Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

Boston, Cape Cod, and New York Adventure Road Trip

Viewed by 109 travelers

Day 1: Boston Delights

Boston, Massachusetts

8:00AM

Start at Quincy Market

Begin your day with a hearty breakfast at Quincy Market, a historic market offering a wide range of food options.
Quincy Market is centrally located in downtown Boston and easily accessible by public transport or a short walk from most hotels.
£10, 1 hour

12:00PM

Freedom Trail Exploration

Embark on the famous Freedom Trail tour to discover Boston's rich history, passing by landmarks such as Paul Revere's House and Faneuil Hall.
Join a guided tour or follow the red-brick trail starting from Boston Common.
£15, 3 hours

7:00PM

Dinner at North End

Indulge in mouth-watering Italian cuisine at North End, Boston's vibrant Italian neighbourhood.
North End is a short walk from the Freedom Trail, filled with charming restaurants.
£30, 2 hours
Find Hotels in Boston

Day 2: Exploring Boston Further

Boston, Massachusetts

9:00AM

Breakfast at Tatte Bakery

Start your day with a delicious breakfast at Tatte Bakery known for its fresh pastries and artisanal coffee.
Tatte Bakery has multiple locations in Boston, offering a cosy atmosphere for a delightful morning meal.
£15, 1 hour

11:00AM

Fenway Park Tour

Visit Fenway Park, home of the Boston Red Sox, and take a guided tour of this iconic baseball stadium.
Fenway Park is located in the Fenway-Kenmore neighbourhood, offering a unique insight into baseball history.
£20, 2 hours

2:00PM

Shop on Newbury Street

Explore the trendy boutiques and designer stores on Newbury Street for a shopping spree in Boston's chic neighbourhood.
Newbury Street is a famous shopping destination in Back Bay, perfect for discovering unique finds.
Variable, 2 hours

7:00PM

Seafood Dinner at Legal Sea Foods

Enjoy a classic New England seafood dinner at Legal Sea Foods, a renowned restaurant chain serving fresh and sustainable seafood dishes.
Legal Sea Foods has several locations in Boston, offering a range of seafood options for a delightful dinner experience.
£40, 2 hours
Find Hotels in Boston

Day 3: Cape Cod Beach Bliss

Cape Cod, Massachusetts

9:00AM

Drive to Cape Cod

Embark on a scenic drive from Boston to Cape Cod, enjoying picturesque views as you head towards the coastal destination.
Take Route 6 from Boston for a beautiful journey to Cape Cod in approximately 2 hours.
£20 (fuel), 2 hours

12:00PM

Beach Day at Coast Guard Beach

Relax on the sandy shores of Coast Guard Beach, known for its natural beauty and serene atmosphere ideal for a tranquil beach day.
Coast Guard Beach is part of the Cape Cod National Seashore and can be accessed via a short walk from the parking area.
Free, 3 hours

5:00PM

Sunset Clambake at The Beachcomber

Experience a traditional Cape Cod clambake during sunset at The Beachcomber, a beachfront restaurant offering a taste of local seafood delights.
The Beachcomber is located in Wellfleet, providing a stunning setting for a memorable dining experience by the ocean.
£50, 2 hours
Find Hotels in Cape Cod

Day 4: Cape Cod Coastal Exploration

Cape Cod, Massachusetts

10:00AM

Bike the Cape Cod Rail Trail

Embark on a scenic bike ride along the Cape Cod Rail Trail, a picturesque cycling route passing through charming towns and scenic landscapes.
Rent a bike from one of the local shops near the trail and start your cycling adventure through the natural beauty of Cape Cod.
£25 (bike rental), 2 hours

1:00PM

Lunch at The Raw Bar

Enjoy a casual seafood lunch at The Raw Bar in Mashpee, known for its fresh oysters and laid-back waterfront dining experience.
The Raw Bar overlooks the water in Popponesset Bay, creating a relaxing setting for a delicious meal.
£35, 1.5 hours

4:00PM

Visit Provincetown

Explore the vibrant town of Provincetown at the tip of Cape Cod, known for its colourful buildings, diverse community, and artistic heritage.
Drive to Provincetown for a leisurely afternoon exploring art galleries, shops, and enjoying the seaside charm of the town.
£10 (parking), 3 hours

7:00PM

Dinner at The Mews Restaurant & Cafe

Dine at The Mews Restaurant & Cafe in Provincetown, offering a diverse menu with fresh seafood dishes and stunning waterfront views.
The Mews is located in the heart of Provincetown, providing a delightful dining experience with a blend of flavours and ocean vistas.
£45, 2 hours
Find Hotels in Cape Cod

Day 5: New York City Arrival

New York City, New York

9:00AM

Arrive in New York City

Travel from Cape Cod to New York City, immersing yourself in the vibrant energy of the Big Apple as you approach the bustling metropolis.
Drive down I-95 South to enter New York City via one of the bridges or tunnels, marking the beginning of your urban adventure.
£30 (tolls), 5 hours

1:00PM

Lunch at Chelsea Market

Indulge in a diverse culinary experience at Chelsea Market, a renowned food hall offering an array of delicious options from local vendors.
Chelsea Market is situated in the vibrant neighbourhood of Chelsea, easily accessible by public transport or a short walk from the High Line.
£20, 1 hour

4:00PM

Central Park Relaxation

Take a leisurely stroll through Central Park, enjoying the green oasis amidst the urban landscape with its picturesque paths and serene lakes.
Central Park spans from 59th Street to 110th Street, providing multiple entry points for a calming escape in the heart of the city.
Free, 2 hours

8:00PM

Dinner in Times Square

Experience the vibrant atmosphere of Times Square while dining at one of the iconic restaurants surrounding the dazzling hub of entertainment.
Times Square is easily reachable by public transport, offering a memorable dining setting amidst the bright lights and excitement of the city.
£50, 2 hours
Find Hotels in New York City

Day 6: Art and Culture in NYC

New York City, New York

10:00AM

The Met Museum Visit

Immerse yourself in art at The Met, one of the world's largest museums, housing diverse collections from various eras and regions.
Located on the eastern edge of Central Park along Museum Mile, The Met is accessible by public transport or a pleasant walk through the park.
£25, 3 hours

2:00PM

Broadway Show

Experience the magic of Broadway with a captivating theatre show, showcasing world-class performances and engaging storytelling.
Book tickets in advance for a popular show and arrive early at the theatre to secure great seats for the performance.
£80, 3 hours

7:00PM

Dinner at Little Italy

Delight in a taste of Italy with a dinner at the vibrant neighbourhood of Little Italy, savouring delicious pasta and authentic Italian dishes.
Little Italy in Lower Manhattan is easily accessible by public transport, offering a charming setting for a culinary journey to Italy.
£35, 2 hours
Find Hotels in New York City

Day 7: Exploring NYC Highlights

New York City, New York

9:00AM

Statue of Liberty Visit

Embark on a ferry to visit the iconic Statue of Liberty on Liberty Island and explore the Ellis Island National Museum of Immigration.
Ferries depart from Battery Park, providing stunning views of Lady Liberty and the Lower Manhattan skyline.
£25 (ferry ticket), 4 hours

2:00PM

Brooklyn Bridge Walk

Take a scenic stroll across the historic Brooklyn Bridge, admiring panoramic views of the Manhattan skyline and the East River.
Start your walk from Brooklyn Bridge Park or near City Hall on the Manhattan side for a picturesque experience.
Free, 1.5 hours

6:00PM

Dinner at Hudson Yards

Enjoy a dining experience with a view at one of the restaurants in Hudson Yards, providing panoramic vistas of the city skyline.
Hudson Yards is a modern neighbourhood on Manhattan's west side, easily accessible by public transport or a short taxi ride.
£60, 2 hours
Find Hotels in New York City

Day 8: Farewell Adventures in NYC

New York City, New York

9:00AM

High Line Park Walk

Take a relaxing stroll along the High Line, an elevated park converted from a disused railway line, offering green spaces and city views.
Access the High Line from various points in Chelsea, providing a serene path with urban landscapes and art installations.
Free, 2 hours

12:00PM

Brunch in West Village

Indulge in a leisurely brunch in the charming West Village, known for its historic streets, townhouses, and cosy cafes.
West Village boasts numerous brunch spots, each offering a unique culinary experience infused with local charm.
£25, 2 hours

3:00PM

Explore Times Square

Spend your afternoon exploring the vibrant hub of Times Square, immersing yourself in the excitement of the bustling intersection.
Times Square is a major attraction in Midtown Manhattan, teeming with shops, theatres, and bustling energy.
Free, 2 hours

7:00PM

Dinner Cruise Experience

Embark on a scenic dinner cruise along the Hudson River, enjoying a delightful meal with stunning views of the Manhattan skyline.
Book a dinner cruise for a memorable evening on the water, savouring the city lights and notable landmarks.
£100, 3 hours
Find Hotels in New York City
0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version
Itinerary created by AI-assisted, human-reviewed

Plan Your Boston, Cape cod and New York Trip

Cost Estimator
Estimate your trip budget
Packing List
Get a custom checklist
Weather Expert
Check weather & best time to go