9-Day Boston to Bar Harbor Road Trip Itinerary: Nature, Luxury, and Culinary Delights via Newport, RI, and Connecticut

Day 1: Explore Boston

Boston, MA

8:00AM

Breakfast at Tatte Bakery & Café

Start your day with a delicious almond croissant and a cappuccino in this artisanal bakery.
Walk to Boston Common after breakfast.
USD 15, 1 hour

9:30AM

Boston Freedom Trail

Walk the Freedom Trail to discover the history of Boston, visiting iconic sites like Paul Revere’s House and the Old North Church.
The trail begins in Boston Common.
FREE, 3 hours

1:00PM

Lunch at Union Oyster House

Enjoy some of the best clam chowder in the historic Union Oyster House, America’s oldest restaurant.
A short walk from the Freedom Trail.
USD 25, 1.5 hours

2:30PM

Visit the Museum of Fine Arts

Explore world-class collections and breathtaking art at this acclaimed museum.
Take the Green Line subway from Haymarket to Museum of Fine Arts.
USD 25, 3 hours

6:00PM

Dinner at Oleana

Savor Mediterranean dishes in a beautiful garden setting at Oleana, which is widely considered one of Boston's best.
Drive or take a cab from the museum.
USD 60, 2 hours

8:30PM

Evening Stroll at the Esplanade

Walk along the scenic Charles River Esplanade, enjoying the breeze and views of the city skyline.
Short drive to the Esplanade.
FREE, 1 hour
View Hotel Availability

Day 2: Boston to Newport

Newport, RI

8:00AM

Breakfast at Flour Bakery

Enjoy a breakfast sandwich and freshly baked pastries at Flour Bakery, a local favorite.
Drive to Newport; approximately 1.5 hours.
USD 20, 1 hour

9:30AM

Visit The Breakers

Tour this opulent mansion, a symbol of the Gilded Age and a must-see in Newport.
Short drive from breakfast to the mansion.
USD 30, 2 hours

12:00PM

Lunch at The Black Pearl

Indulge in fresh seafood, particularly their renowned clam chowder, at this waterfront restaurant.
Short drive or walk from The Breakers.
USD 30, 1.5 hours

1:30PM

Explore Cliff Walk

Stroll along this scenic 3.5-mile path along the shoreline for breathtaking ocean views.
Walk to the beginning of the path.
FREE, 2 hours

4:00PM

Visit the International Tennis Hall of Fame

Learn about the history of tennis and explore the beautiful grounds.
Short drive from Cliff Walk.
USD 20, 1.5 hours

6:00PM

Dinner at 22 Bowen's

Enjoy a fine dining experience with stunning views of the harbor and a seafood-focused menu.
A short walk from the tennis hall.
USD 70, 2 hours
View Hotel Availability

Day 3: Newport to New Haven

New Haven, CT

8:00AM

Breakfast at Belle’s Café

Start with a cozy breakfast with locally sourced ingredients, located along the waterfront.
Drive to New Haven; roughly 2 hours.
USD 18, 1 hour

9:30AM

Explore Yale University Campus

Wander through the historic Yale campus, taking in its beautiful architecture.
Short drive around the campus.
FREE, 2 hours

11:30AM

Visit the Yale University Art Gallery

Explore world-class collections that span from ancient to modern art.
Walk from the campus.
FREE, 1.5 hours

1:00PM

Lunch at Frank Pepe Pizzeria

Savor the iconic New Haven-style apizza at this legendary pizzeria.
Short walk from the art gallery.
USD 20, 1.5 hours

3:00PM

Visit the Peabody Museum of Natural History

Discover fascinating exhibits including dinosaur skeletons and ancient cultures.
Drive from the pizzeria to the museum.
USD 15, 2 hours

6:00PM

Dinner at The 116 Crown

Enjoy creative, locally sourced dishes in a relaxed setting.
Short drive from the museum.
USD 60, 2 hours
View Hotel Availability

Day 4: New Haven to Portsmouth

Portsmouth, NH

8:00AM

Breakfast at Willoughby’s Coffee & Tea

Grab a fresh brewed coffee with a pastry before heading out.
Drive to Portsmouth; approximately 2 hours.
USD 10, 1 hour

9:30AM

Visit Strawbery Banke Museum

Explore this outdoor history museum showcasing life in a waterfront neighborhood from the 1600s to the 1950s.
Short drive from the café.
USD 20, 2 hours

12:00PM

Explore Historic Downtown Portsmouth

Wander the cobblestone streets, visiting boutique shops and vibrant art galleries.
Walking distance from the museum.
FREE, 2 hours

2:00PM

Lunch at The Green Elephant

Relish unique Asian-inspired vegetarian dishes at this popular eatery.
Short walk from downtown.
USD 25, 1.5 hours

3:30PM

Head to Cape Neddick Lighthouse

A beautiful coastal spot, perfect for a short hike and stunning ocean views.
Drive for about 30 minutes from restaurant.
FREE, 2 hours

6:30PM

Dinner at The Library Restaurant

Enjoy a fine dining experience with exquisite dishes served in a former library setting.
Short drive back to downtown Portsmouth.
USD 75, 2 hours
View Hotel Availability

Day 5: Portsmouth to Portland

Portland, ME

8:00AM

Breakfast at Beale Street Barbeque

Savor a hearty BBQ breakfast to kick-start your day.
Drive to Portland; it's about a 30-minute journey.
USD 20, 1 hour

9:30AM

Visit the Portland Head Light

The most photographed lighthouse in the U.S. offers breathtaking views and a great photo op.
Drive for around 20 minutes from the restaurant.
FREE, 1 hour

10:30AM

Explore Fort Williams Park

Stroll around the park with historic sites and beautiful coastal trails.
Within walking distance from the lighthouse.
FREE, 1.5 hours

12:00PM

Lunch at Eventide Oyster Co.

Indulge in fresh seafood, particularly the famous brown butter lobster roll.
Drive into downtown Portland for lunch.
USD 30, 1.5 hours

2:00PM

Visit the Portland Museum of Art

Explore impressive galleries featuring American and European art.
Just a short walk from the restaurant.
USD 20, 2 hours

4:30PM

Shopping at Old Port District

Discover chic boutiques and craft shops in this iconic waterfront neighborhood.
Walking distance from the museum.
FREE, 2 hours

6:30PM

Dinner at Fore Street

Experience locally sourced farm-to-table dishes in a rustic setting.
Drive from the Old Port to the restaurant.
USD 80, 2 hours
View Hotel Availability

Day 6: Portland to Freeport

Freeport, ME

8:00AM

Breakfast at The Holy Donut

Enjoy artisanal potato donuts to treat your taste buds to a sweet start.
Drive to Freeport; it's about a 20-minute journey.
USD 15, 1 hour

9:00AM

Shopping at L.L. Bean Flagship Store

Enjoy shopping at this iconic outdoor retailer and explore the 24-hour store.
Walk to the store from the donut shop.
FREE, 2 hours

11:00AM

Visit Wolfe's Neck Woods State Park

Walk through beautiful coastal trails and enjoy the tranquil environment of this state park.
Drive for about 15 minutes to the park.
USD 5, 2 hours

1:00PM

Lunch at The Lobster Shack

Dig into authentic Maine lobster rolls in a picturesque setting with ocean views.
Drive back to Freeport for lunch.
USD 30, 1.5 hours

2:30PM

Explore Desert of Maine

It's a unique area of sand dunes surrounded by forests, offering walking trails.
A 10-minute drive from the restaurant.
USD 10, 2 hours

5:00PM

Dinner at Azure Cafe

Enjoy Mediterranean flavors and fresh seafood in a cozy atmosphere.
Short drive back to Freeport.
USD 60, 2 hours
View Hotel Availability

Day 7: Freeport to Camden

Camden, ME

8:00AM

Breakfast at the Camden Diner

Savor a classic American breakfast at this charming local spot.
Drive to Camden; about a 30-minute journey.
USD 20, 1 hour

9:30AM

Visit Camden Hills State Park

Hike up the Mt. Battie trail for panoramic views of Camden and Penobscot Bay.
Short drive from the diner to the park.
USD 5, 3 hours

12:30PM

Lunch at Cappy's Chowder House

Enjoy fresh seafood chowder at this cozy eatery that locals love.
Return to downtown Camden for lunch.
USD 25, 1.5 hours

2:00PM

Visit the Farnsworth Art Museum

Discover Maine’s art history, featuring works by Wyeth and other celebrated artists.
Walking distance from Cappy's.
USD 15, 2 hours

4:30PM

Stroll along Camden Harbor

Take in the views and watch the boats in Camden Harbor.
Just a short walk from the museum.
FREE, 1 hour

6:00PM

Dinner at Primo

Taste innovative farm-to-table dishes at this exquisite restaurant set in a renovated house.
Short drive from the harbor.
USD 90, 2 hours
View Hotel Availability

Day 8: Hiking in Acadia National Park

Acadia National Park, ME

7:30AM

Breakfast at The Park Loop Cafe

Fuel up with breakfast sandwiches and coffee before a full day of adventure.
Head directly to Acadia; about a 1-hour drive.
USD 15, 1 hour

9:00AM

Hike Cadillac Mountain

Ascend the highest point on the East Coast for breathtaking views and a rewarding experience.
Drive to the trailhead within Acadia.
FREE (National Park Entry Fee: USD 30), 4 hours

1:00PM

Picnic Lunch at Jordan Pond

Enjoy a scenic picnic with pre-packed sandwiches at this picturesque spot.
Short drive to Jordan Pond.
USD 15 (sandwiches), 1.5 hours

2:30PM

Walk the Jordan Pond Path

Take a leisurely walk around the pond, soaking in stunning views.
Starting point is at the Jordan Pond parking area.
FREE, 2 hours

5:00PM

Dinner at The Sea Lady

Dine on fresh seafood options in a charming atmosphere close to the park.
Drive to Bar Harbor for dinner.
USD 60, 2 hours
View Hotel Availability

Day 9: Acadia National Park to Bar Harbor

Bar Harbor, ME

7:30AM

Breakfast at Bagels & Beans

Get your day started with delicious bagels and fresh coffee.
Drive back into the park for further exploration.
USD 12, 1 hour

9:00AM

Hike the Beehive Trail

Take an exhilarating morning hike on the Beehive for stunning views and some fun scrambling.
Drive to the Beehive Trailhead.
FREE (National Park Entry Fee: already paid), 3 hours

12:00PM

Lunch at Jordan Pond House

Enjoy popovers and soups in a lovely setting with lake views.
Head back to Jordan Pond for lunch.
USD 30, 1.5 hours

1:30PM

Visit Bass Harbor Head Light

Explore the iconic lighthouse and enjoy lovely photo opportunities.
Drive to Bass Harbor; about a 20-minute drive.
FREE, 1 hour

3:00PM

Explore Sand Beach

Spend some time relaxing or taking a stroll on the beautiful sandy beach.
Drive to Sand Beach within Acadia.
FREE (National Park Entry Fee: already paid), 2 hours

5:30PM

Dinner at Restaurant Flow

Indulge in a creative dining experience overlooking the water.
Drive to Bar Harbor for dinner.
USD 70, 2 hours
View Hotel Availability

Day 10: Return to Boston

Boston, MA

8:00AM

Breakfast at Paul Bakery

Savor French pastries and coffee before hitting the road back to Boston.
Timeline permits allowing for a leisurely drive back to Boston.
USD 20, 1 hour

9:00AM

Drive to Boston

Enjoy the scenic route as you make your way back to the bustling city.
Approximately a 4-hour drive.
FREE, 4 hours

1:00PM

Lunch at Legal Sea Foods

Experience a quintessential Bostonian meal at this renowned seafood restaurant.
After arriving in Boston, head to Legal Sea Foods.
USD 40, 1.5 hours

2:30PM

Visit the New England Aquarium

End your trip with a visit to the iconic aquarium, featuring diverse marine life.
Walk from the restaurant to the aquarium.
USD 30, 2 hours

5:00PM

Departure

Your unforgettable journey comes to an end as you reflect on the adventures experienced along the way.
Prepare for your departure.
FREE, N/A
View Hotel Availability