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Ports of Maine by Rail

6 Days / 5 Nights (May be Customized) Freeport – Portland – Kennebunkport
The Ports of Maine is one of our most popular packages, giving travelers a unique look and feel at every stop. Shop in Freeport, explore in Portland and peruse in Kennebunkport. This great package can be done year-round with various seasonal offerings.


Day 1 – Depart for Freeport, Maine and enjoy a Wilbur’s of Maine chocolate activity or an LL Bean Discover Series activity (Overnight in Freeport)
Day 2 – Depart Freeport for Portland and take in an area Trolley Tour (Overnight in Portland)
Day 3 – Your choice of a Portland Foodie or Craft Beer Tour of Portland (Overnight in Portland)
Day 4 – Depart Portland for Kennebunkport with a scenic day trip down the coast. Let your driver guide show you all the sights from Portland to York. (Overnight in Kennebunkport)
Day 5 – Relax and peruse Dock Square or other sites in Kennebunkport. Enjoy dinner at Ports of Italy or Hurricane Restaurant. (Overnight in Kennebunkport)
Day 6 – Transfer back to Amtrak Station for your return trip home.

  • Round-trip Amtrak Downeaster
  • Amtrak station transfers throughout
  • Five-night hotel stay
  • Wilbur’s or LL Bean Discovery Series activity
  • Maine Coast Day Trip and Transfer
  • Portland Trolley Tour + choice of foodie or craft beer tour
  • Dinner in Freeport at Broad Arrow Tavern
  • $100 in dining certificates
  • All Taxes
Package Pricing
Departure City Boston
Adult Per Person $999-$1399
*Prices are per person double occupancy and based on availability. Package inclusions may not be available year-round therefore substitutions may be made. Prices based on midweek departures and subject to change.