29 days in New England Itinerary

29 days in New England Itinerary

Created using Inspirock New England route builder

Make it your trip
Fly to Boston, Ferry to New Shoreham
1
New Shoreham, Block Island
— 2 nights
Ferry to Montauk, Ferry to Martha's Vineyard
2
Oak Bluffs, Martha's Vineyard
— 2 nights
Ferry
3
Nantucket
— 3 nights
Ferry to Ocean Street Terminal, Hyannis, MA, Taxi to Eastham
4
Eastham
— 4 nights
Drive
5
Boston
— 5 nights
Drive
6
Lincoln
— 4 nights
Drive
7
North Conway
— 3 nights
Drive
8
Bar Harbor, Mount Desert Island
— 5 nights
Fly

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New Shoreham, Block Island

— 2 nights
New Shoreham is a town in Washington County, Rhode Island, United States. Kick off your visit on the 5th (Sun): experience rural life at Abrams Animal Farm, take in the waterfront at Mansion Beach, then visit a coastal fixture at North Lighthouse, and finally relax in the rural setting at 1661 Farm and Gardens. Keep things going the next day: stroll through Fred Benson Town Beach, then take in the dramatic natural features at Mohegan Bluffs, then visit a coastal fixture at South East Lighthouse, and finally view the masterpieces at Spring Street Gallery.

For where to stay, reviews, and other tourist information, go to the New Shoreham online route planner.

Phoenix to New Shoreham is an approximately 12-hour combination of flight and ferry. You can also do a combination of bus and ferry; or do a combination of bus, train, and ferry. The time zone difference when traveling from Phoenix to New Shoreham is 2 hours. While traveling from Phoenix, expect cooler days and slightly colder nights in New Shoreham, ranging from highs of 71°F to lows of 61°F. Wrap up your sightseeing on the 6th (Mon) early enough to travel to Oak Bluffs.

Things to do in New Shoreham

Outdoors · Beaches · Parks · Trails

Side Trip

Oak Bluffs, Martha's Vineyard

— 2 nights
Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. On the 7th (Tue), stroll through Inkwell Beach, make a trip to Flying Horses Carousel, then admire the striking features of Trinity Park Tabernacle, and finally take a stroll through Martha's Vineyard Camp meeting Association (MVCMA). On the 8th (Wed), you'll have a packed day of sightseeing: tour the pleasant surroundings at Menemsha Public Beach, then take in the dramatic natural features at Aquinnah Cliffs, and then enjoy the sand and surf at Katama Beach/ South Beach.

For where to stay, maps, and other tourist information, go to the Oak Bluffs travel planner.

You can ride a ferry from New Shoreham to Oak Bluffs in 5 hours. Traveling from New Shoreham in September, you can expect nighttime temperatures to be slightly colder in Oak Bluffs, with lows of 54°F. Wrap up your sightseeing on the 8th (Wed) to allow time to ride a ferry to Nantucket.

Things to do in Oak Bluffs

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Nantucket

— 3 nights
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Step off the beaten path and head to Madaket Beach and Brant Point Lighthouse. Attractions like Siasconset Beach and Jetties Beach make great kid-friendly stops. And it doesn't end there: enjoy the sea views from Sankaty Head Lighthouse, examine the collection at Whaling Museum, tour the pleasant surroundings at Surfside Beach, and get engrossed in the history at Egan Maritime's Nantucket Shipwreck & Lifesaving Museum.

To find ratings, traveler tips, and more tourist information, go to the Nantucket trip planner.

Ride a ferry from Oak Bluffs to Nantucket in 2 hours. September in Nantucket sees daily highs of 71°F and lows of 59°F at night. Finish your sightseeing early on the 11th (Sat) to allow enough time to travel to Eastham.

Things to do in Nantucket

Outdoors · Beaches · Parks · Historic Sites

Eastham

— 4 nights
Eastham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. Kids will enjoy Skaket Beach and Coast Guard Beach. You'll discover tucked-away gems like Nauset Light Beach and Nauset Beach. The adventure continues: stroll through Cape Cod National Seashore, enjoy the sea views from Chatham Lighthouse, take in the views from Uncle Tim's Bridge, and examine the collection at Chatham Railroad Museum.

To see traveler tips, photos, reviews, and more tourist information, you can read our Eastham vacation planner.

Traveling by combination of ferry and taxi from Nantucket to Eastham takes 2.5 hours. Alternatively, you can do a combination of ferry and bus. In September, daytime highs in Eastham are 72°F, while nighttime lows are 59°F. Finish your sightseeing early on the 15th (Wed) to allow enough time to drive to Boston.

Things to do in Eastham

Outdoors · Beaches · Parks · Historic Sites

Side Trips

Boston

— 5 nights

Beantown

Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Explore hidden gems such as Long Sands Beach and St. Ann's Episcopal Church. Bring the kids along to Whydah Pirate Museum and Museum of Fine Arts. Venture out of the city with trips to Wells Beach (in Wells), Sandwich (Sandwich Glass Museum & Heritage Museums & Gardens) and Marginal Way Walkway (in Ogunquit). There's lots more to do: stroll around Boston Public Garden, stop by North End, steep yourself in history at Granary Burying Ground, and appreciate the history behind New England Holocaust Memorial.

For more things to do, reviews, where to stay, and tourist information, refer to the Boston road trip planning tool.

You can drive from Eastham to Boston in 2 hours. Expect a daytime high around 75°F in September, and nighttime lows around 59°F. Finish up your sightseeing early on the 20th (Mon) so you can go by car to Lincoln.

Things to do in Boston

Museums · Historic Sites · Parks · Outdoors

Side Trips

Lincoln

— 4 nights
Stretching through the White Mountain National Forest, Lincoln welcomes hikers along the Appalachian Trail.
Kids will enjoy Clark's Trading Post and Polar Caves Park. You'll discover tucked-away gems like Lost River Gorge and Boulder Caves and Quechee Gorge. Explore the numerous day-trip ideas around Lincoln: Woodstock (Taftsville Covered Bridge & Sugarbush Farm). Next up on the itinerary: immerse yourself in nature at Franconia Notch State Park, get interesting insight from Tours, take in the dramatic natural features at The Basin at Franconia Notch State Park, and take in the awesome beauty at Cannon Mountain.

To find ratings, traveler tips, maps, and more tourist information, you can read our Lincoln travel itinerary planner.

You can drive from Boston to Lincoln in 2.5 hours. Alternatively, you can take a bus. Traveling from Boston in September, you can expect nighttime temperatures to be slightly colder in Lincoln, with lows of 48°F. Finish your sightseeing early on the 24th (Fri) to allow enough time to drive to North Conway.

Things to do in Lincoln

Parks · Nature · Outdoors · Wildlife

Side Trips

North Conway

— 3 nights
North Conway combines colonial New England architecture with outlet shops selling goods from some of the world's most recognizable brands, all set amid the scenery of the White Mountains.
Explore hidden gems such as Story Land and White Mountain National Forest. Attractions like Mount Washington Observatory Weather Discovery Center and Glen Ellis Falls make great kid-friendly stops. Step out of North Conway to go to Moultonborough and see Castle in the Clouds, which is approximately 52 minutes away. And it doesn't end there: take in the dramatic natural features at Cathedral Ledge, explore and take pictures at Kancamagus Highway, shop like a local with The Cassidy Gallery, and look for gifts at Zeb's General Store.

To see more things to do, reviews, and more tourist information, read North Conway online trip itinerary planner.

You can drive from Lincoln to North Conway in 1.5 hours. Traveling from Lincoln in September, plan for a bit warmer nights in North Conway, with lows around 54°F. Cap off your sightseeing on the 27th (Mon) early enough to go by car to Bar Harbor.

Things to do in North Conway

Nature · Parks · Shopping · Outdoors

Side Trips

Bar Harbor, Mount Desert Island

— 5 nights
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. You'll discover tucked-away gems like Frenchman Bay and Village Green. You'll visit kid-friendly attractions like Schoodic Peninsula and Pirate's Cove Miniature Golf. Take a break from Bar Harbor with a short trip to Schoodic Point in Winter Harbor, about 46 minutes away. The adventure continues: stroll around Agamont Park, tour the pleasant surroundings at Sand Beach, trek along Ocean Path, and explore the landscape on two wheels at Carriage Roads.

For maps, more things to do, traveler tips, and other tourist information, use the Bar Harbor day trip website.

Drive from North Conway to Bar Harbor in 4.5 hours. Alternatively, you can do a combination of car and bus; or do a combination of bus and flight. September in Bar Harbor sees daily highs of 70°F and lows of 52°F at night. Finish up your sightseeing early on the 2nd (Sat) so you can travel back home.

Things to do in Bar Harbor

Parks · Outdoors · Trails · Nature

Side Trips