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Sun, Fun and Cycling Holiday USA

Cape Cod and Martha’s Vineyard are famed for their coastal beauty and on this tour you’ll spend 3 nights in charming Yarmouth, MA, where you’ll cycle on the Cape Cod rail trail with incredible coastline scenery. Then it’s 2 nights in quaint Falmouth with cycling along the beautiful Shining Sea Bikeway, and a day trip to explore gorgeous Martha’s Vineyard with its famous Gingerbread Cottages.

Key information

  • Trip type: Guided
  • Lodging: Point to Point
  • Terrain: Paved bike trails
  • Starts in: Yarmouth
  • Ends in: Falmouth
  • Total Distance: Up to 132-150 Miles / 212-241 Kilometers
  • Private tour is possible / minimum 4 people

Meet the instructors

Diane, Steve, & Ron

Highlights

  • 4 days of fully guided cycling
  • Difficulty: Easy
  • Fully guided tour of Martha's Vineyard with its famous Gingerbread Cottages
  • Fully supported with van, bike trailer, and team members
  • Group socials and fun activities
  • 5 nights accommodation
  • Several meals included

Skill level

  • Beginner

5 days with instruction in English
Group size: Maximum of 14 participants
Airport transfer included: Logan International Airport
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Accommodation

You will stay in boutique inns during the tour:

  • 3 nights in Yarmouth, Massachusetts, at the fabulous Bayside Resort
  • 2 nights in Falmouth at charming Shoreway Acres

Program

The essentials

  • Difficulty: Easy
  • Daily distance: Rider's choice between 25-50 miles / 40-80 kilometers

Itinerary

Day 1: Arrival at Yarmouth and/or pick-up at Boston Logan Airport

  • 11:00 Optional pick-up at Logan Airport
  • 19:00 Tour orientation at the hotel (meet in the breakfast area)
  • Lodging: Bayside Resort, 225 Rte. 28 West Yarmouth, MA

Arrive in Yarmouth and explore the quaint main streets and beautiful seashore before meeting for trip orientation.

Day 2: Cape Cod Rail Trail to Chatham Lighthouse

  • Lodging: Bayside Resort, 225 Rte 28 West Yarmouth, MA

Enjoy breathtaking scenery as you cycle along this perfect, paved bikeway heading for historic Chatham with its quaint Main Street and historic, lovely lighthouse. You'll take time to drop the kickstands and spend some time relaxing on the beautiful beach. For those looking for a longer ride, you can elect to cycle back to the hotel for a 42-mile day.

  • Distance: 25 or 42 mi / 40 or 68 km
  • Terrain: Paved bikeways

Day 3: Cape Cod Rail Trail to Province Town

  • Lodging: Bayside Resort, 225 Rte 28 West Yarmouth, MA

Enjoy breathtaking scenery as you cycle along the Atlantic shoreline, part of the national seashore, with great wildlife-viewing including sea birds, seals, and possibly sharks! You can cycle the full 40 miles (64 kilometers), or jump in the SAG van and chill while they get you up to P-town with its endless beaches and charming shops.

  • Distance: Rider's choice up to 45 mi / 72 km

Day 4: Cape Cod Canal Trail and Shining Sea Bikeway

  • Lodging: Shoreway Acres, 59 Shore St, Falmouth, MA

You’ll start with a gorgeous morning ride on the Cape Cod Canal Trail and the Shining Sea Bikeway. After the ride, the rest of the day is yours to explore charming Falmouth and spend time at the awesome swimming beaches right along the bike trail! For those opting for the extended ride, you’ll cycle from the Bayside Inn following a section of the East Coast Greenway.

  • Distance: 22 or 40 mi / 35 or 64 km

Day 5: Martha’s Vineyard

  • 08:30 Ferry to Martha’s Vineyard
  • Lodging: Shoreway Acres, 59 Shore St, Falmouth, MA

Enjoy a great ferry ride to Martha's Vineyard with views of the New England coastline that will take your breath away. On the Vineyard, you will be delighted by the colorful and unique Gingerbread Cottages and gorgeous scenery to be found throughout the island. You can explore on your own or join the guided tour which takes in all the island has to offer!

  • Distance: 30 mi / 48 km

Day 6: Return

  • 09:00 Optional return shuttle to Logan Airport.

On demand: This tour is also available for custom dates for groups of 4 or more. Please send an inquiry to discuss dates, details, and availability.

Location

You will cycle from Yarmouth to Falmouth in Massachusetts.

Food

Meals included

  • Daily breakfast
  • Snacks and beverages
  • 1 lunch
  • 1 happy hour

The following meals are included:

  • Breakfast
  • Snacks
  • Drinks

The following drinks are included:

  • Water

The following dietary requirement(s) are served and/or catered for:

  • Regular (typically includes meat and fish)
If you have special dietary requirements it's a good idea to communicate it to the organiser when making a reservation

What's included

  • 5 nights premium accommodation
  • All transportation while on the tour
  • Roundtrip shuttle to and from Logan Airport
  • Full ride support
  • Tour guides
  • Daily breakfast
  • 1 lunch

What's not included

  • Bike rental (Standard bike: 100 USD, E-Bike: 250 USD)
  • Airfare
  • Extra meals
  • Personal expenses

How to get there

Recommended Airports

Arrival by airplane

Please book your flight to arrive at Logan International Airport (BOS). Shuttle to and from Boston Logan Airport is free of charge. If using the shuttle, you must reserve in advance. Pick up is from the Logan Airport only.

If you are driving to the tour, free parking is available for the duration of the tour.

Airport: Logan International Airport Airport transfer included: Logan International Airport No additional charges. You can request this in the next step.

Cancellation Policy

  • A reservation requires a deposit of 50% of the total price.
  • The deposit is non-refundable, if the booking is cancelled.
  • The rest of the payment should be paid 30 days before arrival.
6 days / 5 nights
from --
Friday June 20, 2025
(6 days / 5 nights)

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