Hyannis is the quintessential Cape Cod town. It’s where salty ocean breezes meet the charm of small-town New England. Whether you’re wandering through its historic Main Street or catching a ferry to the nearby islands, there’s something uniquely magical about this place. Having explored Hyannis myself, I can tell you it’s full of hidden gems—from strolling down Main Street and soaking in the maritime history to indulging in fresh seafood. Here are 15 must-do activities to make your Hyannis getaway special.
Top Things to Do in Hyannis, Cape Cod
Visiting Hyannis? Spend the day on Kalmus Beach, take a ferry to Nantucket or Martha’s Vineyard, or explore the John F. Kennedy Hyannis Museum. Stroll along Main Street for shopping and dining, embark on a whale-watching tour, or enjoy fresh seafood at a waterfront restaurant. Whether you’re into history, outdoor adventures, or coastal charm, Hyannis has plenty to offer.
1. Windsurf and swim at Kalmus Beach
Kalmus Beach is a must-visit in Hyannis, especially for windsurfers and beach lovers. Its two sections—one facing the harbor and the other the open ocean—offer different experiences. The calm waters on the harbor side are perfect for wading and relaxing, while the ocean side provides steady breezes ideal for windsurfing. The soft sand and shallow entry make it great for families, and the stunning views of sailboats drifting by add to its charm. I once spent an afternoon here just watching the colorful kitesurfers dance over the waves—it’s an experience that sticks with you.
Beyond the beach, amenities like a snack bar, picnic tables, and restrooms make it a convenient spot for a full-day outing. Shell collectors will love strolling along the shoreline, and the sunsets here are breathtaking. Whether you’re looking to swim, sunbathe, or enjoy water sports, Kalmus Beach delivers a true Cape Cod experience.
2. Cruise past the Kennedy compound at sunset
Watching the sun melt into Hyannis Harbor from the deck of the Bay Spirit feels like pure Cape Cod magic. This 75-minute sunset cruise is all about slowing down, sipping something cold, and soaking up those postcard views of Hyannis Port.
The crew keeps things easygoing with light music and a stocked bar below deck serving beer, wine, cocktails, and snacks. It’s not a narrated tour, but the captain points out the Kennedy homes as you cruise past them, which always feels like a special local touch.
I really like recommending this one for couples or small groups who want a relaxing evening without the crowds. Just make sure to arrive early to find parking at Ocean Street, then head over to Spanky’s Clam Shack afterward for dinner right by the docks. It’s the perfect Cape Cod night out.
3. Shop and eat on Main Street
Hyannis’ Main Street is the heart of the town, lined with unique shops, art galleries, and some of the best local eateries. Walking down this bustling strip, you’ll find everything from Cape Cod souvenirs to handcrafted jewelry and boutique clothing stores. One of my favorite stops is Katie’s Ice Cream, where you can try flavors inspired by the Cape. The street has a mix of old-school charm and modern appeal, making it the perfect place to explore at a leisurely pace.
Beyond shopping, Main Street is a hub for entertainment and dining. The historic Cape Cod Melody Tent hosts live concerts and comedy shows, while seafood lovers can’t miss a meal at Spanky’s Clam Shack near the harbor. Whether you’re grabbing a coffee at a cozy café or enjoying fresh lobster rolls, this street is the perfect blend of local flavor and coastal charm.
4. Learn maritime history at Cape Cod Maritime Museum
For a deep dive into Cape Cod’s seafaring past, the Cape Cod Maritime Museum is a must-visit. This small yet fascinating museum sits right on the Hyannis waterfront, offering exhibits on shipbuilding, marine conservation, and the region’s rich maritime history. The Boatbuilding Shop is a highlight, where you can watch craftsmen restore traditional wooden boats—a process that takes incredible skill. One exhibit that stood out to me showcased artifacts from old shipwrecks, giving a glimpse into the area’s treacherous waters.
Outside, the museum offers a scenic spot to enjoy views of Hyannis Harbor. You can also take a guided boat tour, learning about the harbor’s history while spotting fishing boats and luxury yachts. It’s an engaging stop for anyone interested in maritime culture, whether you’re a sailing enthusiast or just love learning about coastal history.
5. Drink wine and eat charcuterie at Pour Decisions
If you’ve ever wished wine tasting felt a little more fun and laid-back, Pour Decisions Wine Bar is your spot. This new self-serve wine bar in downtown Hyannis lets you explore 48 rotating wines at your own pace, choosing 2, 4, or 6-ounce pours as you go. It’s part tasting room, part hangout, and all good vibes, with cozy seating nooks, charcuterie boards, and small bites that pair perfectly with whatever’s in your glass.
I really enjoy how approachable it feels. There’s no pretentious wine talk here, just good wine and friendly staff happy to help you discover something new. After your tasting, take a short stroll down Main Street to browse the local shops or grab dessert at Katie’s Homemade Ice Cream. It’s exactly the kind of night out that makes Hyannis so charming.
6. Watch boats and grab lobster rolls at Hyannis Harbor
Hyannis Harbor is the heart of this coastal town, offering stunning waterfront views and a gateway to Cape Cod’s islands. The harbor is always bustling, with ferries departing for Martha’s Vineyard and Nantucket, and local fishing boats unloading the day’s catch. Walking along the boardwalk, you’ll see sailboats bobbing in the water while seagulls circle above. A harbor cruise is a great way to take in the scenery, and if you’re up for adventure, kayaking and paddleboarding rentals let you explore at your own pace.
For fresh seafood, waterfront restaurants like Spanky’s Clam Shack serve up some of the best lobster rolls in town. If you visit in the evening, the sunset over the harbor is a sight to behold. Whether you’re taking a ferry to the islands, enjoying a seafood feast, or simply soaking up the salty air, Hyannis Harbor is a must-visit.
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7. See JFK history at the Kennedy Museum
A visit to The John F. Kennedy Hyannis Museum offers an intimate look at JFK’s deep connection to Cape Cod. Located in downtown Hyannis, this museum is filled with rare photographs, multimedia exhibits, and personal artifacts that highlight the Kennedy family’s time in their Hyannis Port home. Walking through the displays, you’ll see how Hyannis served as the family’s summer retreat, shaping JFK’s love for the ocean and sailing.
One of the highlights is the video presentation featuring firsthand accounts from those who knew the Kennedys. The museum also offers guided tours that delve into the family’s legacy, making it a compelling stop for those interested in American history. After your visit, take a short walk to Veterans Memorial Park, where a memorial honors the 35th president. Whether you admire JFK’s leadership or just love a good story, this museum provides a meaningful glimpse into his life.
8. Hike Skunknett River’s wooded trails
Ever wanted to step into a quiet slice of Cape Cod nature without leaving Hyannis? Skunknett River Wildlife Sanctuary is in Barnstable, just 3 to 5 miles from downtown Hyannis and about a 10-minute drive, making it an easy escape for a morning or afternoon hike. The trails wind through ponds, wetlands, and rare Atlantic White Cedar stands, giving you a chance to see ospreys, black-crowned night herons, and migrating ducks.
The Overlook Trail offers peaceful views of West Pond, while the Holly Trail leads past vernal pools alive with wood frogs in spring. The sanctuary is ideal for birdwatchers, photographers, or anyone wanting to enjoy Cape Cod’s natural beauty at a gentle pace.
Bring sturdy shoes, water, and bug spray, and plan to spend an hour or two wandering before heading back to Hyannis for lunch or a harbor stroll.
9. Meet local artists at HyArts Artist Shanties
Ah, the arts! If you appreciate a good brushstroke or the delicate chisel of a sculpture, HyArts Artist Shanties is your go-to spot in Hyannis. Tucked away near Bismore Park, these quaint little huts are more than just a visual treat; they’re a testament to the town’s vibrant arts scene. Overlooking the harbor, they offer a picturesque setting for discovering local talent while enjoying the sea breeze.
Walking in, it’s like stepping into a different world—one where color, texture, and imagination reign supreme. From handcrafted jewelry to intricate paintings, there’s something here for every art lover. And the exciting part? You get to meet the artists! Many work right in their shanties, sharing their inspiration and techniques. With a rotating lineup of artists, every visit offers a fresh experience. Whether you’re an art enthusiast or just browsing, the HyArts Artist Shanties add a creative touch to any Hyannis itinerary.
10. Grab a beer at Cape Cod Beer
If you’re a fan of craft beer, a visit to Cape Cod Beer is a must. Located just minutes from downtown Hyannis, this local brewery has been crafting small-batch beers since 2004. Their spacious taproom offers a rotating selection of brews, from the flagship Cape Cod Red to seasonal favorites like the cranberry-infused Harvest Ale. You can take a behind-the-scenes tour to see the brewing process or simply relax in their outdoor beer garden with a pint in hand.
Beyond beer, Cape Cod Beer is a community hub, hosting events like trivia nights, live music, and food truck gatherings. I stopped by on a summer afternoon and ended up staying for hours, enjoying the laid-back vibe and sampling their signature flights. If you’re looking for a taste of local flavor, this brewery is the perfect place to sip and unwind.
11. Spot humpback whales on a boat tour
For an unforgettable marine adventure, Hyannis Whale Watcher Cruises offers some of the best whale-watching excursions in New England. Departing from Barnstable Harbor, these tours take you to Stellwagen Bank National Marine Sanctuary, a prime feeding ground for humpback, minke, and fin whales. Seeing a massive humpback breach the surface just a few feet from the boat is a breathtaking experience.
Naturalists on board provide fascinating insights into the whales’ behavior and migration patterns, making the trip both thrilling and educational. On my last trip, I spotted a mother whale teaching her calf how to dive—an unforgettable sight. The three- to four-hour journey offers plenty of opportunities for photography, so bring your camera. Whether you’re a wildlife enthusiast or just looking for a unique experience, Hyannis Whale Watcher Cruises is a must-do.
12. Catch live music at The Melody Tent
For live entertainment in a unique setting, The Cape Cod Melody Tent delivers an intimate concert experience. Unlike traditional venues, this theater-in-the-round has a rotating stage, ensuring every seat provides a great view. Located just off Main Street, it hosts big-name musicians, comedians, and theatrical performances throughout the summer. Past performers have included legendary acts like The Beach Boys and Chris Isaak, making it a go-to spot for live entertainment.
The atmosphere is casual yet lively, with audiences singing along under the tented canopy. I once caught a jazz performance here, and the energy was electric, with the rotating stage making the experience even more immersive. Tickets sell out quickly, especially for major acts, so booking in advance is recommended. Whether you’re a music lover or just looking for a fun night out, The Melody Tent offers an unforgettable experience.
13. Rent a kayak at Bismore Park
If you’re looking for a peaceful escape without leaving the heart of Hyannis, Bismore Park is the perfect spot. Nestled by Hyannis Harbor, this scenic waterfront retreat offers a relaxing atmosphere where you can watch boats drift by, breathe in the salty air, and soak in the Cape Cod charm. It’s a go-to place for a quiet break amid the town’s lively energy.
Beyond the views, Bismore Park is a hub for fun water activities. Kayak rentals? Check. Paddleboard lessons? Absolutely. Whether you’re up for adventure or just want to enjoy a picnic by the harbor, this park has something for everyone. Just steps from Main Street’s restaurants and shops, it feels both central and secluded. It’s the kind of place where you can unwind, recharge, and enjoy Hyannis’ coastal charm at your own pace.
14. Tour the 1690 Barnstable jail
One of the most intriguing historic sites in the area, Barnstable Old Gaol is Cape Cod’s oldest wooden jail, dating back to 1690. Located in Barnstable Village, this small but fascinating site offers a glimpse into the region’s colonial past. The jail once housed accused pirates and local criminals, and its hand-hewn wooden cells remain largely intact. Walking through the dimly lit space, it’s easy to imagine what life was like for those confined within its walls.
Guided tours provide insights into early law enforcement and even share stories of supposed hauntings. On a nighttime tour, I heard tales of eerie noises and unexplained cold spots—a chilling but fun experience. The Old Gaol is a quick but worthwhile stop for those interested in colonial history or looking for an off-the-beaten-path attraction. It’s a great way to step back in time and experience Cape Cod’s past firsthand.
15. See antique sailboats at Osterville Historical Museum
For a deeper dive into Cape Cod’s maritime heritage, Osterville Historical Museum is a hidden gem. Located just a short drive from downtown Hyannis, this museum is home to Cape Cod’s largest collection of antique boats, including the famous Crosby catboats. These historic wooden sailboats played a crucial role in the area’s fishing and sailing traditions, shaping the region’s nautical identity.
The museum also features exhibits on Cape Cod’s shipbuilding history, local families, and 19th-century life. A highlight for me was the vintage boat shop, where skilled craftsmen still practice traditional boatbuilding techniques. The museum hosts seasonal events like antique sales and maritime festivals, making it a lively stop during the summer. If you’re fascinated by Cape Cod’s seafaring history, Osterville Historical Museum offers a fascinating and authentic look at the region’s past and craftsmanship.
