The High Pointe Inn on Cape Cod: Award-winning Bed and Breakfast Overlooking Cape Cod Bay

In our last post we gave you ideas for your Cape Cod vacation itinerary of 3-, 5-, or 7-days. As promised, we have even more ideas to extend your trip to Cape Cod and enjoy more of what we have to offer throughout the year. These ideas are well-suited to  the adventure traveler who wants to play hard and challenge the elements, or for those who prefer a little bit more laid-back approach to travel with time to soak up the atmosphere and “go native”.

Here are some ideas if you have more than one week of vacation time:

Day Eight: Cape Cod Rail Trail
Grab your bike and tackle the 26-mile Cape Cod Rail Trail that starts in Dennis and ends in Provincetown. This trail runs along a former railroad track, so for the most part it is flat with few hills. Upgraded in 2020, the trail is shared with walkers, in-line skaters, runners, and baby strollers, but for the most part it is smooth sailing, especially on week days and in the shoulder seasons. Along the trail are numerous opportunities to “stop and smell the roses” or the fried clams, ice cream, and salty air. You can pack a lunch for a picnic along the trail, or sample one of the clam shacks and ice cream parlors that dot the route. Take a detour into Nickerson State Park for a more challenging and hilly bike track, and reward yourself with a swim in the one of the lovely ponds. A number of bike rental shops abut the trail heads in Dennis, Brewster, and Orleans. When you are done “riding the rails” for the day, return via Route 6A and stop at the Sesuit Harbor Café in Dennis for a lobster roll or perhaps a sunset cruise on Cape Cod Bay.

Day Nine: Cape Cod at Play
Spend the day at any one of Cape Cod’s beautiful beaches soaking up the sun, reading the latest novel, walking the coastline in search of treasures from the sea, or frolicking in the waves. For the more adventuresome in your party, plan a kayak excursion in Pleasant Bay or Nauset Marsh with Osprey Sea Kayak Adventures. A day on the ocean with owner Dick Hilmer will inform, delight, and inspire. And for the duffers in the group, choose from among dozens of challenging golf courses from Ballymeade in Falmouth to Highland Links in Truro. Looking for even more adventure? Then set sail aboard a chartered fishing vessel from Sandwich, Hyannis, Chatham, or Rock Harbor for an afternoon of sport-fishing for striped bass, bluefish, shark, and bluefin tuna. Looking for dinner with a view of the ocean? Try the Aqua Grille, the Boat House, the Chart Room, the Ocean House, Mattakeese Wharf, 28 Atlantic, the Beachcomber, or the Mews. After dinner, catch a play at the Cape Cod Playhouse, America’s oldest professional summer theatre (in season).

Day Ten: Rail and Sail
Ride the rails on the Cape Cod Scenic Train, a 2-hour journey through beautiful cranberry bogs, natural woodlands, lush marshes and more as you make your way between Hyannis and the Cape Cod Canal. The perfect antidote to a sun-scorched day at the beach, a combination “rail and sail” package from the Cape Cod Scenic Railroad affords you a leisurely pace on both land and sea. After your narrated scenic trip on the “fun train” stop for lunch at Baxter’s Boat House on the harbor. In the afternoon, set sail for a leisurely one-hour harbor cruise aboard the Maine coastal steamer replica, Prudence, which will take you on a journey across Lewis Bay and Hyannis Harbor. After your cruise, visit the Cape Cod Maritime Museum at the head of the harbor for a lesson in maritime traditions and heritage. End you day with a concert at the Cape Cod Melody Tent (in season) or stop for a nightcap and some jazz at Harry’s Blues Bar on Main St.

Still have more time to play? Stay tuned for our next installment: Six Fabulous Day Trips 90 Minutes or Less from Cape Cod

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70 High Street,West Barnstable, MA 20208
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