Cape Cod is a peninsula in the Massachusetts State of USA, and it is renowned as a summer vacation destination. The area is full of quaint villages, seaside resorts, lighthouses, picturesque beaches, boutique hotels, bays and ponds, as well as seafood shacks and other dining and entertainment. Tourists will find plenty of comfy condos for rent when they visit. Among the larger towns, Hyannis offers the Kennedy Legacy Trail, which includes the John F. Kennedy Museum. Ferries can be caught from Hyannis to the popular resort islands of Nantucket and Martha’s Vineyard. In the area, visit the Pilgrim Monument with its sweeping views across the countryside and the Heritage Museums and Gardens. While visiting the area, make sure to enjoy a stroll through one of the vineyards. Scroll down to find a list of the best wine tours in Cape Cod, Massachusetts.
1. Enjoy a three-hour tour of Martha's Vineyard Island from Oak Bluffs (from USD 60.0)
The winery tour of Martha’s vineyard starts off in Oak Bluffs, a Victorian seaside resort with its beautiful Victorian gingerbread cottages, where you will head out to visit the Flying Horse Carousel, one of the oldest still in use. Head to picturesque Edgartown with its waterfront and harbor and stately Greek Revival homes built by whaling captains. Visit the Old Whaling Church and the historic Harborview Hotel. Next stop is Vineyard Haven, where you will head to the historic farming towns of Chilmark and West Tisbury. Enjoy the famous “lobstah bisque” and “clam chowdah” in Menemsha. Also, view the multi-colored clay cliffs at Aquinnah with its lighthouse and views. Along the way, enjoy scenes of the Atlantic shoreline, rolling hills and countryside.
Martha's Vineyard Small Group Island Tour from Oak Bluffs
Duration: 3 hours
2. Experience a wine and wine jelly sauce tasting on Plymouth Bay (from USD 13.0)
Relax on historic Plymouth Bay, steps from Plymouth Rock, while enjoying award-winning wines, wine sauces, and wine jellies. The winery tour in Cape Cod is hosted by Plymouth Bay Winery where wine and food lovers can “experience delicious.” All products are crafted from fruits native to the Northeast USA and the wines, wine jellies, and sauces are versatile, delicious and are ideal companions to every meal. Guests sample the entire wine collection and get to take home a beautiful etched commemorative glass as a souvenir of the experience.
Wine and Wine Jelly-Sauce Tasting on Plymouth Bay
Duration: Flexible
3. Enjoy a two-hour sunset cruise from Martha's Vineyard (from USD 98.0)
A Martha’s Vineyard sunset cruise takes visitors from the Edgartown Harbor out to sea in an authentic New England lobster boat named “Plan Sea.” Enjoy cruising past the beautiful residences along the coastline, while watching yachts sail by and experiencing beautifully scenic views. Guests take their own food and drink on board to enjoy during the slow cruise while listening to the gossip of the locally based crew. Leave the harbor and head past the Edgartown lighthouse before entering Nantucket Sound. Here, it is now time for a beautiful sunset over Martha’s Vineyard.
Two Hour Martha's Vineyard Sunset Cruise
Duration: 2 hours
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4. Go on a unique pedicab tour in Provincetown (from USD 117.0)
This adventure presents a charming and leisurely exploration of Provincetown aboard a comfortable pedicab. Led by a friendly and knowledgeable local expert, this tour allows you to soak in the picturesque beauty and rich history of this coastal town. As you traverse the scenic streets, you’ll pass by iconic landmarks, historic sites, and picturesque waterfront views. The open-air setup provides an unobstructed experience, making it perfect for capturing memorable photos and enjoying the fresh sea breeze.
The guide’s insightful commentary adds depth to your journey through the scenic spots in Cape Cod, sharing fascinating stories about Provincetown’s art, culture, and maritime heritage.
Private Provincetown Open-Air Pedicab Tour
Duration: 60 to 90 minutes
5. Embark on a self-guided driving tour (from USD 16.0)
This tour is one of the fun things to do in Cape Cod. You’ll embark on a self-guided adventure that allows you to drive at your own pace while enjoying fascinating audio commentary along the way. The audio guide offers insightful storytelling, sharing captivating tales about the region’s maritime roots, charming villages, and iconic landmarks. You’ll learn about the area’s role in American history, from the Pilgrims’ arrival to its maritime trade significance.
The tour covers famous locations such as Provincetown, Chatham, and the Cape Cod National Seashore, ensuring you discover the best of what Cape Cod has to offer.
Cape Cod Self-Guided Audio Driving Tour
Duration: 3 hours
6. Sunset charter on a private yacht (from USD 552.0)
Enjoy a luxury, three-hour sunset cruise on a trawler from Hyannis Port in Cape Cod, including a visit to the Kennedy Compound. All alcoholic beverages and snacks are included in the price of the cruise, as is entry to the Kennedy Compound.
Sunset Charter on Private Yacht for 6 people
7. Deep sea fishing trip from Plymouth (from USD 43.0)
Head out to Cape Cod Bay for a deep sea fishing adventure, where you will experience catching cod, haddock, mackerel, Pollack and flounder. The crew of the boat will teach you all the best fishing techniques and will clean and fillet your catch for you with pleasure. The trip leaves from Town Wharf in Plymouth, where you can view Plymouth Harbor from the upper deck. The boat has a full galley service supplying food and drink, but guests can feel free to bring their own food with them.
Deep Sea Fishing Trip from Plymouth with Fishing Rod Rental
8. Personalized private photo tour (from USD 78.0)
This tour is ideal for budding photographers, wishing to learn more about their skill. Spend the day with a local photographer who knows the best spots for great images of nature, beaches, harbor life and architecture in Cape Cod. The tour is adaptable to suit your wishes, while you improve your photography with special tricks and tips from the expert.
Personalized Cape Town Private Photo Tour: Nature & City
Experience the beauty of Cape Cod
Whether on the beach or in the romantic hotels, enjoy your stay in this lovely part of the world by partaking of wine and other tours in Cape Cod, Massachusetts, USA. With our list above, you have lots of tour options to keep you busy when you do visit this awesome destination.
Frequently asked questions about wine tours in Cape Cod
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