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Trip List by GotWanderlust

Insider Tips! The Perfect Weekend in Perfect Portsmouth, NH.

May 20, 2006  I've been traveling as long as I can remember . . . and loving it!
4.0 of 5 stars based on 30 votes

I moved to Portsmouth, NH when I was 15 . . . so I have the unique perspective of being both a visitor and a local. Let me share with you some insider tips that will make your visit to this "Top 10 Town" a real delight.

  • Explore locations featured in this Trip List: Portsmouth, Dover, New Castle
  • Category: Perfect weekend
  • Traveler type: Culture, Sightseeing, Shopping, Active/Outdoors
  • Appeals to: Couples/romantics, Honeymooners, Families with small children, Families with teenagers, Seniors, Budget travelers, Active/adventure, Tourists
  • Seasons: Summer
  • 1. Friendly Toast
    The Friendly Toast, Portsmouth, New Hampshire

    THE BEST BREAKFAST.

    Okay, I love this place so much, I almost don't want to share it with you. Almost. The Friendly Toast is a unique place - with its garage sale decor and tattooed wait staff. But don't let it fool you. The food is seriously good. And there's something for everyone - even the vegetarians in your group.

  • 2. Market Square
    Market Square, Portsmouth, New Hampshire

    TAKE A WALK.

    Head up the street (towards the church, smack dab in the middle of downtown) to Market Square. This is the center of activity with coffee shops, art galleries, bookstores, antique shops, and many original 17th-century buildings.

    From here, follow the Portsmouth Harbour Trail, a self-guided walking tour highlighting the town's history and character (pick up the trail guide at the Information Kiosk in front of Breaking New Grounds coffee shop).

  • 3. Portsmouth Brewery
    Portsmouth Brewery, Portsmouth, New Hampshire

    HAVE A COLD ONE.

    Okay, so you worked up a bit of an appetite (and a thirst) on your walk. Just around the corner from Market Square is the Portsmouth Brewery, this lively brewery serves up great beer and equally tempting lunch items.

  • 4. Prescott Park
    Prescott Park, Portsmouth, New Hampshire

    STOP AND SMELL THE OCEAN.

    Put your nose to the wind and follow the ocean scents and you head towards the water. Prescott Park, about a 5-minute walk from Market Square, is situated on some of the most impressive real estate in Portsmouth, sitting right on the water's edge. Take in the water views, the flower views, or bring a blanket and take a nap under one of the many trees.

  • 5. Strawbery Banke Museum
    Strawbery Banke Museum, Portsmouth, New Hampshire

    YOU CAN BANKE ON IT.

    Turn your back to the sea and you'll see Strawbery Banke Museum. This 10-acre outdoor museum traces the history of the town, with costumed interpreters providing demonstrations of trades and insights into earlier Portsmouth times.

  • 6. Children's Museum of Portsmouth
    Children's Museum of New Hampshire, Dover, New Hampshire

    MAKE THE KIDS HAPPY.

    If you've got energetic children, Strawbery Banke might not be the right place but literally steps away, you'll find the perfect place. A sense of energy and excitement pervades the Children's Museum of Portsmouth, an arts and sciences museum where kids aged 1 - 11 get to put their hands on lots of fun and educational exhibits, from a working telegraph to a space shuttle cockpit.

  • 7. Black Trumpet Bistro
    Black Trumpet Bistro, Portsmouth, New Hampshire

    CROSS ON OVER.

    In the mood for a little elegance? How about some eclectic international fare? This is your place. Lindbergh's Crossing is housed in a historical brick colonial row building, with water views. It's casual and welcoming yet with an air of sophistication.

  • 8. Press Room Bar
    Press Room Bar, Portsmouth, New Hampshire

    A PRESSING ENGAGEMENT.

    This bar is popular with locals because it offers an inviting atmosphere and casual entertainment almost every night (usually upstairs).

  • 9. Wentworth by the Sea, A Marriott Hotel & Spa
    Wentworth by the Sea, A Marriott Hotel & Spa, New Castle, New Hampshire
    Show Prices
    Avg price: $277

    TAKE A TRIP BACK IN TIME.

    While not in Portsmouth, this is - hands down - this is the best place to stay in the area. Wentworth By The Sea is in New Castle, a little island off Portsmouth. This grand hotel was built in the 1870s, fell into a state of glorious disrepair and closed its doors in 1982, was slated for demolition time and time again (each time locals fought to save the landmark) and was finally purchased and totally redone--and I mean totally--in 2003.

  • 10. Golden Egg
    Golden Egg, Portsmouth, New Hampshire

    AN EGG-CELENT CHOICE.

    Lines out the front door, snaking alongside the building mean one thing - the breakfasts here are delicious. If you stay at Wentworth By The Sea, you'll drive right past on your way in.

  • 11. Isles of Shoals Steamship Company
    Isles of Shoals Steamship Company, Portsmouth, New Hampshire

    TAKE A 3-HOUR TOUR.

    Hop on board and see Portsmouth from the water and then sail out to the Isles of Shoals. You don't get off the boat, but you do see several islands, a lighthouse, Portsmouth Naval Shipyard, and "the Alcatraz of the east," the now defunct navy prison. The views are always wonderful.

  • 12. Currents Mediterranean Bistro

    OFF THE OCEAN BUT STILL ON THE CURRENT.

    Across the street from the Portsmouth Brewery, you'll find a little gem of a restaurant: Currents. You've really got to look for it and, when you find it, the food is fresh and light. Dining outside, if there's a seat, is refreshing. And sipping the champagne sangria is an out-of-body experience.

  • 13. Attrezzi

    FREE WINE IS THE BEST.

    Head around the corner to Attrezzi, a food, wine and housewares shop for complimentary wine tastings of unusual vintages.

  • 14. Shop, Shop, Shop

    CHARGE!

    Portsmouth has a range of shopping opportunities, from the not-so-unique (Banana Republic) to the oh-so-unique (Macro Polo, where you'll find the craziest things for your house . . . I promise). Get your credit card ready and hit the streets. Remember, you're trying to work up an appetite for dinner.

  • 15. Ristorante Massimo
    Ristorante Massimo, Portsmouth, New Hampshire

    GIVE YOURSELF A TREAT.

    Just off Market Street is Portsmouth's version of Little Italy. Okay, it's just one restaurant. But - Mama Mia - what a restaurant. At Anthony Alberto's, you'll enjoy authentic Italian offerings. Warning: it's upscale so I hope you left some room on your credit card after an afternoon of shopping.