My tour

Charming Cape Cod & Nantucket


cape cod black sheep

Rich with coastal New England charm, Cape Cod is at its most beautiful during our summer and autumn visits. You’ll cycle the car-free Cape Cod Rail Trail through coastal villages alongside cranberry bogs, lush marshlands and rolling sand dunes. With visits to Chatham, Nantucket, Provincetown and points in between, you'll discover why so many people are drawn to the region. Off the bike, you’ll stroll the beaches and nature trails, kayak and whale watch. All this and you’ll still have free time to relax and explore.

6 Tage
168 km / 104 mi
$ 3,395.- / € 3,465.-
  • Ride the Cape Cod Rail Trail from Chatham all the way to Wellfleet passing kettle ponds and quaint towns
  • Take a ferry to Nantucket and visit a whaling museum to learn the whaling past and Quaker roots of the famous island
  • Enjoy a whale watching boat trip with the chance to see majestic humpback whales
  • Kayak the local waters
  • Deposit for this tour is $750 pp



6 Tage
Leicht = Untrainiert, normale Kondition
Moderat = guter Radfahrer mit guter Kondition
Anspruchsvoll = sehr Erfahren, sehr gut trainiert
Tour führung
Gruppentour = Mit Führung und Support
Individuell = mit Beschreibung und Karten
60-80 km / 37-50 mi
168 km / 104 mi
DeLuxe = 4-5 Sterne Hotel oder Excellence B&B
Basic = 1-2 Sterne Hotel/Motel oder B&B
Camping = Zelt, Sporthalle oder Firmegelände
Luxus, Vollpension
Daily luggage transfers
01 Jun 2023 - 30 Sep 2023
Between June and September you can choose any date you like for a private tour for
a minimum of four participants in one booking

Price mention is a starting price, please ask for a quote.
Flughafen Anfang
Int. airport Boston
Flughafen Ende
Int. airport Boston

Preise *Please note the prices are subject to change depending availability*

Preis pro Person / please note the prices are subject to change depending availability
The tour price per person
$ 3,395.-
Zuschlag zur Einzel
Wenn Sie auf Reisen nur eine einzige zusätzliche Gebühr. With some group tours you can avoid a single supplement by sharing a room with another rider.
$ 995.-


Included / Not included

Day 1: Biking in Chatham

You’ll start your trip shuttling from Boston to your first night’s lodging in Chatham on Cape Cod. After a brief orientation, you’ll go for a short spin passing Chatham Lighthouse along the way and have the chance to hike on Morris Island. Tonight you’ll enjoy your first dinner together with the group at a local favorite restaurant, just a short walk from our lodging.
Meals included: Dinner. Biking: 8 miles, Optional Hiking – 1 mile

Day 2: Kayaking Pleasant Bay & Biking to Nickerson

Today you head into Orleans to enjoy a relaxing two-hour kayak on Nauset Marsh before lunch. After your paddle, you’ll head on to Brewster and Nickerson State Park on the blissfully car-free Cape Cod Rail Trail. If you’re looking for more mileage, you can pedal on to the town of Dennis before making your way back to Chatham. Tonight you’ll dine at the Impudent Oyster in downtown Chatham.
Breakfast, Lunch & Dinner. Distance: 19, 30, or 37 miles

Day 3: Ferry to Nantucket,

After breakfast you’ll make the 80-minute ferry crossing to the former whaling port of Nantucket. You can learn about the island’s history at the whaling museum as a docent explains the whaling past and Quaker roots of Nantucket. If you’d rather, take a bike ride to Siasconset at the easternmost part of the island, or you can stay in town and visit more historical sights along the cobblestoned streets of the town center. At the end of the day you’ll ferry back to the Cape then shuttle to Chatham, where you’ll enjoy a delicious clambake.
Meals included: Breakfast & Dinner. Optional Biking 20 miles

Day 4: Biking to Provincetown

This morning you bid farewell to Chatham and head down the Cape to Provincetown. You’ll return to the Cape Cod Rail Trail and take it to the end in Wellfleet before spinning along the country roads to the tip of the Cape. Along the way, you’ll be able to stop and tour a lighthouse and hike the surreal White Cedar Swamp Trail. As you travel through Wellfleet and Provincetown, the number of art galleries and unique shops you’ll pass are testimony to the thriving artist community on the Lower Cape.
Meals Included: Breakfast & Lunch. Distance: 17, 39, or 58 miles & Hiking – 2 miles

Day 5: Whale watching cruise

After yesterday, you’ve earned the right to relax a bit. You’ll enjoy a pleasant four-hour cruise on our whale watching vessel out to the plankton-rich feeding grounds where you may see minke, finback or maybe even the majestic white-fluked humpback whales. After your cruise, you’re free to enjoy lunch at the restaurant of your choice and explore, at your own pace, the many shops and sights of Commercial Street in Provincetown. You’ll enjoy a farewell dinner by the water as you recall the week’s events and stories.
Meals included: Breakfast & Dinner

Day 6: Biking the Province Lands

After yet another delicious breakfast, you’ll hop on your bike and head toward the very tip of the Cape. You’ll be able to stop at the Cape Cod National Seashore Visitor Center and learn more of the natural history of this coastal region. After our ride, you’ll have the chance to shower & pack up before we shuttle you back to Boston.
Meals included: Breakfast. Biking – 8 miles

* This is a general itinerary. Tour itineraries are subject to change based on the group, available accommodations and other unforeseen circumstances such as the weather, local conditions, government intervention, that may affect the quality of the trip and/or safety of the participants. Please view this itinerary as an outline as to what to expect on this tour.


Lodging in charming Inns
Meals included: 4x breakfast, 2 x lunch and 4 x dinner.
Ride-friendly snacks and beverages throughout each day
Hybrid or alloy road bike rental – carbon road bike or E-bike available for an upgrade fee
Whale watch tour, Kayak trip.
Services of professional trip leader(s)
Van support during the trip & porterage service
Tour operators T-shirt, wool socks, water bottles & luggage tags.

Not included:

Pre & post tour travel
Alcoholic beverages
Optional activities such as spa treatments
Gratuities for your guides

Map & Routes



cycle2 Hybrid or alloy road bike rental ( carbon road bike or
available for an upgrade fee)
Road Bikes: Alloy or carbon
While we often use other brands we prefer to use our fleet of Cannondale Synapse bikes. Our bikes come in Alloy and Carbon with a range of components always outfitted with quality Shimano parts.
Hybrid bikes: Flat handlebars
We have a fantastic fleet of Cannondale Quick 3 Hybrid Bikes. All bikes have flat handlebars, disc brakes, and a more relaxed fit. If you don’t feel you’re a “serious” bike rider this is often best option for you.
E-bikes: pedal assisted
Our fleet of Cannondale Quick Neo E-Bikes can’t be beat. With a Shimano pedal-assisted drive train this bike a great option for someone who feels they might have trouble keeping up or just wants to sweat less.


Cape Cod lodging
This website uses cookies to save your search preferences on this website, thereby improving your user experience. In addition, we place cookies for measuring and tracking visitor statistics. By clicking Accept, or continuing to use this site, you agree with this.