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View Cape Cod Day Trip Ideas in a larger map
Many of our European guests stay for more than one week, take advantage of our central location to use as a base for an extended exploration of southern New England. It’s easy to explore Cape Cod in a few days, but there are also a wealth of things to see and do on the nearby islands of Nantucket and Martha’s Vineyard, as well as in the capital city of Boston, MA; Plimoth Plantation in nearby Plymouth, MA; and Newport, R.I. By extending your stay for as much as two weeks, here, in no particular order, are some of our favorite daytrips less than 90 minutes from Cape Cod.
Newport
A trip to Newport, R.I., which is 90 minutes by car from our location, allows you to take a step back in time by touring the magnificent mansions that were once the summer homes of the Vanderbilts and Astors and many other wealthy Americans. Rich and I spent 3 days there in April last year and thoroughly enjoyed our stay. Our first stop was the Breakers, a 70-room estate that was the summer home of Cornelius Vanderbilt. Nearby is Marble House, with its fanciful re-creation of a Japanese tea house in the ocean-front gardens. Across the street is the Elms, where we were treated to a “behind the scenes” tour of the basement and sub-basement, as well as the servants’ quarters. Had the day been nicer we would have been able to go up to the roof for a rooftop view of the surrounding gardens. A leisurely drive along the 10-mile Ocean Drive is a must-do in Newport, as is a walk along the Cliff Walk, which runs in front of The Breakers, Marble House, and Chateau Sur Mer. And if you want a quintessential bowl of steaming New England clam chowder, try the Black Pearl on Bannister’s Wharf.
Nantucket
Although both of Cape Cod’s off-shore islands are worth visiting, we prefer Nantucket. If you take the Hy-Line high-speed ferry from Hyannis, which is only 15 minutes from the Inn, in one hour you’ll be walking the cobbled streets of Nantucket Town. There are lovely shops and galleries to browse and a magnificent view of the harbor from atop the First Congregational Church belltower on Center Street.
Of course, no visit to Nantucket would be complete without a tour of the Whaling Museum, which is located on Broad Street just up from the ferry docks. Having undergone a recent multi-million dollar restoration, the Museum now hosts several informative daily lectures that offer a glimpse into what life may have been like in the heyday of its whaling history. Be sure to take the elevator to the roof for a breathtaking view of Nantucket Town and harbor. Just up Broad Street from the Whaling Museum are two of our favorite spots fro lunch, the Brotherhood of Thieves and Le Languedoc.
In the afternoon we usually rent a bike form Young’s Bike Shop and ride the Polpis Road out to Siasconset (or ‘Sconset, as the locals call it) to see the famed rose-covered fishing cottages. You’ll ride through the Moors past some lovely homes and a spectacular golf course. As you ride you will see Sankaty Head lighthouse in the distance, which had to be relocated several years ago due to erosion. You can ride the Airport Road back into to town to catch the ferry back to the mainland. Be sure to throw a penny off the stern as you pass Brant Point Lighthouse to ensure your return trip to the island one day.
Plimoth Plantation
Plimoth Plantation, the first permanent European settlement in the “New World”, is a living history museum dedicated to recreating the 17th century lifestyle. Less than a 45 minute drive from the Inn, Plymouth is home to the Mayflower II, which is a recreation of the original vessel that brought the Pilgrims to America. Take a tour to learn about the perils of the famous 2020 journey. At the Plantation itself, exhibits include a 17th century crafts center, the Nye Barn with its rare and heritage breed livestock, a re-creation of a 2020 English village, plus much, much more. Nearby you can visit Plymouth Rock, located on the waterfront in town, close to where Mayflower II is anchored. When it’s time for lunch, try the Lobster Hut for fresh New England seafood served up on the harbor.
Martha’s Vineyard
Although you can take the Steamship Authority ferry to Martha’s Vineyard from Woods Hole or the Hyline fast ferry from Hyannis, we prefer to take the passenger-only Island Queen ferry from Falmouth Harbor to Oak Bluffs. The dock is just 35-minutes by car from the Inn and a 45-minute ferry trip will land you in Oaks Bluff. There you can visit the gingerbread house of the old Methodist Camp. Each cottage is brightly colored and sports an unique name. Just around the corner is the the Flying Horses Carousel. A great attraction for the kids, adults enjoy trying to grasp the proverbial “brass ring” as they whirl around on antique wooden horses. 
You can take a shuttle bus into Edgartown, or rent a bike and ride into town via the designated bike path, a short 5-mile journey that takes you along the water. Edgartown is a bustling community in the height of summer, but can be pretty desolate in the off-season. There are some cute shops and a wonderful sidewalk cafe by the name of Alchemy for lunch. If you’re lucky they’ll have Rich’s favorite sandwich on special–a softshell crab BLT. Yum!
Be sure to take the 5-minute ferry trip to Chappaquiddick where you can take a tour of the lighthouse or visit Mytoi Japanese Gardens. Back in Edgartown, take a ride out to Katama Beach for great body surfing or a lazy afternoon on the beach. Alternatively, rent a car or hire a taxi for a tour of the rest of the island, driving through the fishing village of Menemsha, Aquinnah, and the cliffs at Gay Head. If you need a snack, keep an eye out for the Bite, a true roadside clam shack for authentic fried clams or fish and chips.
Boston
Boston is a small city that is easily walkable. Just one hour by car from the High Pointe Inn, we like to park down by the waterfront and visit the New England Aquarium and nearby Imax Theater in the morning, then perhaps take a walking tour along the Freedom Trail or a Beantown Trolley tour of the city in the afternoon.
As you enter the Aquarium, you’ll be greeted by a very vocal penguin exhibit, where several times throughout the day a docent will get in the water to feed the birds and explain to gathered guests about their eating, migration, and procreation habits. It’s fascinating stuff. Outside is the Atlantic Harbor Seal exhibit, which you can actually view for free before you even enter the Aquarium, and just inside the entrance is an amazing collection of jelly fish. Next door, the Imax Theater shows a variety of 3D movies featuring undersea life. It’s a hoot to put on your 3D glasses and see marine life up close and personal.
Our favorite spots for lunch are Legal Seafood, of which there are several locations throughout the city.
In the afternoon take a Duck Mobile tour if you can score a reservation. Their guides are among the best-trained and most-coveted positions in the city. It’s a laugh-out-loud experience by land and sea. In Charlestown, visit Old Ironsides and the Bunker Hill Monument, then come back for some shopping or thirst-quenching at the market stalls of Quincy Market and Faneuil Hall. Alternatively walk up to Boston Commons and the Public Garden for a ride on the swan boats or a walk along the Emerald Necklace parkway, designed by Frederick Law Olmstead.