This one-week Boston and Cape Cod itinerary blends big-city history with classic New England coastal charm, giving you a seamless mix of iconic landmarks, great food, and relaxed seaside moments. With memorable stops in Boston, a scenic drive through Plymouth, and a luxurious stay in Chatham, it’s the perfect plan for couples or families craving a balanced, well-paced getaway.
My husband had talked about going to Boston for years. He’s an avid baseball fan, so Fenway Park had always been on his list, and he loves soaking up history, so the city made perfect sense. As for me, I’m all about the coast, and visiting Cape Cod had been on my dream list for just as long. Pairing the two made for the perfect New England getaway in early September. Boston greeted us with sunny 70–80° weather, and while Cape Cod gave us mostly overcast skies and a few light showers, the charm of Chatham still stole the show.
So if you’ve been dreaming of a trip that blends big-city history and culture with coastal New England charm, a week in Boston and Cape Cod is the perfect plan. I created this Boston and Cape Cod itinerary to give the best of both worlds: bustling city streets, iconic landmarks, fresh seafood, and serene seaside escapes. The plan includes three nights in Boston at The Newbury Boston and three nights in Chatham at the luxurious Chatham Bars Inn.
Boston is a walkable, safe city with a vibrant energy fueled by its 30+ colleges and universities. Historic streets, charming brownstones, and lively neighborhoods make it ideal for strolling, dining, and exploring. Chatham, on the other hand, feels like a storybook coastal town- quaint, peaceful, and picture-perfect. Renting a car for the drive between Boston and Chatham is highly recommended, with a scenic stop in Plymouth for lunch and a quick visit to Plymouth Rock.
Day 1: Arrival in Boston
- Check into The Newbury Boston, a chic hotel overlooking the Public Garden.
- Stroll through Boston Common and the Public Garden to get a first glimpse of the city.
- Dinner at Saltie Girl– don’t miss the tuna carpaccio and their famous lobster roll.
- Cap the night with drinks at a cozy pub and a quick photo at the Cheers bar.
Day 2: History, Culture & Iconic Food
- Morning walk along the Freedom Trail (stop at Faneuil Hall Marketplace for shopping and snacks).
- Lunch at Florina, near the start of the Freedom Trail behind the Statehouse, known for its pizza with the freshest ingredients.
- Stop by Omni Parker House, the birthplace of the iconic Boston cream pie (it’s a classic experience!).
- Stroll through the streets of the North End, soaking up Little Italy vibes.
- Afternoon drinks at the Samuel Adams Brewery or Bell in Hand Tavern, the oldest tavern in the U.S.
- Dinner at Row 34 Seaport. The fresh tomato salad and clam chowder are standouts.
Day 3: Art, Fenway & Game-Day Vibes
- Explore the Isabella Stewart Gardner Museum, a beautiful and easily walkable art haven.
- Lunch at Flour, known for its sandwiches and fresh bread.
- Afternoon at Fenway Park, either cheering on the Red Sox or touring the historic ballpark.
- Dinner and drinks at Dillons Sports Bar, perfect for soaking up authentic Boston game-day energy.
Day 4: Boston to Cape Cod (with Plymouth Stop)
- Pick up your rental car and begin the scenic drive to Cape Cod.
- Stop in Plymouth to see Plymouth Rock, then enjoy a seaside lunch at East Bay Grille.
- Continue to Chatham and check into Chatham Bars Inn, your luxury coastal retreat.
- Stroll through downtown Chatham for boutique shopping and galleries.
- Dinner at Beach House Grill—try the tenderloin with truffle for a special treat.
Day 5: Cape Cod Adventure
- Breakfast at Captain’s Table, a local favorite—don’t miss the shrimp & grits.
- Rent bikes and ride to Chatham Lighthouse for breathtaking ocean views.
- Afternoon whale watching excursion—a quintessential Cape Cod experience.
- Dinner at Wild Goose Tavern, famous for its lobster toast.
- Cap the evening with drinks at The Squire, a lively and fun local spot.
Day 6: Relaxation & Coastal Indulgence
- Start the morning at the Chatham Bars Inn Spa with a restorative treatment.
- Spend the afternoon relaxing by the beach or pool, or browsing Chatham’s charming shops.
- Casual lunch at Mac’s Chatham Fish & Lobster, a counter-service local favorite.
- Dinner at the inn or one last seafood feast in town, followed by optional drinks at Sacred Cod Tavern.
Day 7: Departure
- Breakfast on the terrace at the inn with stunning ocean views.
- Drive back to Boston for your flight home, taking home memories of New England’s best cities and coastal charm.
I think this Boston and Cape Cod itinerary perfectly balances city excitement with coastal relaxation. It’s a fantastic domestic getaway for couples, and families with older kids will love it too.
You can spend three nights diving into Boston’s history, culture, and culinary scene, then unwind with seaside strolls, spa treatments, and fresh seafood in Chatham.
When you’re ready to start planning your New England adventure, contact us for a tailored luxury experience.
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FAQ’s
1. When is the best time to visit Boston and Cape Cod for a one-week trip?
The best months are late May through early October, when the weather is warm, the coastal towns are lively, and outdoor activities are at their peak.
2. Do I need a rental car for this itinerary?
You won’t need a car while staying in Boston, but renting one for the drive to Cape Cod is highly recommended. It gives you flexibility and lets you stop in Plymouth along the way.
3. Is this trip suitable for families?
Yes! While couples love this itinerary, families with older kids especially enjoy the mix of history, great food, beaches, and outdoor adventures like whale watching.
4. How many days should I spend in each destination?
Three nights in Boston and three nights in Chatham offer the perfect balance between city exploration and coastal relaxation, without feeling rushed. You can easily bump up to 4 nights in each, if you have the time.
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