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The Pinehills · Plymouth · Massachusetts

Day Trips & Islands

Couples Escapes

Two people, one day, no agenda. Sunset spots, quiet harbors, long lunches.

While you’re planning — book an experience

Provincetown Ghost & History Walking TourCape Classics
After Dark

Provincetown Ghost & History Walking Tour

A lantern-lit 90-minute walk through 400-plus years of Provincetown legend and seafaring lore, including the town's historic cemeteries. A fun after-dark take on local history.

~$20See Pricing & Availability
Boston: Martha's Vineyard Day Trip with Optional Island TourCape Classics
Day Trip from Boston

Boston: Martha's Vineyard Day Trip with Optional Island Tour

Explore Martha's Vineyard on a day trip from Boston and see the cottages in Oak Bluffs, the quaint shops of Edgartown, and the Gay Head Cliffs. Upgrade your trip with a guided tour of the island.

$129 per adultSee Pricing & Availability
Albatross Deep Sea Fishing & Live Music CruisesBeach Day
Party Fishing + Live Music Sunsets · Sesuit Harbor

Albatross Deep Sea Fishing & Live Music Cruises

Head out from Sesuit Harbor in East Dennis for 4-hour bottom-fishing trips in Cape Cod Bay on the 52-foot Albatross. In summer, catch a live-music sunset cruise every last Wednesday in June through Labor Day — same boat, open bar, different vibe.

from $16See Pricing & Availability
Chatham Seal & Harbor CruiseLuxury Weekend
Resort-Run · Small Group

Chatham Seal & Harbor Cruise

A one-hour cruise along Chatham's coastline for close views of seals on the sandbars, passing the iconic Chatham Lighthouse and Fish Pier. A polished, resort-run outing.

VariesSee Pricing & Availability
Schooner Hindu — Historic Tall Ship SailingCape Classics
1925 Schooner · Day & Sunset Sails · MacMillan Pier

Schooner Hindu — Historic Tall Ship Sailing

Sail on a 1925 wooden gaff-rigged schooner — the longest-running sailing charter on Cape Cod. Day sails depart MacMillan Pier at 10am and 1pm (1.5 hours each); sunset sails run 2 hours. Dog and picnic-friendly; adults-only sunset sail is BYOB.

See Pricing & Availability
Martha’s Vineyard Self-Guided GPS Audio Walking TourCape Classics
Go at Your Own Pace

Martha’s Vineyard Self-Guided GPS Audio Walking Tour

A self-guided GPS audio walking tour. Booked on Viator.

from $10See Pricing & Availability
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Cape Cod Fall Day Trips: 7 One-Day Itineraries for the Cape's Best Season

Visiting Cape Cod

Cape Cod Fall Day Trips: 7 One-Day Itineraries for the Cape's Best Season

Seven one-day fall itineraries on Cape Cod — Route 6A antiques, Wellfleet oysters, Sandwich heritage, Chatham lighthouse, Provincetown galleries, and more.

Cape Cod Once School Starts: The Adults-Only September Playbook

Visiting Cape Cod

Cape Cod Once School Starts: The Adults-Only September Playbook

Walk-in restaurants, weekday golf, warm empty beaches, and spontaneous overnights — the September moves that only work once families leave Cape Cod after Labor Day.

The Cape Cod Wine Trail: Two Vineyards, One Great Day

Visiting Cape Cod

The Cape Cod Wine Trail: Two Vineyards, One Great Day

The complete guide to doing Cape Cod's two vineyards in one day — Cape Cod Winery in East Falmouth and Truro Vineyards in North Truro, with the route, timing, and where to eat between stops.

The Cape Cod Girls Weekend That Actually Delivers

Visiting Cape Cod

The Cape Cod Girls Weekend That Actually Delivers

2-day Cape Cod girls weekend guide built around Provincetown — Tea Dance at the Boatslip, Ross' Grill, Race Point Beach, and the bars and restaurants actually worth your time.

A Perfect Day in Provincetown, Cape Cod: Whales, Art, Commercial Street & Land's End

Visiting Cape Cod

A Perfect Day in Provincetown, Cape Cod: Whales, Art, Commercial Street & Land's End

Whale watching from MacMillan Pier, climbing Pilgrim Monument, gallery-hopping on Commercial Street, and catching sunset at Long Point — your perfect day at the tip of Cape Cod.

A Perfect Day in Harwich, Cape Cod: Cranberry Bogs, Nantucket Ferry & South Beach

Visiting Cape Cod

A Perfect Day in Harwich, Cape Cod: Cranberry Bogs, Nantucket Ferry & South Beach

Spend a perfect day in Harwich, Cape Cod — Wychmere Harbor at sunrise, Red River Beach, the Nantucket Fast Ferry, and a quiet evening in Harwich Port village.

Chatham vs. Falmouth vs. Brewster vs. Provincetown: Which Cape Cod Town Is Right for Your Wedding?

Cape Cod Celebrations

Chatham vs. Falmouth vs. Brewster vs. Provincetown: Which Cape Cod Town Is Right for Your Wedding?

Comparing Chatham, Falmouth, Brewster, and Provincetown for your Cape Cod wedding? Real venue prices, beach permit rules, and which town fits which couple.

A Perfect Day in Barnstable, Cape Cod: Historic Villages, Hyannis & the Harbor

Visiting Cape Cod

A Perfect Day in Barnstable, Cape Cod: Historic Villages, Hyannis & the Harbor

Spend a perfect day in Barnstable, Cape Cod — from the oldest library building in the US on Route 6A to JFK's harbor, Craigville Beach, and a sunset over Nantucket Sound.

The Sandwich Boardwalk: Salt Marsh, Blue Herons & Bay Sunsets

Wild Cape Cod

The Sandwich Boardwalk: Salt Marsh, Blue Herons & Bay Sunsets

Walk the historic Sandwich Boardwalk over Mill Creek salt marsh, spot blue herons and green crabs at low tide, and end at Town Neck Beach for a Bay sunset. One of the most peaceful spots on the Upper Cape.

A Perfect Day in Falmouth, Cape Cod: Beaches, Vineyard Ferry & Local Eats

Visiting Cape Cod

A Perfect Day in Falmouth, Cape Cod: Beaches, Vineyard Ferry & Local Eats

Spend a perfect day in Falmouth, Cape Cod: bike the Shining Sea Bikeway, swim at Old Silver Beach, catch a ferry to Martha's Vineyard, and watch the sun set over Vineyard Sound.

A Perfect Day in Yarmouth, Cape Cod: Sound Beaches, Bass River & Village Strolls

Visiting Cape Cod

A Perfect Day in Yarmouth, Cape Cod: Sound Beaches, Bass River & Village Strolls

Spend a perfect day in Yarmouth, Cape Cod — from the historic 6A village and Edward Gorey House to Bass River kayaking and warm Sound beaches.

A Perfect Day in Mashpee, Cape Cod: Wampanoag Heritage, Commons & South Cape Beach

Visiting Cape Cod

A Perfect Day in Mashpee, Cape Cod: Wampanoag Heritage, Commons & South Cape Beach

Spend a perfect day in Mashpee exploring Wampanoag history, South Cape Beach State Park, Mashpee Commons, and freshwater ponds — a local's honest guide.

A Perfect Day in Sandwich, Cape Cod: Heritage, Dunes & Hidden Gems

Visiting Cape Cod

A Perfect Day in Sandwich, Cape Cod: Heritage, Dunes & Hidden Gems

Sandwich is Cape Cod's oldest town and most underrated day — Glass Museum, Heritage Gardens, a boardwalk through salt marsh, and Bay-side sunsets few tourists find.

A Perfect Day in Chatham, Cape Cod: Lighthouse, Outer Beach & Main Street

Visiting Cape Cod

A Perfect Day in Chatham, Cape Cod: Lighthouse, Outer Beach & Main Street

Spend a perfect day in Chatham, Cape Cod: gray seals at the lighthouse, fresh fish off the pier, walking Main Street, and a Friday night band concert.

A Perfect Day in Eastham, Cape Cod: Fort Hill, Coast Guard Beach & the Outer Cape

Visiting Cape Cod

A Perfect Day in Eastham, Cape Cod: Fort Hill, Coast Guard Beach & the Outer Cape

Spend a perfect day in Eastham, MA — Fort Hill's marsh views, Coast Guard Beach, First Encounter's tidal flats, and the best of Cape Cod National Seashore.

A Perfect Day in Bourne, Cape Cod: Canal, Beaches & the Gateway Town

Visiting Cape Cod

A Perfect Day in Bourne, Cape Cod: Canal, Beaches & the Gateway Town

Bourne is more than a bridge crossing — it's canal bike paths, calm bay beaches, herring runs, and quiet villages that most Cape visitors drive straight past.

Cape Cod Day Trip from Boston: What to Do, Where to Go & How to Beat Traffic

Visiting Cape Cod

Cape Cod Day Trip from Boston: What to Do, Where to Go & How to Beat Traffic

Plan the perfect Cape Cod day trip from Boston with real traffic advice, two driving routes, the Cape Flyer train option, and itineraries for 4-hour, 6-hour, and full-day trips to Sandwich, Chatham, and Nauset Beach.

A Perfect Day Trip to Martha's Vineyard from Cape Cod

Visiting Cape Cod

A Perfect Day Trip to Martha's Vineyard from Cape Cod

Ferry from Woods Hole to Martha's Vineyard and back in a day. A local's itinerary covering Oak Bluffs, Edgartown, South Beach, and the Aquinnah Cliffs.

Rock Harbor, Orleans: Sunset Fishing Charters, Charter Boats & the Most Picturesque Harbor on the Mid-Cape

Cape Cod Pursuits

Rock Harbor, Orleans: Sunset Fishing Charters, Charter Boats & the Most Picturesque Harbor on the Mid-Cape

Rock Harbor in Orleans is Cape Cod's most photogenic bay-side harbor — fishing charters for striped bass, bluefish & fluke, plus legendary Bay sunsets.

Romantic Cape Cod Weekend Getaway

Cape Cod Celebrations

Romantic Cape Cod Weekend Getaway

Discover the most romantic Cape Cod weekend getaways for every season.

A Perfect Day Trip to Nantucket from Cape Cod

Visiting Cape Cod

A Perfect Day Trip to Nantucket from Cape Cod

Catch the Hy-Line ferry from Hyannis and spend a perfect day on Nantucket — cobblestone streets, whaling history, Atlantic surf, and rose-covered cottages in 'Sconset.

Best Sunset Beaches on Cape Cod: Where to Watch the Cape Most Beautiful Sunsets

Visiting Cape Cod

Best Sunset Beaches on Cape Cod: Where to Watch the Cape Most Beautiful Sunsets

Find the best sunset beaches on Cape Cod — from Herring Cove in Provincetown to Rock Harbor in Orleans. All bay-facing spots where the sky actually turns gold.

Day Trip to Marthas Vineyard from Cape Cod: Ferries, What to Do & How to Make It Worth It

Visiting Cape Cod

Day Trip to Marthas Vineyard from Cape Cod: Ferries, What to Do & How to Make It Worth It

Everything you need to plan a day trip to Marthas Vineyard from Cape Cod — which ferry to take, where to park, what to do in Edgartown, Oak Bluffs, and Aquinnah, and how to make the most of one full day on the island.

A Perfect Day in Buzzards Bay: Canal Bikes, Bay Breezes, and No Crowds

Visiting Cape Cod

A Perfect Day in Buzzards Bay: Canal Bikes, Bay Breezes, and No Crowds

Skip the tourist crowds and spend a perfect day in Buzzards Bay — canal bike path, fishing off the breakwater, and a real working-waterfront sunset on the bay.

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