mid-Cape, Hyannis offers a mix of history and coastal activity. Pay respects at the serene John F. Kennedy Memorial, which overlooks Lewis Bay (President Kennedy often sailed here). Adjacent is a beach and the Korean War Memorial, making this a reflective stop. Stroll Hyannis Harbor, where in summer you can watch the ferries depart for Martha’s Vineyard and Nantucket a tempting side trip if you have a full day. The harbor area has shops, artist shanties, and the Cape Cod Maritime Museum. If you fancy a cruise, Hyannis is a departure point for harbor cruises and fishing charters.
• Chatham: Located at the “elbow” of Cape Cod, Chatham is a postcard-perfect seaside town. As you approach, consider detouring to Chatham Lighthouse Beach. The Chatham Light (an active lighthouse originally built in 1808) stands guard here near dangerous shoals; it’s one of Cape Cod’s notable beacons. From the bluff by the lighthouse, you get sweeping views of the Atlantic in summer, you might spot seals just offshore. Next, wander Main Street Chatham, filled with boutiques, galleries, and ice cream parlors. This is an ideal late-afternoon or evening stop: grab some homemade ice cream or saltwater taffy, and pop into shops selling coastal souvenirs. Don’t miss the Chatham Squire or another local seafood spot for a lobster roll or fresh fish and chips.
• Cape Cod Beaches & National Seashore: If you crave beach time, the Cape Cod National Seashore (on the Atlantic side of the Outer Cape) offers some of the finest. From Chatham, you’re a short drive to Nauset Beach in Orleans or a bit farther to Coast Guard Beach in Eastham both routinely ranked among the best beaches in the U.S. for their wide sands and rolling surf. Coast Guard Beach in particular offers gorgeous ocean views and frequent seal sightings. In summer, arrive early; parking lots at popular beaches often fill by mid-morning (National Park Service rangers advise finding beach parking before 10 am or after 3 pm to avoid crowds). If you venture all the way to Provincetown at the Cape’s tip, you’ll not only experience a lively artsy town with galleries and Portuguese bakeries, but you can also visit the dramatic dunes of Race Point Beach or climb the Pilgrim Monument for a panoramic view. Ptown is about a 3-hour drive from Boston, so only attempt this extension if you have ample time.

Where to Eat & Stay

For lunch, consider a classic seafood shack or pub in Plymouth’s waterfront (try a hearty bowl of chowder or fish n’ chips). On Cape Cod, seafood is a must: in Sandwich, Seafood Sam’s is a casual favorite for fried clams; in Hyannis, you might enjoy fresh oysters atSpanky’s Clam Shack by the harbor. For a sweet treat, Four Seas Ice Cream in Centerville (just off Route 6 on the way to Hyannis) is a local institution scooping homemade ice cream since the 1930s.

If you’re extending to dinner, Chatham has upscale options and family eateries alike Chatham Squire is a lively tavern beloved by both locals and visitors. For something more intimate, many Cape towns have inn restaurants featuring local catch; for example, Belfry Inn & Bistro in Sandwich (a converted church setting) or Ocean House in Dennisport for oceanfront dining.

Staying overnight? There’s a range from cozy B&Bs to resorts. In Plymouth, you could overnight at the historic John Carver Inn (walking distance to the sights). On the Cape, Inn at Sandwich offers B&B charm, while Hyannis has familiar hotels and resorts (like the family-friendly Cape Codder Resort with its pools). For a special splurge, Chatham Bars Inn is an iconic luxury resort right on the shore in Chatham, complete with a private beach and classic New England elegance. Booking ahead is essential in summer and fall weekends, as accommodations fill up quickly.

Practical Tips

• Timing & Traffic: In summer, Cape traffic can be intense. Avoid driving to the Cape on a Friday afternoon or back to Boston on a Sunday evening if you can the bridges back up for miles. The local advice is to travel at off-peak times (e.g. leave Boston early in the morning or later in the evening). If doing a weekend trip, consider leaving Thursday night or very early Saturday, and returning late Sunday or Monday morning to beat the worst jams.
• Beach Logistics: Many Cape Cod town beaches charge for daily parking in peak season (roughly Memorial Day to Labor Day), and lots often fill up by mid-morning on nice days. Plan to arrive early (before 9–10am) or opt for late afternoon beach visits when some crowds have left (bonus: sunset on a Cape beach!). National Seashore beaches have larger lots but still can reach capacity have a backup beach in mind or be flexible. Also, bring cash for parking fees as not all accept cards.
• What to Pack: Even in summer, bring layers. Sea breezes can make mornings and evenings cool (and if you do a ferry or whale watch, a light jacket is handy). Don’t forget sunscreen, bug spray (greenhead flies can bite on marshy beaches in July), and comfortable walking shoes for village strolls and dunes. A beach towel or foldable chair is great if you plan to dip your toes in the ocean.
• Ferries: If you decide on a day trip to Martha’s Vineyard or Nantucket, the fastest ferries depart from Hyannis (foot passengers only on the high-speed catamarans). Allocate a full day for either island for example, a morning ferry to Nantucket, renting a bike or taking a tour on-island, and an evening return. Ferry reservations (especially for cars) must be made well in advance in summer.
• Alternate Routes: On the way back, taking I-495 instead of retracing Route 3 can sometimes save time. It’s a slightly longer distance but often a smoother drive, especially if you’re returning on a Sunday when Route 3 north can be very congested near the Sagamore Bridge. Watch electronic signs for traffic updates on both bridges if one is backed up, try the other. And remember Massachusetts’ hands-free driving law: no handheld phone use while driving.

Rentals & Logistics

Planning to rent a car for this adventure? Reserve in advance, especially in summer when demand is high. A mid-size SUV or comfortable sedan is ideal for both highway cruising and carrying beach gear. Before leaving Boston, familiarize yourself with the rental’s toll policy you’ll encounter tolls on the Mass Pike (I-90) or I-495 if you use those on your return. On the Cape, roads are free of tolls, but be prepared for rotaries (traffic circles) which are common in Massachusetts. Pro tip: fill up the gas tank before crossing onto Cape Cod; fuel is available on Cape, of course, but prices might be a bit higher in the tourist areas.

Lastly, embrace “Cape time” things move a little slower in these charming towns, especially with summer crowds. Build some flexibility into your schedule so you can linger on a beach or enjoy an impromptu lobster roll break. With a trusty set of wheels and this itinerary, you’re set to explore coastal Massachusetts at your own pace. Ready to hit the road? Buckle up, cue up a Cape Cod playlist (the song “Old Cape Cod” is a classic), and enjoy the salty air and scenery on this unforgettable drive.

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