Cape Cod dune shack with winding path through sand dunes

Outer Cape Weekend 2025

Two nights in Provincetown

Saturday Itinerary

Morning

Early Departure
Leave Mashpee early for a full day on the Outer Cape
Hole in One, Eastham
Breakfast stop

Potential stops on the way out Saturday

Longnook Beach, Truro
Trails & scenic walk
Jenny Lind Tower
Historic Air Force base site, Truro
Truro Hills
Off Pamet Road
Pilgrim Springs Trails
Site of first fresh water found by Pilgrims

Pre-Dinner

Red Inn
Fancy drinks option
Old Colony Tap
Dive bar alternative

Evening

Ciro & Sal's — 6:15 PM
Classic Italian dinner reservation
Herring Cove Beach
Sunset viewing around 8:20 PM

Weekend Activities

Dune Shack Trail
Direct access from front door — long trek through dunes & historic shacks
Whale Watch
Trips departing daily at 10am, 12pm, 2pm, 4pm - Dolphin Fleet, MacMillan Wharf
High Head Beach, Truro
Remote beach near previous hotel - where we ran into the crazy hedgehog lady
Long Point Lighthouse
Hike the spit to P-town's tip
Race Point Loop
Dunes-to-beach trail, ideal for sunset
Blessing of the Fleet
Sunday 12-3 PM, MacMillan Pier
Art Galleries
Stroll Provincetown's galleries

Dining

Coffee
Kohi Coffee Company
Highly rated
Joe Coffee & Café
361 Coffee & Espresso Bar
Lunch
Far Land Provisions
Deli-style lunch & baked goods
East End Market
Fresh sandwiches, drinks & provisions
Additional Dinner Options
Nor'East Beer Garden
Walk-in, casual
The Red Inn
Upscale, drinks on deck
Kong Fu Dumplings
Quick takeout
The Squealing Pig
Pub grub, live music
The Patio American Grill
Outdoor American fare

Sunset Spots

Harbor Hotel Fire Pits
Bay front views near the Airbnb
Herring Cove Beach
West-facing sunset with easy parking

Ptown Memories

The Dune Trail
The Dune Trail
The Graffiti Ruin
The Graffiti Ruin
Click for location
Herring Cove Beach at Sunset
Herring Cove Beach at Sunset
Race Point Lighthouse
Race Point Lighthouse
Where we wished the long hike had ended
Happy Birthday, Leah!

I'm so excited to get away with you to the Outer Cape. I can't wait to get lost with you in the dunes — it reminds me of that epic walk we did, laughing and being thankful we're not responsible for the historic upkeep of one of those shacks (though… maybe one day! 😘).

I'm looking forward to long hikes, salty air, great meals and drinks, and wandering Commercial Street with you. Most of all, I can't wait to have you all to myself.

Love,
Mike