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Nature Road Trip: Boston, Vermont, New York

Viewed by 58 travelers

Day 1: Exploring Boston

Boston, MA, USA

8:00AM

Breakfast at Flour Bakery + Cafe

Start your day with delicious pastries and coffee at Flour Bakery + Cafe to fuel up for exploring Boston.
Walk or take a short drive to Flour Bakery + Cafe.
15 USD, 1 hour

10:00AM

Freedom Trail

Embark on a historical journey along the Freedom Trail, visiting iconic sites like Faneuil Hall and Paul Revere's House.
Walk to the starting point of the Freedom Trail.
Free, 3 hours

1:00PM

Lunch at Neptune Oyster

Indulge in fresh seafood at Neptune Oyster, known for its lobster rolls and oysters.
Walk or take a short drive to Neptune Oyster.
30 USD, 1 hour

3:00PM

Explore Boston Common

Take a leisurely stroll through the picturesque Boston Common, the oldest city park in the United States.
Walk to Boston Common.
Free, 2 hours

6:00PM

Dinner at Union Oyster House

Experience a historic dining experience at Union Oyster House, serving seafood since 1826.
Walk or take a short drive to Union Oyster House.
40 USD, 2 hours
Find Hotels in Boston

Day 2: Sightseeing in Boston

Boston, MA, USA

9:00AM

Breakfast at Tatte Bakery & Cafe

Enjoy a cozy breakfast at Tatte Bakery & Cafe, known for its delicious pastries and coffee.
Walk or drive to Tatte Bakery & Cafe.
20 USD, 1 hour

11:00AM

Visit Harvard University

Explore the prestigious Harvard University campus and its historic landmarks like Harvard Yard and Widener Library.
Drive or take public transportation to Harvard University.
Free, 2 hours

1:00PM

Lunch at Regina Pizzeria

Savor authentic Italian pizza at Regina Pizzeria, a Boston institution since 1926.
Drive or walk to Regina Pizzeria.
25 USD, 1 hour

3:00PM

Shop on Newbury Street

Indulge in some retail therapy on Newbury Street, lined with trendy boutiques and designer stores.
Walk or drive to Newbury Street.
Varies, 2 hours

6:00PM

Dinner at Legal Sea Foods

Treat yourself to a seafood feast at Legal Sea Foods, known for its fresh catches and chowder.
Drive or walk to Legal Sea Foods.
45 USD, 2 hours
Find Hotels in Boston

Day 3: Exploring Vermont

Vermont, USA

9:00AM

Breakfast at Penny Cluse Cafe

Start your day with a hearty breakfast at Penny Cluse Cafe, known for its delicious pancakes and maple syrup.
Drive to Penny Cluse Cafe in Vermont.
15 USD, 1 hour

11:00AM

Hike in Green Mountain National Forest

Immerse yourself in nature with a scenic hike in Green Mountain National Forest, known for its lush greenery and trails.
Drive to the trailhead in Green Mountain National Forest.
Free, 3 hours

2:00PM

Lunch at Hen of the Wood

Enjoy farm-to-table cuisine at Hen of the Wood, a renowned restaurant offering seasonal dishes.
Drive to Hen of the Wood for lunch.
35 USD, 1 hour

4:00PM

Ben & Jerry's Factory Tour

Take a tour of the Ben & Jerry's Factory to learn about the ice cream making process and enjoy sweet samples.
Drive to the Ben & Jerry's Factory for the tour.
15 USD, 2 hours

7:00PM

Dinner at Prohibition Pig

Savor craft beers and barbecue at Prohibition Pig, a popular spot for delicious brews and smoked meats.
Drive to Prohibition Pig for dinner.
40 USD, 2 hours
Find Hotels in Vermont

Day 4: Nature in Vermont

Vermont, USA

9:00AM

Breakfast at The Skinny Pancake

Enjoy a cozy breakfast with sweet and savory crepes at The Skinny Pancake, a local favorite in Vermont.
Drive to The Skinny Pancake for breakfast.
20 USD, 1 hour

11:00AM

Scenic Drive on Route 100

Embark on a picturesque drive along Route 100, known for its stunning fall foliage and charming towns.
Start your scenic drive on Route 100.
Gas Cost, 3 hours

2:00PM

Visit Quechee Gorge

Explore the breathtaking Quechee Gorge, often called the 'Grand Canyon of Vermont', for stunning views and hiking opportunities.
Drive to Quechee Gorge for exploration.
5 USD, 2 hours

5:00PM

Cheese Tasting at Cabot Creamery Annex

Indulge in a cheese tasting experience at Cabot Creamery Annex, sampling a variety of award-winning Vermont cheeses.
Drive to Cabot Creamery Annex for cheese tasting.
10 USD, 1 hour

7:00PM

Dinner at Simon Pearce Restaurant

Dine at Simon Pearce Restaurant overlooking a waterfall, known for its elegant ambiance and farm-to-table cuisine.
Drive to Simon Pearce Restaurant for dinner.
50 USD, 2 hours
Find Hotels in Vermont

Day 5: Urban Exploration in New York

New York, NY, USA

9:00AM

Breakfast at Clinton St. Baking Company

Start your day with a delicious breakfast at Clinton St. Baking Company, known for its famous blueberry pancakes.
Walk or take public transportation to Clinton St. Baking Company.
25 USD, 1 hour

11:00AM

Central Park Exploration

Discover the beauty of Central Park with a leisurely stroll, boat ride on the lake, or visit to iconic landmarks like Bethesda Terrace.
Walk to Central Park for exploration.
Free, 3 hours

2:00PM

Lunch at The Halal Guys

Satisfy your cravings with flavorful halal street food at The Halal Guys, a must-visit spot in New York City.
Walk or take public transportation to The Halal Guys.
15 USD, 1 hour

4:00PM

Explore The Metropolitan Museum of Art

Immerse yourself in art and culture at The Met, one of the world's largest and most prestigious art museums.
Walk or take public transportation to The Met.
25 USD, 2 hours

7:00PM

Dinner at Eataly NYC Flatiron

Experience Italian culinary delights at Eataly NYC Flatiron, a bustling market with various dining options.
Walk or take public transportation to Eataly NYC Flatiron for dinner.
40 USD, 2 hours
Find Hotels in New York

Day 6: Sightseeing in New York

New York, NY, USA

9:00AM

Breakfast at Two Hands

Enjoy a trendy breakfast at Two Hands, known for its delicious avocado toast and specialty coffee.
Walk or take public transportation to Two Hands.
20 USD, 1 hour

11:00AM

Statue of Liberty Cruise

Embark on a Statue of Liberty cruise for panoramic views of the iconic statue and the New York City skyline.
Take a short walk to the Statue of Liberty cruise departure point.
30 USD, 2 hours

2:00PM

Visit One World Observatory

Take in breathtaking views of Manhattan from the One World Observatory, located atop the One World Trade Center.
Take public transportation or a short drive to One World Observatory.
35 USD, 1.5 hours

4:00PM

Shopping in SoHo

Indulge in shopping at trendy boutiques and designer stores in the fashionable neighborhood of SoHo.
Walk or take public transportation to SoHo.
Varies, 2 hours

7:00PM

Farewell Dinner at Gramercy Tavern

Enjoy a memorable farewell dinner at the acclaimed Gramercy Tavern, known for its seasonal American cuisine.
Take public transportation or a short drive to Gramercy Tavern.
60 USD, 2 hours
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More About Boston, Vermont, New York

Trip Packing List: United States multi-city tour (30 Aug 2026 — early Nov 2026)
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