The Ultimate 5-Day New Haven Adventure

Discover the historic charm and vibrant culture of New Haven.

22 April 2023

New Haven, located in Connecticut, is a vibrant college town that offers plenty of attractions for tourists. Visitors can explore the beautiful campus of Yale University, take a stroll through the picturesque East Rock Park, and indulge in New Haven's famous collection of pizza restaurants. The city is also home to several museums, including the Yale University Art Gallery and Peabody Museum of Natural History.

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Travel plan

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Day 1

Welcome to New Haven!

  • Check-in at The Study at Yale, a charming boutique hotel with an Ivy League ambiance
  • Grab a coffee at Book Trader Cafe and browse their impressive book collection
  • Visit the Yale University Art Gallery for a dose of art and culture
  • Take a stroll down Chapel Street, with its quirky shops and restaurants
  • End the day with a pizza feast at Frank Pepe Pizzeria Napoletana, a legendary New Haven landmark
Day 2

Outdoor Adventures

  • Start with a hearty breakfast at Bella's Cafe
  • Head to East Rock Park for a scenic hike and breathtaking views of the city
  • Rent a bike and pedal along the Farmington Canal Trail
  • Visit Lighthouse Point Park for a beach day and a tour of the historic lighthouse
  • Dine at The Place, an unassuming seafood joint with picnic tables and a BYOB policy
Day 3

Cultural Gems

  • Explore the New Haven Museum and learn about the city's rich history
  • Visit the Beinecke Rare Book and Manuscript Library, a stunning modernist building that houses rare books and manuscripts
  • Take a guided tour of the historic Grove Street Cemetery, final resting place of many notable figures
  • Catch a show at the Yale Repertory Theatre or Shubert Theatre
  • Dine at Olmo Kitchen, a farm-to-table restaurant with Italian influences
Day 4

Day Trips

  • Take a train to Mystic Seaport, an open-air maritime museum that offers a glimpse into New England's seafaring past
  • Visit the picturesque town of Guilford and stroll along the Green, with its quaint shops and historic buildings
  • Tour the Thimble Islands by boat, a collection of tiny islands off the coast of Branford
  • Snack on lobster rolls at Lenny & Joe's Fish Tale, a seafood shack that's been around since 1979
  • Return to New Haven for a nightcap at Ordinary, a hip bar that specializes in craft cocktails
Day 5

Farewell, New Haven

  • Savor a final breakfast at Claire's Corner Copia, a vegetarian haven with a cozy ambiance
  • Visit the Yale Center for British Art, with its outstanding collection of British masterpieces
  • Take a leisurely walk in Edgerton Park, a peaceful oasis with beautiful gardens
  • Shop for souvenirs at Atticus Bookstore Cafe, a cozy shop with books, gifts, and coffee
  • Say goodbye to New Haven with a dinner at Zinc, a sophisticated restaurant with a modern American menu.

Length of stay

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Type of trip

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How to get there

Plane

The easiest way to get to New Haven is to fly to Tweed-New Haven Regional Airport. Airlines like American Eagle and Delta operate frequent flights to this airport from major cities in the US.

Car

Driving to New Haven from nearby cities is a good option. Major highways such as I-95 and I-91 connect to New Haven. It takes about 2 hours to reach New Haven from New York City and 2.5 hours from Boston.

Train

One of the best ways to get to New Haven is by taking the Amtrak Northeast Regional train. The New Haven Union Station connects to several major cities including New York City, Boston, and Providence.

Boat

Travelling by boat to New Haven is not recommended because the city doesn’t have a major port. However, nearby cities like Bridgeport have a ferry service to Port Jefferson, Long Island.

Bus

Taking a bus to New Haven is also a convenient option. Greyhound and Peter Pan Bus Lines have regular services to New Haven from major cities. The bus terminal is located at 50 Union Avenue, New Haven.

Destination

New Haven

New Haven is a city that takes its pizza seriously – like, “trying to create world peace through the perfect pie” seriously. But don't let the pizza dominance fool you, there's plenty of other reasons to visit this charming Connecticut town.

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Number of days

1 2 3 4 5

Type of trip

Standard trip Budget Family Friendly Romantic Stag do

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