Massachusetts Tours
Wind in your ears. Chowder in reach. From dune grass to dock line, do it the Backroads way.
5 Trips
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Biking
Families with Teens & 20s
Cape Cod Family Bike Tour
5 days
1-3
Casual Hotels
$3,799/person
(+$900 for optional single occ.)
Available
May 25, 2026
Monday
May 29, 2026
Friday
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Biking
Couples, Friends & Solos
Martha's Vineyard & Nantucket Bike Tour
5 days
1-3
Premiere Hotels
$4,399/person
(+$1,350 for optional single occ.)
Available
May 25, 2026
Monday
May 29, 2026
Friday
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Biking
Families with Kids & Teens
Cape Cod Family Bike Tour
5 days
1-3
Casual Hotels
$3,499/person
(+$850 for optional single occ.)
Available
May 31, 2026
Sunday
Jun 4, 2026
Thursday
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Biking
Couples, Friends & Solos
Martha's Vineyard & Nantucket Easygoing E-bike Tour
5 days
1-2
Premiere Hotels
$4,649/person
(+$1,500 for optional single occ.)
Available
May 31, 2026
Sunday
Jun 4, 2026
Thursday
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Biking
Families with Teens & 20s
Cape Cod Family Bike Tour
5 days
1-3
Casual Hotels
$3,799/person
(+$900 for optional single occ.)
Available
Jun 7, 2026
Sunday
Jun 11, 2026
Thursday
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Biking
Couples, Friends & Solos
Martha's Vineyard & Nantucket Bike Tour
5 days
1-3
Premiere Hotels
$4,399/person
(+$1,500 for optional single occ.)
Available
Jun 7, 2026
Sunday
Jun 11, 2026
Thursday
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Biking
Families with Kids & Teens
Cape Cod Family Bike Tour
5 days
1-3
Casual Hotels
$3,499/person
(+$1,250 for optional single occ.)
Available
Jun 14, 2026
Sunday
Jun 18, 2026
Thursday
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Biking
Families with Kids & Teens
Cape Cod Family Bike Tour
5 days
1-3
Casual Hotels
$3,499/person
(+$1,450 for optional single occ.)
Available
Jun 28, 2026
Sunday
Jul 2, 2026
Thursday
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Biking
Families with Teens & 20s
Cape Cod Family Bike Tour
5 days
1-3
Casual Hotels
$3,799/person
(+$1,400 for optional single occ.)
Available
Jul 5, 2026
Sunday
Jul 9, 2026
Thursday
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Biking
Families with Kids & Teens
Cape Cod Family Bike Tour
5 days
1-3
Casual Hotels
$3,499/person
(+$1,450 for optional single occ.)
Available
Jul 12, 2026
Sunday
Jul 16, 2026
Thursday
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Biking
Families with Teens & 20s
Cape Cod Family Bike Tour
5 days
1-3
Casual Hotels
$3,799/person
(+$1,400 for optional single occ.)
Available
Jul 19, 2026
Sunday
Jul 23, 2026
Thursday
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Biking
Families with Kids & Teens
Cape Cod Family Bike Tour
5 days
1-3
Casual Hotels
$3,499/person
(+$1,450 for optional single occ.)
Available
Jul 26, 2026
Sunday
Jul 30, 2026
Thursday
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Biking
Families with Teens & 20s
Cape Cod Family Bike Tour
5 days
1-3
Casual Hotels
$3,799/person
(+$1,400 for optional single occ.)
Available
Aug 2, 2026
Sunday
Aug 6, 2026
Thursday
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Biking
Families with Kids & Teens
Cape Cod Family Bike Tour
5 days
1-3
Casual Hotels
$3,499/person
(+$1,400 for optional single occ.)
Available
Aug 9, 2026
Sunday
Aug 13, 2026
Thursday
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Biking
Families with Teens & 20s
Cape Cod Family Bike Tour
5 days
1-3
Casual Hotels
$3,799/person
(+$1,400 for optional single occ.)
Available
Aug 16, 2026
Sunday
Aug 20, 2026
Thursday
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Biking
Couples, Friends & Solos
Martha's Vineyard & Nantucket Bike Tour
5 days
1-3
Premiere Hotels
$4,399/person
(+$2,300 for optional single occ.)
Available
Aug 16, 2026
Sunday
Aug 20, 2026
Thursday
Log in to save!
Biking
Families with Kids & Teens
Cape Cod Family Bike Tour
5 days
1-3
Casual Hotels
$3,499/person
(+$1,450 for optional single occ.)
Available
Aug 23, 2026
Sunday
Aug 27, 2026
Thursday
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Biking
Couples, Friends & Solos
Martha's Vineyard & Nantucket Easygoing E-bike Tour
5 days
1-2
Premiere Hotels
$4,649/person
(+$2,300 for optional single occ.)
Available
Aug 23, 2026
Sunday
Aug 27, 2026
Thursday
Log in to save!
Biking
Couples, Friends & Solos
Martha's Vineyard & Nantucket Bike Tour
5 days
1-3
Premiere Hotels
$4,399/person
(+$2,300 for optional single occ.)
Available
Aug 30, 2026
Sunday
Sep 3, 2026
Thursday
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Biking
Couples, Friends & Solos
Cape Cod Bike Tour
5 days
1-3
Casual Hotels
$3,549/person
(+$950 for optional single occ.)
Available
Sep 7, 2026
Monday
Sep 11, 2026
Friday
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Biking
Couples, Friends & Solos
Martha's Vineyard & Nantucket Easygoing E-bike Tour
5 days
1-2
Premiere Hotels
$4,649/person
(+$2,200 for optional single occ.)
Available
Sep 7, 2026
Monday
Sep 11, 2026
Friday
Log in to save!
Biking
Couples, Friends & Solos
Martha's Vineyard & Nantucket Bike Tour
5 days
1-3
Premiere Hotels
$4,399/person
(+$1,950 for optional single occ.)
Available
Sep 13, 2026
Sunday
Sep 17, 2026
Thursday
Log in to save!
Biking
Couples, Friends & Solos
Cape Cod Bike Tour
5 days
1-3
Casual Hotels
$3,549/person
(+$950 for optional single occ.)
Available
Sep 13, 2026
Sunday
Sep 17, 2026
Thursday
Log in to save!
Biking
Couples, Friends & Solos
Martha's Vineyard & Nantucket Bike Tour
5 days
1-3
Premiere Hotels
$4,399/person
(+$1,500 for optional single occ.)
Available
Sep 20, 2026
Sunday
Sep 24, 2026
Thursday
Log in to save!
Biking
Couples, Friends & Solos
Cape Cod Bike Tour
5 days
1-3
Casual Hotels
$3,549/person
(+$900 for optional single occ.)
Available
Sep 20, 2026
Sunday
Sep 24, 2026
Thursday
Massachusetts Tours
Simple pleasures, small-town hospitality and the relaxed pace of island life await off the coast of Cape Cod, Massachusetts. Join Backroads for carefree biking Nantucket and Martha’s Vineyard. Ride past scenic beaches, historic homes, woodland and cranberry bogs. Explore Chappaquiddick Island’s famed Cape Poge Lighthouse. Fill your next vacation with New England charm, fresh seafood and the luxuries of welcoming inns.