Provincetown (Ptown), Massachusetts
“It is the Morocco of America, the New Orleans of the north.” ― Michael Cunningham, Land's End: A Walk in Provincetown


- More about your Oliver Guide: Rachel Wynne
- Trip type: Adult, Beach
- Activity level: moderate
- Ideal length of trip: Long weekend
to & from
During the summer there are regular Cape Air flights from Boston Logan and Provincetown Airport but better still, take the 90-minute ferry from Boston run by Bay State Cruise Company and Boston Harbor Cruises at the South Station.
Where to Stay
There are dozens of amazing small boutique hotels tucked away in Provincetown. I suggest checking out the location before booking- in town vs out of town. If you want quiet retreat do not stay in the heart of town.
Truro, Massachusetts
'The sea-shore is a sort of neutral ground, a most advantageous point from which to contemplate this world.' ― Henry David Thoreau, Cape Cod







- More about your Oliver Guide: Rachel Wynne
- Trip type: Family, Beach
- Activity level: easy
- Ideal length of trip: One or Two Weeks
to & from
Drive from Boston or during the summer there are regular Cape Air flights from Boston Logan and Provincetown Airport but better still, take the 90-minute ferry from Boston run by Bay State Cruise Company and Boston Harbor Cruises at the South Station. (Provincetown is 9 miles up the road).
Where to Stay
Rent for a week in Truro, but make *note* there is a difference between Truro and North Truro; staying in Truro you will not have to be on Rt 6 as much.
Wellfleet,Massachusetts
Swing down to Mac's Shack for fresh oysters and a Devil's Purse to wash it down.





- More about your Oliver Guide: Rachel Wynne
- Trip type: Family, Beach
- Activity level: moderate
- Ideal length of trip: One to Two weeks
to & from
During the summer there are regular Cape Air flights from Boston Logan and Provincetown Airport but better still, take the 90-minute ferry from Boston run by Bay State Cruise Company and Boston Harbor Cruises at the South Station. Provincetown to Wellfleet is a 20 minute drive. Drive from Boston.
Where to Stay
Rent a home. Wellfleet offers every accommodation from Cape Classic to 50s Modern.