Family Friendly Getaway Near Boston

Day 1: Travel to Portland

Portland, Maine

8:00AM

Depart from Boston

Embark on a scenic drive from Boston to Portland, Maine, a charming waterfront city known for its lobster shacks and vibrant arts scene.
Take I-95 north for about 2.5 hours until reaching Portland.
Gas and tolls, 3 hours

12:00PM

Check into Airbnb

Settle into a cozy 2-bedroom Airbnb near the waterfront, offering the perfect home base for your family getaway.
Follow instructions from the host to access the accommodation.
Accommodation cost, 1 hour

1:00PM

Lunch at DiMillo's On The Water

Enjoy fresh seafood with picturesque views at DiMillo's On The Water, a unique restaurant housed in a converted car ferry.
Navigate to 25 Long Wharf, where the restaurant is located.
$$, 1.5 hours

3:00PM

Explore Old Port District

Stroll through the cobblestone streets of Old Port, lined with boutique shops, galleries, and historic buildings, offering a charming atmosphere for a leisurely walk.
Walk from the waterfront to the Old Port area.
Free, 2 hours

6:00PM

Dinner at Street & Co.

Indulge in a delicious seafood dinner at Street & Co., a top-rated restaurant known for its fresh and flavorful dishes.
Make a reservation or walk in for dinner at 33 Wharf St.
$$$, 2 hours
View Hotel Availability

Day 2: Discover Acadia National Park

Bar Harbor, Maine

8:00AM

Drive to Acadia National Park

Embark on a scenic drive from Portland to Acadia National Park, known for its stunning coastal views, hiking trails, and wildlife.
Take I-95 North and follow signs to Acadia National Park.
Gas and park entrance fees, 3 hours

11:00AM

Hike the Great Head Trail

Embark on a family-friendly hike on the Great Head Trail, offering panoramic views of the rugged coastline and surrounding islands.
Follow signs to the trailhead and begin your hike.
Free, 2 hours

1:00PM

Picnic at Sand Beach

Enjoy a relaxing picnic on the sandy shores of Sand Beach, surrounded by the beauty of Acadia's coastline.
Drive to Sand Beach and find a spot for your picnic.
Picnic supplies, 1 hour

3:00PM

Visit Bar Harbor Village

Explore the quaint shops and eateries of Bar Harbor Village, a picturesque coastal town near Acadia National Park.
Drive back to Bar Harbor and park in the village.
Free, 2 hours

6:00PM

Dinner at Burning Tree

Enjoy a hearty dinner at Burning Tree, a cozy restaurant known for its seasonal New England cuisine and warm ambiance.
Head to 69 Otter Creek Dr, just outside of Bar Harbor.
$$, 2 hours
View Hotel Availability

Day 3: Relax at Ogunquit Beach

Ogunquit, Maine

9:00AM

Drive to Ogunquit Beach

Travel to the beautiful Ogunquit Beach, a family-friendly sandy shore perfect for relaxing and playing by the ocean.
Take I-95 south to Ogunquit.
Gas and parking fees, 1 hour

10:00AM

Beach Day

Spend the day building sandcastles, swimming in the ocean, and strolling along the scenic Marginal Way coastal walkway.
Set up on the beach and enjoy the day.
Beach gear, 4 hours

2:00PM

Lunch at Beach Plum Lobster Farm

Enjoy a delicious seafood lunch at Beach Plum Lobster Farm, offering a casual dining experience with ocean views.
Head to 16 Godfrey Ln for a laid-back meal.
$$, 1 hour

4:00PM

Relax at Accommodation

Take some time to relax and enjoy the comforts of your Airbnb accommodation, allowing the little one to nap and recharge.
Return to your Airbnb and unwind.
Free, 2 hours

6:00PM

Dinner at That Place in Ogunquit

Dine at That Place in Ogunquit, a family-friendly restaurant with a diverse menu to satisfy every palate.
Head to 331 Shore Rd for a pleasant dining experience.
$$, 1.5 hours
View Hotel Availability

Day 4: Return to Boston

Boston, Massachusetts

9:00AM

Drive back to Boston

Prepare for the journey back to Boston, reflecting on the wonderful memories made during your family-friendly getaway.
Take I-95 south to return to Boston.
Gas and tolls, 3 hours
View Hotel Availability