Wine Tours from the South Shore: Westport to Newport

The closest wine country to the South Shore is along the coast where Massachusetts meets Rhode Island: Westport and Dartmouth on the Massachusetts side, Little Compton, Portsmouth and Middletown on the Rhode Island side. Westport is a little over an hour from Hingham and Newport about an hour and a half, so a chauffeured wine tour fits in one relaxed day, with two or three tastings, lunch, and nobody in your group who has to drive home.

Here are two routes that work well, and how to plan the day.

Why book a driver for a wine tour

• Everyone tastes. No designated driver sitting out the day.
• No navigating back roads. The vineyards are spread along country roads with little signage.
• One vehicle for the group. Arrive together, leave together, and keep your purchases safely in the car between stops.
• A flexible day. Booked by the hour, your chauffeur waits at each winery and moves on when you are ready.

Route 1: Westport and Little Compton

This route stays in the farm country on both sides of the state line, among stone walls, farm stands and views of the water.

• Westport Rivers Vineyard, Westport, Massachusetts. A long-established family vineyard, well known for its sparkling wines.
• Running Brook Vineyards & Winery, North Dartmouth, Massachusetts, a short drive inland from Westport.
• Sakonnet Vineyard, Little Compton, Rhode Island. One of New England's oldest vineyards, a scenic drive south of Westport.

Drive: about 55 miles from Hingham to Westport, roughly 1 hour 15 minutes in light traffic, and a little less from Braintree or Weymouth. The wineries are 15 to 25 minutes apart.

Route 2: Aquidneck Island and Newport

This route crosses into Rhode Island to the island that holds Portsmouth, Middletown and Newport, so you can pair the tastings with lunch by the harbor.

• Greenvale Vineyards, Portsmouth, Rhode Island. A historic farm with vineyard views down to the Sakonnet River.
• Newport Vineyards, Middletown, Rhode Island. A large winery with a restaurant, a few minutes from downtown Newport.
• Lunch in Newport, then the drive home, or an evening stop on Bellevue Avenue before you leave.

Drive: about 65 miles from Hingham to Newport, roughly 1 hour 40 minutes in light traffic. Summer weekend traffic into Newport can add more.

Planning the day

Plan on six to eight hours door to door. Two wineries and a long lunch make a relaxed day; three is about the maximum before the tastings blur together.

A few practical tips

• Bring ID. Everyone who tastes must be 21 or older and may be asked for identification.
• Eat lunch. Tasting pours add up over an afternoon.
• Bring a cooler bag for bottles on a hot day. The car is air-conditioned, but bottles still prefer the shade.
• Go in the fall. September and October are harvest season and the prettiest time on the coast, which also makes them the busiest. Book the car early.

Which vehicle?

• 2 to 7 guests: a luxury SUV: a Cadillac Escalade or Jeep Grand Wagoneer L for up to 7, a Chevrolet Suburban for up to 6.
• Up to 12 guests: a passenger van, for a birthday or a company outing.
• A celebration for up to 10: a stretch limousine, if the wineries on your route have room to park it. Ask us when you plan the route.

Book the day by the hour, and see our fleet for every vehicle.

Frequently asked questions

How far are the wineries from the South Shore?

Westport is about an hour and 15 minutes from Hingham in light traffic, and Newport about an hour and 40 minutes. From Braintree and Weymouth, both are a little closer.

Can we bring food or drinks in the car?

Ask us when you book, and we will tell you what is allowed in the vehicle you choose.

Can you plan the route for us?

Tell us how many wineries you want to visit and where you would like to have lunch, and we will plan the timing and the drive between stops with you.