TOP 30 Best Romantic wine vacations in Massachusetts

Italian Exclusive Vacation is a premier travel agency located in Waltham, Massachusetts, specializing in creating luxurious and unforgettable vacations to Italy. Our team of experienced travel experts is dedicated to crafting personalized itineraries that cater to the unique preferences and interests of each client. From exploring the historic streets of Rome to savoring the finest wines in Tuscany, we ensure that every aspect of your Italian getaway is meticulously planned and executed. Whether you seek a romantic honeymoon, a family adventure, or a solo retreat, Italian Exclusive Vacation is your gateway to experiencing the beauty, culture, and cuisine of Italy in style and comfort. Visit us at 24 Crescent Street to start planning your dream vacation today.

Located at 6 North Beach Street in Nantucket, Massachusetts, The Brant is a luxurious lodging institution that offers a unique and unforgettable island experience. Situated in the picturesque Brant Point area, guests can enjoy the convenience of being just minutes away from downtown and steps from the beach. The Brant redefines Nantucket hospitality with its exclusive amenities, impeccable design, and intuitive service. With a variety of room types to choose from, guests can personalize their stay to their preferences. Whether you prefer a room with a kitchenette for longer visits, a lofted ceiling, or a private porch, The Brant has everything you need to make your stay comfortable.

The Captain Freeman Inn, located at 15 Breakwater Road in Brewster, Massachusetts, is a beautifully restored Sea Captain's mansion just a short walk away from Breakwater Beach. This award-winning Bed and Breakfast has been recognized with the Tripadvisor Certificate of Excellence for the past 11 years, offering guests a deluxe seaside experience year-round. Guests can enjoy the outdoor heated salt water swimming pool and custom firepit, providing the ultimate in luxury and relaxation in every season. The inn also offers a gourmet three-course breakfast made with farm-to-table ingredients, served in a charming indoor dining area or on the screened porch.

Located at 30 East Street in Stockbridge, Massachusetts, The Inn at Stockbridge is a charming Georgian-style bed and breakfast nestled on six beautifully landscaped acres in the tranquil Berkshires. Offering three distinct lodging options to cater to every traveler's preferences, guests can choose between the elegant Main House, the cozy Cottage House, or the rustic-chic Barn. Immerse yourself in the thriving arts and culture scene of the Berkshires, with world-class museums and entertainment venues just minutes away. Explore attractions like the Norman Rockwell Museum, MASS MoCA, and Tanglewood, or enjoy exclusive offerings such as tee times at Stockbridge Golf Club and deals at local ski resorts.

Bearskin Neck Motor Lodge is an ocean front lodging located at 64 Bearskin Neck in Rockport, Massachusetts. Despite the term "motor lodge," our rooms are clean and provide a pleasant atmosphere for your stay. Enjoy a bottle of wine and some steamed lobsters on the back deck while watching the sunset. Our friendly staff is always available to provide restaurant recommendations or trip ideas. Each room is equipped with air conditioning, refrigerators, cable TV, and free WiFi. All rooms have ocean front views and a shared balcony with chairs right outside your door. Additional deck tables are available adjacent to the hotel. Free parking is available on Bearskin Neck, with one parking spot per room. We also offer Express Check-In for your convenience. Our central location allows easy access to shops, restaurants, and Front Beach. The office is open from 9 am to 7 PM daily, and assistance is available after hours by calling (978) 546-6677. The deck behind the main office is currently being renovated to create a new alfresco seating area called The Hideaway, which will offer cocktails, beer, wine, and light bites like charcuterie. We look forward to welcoming you to Bearskin Neck Motor Lodge for a relaxing and enjoyable stay.

Chatham Inn is a luxurious institution located at 359 Main Street in Chatham, Massachusetts, United States. This establishment offers a unique experience, being Cape Cod’s only Relais & Châteaux and Forbes Five-Star hotel. Renovated between 2016 and 2019, Chatham Inn seamlessly blends modern decor, top-notch amenities, and exceptional service with the rich history of the oldest inn on the Cape. It has been recognized as one of the top hotels for service and romance in the United States, as well as being rated the number one hotel in Chatham and Cape Cod. The 18 beautifully renovated guest rooms and suites at Chatham Inn feature modern luxuries while preserving the inn's historic charm. Guests can choose from twin, queen, or king bed options, as well as spacious Premier King Rooms or Suites with private balconies, fireplaces, and wet bars. A Chef’s à la carte Breakfast is included in the stay, served in the elegant dining room.

The Duck Inn is a charming lodging establishment located at 10 Duck Pond Way in the picturesque town of Aquinnah, Massachusetts. Nestled amidst nature, this cozy inn offers comfortable accommodations and a peaceful atmosphere for guests looking to relax and unwind. With its serene surroundings and welcoming ambiance, the Duck Inn is the perfect retreat for those seeking a tranquil getaway in the United States.

Foxy Travel, Inc is a premier travel agency located at 38 Providence Road in Northbridge, Massachusetts, United States. With a reputation for providing exceptional customer service and personalized travel experiences, Foxy Travel, Inc is your go-to destination for all your travel needs. Whether you're looking to book a family vacation, a romantic getaway, or a group tour, our team of experienced travel experts will help you plan the perfect trip. Contact us today to start planning your next adventure with Foxy Travel, Inc.

Pilgrim Belle Cruises LLC, located at 77 Water Street in Plymouth, Massachusetts, is a travel agency specializing in scenic cruises on their classic paddlewheel boat, the Pilgrim Belle. Whether you prefer to soak up the sun on deck or relax in the climate-controlled cabin with galley service and a full bar, a cruise on the Pilgrim Belle is the perfect way to experience the beauty of Plymouth Harbor. Watch the sunset over the harbor while enjoying a cocktail, beer, or wine from the full-service bar. In addition to leisure cruises, the Pilgrim Belle is also available for special events and occasions, providing a unique and memorable venue for celebrations. Conveniently located in Plymouth, Captain John Boats offers easy access to the stunning coast of New England, with Boston and New Bedford just a short drive away. For those looking to explore further, the ferry to Provincetown is just a 90-minute ride from Plymouth. Embark on a journey with Pilgrim Belle Cruises LLC and create unforgettable memories on the water.

The Red Lion Inn is a charming and historic establishment located in Cohasset, Massachusetts. Situated at 71 South Main Street, this institution offers a unique combination of food, lodging, and dining experiences. Guests can enjoy comfortable accommodations in a picturesque setting, along with delicious meals served at the on-site restaurant. With its warm and welcoming atmosphere, The Red Lion Inn is the perfect destination for a relaxing getaway or a memorable dining experience.

Located at 304 Cambridge Road in Woburn, Massachusetts, Sogno is a charming Italian restaurant that offers a warm and inviting atmosphere for guests to enjoy delicious meals inspired by the rich culture and history of Italy. Owned by Ron Martignetti, Sogno aims to recreate the feeling of a traditional Italian family gathering, where everyone is welcome to come together and share a meal. The menu at Sogno showcases the diversity of Italian cuisine, featuring dishes from various regions of Italy that are prepared using fresh, locally sourced ingredients as well as imported Italian products. Guests can watch as their meal is being prepared in the restaurant's exposition kitchen, adding to the overall dining experience. From handcrafted cocktails at the bar to Neapolitan brick oven pizzas, Sogno offers a wide range of options for guests to enjoy.

The Club at New Seabury's Popponesset Inn is a charming seaside destination located at 252 Shore Drive in Mashpee, Massachusetts. This institution offers a unique blend of food, lodging, and dining experiences, making it the perfect place for a relaxing getaway or a special event. With stunning views of the ocean, delicious cuisine, and luxurious accommodations, The Popponesset Inn is a must-visit destination for those looking to enjoy the best that Cape Cod has to offer. Whether you're looking for a romantic dinner for two or a weekend retreat with friends, this institution has something for everyone.

Riverboat is a vibrant and lively institution located at 11 South End Bridge in Agawam, Massachusetts. This unique establishment offers a combination of a bar, food, and restaurant all in one. With its cozy atmosphere and picturesque views of the nearby river, Riverboat is the perfect spot to unwind and enjoy a delicious meal or drinks with friends and family. Whether you're looking for a casual night out or a special occasion, Riverboat has something for everyone. Come visit us and experience the charm of this hidden gem in Agawam.

New England Trips Inc. is a premier travel agency located at 90 Canal Street in the heart of Boston, Massachusetts. We specialize in creating unforgettable travel experiences throughout the picturesque New England region. Our team of expert travel advisors are dedicated to crafting unique and personalized itineraries that showcase the best of what New England has to offer. Whether you're looking to explore historic sites, enjoy outdoor adventures, or indulge in delicious local cuisine, we have the perfect trip for you. Contact us today to start planning your dream vacation in New England!

Porto is a vibrant and trendy bar and restaurant located on the Ring Road in Boston, Massachusetts. Known for its delicious food and lively atmosphere, Porto offers a unique dining experience with a menu that highlights fresh seafood and Mediterranean-inspired dishes. The sleek and modern decor creates the perfect setting for enjoying a meal with friends or grabbing a drink at the bar. Whether you're looking for a casual night out or a special occasion, Porto is the ideal spot to indulge in delicious food and drinks in the heart of the city.

The Royal is a charming bar located at 160 Center Avenue in Middleborough, Massachusetts. With its cozy atmosphere and friendly staff, it is the perfect spot to unwind after a long day or catch up with friends over a drink. The Royal offers a wide selection of beers, wines, and cocktails, as well as delicious bar snacks to enjoy. Whether you're looking for a laid-back evening or a lively night out, The Royal is the place to be. Come and experience the royal treatment at this beloved neighborhood bar.

HomeGrown Tours is a premier travel agency located at 1 Seaview Avenue in Oak Bluffs, Massachusetts, United States. We specialize in providing personalized and unique travel experiences for our clients, showcasing the best that the local area has to offer. Our team of experienced travel experts are dedicated to creating unforgettable vacations, whether you're looking for a relaxing beach getaway, a cultural exploration, or an adventure-filled excursion. Let HomeGrown Tours help you plan your next dream vacation and make memories that will last a lifetime.

Santorini is a charming Mediterranean-inspired institution located at 376 Revere Beach Boulevard in Revere, Massachusetts. This establishment offers a delightful blend of food, restaurant, and store services, providing customers with a taste of authentic Greek cuisine and culture. With a warm and inviting atmosphere, Santorini is the perfect place to enjoy delicious dishes, shop for unique Greek products, and experience the vibrant flavors of the Mediterranean. Whether you're looking for a cozy meal, a quick snack, or a special gift, Santorini has something for everyone to enjoy.

The Cottage at Blue Heron Farm is a charming lodging option located at 212 Warner Hill Road in the picturesque town of Charlemont, Massachusetts, United States. Situated on a serene farm property, guests can enjoy a peaceful retreat surrounded by nature. The cozy cottage offers comfortable accommodations and a tranquil atmosphere, perfect for a relaxing getaway. Whether you're looking to unwind in the countryside or explore the nearby attractions, The Cottage at Blue Heron Farm provides a unique and inviting place to stay.

Moorlands Inn is a charming lodging establishment located at 11 Hughes Road in Truro, Massachusetts. Nestled in a picturesque setting, this cozy inn offers comfortable accommodations for travelers looking to unwind and relax. The welcoming atmosphere and attentive staff make Moorlands Inn the perfect destination for a peaceful getaway. With its convenient location in the United States, guests can easily explore the nearby attractions and enjoy a memorable stay. Whether you're seeking a romantic retreat or a family vacation, Moorlands Inn provides a tranquil setting for all types of travelers.

Kutrubes Travel Agency is a premier travel agency located at 328 Tremont Street in the heart of Boston, Massachusetts. With a team of experienced travel experts, we specialize in creating unforgettable travel experiences for our clients. From booking flights and accommodations to arranging tours and activities, we handle every aspect of your trip with care and attention to detail. Whether you're planning a family vacation, romantic getaway, or business trip, Kutrubes Travel Agency is your go-to destination for all your travel needs. Let us help you turn your travel dreams into reality.

Boston Travel Guide is a premier travel agency located at 1 Long Wharf in Boston, Massachusetts. Our team of experienced travel experts are dedicated to helping you plan and book your dream vacation to this historic city. Whether you're looking to explore the Freedom Trail, visit the renowned museums, or indulge in the local cuisine, we have the knowledge and resources to make your trip unforgettable. Let us take the stress out of travel planning and help you create memories that will last a lifetime. Contact us today to start planning your Boston adventure!

Blue Travel LLC d.b.a. KissFromItaly is a premier travel agency located at 32 Papile Lane in Quincy, Massachusetts, United States. Specializing in Italian travel experiences, they offer personalized and unforgettable trips to some of the most beautiful destinations in Italy. With a team of knowledgeable and experienced travel experts, KissFromItaly ensures that every detail of your trip is taken care of, allowing you to relax and enjoy the journey. Whether you're looking for a romantic getaway in Florence, a culinary tour of Sicily, or a cultural exploration of Rome, Blue Travel LLC d.b.a. KissFromItaly is your go-to agency for all things Italy. Start planning your dream Italian vacation today with KissFromItaly.

Halcyon Days Sailing Charters is a premier travel agency located in Gloucester, Massachusetts, United States. Specializing in unforgettable sailing experiences, Halcyon Days offers a variety of charter options for individuals and groups looking to explore the scenic waters of the New England coast. With expert captains and top-of-the-line vessels, guests can relax and enjoy a luxurious and personalized sailing adventure. Whether you're a seasoned sailor or a first-time explorer, Halcyon Days Sailing Charters promises an unforgettable journey on the open sea.

My Vineyard Concierge is a premier travel agency located in the picturesque town of Tisbury, Massachusetts. Our dedicated team of professionals is committed to providing exceptional service and personalized attention to every aspect of your travel experience. Whether you are looking to plan a romantic getaway, a family vacation, or a corporate retreat, we are here to cater to your every need. From booking accommodations and arranging transportation to organizing tours and activities, we will take care of all the details so you can relax and enjoy your time on Martha's Vineyard. Contact us today to start planning your dream vacation!

i tour Puerto Rico, inc. is a travel agency located at 131 Tremont Street in Boston, Massachusetts. Specializing in Puerto Rico travel experiences, our agency offers a wide range of services including personalized itinerary planning, hotel bookings, transportation arrangements, and guided tours. With a team of knowledgeable and experienced travel experts, we strive to provide our clients with unforgettable and authentic Puerto Rican adventures. Whether you're looking for a relaxing beach getaway, a cultural exploration, or an adrenaline-pumping outdoor adventure, i tour Puerto Rico, inc. has you covered. Contact us today to start planning your dream vacation to Puerto Rico!

Martha's Vineyard, MA is a quaint and charming transit station located in Edgartown, Massachusetts, United States. This picturesque destination serves as a gateway to the beautiful island of Martha's Vineyard, offering travelers a convenient and scenic way to explore all that this idyllic location has to offer. With its historic charm, stunning landscapes, and vibrant community, Martha's Vineyard, MA is the perfect starting point for an unforgettable island adventure.

Truro Vineyard is a charming transit station located in Truro, Massachusetts, United States. This picturesque institution offers a unique experience for travelers passing through the area, with a focus on showcasing the beauty and flavors of the local vineyards. Visitors can enjoy tastings of award-winning wines, explore the vineyard grounds, and learn about the winemaking process. With its serene setting and welcoming atmosphere, Truro Vineyard is the perfect stop for those looking to relax and indulge in the pleasures of wine country.

The Rose & Crown is a charming lodging establishment located at 158 Commercial Street in Provincetown, Massachusetts. This historic inn offers a cozy and comfortable atmosphere for guests to relax and unwind during their stay on Cape Cod. With its convenient location near the waterfront and popular attractions, the Rose & Crown is the perfect choice for visitors looking to experience the beauty and charm of Provincetown. Whether you're in town for a romantic getaway or a fun-filled vacation, the Rose & Crown provides a welcoming retreat for all travelers.

Culdesac Cottage Bed and Breakfast is a charming lodging located at 49 Glover Square in the picturesque town of Chatham, Massachusetts. Situated in a peaceful cul-de-sac, this cozy cottage offers a serene and relaxing atmosphere for guests looking to escape the hustle and bustle of everyday life. The accommodations are tastefully decorated and feature modern amenities to ensure a comfortable stay. Guests can enjoy a delicious homemade breakfast each morning, served in the inviting dining area. With its convenient location near beaches, shopping, and dining options, Culdesac Cottage Bed and Breakfast is the perfect choice for a memorable stay on Cape Cod.