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North America · Open jaw · 14 NIGHTS

New England city and coastal parks

More time in the middle and at the far end

Submitted by Quiet City Walks
Use this itinerary

Route and nights

  1. Boston3 nights
  2. Portland, Maine6 nights
  3. Bar Harbor5 nights

Trip format: Open jaw · One hotel or guesthouse per overnight base

Tradeoff: The middle base gets time of its own. Book the last gateway separately and compare the total transport cost.

Compare: Drive or rail and road to compare

Trip stats

Trip days
15
Nights
14
Home Bases
3
Scheduled entries
90

Days by place

Portland, Maine
6
Bar Harbor
6
Boston
3

Hotels and other stays

Portland Harbor Hotel · Portland, Maine
6 nights
Bar Harbor Inn
5 nights
The Godfrey Hotel Boston
3 nights

Schedule by type

Meal
48
Activity
30
Lodging
6
Ground transport
5
Rail
1

Day-by-day agenda

Jump to Calendar View
Day 1 Boston
  1. to · Lodging Check in and drop your bags The Godfrey Hotel Boston
  2. to · Activity Take a short orientation walk near the hotel Boston Common

    Skip this block if you arrive later.

  3. to · Meal Have dinner near the hotel Downtown Crossing, Boston
The Godfrey Hotel BostonBoston
Day 2 Boston
  1. to · Meal Breakfast near the Greenway Rose Kennedy Greenway, Boston
  2. to · Activity Walk part of the Rose Kennedy Greenway Rose Kennedy Greenway, Boston

    Start near the North End and head toward the public market.

  3. to · Meal Compare lunch vendors at Boston Public Market Boston Public Market, Boston

    Check individual vendor hours and choose one meal to carry into the afternoon.

  4. to · Activity Walk the North End's side streets and parks North End, Boston
  5. to · Activity Follow the waterfront from Christopher Columbus Park Christopher Columbus Waterfront Park, Boston
  6. to · Meal Seafood dinner around the North End or waterfront Boston Waterfront, Boston

    Make a reservation if you have one specific restaurant in mind.

The Godfrey Hotel BostonBoston
Day 3 Boston
  1. to · Meal Breakfast in Back Bay Back Bay, Boston
  2. to · Activity Visit the Boston Public Library's Central Library Boston Public Library Central Library, Boston

    Check public hours before setting out. Start with the McKim Building and Bates Hall if open.

  3. to · Activity See the buildings around Copley Square Copley Square, Boston

    Explore the square and see the Trinity Church exterior from the public sidewalk.

  4. to · Meal Lunch around Newbury Street Newbury Street, Boston
  5. to · Activity Follow the Boston Literary District through Beacon Hill Beacon Hill, Boston

    Use publicly visible plaques and streetscapes and respect residential entrances.

  6. to · Activity Browse a bookstore near Boston Common Boston Common, Boston
  7. to · Meal Dinner around Downtown Crossing Downtown Crossing, Boston
The Godfrey Hotel BostonBoston
Day 4 Portland, Maine
  1. to · Meal Have breakfast before checking out Downtown Crossing, Boston
  2. to · Lodging Check out and allow time to reach your departure point The Godfrey Hotel Boston
  3. to · Rail Travel from Boston to Portland, Maine Boston North Station

    Check the current Downeaster timetable, departure from North Station, and onward ride from the Portland Transportation Center. Use the departure and arrival times from your booking.

  4. to · Meal Have lunch near your new base Old Port, Portland, Maine
  5. to · Lodging Drop bags and check in when the room is ready Portland Harbor Hotel
  6. to · Activity Take a short orientation walk if time allows Commercial Street, Portland, Maine
  7. to · Meal Have dinner near your new hotel if time allows Old Port, Portland, Maine
Portland Harbor HotelPortland, Maine
Day 5 Portland, Maine
  1. to · Meal Choose a bakery breakfast in the Old Port Old Port, Portland, Maine
  2. to · Activity Walk Commercial Street and compare the working and public waterfront Commercial Street, Portland, Maine

    Keep to public piers and watch for delivery traffic.

  3. to · Meal Choose seafood or another local lunch near the harbor Old Port, Portland, Maine

    Check current menus and queue times.

  4. to · Activity Take a short route toward the Eastern Promenade if the weather suits Eastern Promenade, Portland, Maine
  5. to · Meal Take a coffee or bakery break Portland, Maine
  6. to · Meal Dinner near the hotel Old Port, Portland, Maine
Portland Harbor HotelPortland, Maine
Day 6 Portland, Maine
  1. to · Meal Breakfast near the hotel Old Port, Portland, Maine
  2. to · Activity Walk the public Old Port streets and wharf approaches Commercial Street, Portland, Maine
  3. to · Activity Choose an open maritime history stop or walk to the waterfront terminals Portland Waterfront, Maine

    Check openings and stay clear of working docks.

  4. to · Meal Have lunch near the waterfront Old Port, Portland, Maine
  5. to · Activity Compare older commercial façades around Exchange and Fore streets Exchange Street, Portland, Maine
  6. to · Meal Take a café break in the Old Port Old Port, Portland, Maine
  7. to · Meal Have dinner near the hotel Old Port, Portland, Maine
Portland Harbor HotelPortland, Maine
Day 7 Portland, Maine
  1. to · Meal Have breakfast in the Old Port Old Port, Portland, Maine
  2. to · Ground transport Travel to Fort Williams Park in Cape Elizabeth Fort Williams Park, Cape Elizabeth

    Confirm parking, local transport, and park conditions before leaving.

  3. to · Activity See Portland Head Light from public park viewpoints Portland Head Light, Cape Elizabeth

    Stay on open paths and well back from exposed edges or surf.

  4. to · Meal Take a picnic lunch or return toward Portland for lunch Cape Elizabeth, Maine
  5. to · Activity Choose a shorter waterfront walk or sheltered Portland stop Eastern Promenade, Portland, Maine

    Use the shorter city fallback in rain or strong wind.

  6. to · Meal Take a seated break in the Old Port Old Port, Portland, Maine
  7. to · Meal Have dinner near the hotel Old Port, Portland, Maine
Portland Harbor HotelPortland, Maine
Day 8 Portland, Maine
  1. to · Meal Have a later breakfast near the hotel Old Port, Portland, Maine
  2. to · Activity Leave time for a stop you missed or want to revisit Old Port, Portland, Maine

    Use this window for a closure, bad weather, or a slower morning.

  3. to · Meal Have lunch near the hotel or your chosen stop Old Port, Portland, Maine
  4. to · Activity Take a short neighborhood walk if time allows Commercial Street, Portland, Maine

    Use the time for a break if the weather or the next transfer calls for a slower day.

  5. to · Meal Take a seated break Old Port, Portland, Maine
  6. to · Meal Have dinner near the hotel Old Port, Portland, Maine
Portland Harbor HotelPortland, Maine
Day 9 Portland, Maine
  1. to · Meal Have a later breakfast near the hotel Old Port, Portland, Maine
  2. to · Activity Leave time for a stop you missed or want to revisit Old Port, Portland, Maine

    Use this window for a closure, bad weather, or a slower morning.

  3. to · Meal Have lunch near the hotel or your chosen stop Old Port, Portland, Maine
  4. to · Activity Take a short neighborhood walk if time allows Commercial Street, Portland, Maine

    Use the time for a break if the weather or the next transfer calls for a slower day.

  5. to · Meal Take a seated break Old Port, Portland, Maine
  6. to · Meal Have dinner near the hotel Old Port, Portland, Maine
Portland Harbor HotelPortland, Maine
Day 10 Bar Harbor
  1. to · Meal Have breakfast before checking out Old Port, Portland, Maine
  2. to · Lodging Check out and allow time to reach your departure point Portland Harbor Hotel
  3. to · Ground transport Travel from Portland, Maine to Bar Harbor Portland, Maine

    Confirm how you will reach Bar Harbor. Driving and coach connections have different schedules. Keep room for lunch, road delays, and parking. Use the departure and arrival times from your booking.

  4. to · Lodging Check in after reaching the new base Bar Harbor Inn

    Keep dinner flexible if the transfer runs late.

  5. to · Meal Have dinner near your new hotel if time allows West Street, Bar Harbor
Bar Harbor InnBar Harbor
Day 11 Bar Harbor
  1. to · Meal Breakfast near the hotel West Street, Bar Harbor
  2. to · Activity Walk from the harbor through the central streets Agamont Park, Bar Harbor

    Compare the town’s shore-facing and commercial streets.

  3. to · Activity Choose a local history or culture stop if open Abbe Museum, Bar Harbor

    Check its current schedule and use downtown public streets as a fallback.

  4. to · Meal Have lunch near Main Street Main Street, Bar Harbor
  5. to · Activity Walk an open section of the Shore Path or choose a town loop Shore Path, Bar Harbor

    Check access and keep to the route that is open.

  6. to · Meal Take a seated break Bar Harbor, Maine
  7. to · Meal Dinner near the hotel West Street, Bar Harbor
Bar Harbor InnBar Harbor
Day 12 Bar Harbor
  1. to · Meal Have a bakery or café breakfast near Main Street Main Street, Bar Harbor
  2. to · Activity Check produce, snacks, and portable lunch options in town Bar Harbor, Maine

    Check seasonal hours and choose supplies that can be stored safely.

  3. to · Meal Have seafood for lunch or choose a picnic meal West Street, Bar Harbor

    Compare prices and portions before ordering. Keep a sheltered backup in poor weather.

  4. to · Activity Choose a public harbor walk or a sheltered town stop Agamont Park, Bar Harbor
  5. to · Meal Take an afternoon coffee break and plan the next morning Bar Harbor, Maine
  6. to · Meal Dinner near the waterfront hotel West Street, Bar Harbor
Bar Harbor InnBar Harbor
Day 13 Bar Harbor
  1. to · Meal Have breakfast before leaving Bar Harbor Bar Harbor, Maine
  2. to · Ground transport Check park access and travel to your first open stop Hulls Cove Visitor Center, Acadia National Park

    Check current roads, shuttle service, and any separate vehicle reservation for Cadillac Summit Road. Confirm before leaving town.

    Official information
  3. to · Activity Choose an open Acadia shore viewpoint or a short marked path Acadia National Park, Maine

    Use current park notices, keep clear of exposed rock and surf, and adjust for closures and weather.

  4. to · Meal Take a packed lunch or return to town for lunch Mount Desert Island, Maine
  5. to · Activity Choose one mountain or inland viewpoint if access fits Acadia National Park, Maine

    Use a confirmed reservation where required, or choose a lower inland route. Keep the afternoon open in poor visibility.

    Official information
  6. to · Ground transport Return to Bar Harbor and take a break Bar Harbor, Maine
  7. to · Meal Have dinner near the hotel West Street, Bar Harbor
Bar Harbor InnBar Harbor
Day 14 Bar Harbor
  1. to · Meal Have a later breakfast near the hotel West Street, Bar Harbor
  2. to · Activity Leave time for a stop you missed or want to revisit West Street, Bar Harbor

    Use this window for a closure, bad weather, or a slower morning.

  3. to · Meal Have lunch near the hotel or your chosen stop West Street, Bar Harbor
  4. to · Activity Take a short neighborhood walk if time allows Agamont Park, Bar Harbor

    Use the time for a break if the weather or the next transfer calls for a slower day.

  5. to · Meal Take a seated break West Street, Bar Harbor
  6. to · Meal Have dinner near the hotel West Street, Bar Harbor
Bar Harbor InnBar Harbor
Day 15 Bar Harbor
  1. to · Meal Have breakfast near the hotel West Street, Bar Harbor
  2. to · Activity Take an optional last walk Agamont Park, Bar Harbor

    Skip the walk if you have an early departure.

  3. to · Lodging Check out and collect luggage Bar Harbor Inn
  4. to · Ground transport Allow time for onward travel West Street, Bar Harbor

    Use the confirmed departure and pickup times from your booking.

Trip calendar

Itinerary map Print itinerary

Suggested schedule · All times are local. Check hours and availability for your dates.

  1. Day 1

    Boston

    America/New_York Open map for Boston
    1. to · Lodging Check in and drop your bags The Godfrey Hotel Boston
    2. to · Activity Take a short orientation walk near the hotel Boston Common

      Skip this block if you arrive later.

    3. to · Meal Have dinner near the hotel Downtown Crossing, Boston
    The Godfrey Hotel BostonBoston
  2. Day 2

    Boston

    America/New_York Open map for Boston
    1. to · Meal Breakfast near the Greenway Rose Kennedy Greenway, Boston
    2. to · Activity Walk part of the Rose Kennedy Greenway Rose Kennedy Greenway, Boston

      Start near the North End and head toward the public market.

    3. to · Meal Compare lunch vendors at Boston Public Market Boston Public Market, Boston

      Check individual vendor hours and choose one meal to carry into the afternoon.

    4. to · Activity Walk the North End's side streets and parks North End, Boston
    5. to · Activity Follow the waterfront from Christopher Columbus Park Christopher Columbus Waterfront Park, Boston
    6. to · Meal Seafood dinner around the North End or waterfront Boston Waterfront, Boston

      Make a reservation if you have one specific restaurant in mind.

    The Godfrey Hotel BostonBoston
  3. Day 3

    Boston

    America/New_York Open map for Boston
    1. to · Meal Breakfast in Back Bay Back Bay, Boston
    2. to · Activity Visit the Boston Public Library's Central Library Boston Public Library Central Library, Boston

      Check public hours before setting out. Start with the McKim Building and Bates Hall if open.

    3. to · Activity See the buildings around Copley Square Copley Square, Boston

      Explore the square and see the Trinity Church exterior from the public sidewalk.

    4. to · Meal Lunch around Newbury Street Newbury Street, Boston
    5. to · Activity Follow the Boston Literary District through Beacon Hill Beacon Hill, Boston

      Use publicly visible plaques and streetscapes and respect residential entrances.

    6. to · Activity Browse a bookstore near Boston Common Boston Common, Boston
    7. to · Meal Dinner around Downtown Crossing Downtown Crossing, Boston
    The Godfrey Hotel BostonBoston
  4. Day 4

    Portland, Maine

    America/New_York
    1. to · Meal Have breakfast before checking out Downtown Crossing, Boston
    2. to · Lodging Check out and allow time to reach your departure point The Godfrey Hotel Boston
    3. to · Rail Travel from Boston to Portland, Maine Boston North Station

      Check the current Downeaster timetable, departure from North Station, and onward ride from the Portland Transportation Center. Use the departure and arrival times from your booking.

    4. to · Meal Have lunch near your new base Old Port, Portland, Maine
    5. to · Lodging Drop bags and check in when the room is ready Portland Harbor Hotel
    6. to · Activity Take a short orientation walk if time allows Commercial Street, Portland, Maine
    7. to · Meal Have dinner near your new hotel if time allows Old Port, Portland, Maine
    Portland Harbor HotelPortland, Maine
  5. Day 5

    Portland, Maine

    America/New_York Open map for Portland, Maine
    1. to · Meal Choose a bakery breakfast in the Old Port Old Port, Portland, Maine
    2. to · Activity Walk Commercial Street and compare the working and public waterfront Commercial Street, Portland, Maine

      Keep to public piers and watch for delivery traffic.

    3. to · Meal Choose seafood or another local lunch near the harbor Old Port, Portland, Maine

      Check current menus and queue times.

    4. to · Activity Take a short route toward the Eastern Promenade if the weather suits Eastern Promenade, Portland, Maine
    5. to · Meal Take a coffee or bakery break Portland, Maine
    6. to · Meal Dinner near the hotel Old Port, Portland, Maine
    Portland Harbor HotelPortland, Maine
  6. Day 6

    Portland, Maine

    America/New_York Open map for Portland, Maine
    1. to · Meal Breakfast near the hotel Old Port, Portland, Maine
    2. to · Activity Walk the public Old Port streets and wharf approaches Commercial Street, Portland, Maine
    3. to · Activity Choose an open maritime history stop or walk to the waterfront terminals Portland Waterfront, Maine

      Check openings and stay clear of working docks.

    4. to · Meal Have lunch near the waterfront Old Port, Portland, Maine
    5. to · Activity Compare older commercial façades around Exchange and Fore streets Exchange Street, Portland, Maine
    6. to · Meal Take a café break in the Old Port Old Port, Portland, Maine
    7. to · Meal Have dinner near the hotel Old Port, Portland, Maine
    Portland Harbor HotelPortland, Maine
  7. Day 7

    Portland, Maine

    America/New_York Open map for Portland, Maine
    1. to · Meal Have breakfast in the Old Port Old Port, Portland, Maine
    2. to · Ground transport Travel to Fort Williams Park in Cape Elizabeth Fort Williams Park, Cape Elizabeth

      Confirm parking, local transport, and park conditions before leaving.

    3. to · Activity See Portland Head Light from public park viewpoints Portland Head Light, Cape Elizabeth

      Stay on open paths and well back from exposed edges or surf.

    4. to · Meal Take a picnic lunch or return toward Portland for lunch Cape Elizabeth, Maine
    5. to · Activity Choose a shorter waterfront walk or sheltered Portland stop Eastern Promenade, Portland, Maine

      Use the shorter city fallback in rain or strong wind.

    6. to · Meal Take a seated break in the Old Port Old Port, Portland, Maine
    7. to · Meal Have dinner near the hotel Old Port, Portland, Maine
    Portland Harbor HotelPortland, Maine
  8. Day 8

    Portland, Maine

    America/New_York Open map for Portland, Maine
    1. to · Meal Have a later breakfast near the hotel Old Port, Portland, Maine
    2. to · Activity Leave time for a stop you missed or want to revisit Old Port, Portland, Maine

      Use this window for a closure, bad weather, or a slower morning.

    3. to · Meal Have lunch near the hotel or your chosen stop Old Port, Portland, Maine
    4. to · Activity Take a short neighborhood walk if time allows Commercial Street, Portland, Maine

      Use the time for a break if the weather or the next transfer calls for a slower day.

    5. to · Meal Take a seated break Old Port, Portland, Maine
    6. to · Meal Have dinner near the hotel Old Port, Portland, Maine
    Portland Harbor HotelPortland, Maine
  9. Day 9

    Portland, Maine

    America/New_York Open map for Portland, Maine
    1. to · Meal Have a later breakfast near the hotel Old Port, Portland, Maine
    2. to · Activity Leave time for a stop you missed or want to revisit Old Port, Portland, Maine

      Use this window for a closure, bad weather, or a slower morning.

    3. to · Meal Have lunch near the hotel or your chosen stop Old Port, Portland, Maine
    4. to · Activity Take a short neighborhood walk if time allows Commercial Street, Portland, Maine

      Use the time for a break if the weather or the next transfer calls for a slower day.

    5. to · Meal Take a seated break Old Port, Portland, Maine
    6. to · Meal Have dinner near the hotel Old Port, Portland, Maine
    Portland Harbor HotelPortland, Maine
  10. Day 10

    Bar Harbor

    America/New_York
    1. to · Meal Have breakfast before checking out Old Port, Portland, Maine
    2. to · Lodging Check out and allow time to reach your departure point Portland Harbor Hotel
    3. to · Ground transport Travel from Portland, Maine to Bar Harbor Portland, Maine

      Confirm how you will reach Bar Harbor. Driving and coach connections have different schedules. Keep room for lunch, road delays, and parking. Use the departure and arrival times from your booking.

    4. to · Lodging Check in after reaching the new base Bar Harbor Inn

      Keep dinner flexible if the transfer runs late.

    5. to · Meal Have dinner near your new hotel if time allows West Street, Bar Harbor
    Bar Harbor InnBar Harbor
  11. Day 11

    Bar Harbor

    America/New_York Open map for Bar Harbor
    1. to · Meal Breakfast near the hotel West Street, Bar Harbor
    2. to · Activity Walk from the harbor through the central streets Agamont Park, Bar Harbor

      Compare the town’s shore-facing and commercial streets.

    3. to · Activity Choose a local history or culture stop if open Abbe Museum, Bar Harbor

      Check its current schedule and use downtown public streets as a fallback.

    4. to · Meal Have lunch near Main Street Main Street, Bar Harbor
    5. to · Activity Walk an open section of the Shore Path or choose a town loop Shore Path, Bar Harbor

      Check access and keep to the route that is open.

    6. to · Meal Take a seated break Bar Harbor, Maine
    7. to · Meal Dinner near the hotel West Street, Bar Harbor
    Bar Harbor InnBar Harbor
  12. Day 12

    Bar Harbor

    America/New_York Open map for Bar Harbor
    1. to · Meal Have a bakery or café breakfast near Main Street Main Street, Bar Harbor
    2. to · Activity Check produce, snacks, and portable lunch options in town Bar Harbor, Maine

      Check seasonal hours and choose supplies that can be stored safely.

    3. to · Meal Have seafood for lunch or choose a picnic meal West Street, Bar Harbor

      Compare prices and portions before ordering. Keep a sheltered backup in poor weather.

    4. to · Activity Choose a public harbor walk or a sheltered town stop Agamont Park, Bar Harbor
    5. to · Meal Take an afternoon coffee break and plan the next morning Bar Harbor, Maine
    6. to · Meal Dinner near the waterfront hotel West Street, Bar Harbor
    Bar Harbor InnBar Harbor
  13. Day 13

    Bar Harbor

    America/New_York Open map for Bar Harbor
    1. to · Meal Have breakfast before leaving Bar Harbor Bar Harbor, Maine
    2. to · Ground transport Check park access and travel to your first open stop Hulls Cove Visitor Center, Acadia National Park

      Check current roads, shuttle service, and any separate vehicle reservation for Cadillac Summit Road. Confirm before leaving town.

      Official information
    3. to · Activity Choose an open Acadia shore viewpoint or a short marked path Acadia National Park, Maine

      Use current park notices, keep clear of exposed rock and surf, and adjust for closures and weather.

    4. to · Meal Take a packed lunch or return to town for lunch Mount Desert Island, Maine
    5. to · Activity Choose one mountain or inland viewpoint if access fits Acadia National Park, Maine

      Use a confirmed reservation where required, or choose a lower inland route. Keep the afternoon open in poor visibility.

      Official information
    6. to · Ground transport Return to Bar Harbor and take a break Bar Harbor, Maine
    7. to · Meal Have dinner near the hotel West Street, Bar Harbor
    Bar Harbor InnBar Harbor
  14. Day 14

    Bar Harbor

    America/New_York Open map for Bar Harbor
    1. to · Meal Have a later breakfast near the hotel West Street, Bar Harbor
    2. to · Activity Leave time for a stop you missed or want to revisit West Street, Bar Harbor

      Use this window for a closure, bad weather, or a slower morning.

    3. to · Meal Have lunch near the hotel or your chosen stop West Street, Bar Harbor
    4. to · Activity Take a short neighborhood walk if time allows Agamont Park, Bar Harbor

      Use the time for a break if the weather or the next transfer calls for a slower day.

    5. to · Meal Take a seated break West Street, Bar Harbor
    6. to · Meal Have dinner near the hotel West Street, Bar Harbor
    Bar Harbor InnBar Harbor
  15. Day 15

    Bar Harbor

    America/New_York Open map for Bar Harbor
    1. to · Meal Have breakfast near the hotel West Street, Bar Harbor
    2. to · Activity Take an optional last walk Agamont Park, Bar Harbor

      Skip the walk if you have an early departure.

    3. to · Lodging Check out and collect luggage Bar Harbor Inn
    4. to · Ground transport Allow time for onward travel West Street, Bar Harbor

      Use the confirmed departure and pickup times from your booking.