2023 Rolling Thru Cape Cod (and Martha’s Vineyard)!

An Exclusive and Rare Tour of the Seacoast

September 25 – 28, 2023



Join us in Cape Cod for one of the most scenic, unforgettable, and unique tours offered in the United States.

We’ve wanted to uncork this tour for years because it’s such a cool trip.  Seacoast riding, ferry rides to/from an Atlantic island, classic inns, lighthouses, etc. It intrigued us. It eluded us.  It’s kept us up at night.  For 2023, we’ve been able to put all the pieces together, and are ready to launch it.  Don’t Miss it! 

The weather this time of year is usually warm, from the upper 60s to mid-70s during the day.  And, the traffic is very low, making for a great ride.

Monday- Welcome to Cape Cod

Your hotel is simply incredible.  It’s a boutique inn that has been offering lodging to Cape Cod for OVER 300 years.  (You read that right)  It’s romantic, it’s elegant and they’re offering you an incredible deal on their rooms.

When you check-in, your Rolling Thru Cape Cod representative will be there to facilitate the process and make sure everything goes smoothly. You’ll receive your Rolling Thru Cape Cod package, with credentials, route maps (in case you decide to ride on your own), and your special gift.

Get ready for dinner – it’s going to be one of the best you’ve had.  The Inn’s restaurant is recognized as a Distinguished Restaurant of North America, placing it in the top 1% of restaurants in the country!  We’ll sit in their cozy tavern, eating like kings and queens.  (Remember, Rolling Thru America lunch and dinner destinations welcome motorcyclists.  Helmet head and jeans are welcome here.

Tuesday: Cape Cod – To the end and back.

Breakfast will be at the Inn each morning.  (Did we mention that this is an award-winning restaurant??).  Afterward, we’ll ride in medium-sized waves with a friendly lead and sweep guide in each wave.  (You can ride on your own too if you prefer).   We’ll ride along the coast to the very tip of the peninsula and back.

The Atlantic will be your riding partner throughout the day, sometimes riding within feet of the sea.  The ride pace as always is a relaxed one, with the natural undulation of the terrain giving us gentle curves shaped by the dunes and mother nature.  You’ll see lighthouses, quaint villages, stunning beachfront, inland ponds, and seafood shacks covered in buoys.  It’s like riding through a postcard.  It’s approximately 4 hours of seat time, with plenty of stops throughout the day.

Lunch awaits you at an incredible inn that we had to wait over a year to reserve.  (It’s that good.)  It’s one of the most famous destinations on the Cape because of its incredible food, and because of its location; the dining room sits right on the shores of the Atlantic, overlooking a beautiful beach, near an inlet with sailboats passing by regularly.  This view is one of THE BEST views Rolling Thru America has ever enjoyed on a tour.

After lunch, we’ll return to the Inn on more enjoyable and scenic roads.  You’ll have time to relax, wash up, and then head out into the town on your own.  It’s your opportunity to explore and perhaps have dinner with newfound friends at a place you discover.   Get some sleep though – tomorrow is going to be an epic day

Wednesday: Martha’s Vineyard – A Day Like No Other

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This is going to be a very memorable day.  You’ll ride a short distance across Cape Cod to the southern shore whereupon you and your bike will hop aboard a large ferry, travel across the sound to one of THE most exclusive islands in the world, and enjoy a several hour trip with breathtaking views.  The villages on the island are very authentic and charming, and our lunch stop is a more casual, laid back restaurant.  Following lunch, we’ll ride a bit more, hop on the ferry, and head back to the mainland.

Martha’s Vineyard is an ideal day-ride destination, but one that you probably wouldn’t try on your own, on your bike. But with Rolling Thru Cape Cod, it’s going to be easy. The island is simply beautiful.  Period.  It’s why some fortunate few spend tens of millions on their homes here. 

The roads on the island have gorgeous views of the ocean, beaches, villages and impressive properties, and are marble-smooth.  They wrap around bays, rise and fall over dunes, and make for a really good ride.  

The lunch destination is in one of the most popular bays, with lovely views of the water and the neighboring seaside village buildings.  It’s a relaxed vibe here, with very good food – you’ll feel like a local (which is either a vw bus driving surfer dude, or a hedgefund manager looking like a vw bus driving surfer dude).  Regardless, it’s the perfect place to take a moment to consider the specialness of today’s ride.

After lunch, we’ll ride a little bit more and then head back to the ferry. 

The ferry ride will be over quickly, given how much scenery you’ll see and from the excitement of the moment.  The ferry ride is 45 min, but will go by in a blink of an eye.

Later that night, you’ll join the rest of the group in the Inn for our farewell dinner.  It’s always a great time, sharing stories from the ride and enjoying one more dinner from this incredible place.  

Thursday- See you Next Year!

A special Farewell Breakfast awaits you. You’ll say goodbye to new and old friends, see photos from the trip, and will likely be thinking about your next Rolling Thru America tour.


SEPTEMBER 25th-28th, 2023

Package Price (not including lodging): $699/per person

Standard Room (Description below):  $219/night (Normally $296/night) for three nights. Total for Rider and Lodging: $1,437 inclusive of all taxes and fees

Suite Room (Description below): $249/night (Normally $399/night) or three nights. Total for Rider and Lodging: $1,539 inclusive of all taxes and fees

You’ll need to be a guest of the hotel (or share a room with a friend who is a guest at the hotel)

Standard Rooms:  Nicely appointed rooms with a queen-sized bed (or two doubles or a king) and a private bath. Please note your choice when booking your trip with us.  (Some details may vary by room) 

Suite Rooms: One-room suites featuring a two-person shower, heated tile floors, and an oversized whirlpool with grand columns and stairs inviting you to bathe in luxury. Most Suites offer a private balcony overlooking the exquisite, manicured gardens and a decorative or gas fireplace. Some details may vary by room.  Note, Suites are not available the prior Saturday and Sunday nights, nor the Thursday night following the tour (they’re sold out on those preceding and following nights).

Additional Night(s)? Want to arrive early, or stay late? Email us and we can secure a longer stay for you at a discounted rate.

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