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5 Fun And Affordable Cruises Out Of Boston This Year

Author Jeff Gorra

When you think of hopping on a cruise ship for a week, you typically envision flying out of the Northeast and heading down south first. Well, if you are willing to wait a few more months, there are some great cruises leaving right out of Boston again this year.

The seaport area of the city has become a well-established hot spot over the past ten years. It has restaurants, night clubs, and high-rise apartments. You can also walk across the street and sail away for a week.

If you haven’t booked a cruise excursion through an all-inclusive program that bundles in the flight, airfare can easily be a good chunk of the vacation cost. Typically you look for a deal and separately pay for roundtrip flights to Florida. It’s then on you to get from the airport to the dock.

Given the costs, it has become increasingly popular to board a cruise out of New York City as well. These trips leave more frequently throughout the year, including in the winter.

However, Cruise Critic has recently outlined a few great, and cost-effective options for you to enjoy a cruise right out of Boston.

Cruises To Canada, Florida, and the Caribbean Right Out of Boston

If you are flexible on timing, it may be worth your while to wait until the fall. The weather still allows you to enjoy time out on the decks while the ship heads down the east coast of the Atlantic.

Here are some great options starting in September. All leave right out of Boston.

  • Celebrity Cruise to Fort Lauderdale, 10 nights
  • Princess Cruise to Canada, 7 nights
  • Holland America Cruise to the southern Caribbean, up to 14 nights
  • Royal Caribbean Cruise  to San Juan, 7 nights
  • Celebrity Cruise to Maine and Canada, 7-11 nights

The best news is, most of these can be booked for under $2,000 per person. Some are even under $1,000. You can time and flight money and have a few extra vacations days out at sea.

From Pizza To Guitars Here Are Your Best I-95 Stops From Boston To New York

There are roughly 220 miles and four and half hours between Boston and New York. On the drive south (or return trip North), it’s likely you’ll need to make a pit stop. Whether it’s to accommodate a bathroom request, grab a bite to eat or get a breath of air, we’ve compiled a list of the best stops along I-95 on the Boston to New York drive.

We’ll assume here that we are driving south. Therefore, your journey begins in Massachusetts. You’ll pull past Providence and a few exit signs for T.F. Green Airport before enduring the meat of the trip. That would be a good two-plus hours through Connecticut, where you will surely slow down at some point. Finally, after trekking through the Constitution State, you start to see the exit sign numbers get down to single digits. The empire state awaits.

This journey can seem like a grueling effort up and down I-95. In a bigger picture, a four-hour route between two major markets is not really that much. Just ask the Midwest. If you want to drive from Chicago to Minneapolis, you are looking at close to a seven-hour drive, with only one state in the way. Nonetheless, the 1-95 Boston to New York route can be grueling. Therefore, we put together a collection of different stops to help make it more enjoyable.

Of course, this exercise does not include kids screaming in the backseat that need an immediate stop. Perhaps that’s another list. Here, we will pinpoint some pleasing attractions you would have the time to stop for. However, we won’t stray too far off the exits. And while taking 12 hours to play blackjack at Foxwoods would be a blast, we will narrow in on relatively short stops only.

So, let’s hop in the car and find the best stops from Boston to New York along I-95.

*Note – we are not going in order of stops from north to south. We are listing in an overall ranking format.

  • #1 Frank Pepe's Pizza

    We’ll start with the best thing to stop for. Pizza. Frank Pepe’s is a legendary establishment in the New Haven pizza scene. The good news here is that you have choices. If the original New Haven spot is too far off the path (or has a long wait), there’s also a location in Fairfield, CT at Exit 24.

     

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    A post shared by Frank Pepe Pizzeria (@frankpepepizza)

  • #2 Hoxie Scenic Overlook Point

    If you need a moment of fresh air or to loosen up the legs, this scenic lookout point offers a nice view of the Mystic River. There’s comfortable parking space, and its an easy pull off or on to the interstate. It’s not uncommon to find people taking photographs here as well.

    A view of the Mystic River in CT. Hoxie overlook

  • #3 Cafe Tempo Coffee House

    Sure there are dozens of Starbucks or Dunkin Donuts right along the path, but pulling into Cafe Tempo Coffee House in Warwick, Rhode Island is well worth the wait. A homemade banana hazelnut iced coffee makes any slow-moving traffic situation more manageable.

  • #4 Milford Service Area Rest Stop

    After all that pizza and coffee somebody is going to need a bathroom. At mile-marker 41, via southbound access, you will find a rest stop in Milford CT that is a direct pull-off I-95. You can fill up on gas, or more food if you still feel like snacking. There are plenty of fast food and candy options at this stop.

    Blue rest Area sign off the highway, pointing to the exit

  • #5 Bay State Vintage Guitars

    This is applicable on your way out or into Massachusetts. Bay State Vintage Guitars is a family owned shop has some of the nicest custom and vintage guitars available. Each instrument on the wall tells a story and his a history that goes back well beyond what’s considered classic rock. They are located on Washington St. in Norwood.

  • #6 Colony Grill

    Hot oil pizza is a thing in Connecticut and it’s delicious. Colony Grill in Stamford is bound to have whatever game that is live playing on their TV’s. Their menu consists of pizza and drinks, so you know they take their pie seriously. Like Pepe’s, you have a few choices in addition to Stamford. Their Fairfield location is also a stone’s throw off I-95.

     

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    A post shared by Colony Grill (@colonygrill)

Jeff Gorra is a Boston-based writer who has been with Beasley Media Group since the beginning of 2023. He writes about restaurants and food, as well as sports and rock music. His experience also includes show hosting and in-depth creative writing in rock and reggae dub music. Jeff’s an avid surfer, New York Giants, and Pearl Jam fan, however, if you make unforgettable pizza, he is sure to find you.

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