The 7 Best Wine Country Day Trips in the USA

1.Napa and Sonoma Wine Country Full-Day Tour from San Francisco

★★★★★★★★★★4.5 · 4,455 reviews · 8 to 9 hours (approx.) · from $165Our pick

Spend 8 to 9 hours crossing the Golden Gate Bridge, tasting at three changing Napa and Sonoma wineries, and enjoying free time in Sonoma Plaza. Guides such as Don, Debbie, Thomas, and Rick are noted for strong commentary, though the full-size coach and changing winery schedule require some flexibility.

“Enjoyable tour visiting 3 wineries. Understand that this tour is on a full sized coach with the driver giving commentary along the way. No problem with that but you don’t get the more personal experience that you do on a smaller bus. That said, our driver was very good.”

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2.Boston to Martha’s Vineyard Day Trip with Optional Island Tour

★★★★★★★★★★4.5 · 3,162 reviews · 12 hours (approx.) · from $129

Leave Boston early in a 24-passenger minibus, ride the Island Queen ferry across Vineyard Sound, then explore Martha’s Vineyard for 5.5 to 6 hours. Choose free time or an added three-hour island tour with stops at Edgartown and Gay Head Cliffs. Guides such as Tom, Elaine, and Johnny Boston are known for lively local narration.

“You are not going to see, not even from a distance, the rich and famous homes. We did enjoy the rich homes in Edgartown but should have had a stop/off the bus by the Gingerbread homes and the Jaws movie area.”

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3.Boston: Martha’s Vineyard Day Trip with Optional Island Tour

★★★★★★★★★★4.6 · 573 reviews · 13 hours · from $129

Travel from downtown Boston to Martha’s Vineyard by minibus and ferry, then choose six hours of guided sightseeing and free time, or explore independently. Local guides such as Tom and Anthony share island stories, while hotel pickup, ferry tickets, snacks, water, and a guidebook simplify this long but rewarding day.

“Anthony was aperfect guide, lots of nice and funny stories and facts We would have liked to stay a little longer in Edgartown and especially at the cliffs of Gay Head”

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4.Martha’s Vineyard Day Trip with Optional Island Tour from Boston

★★★★★★★★★★4.5 · 407 reviews · 13 hours (approx.) · from $130

Travel from Boston to Martha’s Vineyard by minibus and ferry, with commentary from guides such as Keith, Rory, Matt, and Jimmy. Choose six hours of free time or add a three-hour island tour covering Oak Bluffs, Edgartown, and Aquinnah.

“Keith was full of information about Boston & MV, he made sure everyone was familiar with ferry port before leaving us and gave many suggestions for things to do in Boston and on the island. NEX staff was always available when I called with questions and friendly. I would definitely use NEX again if in Boston.”

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5.Boston: Martha’s Vineyard Day Trip with Optional Island Tour

★★★★★★★★★★4.6 · 123 reviews · from $120Best value

Travel from Boston to Woods Hole by comfortable minibus, cross by ferry, then explore Martha’s Vineyard at your own pace or add a three-hour island tour. Guides including Keith, Matt, Rory, and Harry provide local background, history, food tips, and photo stops across the island.

“I had a wonderful time on this day trip to Martha's Vineyard. The tour company was very accommodating. The tour guides were pleasant, knowledgeable, and entertaining. Everything went smoothly. I would definitely recommend New England Excursions.”

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6.San Antonio: Fredericksburg Wineries Day Trip with Tastings

★★★★★★★★★★4.9 · 15 reviews · 6h 30m · from $179

Travel from San Antonio in a small van with an English-speaking guide, stopping at Sister Creek Vineyards and Texas Wine Collective for tastings. Enjoy crackers, chocolate, and water, then spend 90 minutes shopping, eating, or sightseeing in Fredericksburg. Guides may include Matt or Brandy.

“The trip was great! Matt does an awesome job and the two wineries he selected were both excellent. Highly recommend Matt and his tour!”

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7.Martha’s Vineyard & Essex 2-Day Tour from New York | Kids 50% Off

★★★★★★★★★★5.0 · 3 reviews · 2 days (approx.) · from $478Top rated

Leave New York at 6:30 a.m. for a two-day group tour covering Essex, Newport, and Martha’s Vineyard. Expect round-trip transport, one hotel night with breakfast, a narrated island tour, and optional attraction tickets. The summer kids’ offer can cut costs for families.

“The tour is wonderful! It is very relaxing but have lots of entertainments. It is also very well organized. The steam train and river boat was just a fantastic adventure. We also enjoyed very much visiting the Breakers cottages, it really looks like Renaissance luxury cottages. And Martha's Vineyard Island is beautiful, wonderful beaches and relaxing atmosphere.”

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