A Romantic Long Weekend in New Haven

Fall in love all over again in historic New Haven.

22 April 2023

A romantic trip to New Haven will take you to a charming coastal town in Connecticut, known for its Ivy League university and picturesque scenery. You can indulge in cozy and intimate dinners at the many top-rated restaurants and enjoy a stroll through the historic Yale University campus. For a truly romantic experience, take a sunset boat ride along the Long Island Sound and take in the scenic beauty.

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Travel plan

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Day 1

Arrival and Exploration

  • Check into The Study at Yale, a boutique hotel with sleek design and cozy atmosphere
  • Start the day with New Haven-style pizza at Pepe's, featuring charred crust and fresh toppings
  • Walk around Yale University's gothic architecture and visit the Yale Art Gallery or the Beinecke Rare Book & Manuscript Library
  • Stop by Louis' Lunch, the birthplace of the hamburger, for a quick bite
  • Finish the day with craft cocktails at Ordinary, a speakeasy hidden in a former post office
Day 2

Coastal Getaway

  • Drive to the charming town of Guilford for breakfast at The Place, a rustic outdoor spot known for their lobster rolls and live music
  • Spend the morning kayaking or sunbathing at Hammonasset Beach State Park, featuring a scenic coastline and nature trails
  • Head back to New Haven for lunch at Claire's Corner Copia, a vegetarian restaurant with hearty soups and organic juices
  • Take a tour of Yale's campus and see the iconic Bill Clinton–Bob Dole presidential debate site
  • Enjoy artisan ice cream at Arethusa al Tavolo, a cozy dessert spot with unique flavors
Day 3

Art and Culture

  • Visit the Yale Center for British Art, showcasing masterpieces spanning five centuries
  • Grab a bagel and coffee at The Donut Crazy, a trendy cafe with creative donuts
  • Explore the Yale Peabody Museum of Natural History, featuring a dinosaur hall and Native American artifacts
  • Take a stroll through Edgerton Park, a botanical garden with a picturesque greenhouse
  • Finish the day with dinner at Elm City Social, a retro-chic restaurant serving seasonal American fare and craft beer
Day 4

Historic Tour

  • Start the morning with breakfast at Atticus Bookstore Cafe, a quaint spot with homemade pastries and coffee
  • Visit the New Haven Museum, featuring exhibits on the city's history and culture
  • Discover East Rock Park, a scenic recreation area with hiking trails and panoramic views of the city
  • Stop by the Yale University Art Gallery, showcasing ancient to contemporary artworks
  • End the day with a farewell dinner at Zinc, a French-inspired brasserie with an intimate ambiance and impressive wine list.

Length of stay

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Type of trip

Standard trip Budget Family Friendly Romantic Stag do

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

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Type of trip

Standard trip Budget Family Friendly Romantic Stag do

More travel plans

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Four Days of Family Fun in Vibrant New Haven

New Haven, located in Connecticut, is a fantastic destination for a family-friendly trip. Explore the prestigious Yale University campus and visit the Yale Peabody Museum of Natural History, which is home to fascinating dinosaur exhibits. Enjoy a relaxing day at Lighthouse Point Park, where kids can play on the beach, ride the carousel, and even spot some seals.