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Cape Cod Explorer Bike Tour

  • Cape Cod beach with path
  • Lighthouse in Chatham, Massachusetts
  • Lobster dinner on a plate
  • Cape Cod sunset with spit of land
  • Beach near lighthouse Cape Cod
  • Gingerbread house Martha's Vineyard
  • Harbor near Falmouth
  • Chatham from across the grasses on Cape Cod
  • Riding by pond on Cape Cod
DURATION
6 Day(s)
DAILY BIKING
17 to 48 miles
TRIP DIFFICULTY
1-Easier
STARTING FROM
$2600
SINGLES ADD FROM
$900

Trip Overview

This tour allows you to travel the length ... and to the very end ... of New England's treasure: Cape Cod! On the Cape, you follow beach roads and beautiful bike paths as you weave your way past salt marshes, cranberry bogs, bird sanctuaries, barrier beaches, and tidal flats filled with egrets, geese, and ducks. Explore the quintessential Cape communities of Chatham and Provincetown. You cycle breathtaking coastal routes with sweeping Atlantic vistas, passing coffee-colored sandbars, and pristine beaches protected as part of the Cape Cod National Seashore.

A scenic ferry ride takes you for a day trip to Martha’s Vineyard and elegant Edgartown, a colonial seaport with rows of handsome 18th-century homes. Don't miss cycling along a beautiful bike path to Oak Bluffs. Here you explore famous labyrinthine streets lined with fanciful rainbow-colored gingerbread cottages and visit the town’s antique Flying Horses Carousel.

Don't miss this exciting exploration of Cape Cod, Massachusetts, by bike.

Itinerary

From start to finish, check out the route.

DAY 1 - Welcome!
Distance: 17 miles | Terrain: Easier | Inn on the Square
On Sunday, you are welcomed to Cape Cod with a stay at Inn on the Square in Falmouth at 2 p.m. The inn is nestled among the wonderful shops, galleries and restaurants of this village. After introductions, you cycle a section of the Shining Sea Bikeway and weave your way past salt marshes, cranberry bogs, bird sanctuaries, beaches, and harbors. You follow some quiet roads to the shores of Vineyard Sound in Falmouth. Then pedal Surf Drive and Beach Road past Little Pond and Inner Harbor — where hundreds of yachts and sailboats sway at anchor. Skirt past Oyster Pond and pause here to breathe in the sea air or watch osprey and herons. In the evening, the group gathers for a short stroll to your choice of the area’s fine restaurants followed by a friendly get-together in the common area of the inn.
DAY 2 - Martha's Vineyard Day Trip
Distance: 35 miles | Terrain: Easier | Inn on the Square
Ride on the Shining Sea bike path from Falmouth to Woods Hole, then take the ferry to Martha's Vineyard. Do a scenic 25-mile loop or more, with a lunch stop in Edgartown. You have the option to do an extra 10 miles to visit Chappaquiddick Island and visit Vineyard Haven. Return by ferry and bike path to Falmouth.
DAY 3 - Chatham
Distance: 25 miles | Terrain: Easier | The Captain's House
Shuttle from Falmouth to the start of the Cape Cod Rail Trail in Yarmouth, then ride the trail through the quaint town of Brewster into Chatham. Explore Chatham and many back roads and beaches. Chatham is famous for the Monomoy National Wildlife Refuge and scenic lighthouses. Unpack and stay two nights at a small, beautifully landscaped inn.
DAY 4 - Chatham
Distance: 20 miles | Terrain: Easier | The Captain's House
You have a choice today! Bike, go to the beach, or enjoy strolling the town of Chatham. There is an optional 20+ mile route … or take a day off the bike and explore. There are several interesting museums, lighthouses and even the Chatham Pier Fish Market.
DAY 5 - Provincetown
Distance: 48 miles | Terrain: Easier | Surfside Hotel & Suites
Bike the Cape Cod Rail Trail and other trails and back roads to the iconic town at the end of the cape! Provincetown has loads of attractions — including beaches, art galleries, restaurants and enticing shops. If you have extra time, check out the Shark Center.
DAY 6 - Final day
Distance: 16 miles | Terrain: Easier
Bike a loop around and through lovely Provincetown in the morning before a final shower, hotel checkout, and a shuttle back to Falmouth, to say farewell.

Map

Dates & Pricing

Prices are per person based on double occupancy (2 people in one room). Single supplement for private room is listed at the top of this page. A deposit of $500 holds your reservation for most tours. For weekend tours, the deposit is $300.

Start End Cost Availability
Sep 24, 2023 Sep 29, 2023 $2600.00 Private Sold Out Sold Out
Jun 23, 2024 Jun 28, 2024 $3195.00 Available! Reserve Reserve
Sep 22, 2024 Sep 27, 2024 $3195.00 Available! Reserve Reserve
Oct 06, 2024 Oct 11, 2024 $3195.00 Available! Reserve Reserve

What’s Included

5 nights' lodging, 5 breakfasts, 1 lunch, 3 dinners. Round-trip ferry to Martha’s Vineyard.We also include detailed maps and itineraries, experienced guides, full van support — plus use of a bike and helmet. Airfare and car parking at ferry not included.

Dates & Pricing

Prices are per person based on double occupancy (2 people in one room). Single supplement for private room is listed at the top of this page. A deposit of $500 holds your reservation for most tours. For weekend tours, the deposit is $300.

Start: Sep 24, 2023
End: Sep 29, 2023
Cost: $2600.00
Availability: Private
Sold Out
Start: Jun 23, 2024
End: Jun 28, 2024
Cost: $3195.00
Availability: Available!
Reserve
Start: Sep 22, 2024
End: Sep 27, 2024
Cost: $3195.00
Availability: Available!
Reserve
Start: Oct 06, 2024
End: Oct 11, 2024
Cost: $3195.00
Availability: Available!
Reserve

What’s Included

5 nights' lodging, 5 breakfasts, 1 lunch, 3 dinners. Round-trip ferry to Martha’s Vineyard.We also include detailed maps and itineraries, experienced guides, full van support — plus use of a bike and helmet. Airfare and car parking at ferry not included.

Inns

Where you stay along the way.

Inn on the Square
The Inn on the Square showcases historic Cape Cod charm. From the hotel's nautical weathervanes to its rustic stone walls, this boutique property blends into the streetscape of the quaint maritime village. From the downtown location in Falmouth, nestled among cafes, galleries, and boutique shops, you're minutes from Cape Cod's beaches and three blocks from the ferries to Martha's Vineyard. After a day exploring the area, take a refreshing dip in their skylit pool, or grab lunch at the restaurant. Here, boutique charm meets coastal luxury.
The Captain's House
A distinctive Cape Cod bed and breakfast, the Captain’s House Inn offers luxury accommodations that will be sure to make your stay relaxing and memorable. The inn is regarded by many respected lodging reviewers as perhaps “the Cape’s finest small inn.” This Four-Diamond sea captain’s estate on two acres in Chatham, Massachusetts is the perfect choice for a romantic getaway or a peaceful retreat from the workaday world.
Surfside Hotel & Suites
Nestled along beautiful Cape Cod Bay, our beachside hotel offers you sweeping bay sightlines and proximity to the best of Provincetown's activities. Unwind in our seaside rooms, jacuzzi suites, or our apartment with expansive views of Cape Cod Bay.

Gallery

Images from this tour. Click each to see it larger.

Cape Cod beach with path Lighthouse in Chatham, Massachusetts Lobster dinner on a plate Cape Cod sunset with spit of land Beach near lighthouse Cape Cod Gingerbread house Martha's Vineyard Harbor near Falmouth Chatham from across the grasses on Cape Cod Riding by pond on Cape Cod