The Breakers
Boston · Portland · Newport · 7 days itinerary

Boston, Portland and Newport in 7 Days

Photo: User:Itub, CC BY-SA 3.0 via Wikimedia Commons

This 7-day trip covers historic sites in Boston, coastal sights in Portland, Maine, and mansions in Newport. The Boston days focus on Boston Common, the Freedom Trail, Harvard, the Arnold Arboretum and the North End. The route then drives north to Portland for lighthouses and Casco Bay islands, and ends with two days in Newport for the Cliff Walk and the mansions.

7 daysBostonPortlandNewportBy travli· Checked by the travli team, September 2026

Day by day

Day 1

Boston Common and the Freedom Trail

  1. 9:00BostonWalk
  2. 10:00BostonWalk
  3. 11:00Freedom TrailBostonWalk
  4. 14:00BostonSight
Day 2

Arnold Arboretum and Harvard

  1. 9:30BostonWalk
  2. 14:00BostonWalk
  3. 16:00BostonSight
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Day 3

The North End, then Portland

  1. 9:30BostonSight
  2. 10:30BostonSight
  3. 14:00Drive to PortlandBostonTransfer
  4. 18:00PortlandWalk
Day 4

Portland's lighthouses

  1. 9:30PortlandSight
  2. 12:00PortlandWalk
  3. 15:00PortlandWalk
Day 5

Casco Bay, then Newport

  1. 9:00Casco Bay islands ferryPortlandSight
  2. 13:00PortlandSight
  3. 15:00Drive to NewportPortlandTransfer
Day 6

Newport's mansions

  1. 9:30NewportSight
  2. 12:30NewportWalk
  3. 15:00NewportSight
Day 7

Rosecliff and Fort Adams

  1. 10:00NewportSight
  2. 13:00NewportSight
  3. 16:00NewportSight
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Questions about this trip

Is 3 days enough for Boston?

Three days covers the main historic sites and gardens. Walk or use the subway to move between locations.

Do I need to book The Breakers ahead?

Yes, buy tickets online before arrival. Online tickets save time at the entrance on busy days.

How long is the drive from Boston to Portland?

The drive takes two hours on I-95. Rent a car in Boston for the full route to Newport.

Do I need reservations for the Casco Bay ferry?

No advance booking is required for Casco Bay Lines. Buy tickets at the Portland terminal; fares vary by island.

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