Senior Cycling

Tour Schedule

Cape Cod – 2023

Cape Cod 2023 #1

September 10-16, 2023 | $2,650
This form stopped accepting submissions on September 10, 2023 3:00 pm EDT.

Cape Cod 2023 #2

October 1 - 7, 2023 | $2,650
This form stopped accepting submissions on October 1, 2023 3:00 pm EDT.

Sea, sand, sun-dappled scrub pine forests, and ferry rides fill our days on the Cape and its nearby islands. We visit the ports in Hyannis, Provincetown and Falmouth and ferry to Martha’s Vineyard. Our trip to Martha’s Vineyard includes time to bike some of the island’s trails, beaches, or visit the Gingerbread Houses in Oak Bluffs.

On the Cape we bike the Cape Cod Rail Trail between West Yarmouth and Wellfleet, exploring the Cape Cod National Seashore. The next day we wind through quaint Wellfleet and Truro, lunch at the Truro Vineyard and then do some optional road riding to reach the tip of the Cape at Provincetown. While in P’town some riders elect an optional Dunes ride to marvel at the extensive dunes on the ocean side of the area. A climb to the top of the Pilgrim Monument puts all of P’town, Massachusetts Bay and the Atlantic Ocean at your feet. Back at the western end of the Cape we ride the canal bikeway along the Cape Cod Canal. The canal connects Massachusetts Bay on the east with Buzzards Bay on the west. We combine the Canal trail with a ride on the Shining Sea Bikeway that runs between North Falmouth at its northern end and the village of Woods Hole its southern end.

Our lodging on this trip includes a variety of inns and motels. Our locations in Provincetown and Hyannis put us right in the heart of the action. There are diners and pubs and fine dining restaurants sprinkled throughout our travels.

There is something special about this seaside New England landscape with its harbors and windswept woods. The gray shingled houses and the bright white clapboard ones are complimented by the intense colored flowers that only happen in these northern climes. It’s the perfect place to be when time is on the outside edges of the summer months.

Approximately 100 miles of cycling in 6 days.

Tour Leaders: Owner and Massachusetts native Ned Raynolds will lead this tour, along with his very good friend (and also Massachusetts native) Mike Hicks.


  • Overnight accommodations for SIX (6) nights
  • Area-knowledgable and cycling expert tour guides
  • 4 breakfasts, 2 lunches, 3 dinners
  • Gratuities for Meals & Accomodations
  • In-ride drinks & snacks
  • Van support
  • Detailed maps and itineraries
  • Round trip ferry to Martha’s Vineyard


  • Day 1 - Sunday

    We'll meet at 5:00 pm at our hotel, the Hampton Inn West Yarmouth, to introduce ourselves and discuss what the week of cycling and sightseeing will look like. Then we'll hop in the van to go to dinner at restaurant near Hyannis Harbor.

  • Day 2 - Monday

    30 miles – We'll bike the Cape Cod Rail trail and stop for lunch and some exploring in Orleans, a very charming town bisected by the trail. After getting back on our bikes we'll soon arrive at the National Park Service Headquarters of the Cape Cod National Seashore, and whomever wants to can take the bike path extension right to Coast Guard Beach. Then we'll head on up the trail to our accomodations for the night, the Southfleet Motor Inn in South Wellfleet. After relaxing and showering, we'll enjoy a sunset dinner at The Pearl overlooking Wellfleet Harbor.

  • Day 3 - Tuesday

    We'll continue up the last stretch of the Cape Cod Rail Trail to its terminus, then head out to the ocean bluffs along quiet country roads. After enjoying views of the Atlantic from the unspoiled town beaches, we'll wind our way back west and into Wellfleet Town Center, where we'll stop for bit. Then we'll continue along more quiet country roads along salt marshes to Truro Center, before arriving at Truro Vineyards for lunch and some wine tasting, if you wish. After lunch folks can continue riding north to Provincetown along Rt. 6A, which features some moderate hills early on and fairly light traffic). We'll check into our waterfront accommodations to enjoy the rest of the afternoon and evening in Provincetown.

  • Day 4 - Wednesday

    On your own / activity day in Provincetown. Tour leaders will lead an optional morning ride to the dunes of Province Lands, where a 5.45-mile loop trail loops around the Province Lands, passing through pine forests, sandy dunes, and low-lying cranberry bogs with spurs to both Herring Cove and Race Point beaches. Riders will finish by coming back into Provincetown from the west end along Commercial St.
    For the remainder of the day, a whale watching tour to Stellwagen Bank National Marine Sanctuary is just one of many options; ascending the 252 ft, 116 step Pilgrim Monument, browsing art galleries and people watching, or a sunset sail on the bay are others. The day is yours!

  • Day 5 - Thursday

    Up to 31 miles – We van the length of the Cape, from Provincetown to Sandwich to bike the Bourne Canal Bike Path. After lunch at a local seafood restaurant, there is a bit of road riding and then we finish the day on the Shining Sea Bikeway, then on to our night’s lodging in Falmouth. Tonight we'll enjoy a pizza party together in our relaxed Inn.

  • Day 6 - Friday

    All-day adventure to Martha's Vineyard. You'll bring your bike as we ferry to Martha’s Vineyard. Later in the day we will ferry back to Falmouth for our last night together. This iconic island is one of the most scenic places we visit on any tour!

  • Day 7 - Saturday

    After breakfast in Falmouth we will drive back to our opening hotel. We do not have any planned activities for this day. It's been a great tour of Cape Cod!

Difficulty Level: Intermediate-Plus

Due to road riding into Provincetown and again into Falmouth, this tour's difficulty rating is Intermediate-Plus.

This tour’s trails are all paved, and are suitable for all bicycles. 

Suggested bicycle: Touring bikes, road bikes, hybrids

Suggested tire size for this tour: 25mm – 37mm 


$2,650 per person (based on double occupancy)

$725 – Single Supplement (extra price to have your own room)

$150 – Bike Rental (helmet and bike bag included)

Your Travel Plans

For this tour we meet riders at 5:00 pm on Sunday evening at our opening hotel. The trip ends on Saturday. We plan to be back at the hotel by 1:00 PM.

If you are traveling by air you fly into and out of Boston’s Logan Airport and take the bus to Hyannis. They have a regular schedule between the airport and Hyannis for the two hour ride. The bus delivers you to the Transportation Center in Hyannis which is about a mile from the hotel. There are taxis available, or a quick Uber/Lyft ride). We return you to the hotel at the end of the trip.

If you are driving, you drive to the hotel. We return you there at the close of the trip.  You may leave your car there during the trip.

Your Lodging Plans

Your lodging from Sunday through Friday evenings (6 nights) is included

  • The cost of this trip is $2,650. per person (double occupancy)
  • Single supplement fee is $665.
  • 50% of the total is a required deposit, due upon registration
  • The remainder is due 60 days prior to departure date. Cancellation details: If you cancel more than 60 days prior to departure date, you will receive a 90% refund. Cancellations received less than 60 days prior to tour starting date will not be eligible for a refund.
  • Please purchase trip insurance. We trust Allianz Travel Insurance. CLICK HERE to visit their website. 

Not Included

  • Airfare/transportation to and from Hyannis  
  • Alcohol with meals
  • Items of a personal nature such as laundry
  • Gratuities for guides
  • Travel Insurance (please purchase!)
  • Bike rental

Cape Cod 2023 #1

September 10-16, 2023 | $2,650
This form stopped accepting submissions on September 10, 2023 3:00 pm EDT.

Cape Cod 2023 #2

October 1 - 7, 2023 | $2,650
This form stopped accepting submissions on October 1, 2023 3:00 pm EDT.