Spend several days in this charming town in the heart of Cape Cod

Cape Cod Bicycle Tour, Massachusetts

6 days
Site savings
$3,959 USD

One of the largest barrier “islands” in the world, the easternmost arm of Massachusetts is part of a thin line of archipelagic islands formed by retreating glaciers. Artists have long been drawn to the Cape’s landscapes and soft light. Unspoiled sand dunes line beaches for nearly 30 miles along the Cape Cod National Seashore. Charming villages feature historic homes and picturesque harbors that still host working fishing fleets. Country roads and the Cape Cod Rail Trail invite exploration by bicycle. Experience one of New England’s most beloved seacoast vacation destinations on this 6 day Cape Cod bike trip.

  • Category
    Road Cycling
  • Type
    Fully Guided
  • Duration
    6 days
  • Culture Level
  • Skill Level
    2 - Novice
  • Activity Level
    2 - Moderate
  • Elevation
    2 - Moderate
  • Terrain
  • Distance
    110 miles
  • Avg. Daily Distance
    21.7 miles
Best Price Guarantee
No booking or payment fees
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The trip begins and ends in Boston, one of the nation’s most historic cities. Quincy Market, Faneuil Hall, Boston Public Gardens, and the charming North End – Boston’s Italian neighborhood – are all within an easy walking distance. Visit Cape Cod in spring or fall when the weather is lovely and summer crowds absent for an utterly tranquil visit. Pedal along quiet lanes and back roads, through seaside villages whose grey-shingled cottages are framed by white picket fences. Ride along the Cape Cod Rail Trail, whose paved surface and gentle terrain are ideal for leisure cyclists.

This tour encompasses the best of Cape Cod’s unique landscapes and seaside character. A diversity of scenery, cycling routes, and distinctive accommodations allow you to experience “The Cape” in comfort and style. Explore the lovely town of Chatham—one of New England’s hidden gems—where you will enjoy a three-night stay at the renowned Chatham Bars Inn. Venture off the beaten path to visit lighthouses and cranberry bogs, explore seaside villages, and bask in the expanse of the undeveloped Atlantic-facing beaches that make up the Cape Cod National Seashore. Follow a bike path through the incredible dunes of Provincetown, at the outermost point of the Cape, and visit the Old Harbor Lifesaving Museum. Your accommodation in the quiet West End is perched high above town and offer spectacular views over the harbor. The location provides easy walking access to Provincetown’s narrow lanes, harborside shops and galleries. Golfers can play a round of golf on the well-groomed fairways and bright greens of nearby Cape Cod National. Return by passenger ferry from Provincetown to Boston.

**Roar Adventures customers that book a Sojourn tour will get a 5% discount if you book another Sojourn tour with us. Note that this does not apply for multiple bookings for the same departure date.

Tour inclusions and exclusions at a glance:

What's included?
Items included in the cost of the tour

  • Accommodation
  • Support of experienced tour leaders from start to finish
  • Full van support for a variety of route options
  • Custom tour jersey and water bottles – both yours to keep
  • All gratuities at hotels and restaurants
  • Baggage transfers and porterage
  • Daily route directions, maps, and a downloadable GPS
  • 5% Past Traveler Discount to use on your next Sojourn Tour
  • Snacks and drinks on the way
  • Private boat cruise on Pleasant Bay
  • Wine sampling at Truro Vineyards
  • Lighthouse and cranberry bog tours
  • Welcome reception
  • Meals (as indicated in itinerary)
  • Free bike rental is included in the price of this tour (upgrade options are available - please see below).
What's not included?
Items not included in the cost of the tour

  • International / Domestic flights
  • Visas
  • Personal travel insurance

Tour options and upgrades:

5 equipment options available
1 tour add-on available