Are you ready to soak up the sun, savor some seafood, and explore a charming coastal town? Look no further than Portsmouth, New Hampshire! This historic city, located just an hour north of Boston, has something for everyone, from picturesque parks to trendy boutiques.
And with these five unique itineraries, you can take it all in. Pick and choose, or stick around and experience all five days. Let’s get this adventure started.
Getting Here:
The closest commercial airport is the Manchester-Boston Regional Airport (MHT), just 50 miles west of Portsmouth, with service to all major cities. International travelers can fly into Boston’s Logan Airport (BOS), an hour south.
Where to Stay:
For budget-friendly hotel accommodations, check out the Howard Johnson by Wyndham or the Hampton Inn Portsmouth Central. Seeking chic and boutique? Both the historic Martin Hill Inn and Hotel Thaxter are just minutes from downtown. And if you’re traveling in an RV – Portsmouth has you covered – with numerous sites just outside the city, such as Old Stage Campground and the Sea Coast Camping and RV Resort.
Day 1: Museums, Markets and Theatrics
Morning
Begin your week in Portsmouth with breakfast at The Friendly Toast. With bright green walls, funky accents and creative twists on standard breakfast classics, this quirky diner serves up delicious food with a fun atmosphere. Try the chicken and waffles infused with bacon and topped with fire-roasted poblano corn, jalapeno jack cheese, and chipotle maple sour cream
After breakfast, head to the Strawbery Banke Museum, a ten-acre outdoor living history museum showcasing the history of Portsmouth and its inhabitants. Spend the morning exploring dozens of historic buildings like the Pitt Tavern, a Revolutionary War-era tavern built in 1775, and the Gov. Goodwin Mansion, the furnished home of Civil War governor Ichabod Goodwin. Expect to spend 2-3 hours exploring the grounds, where you’ll also interact with actors playing laborers, merchants, millworkers, tradesmen, or politicians going about their daily lives.
Afternoon
Grab lunch at Cavas Tapas & Wine Bar, a rustic-chic bistro specializing in modern Spanish tapas with an extensive wine list. For more casual fare, grab soup and a sandwich at the nearby Geno’s Chowder & Sandwich Shop.
Next, spend the afternoon exploring the historic Market Square in the heart of downtown. This shopping hub features 17th-century buildings, bookstores, art galleries, cafes and antique stores. Browse Pickwick’s Mercantile, a modern-day apothecary and gift shop selling soap, candles, perfumes and journals. Laugh at Off Piste, a novelty store known for its humorous planters, coffee mugs, books and clothing. Or, tour the Museum of New Art, featuring exhibitions from young up-and-coming artists. If you’re interested in learning more about the history of Market Square, guided walking tours take place on Thursdays and Saturdays. Keep an eye out for the kiosk.
Evening:
Enjoy dinner at Moxy, a stylish restaurant specializing in shared plates and creative cocktails, from beef short rib marmalade to the miss frizzle – a sparkling cocktail combining pisco, spiced pear and cucumber.
End the day with an evening of entertainment at the Seacoast Repertory Theatre, just a quick four-minute walk from Moxy. While the theater may be on the smaller side, the talent on stage is larger than life. From Broadway-style musicals to classical plays, it’s the perfect way to end your first day in Portsmouth.
Day 2: Seaside Vibes and Historical Sites
Morning
Wake up to fluffy blueberry pancakes and eggs benedict at Colby’s Breakfast & Lunch, a classic diner with an extensive breakfast menu and quaint atmosphere.
What’s next? How about a little road trip along New Hampshire’s seacoast? Home to rocky shores, sandy beaches and adorable small towns, the coastline offers ample opportunities for photo ops. Spend the rest of the morning exploring Odiorne Point State Park, a 135-acre nature area with miles of stunning hiking trails and ocean views in Rye, New Hampshire, just a short drive from Portsmouth. Hike the Ordiorne Point Loop Trail. See the remains of Fort Dearborn, a historic structure from World War II. Or, tour the Seacoast Science Center and discover exhibits about the Gulf of Maine, reef restoration and even get up close and personal with urchins and sea stars!
Afternoon
Continuing the ocean theme, fresh seafood is on the menu at The Beach Plum. Serving up classic New England fare, you can chow down on massive lobster rolls and steaming bowls of clam chowder. Don’t forget to save room for hand-dipped ice cream for dessert.
After lunch, visit Fort Constitution and New Castle Beach, a fort dating back to the American Revolution and a beach boasting incredible views of Portsmouth Harbor. Finally, take a detour to the iconic Portsmouth Harbor Lighthouse. Built in 1771, the lighthouse was the first light station north of Boston. Tours are currently suspended due to storm damage but are expected to resume soon.
Evening
Back in town, enjoy farm-to-table dining at Black Trumpet, a bistro featuring dishes made from locally sourced ingredients with a Mediterranean twist. There’s also an upstairs wine bar. After dinner, enjoy a concert or comedy show at The Music Hall, the oldest-operating theater in New Hampshire. The hall has been known to host the Great Bay Philharmonic Orchestra, indie artists like Abigail Lapell and comedians such as Howie Mandel and Drew Lynch.
Day 3: Parks, Hiking Trails and Sunset Boat Rides
Morning
Grab a quick breakfast at Cafe Espresso, a laid-back joint known for its creative egg benedicts and breakfast sandwiches and burritos. Then, enjoy a short walk to the USS Albacore Museum and Park, home to a historic naval submarine and museum.
Next, embark on a self-guided tour of the submarine, where you can look through the periscope and walk through the engineering spaces, control room and bunk room. Check out the audio stations that detail the submarine’s features. Afterward, check out the gift shop for souvenirs and stroll through the Memorial Garden, which honors the men and women who served on the Albacore.
Afternoon
Kick off the afternoon by biting into a juicy burger at Lexie’s Joint. Pair it with a craft beer and some truffle fries, and you’re good to go for the next adventure – a self-guided walking tour of Portsmouth Harbour Trail. This trail boasts ten National Historic Landmarks and ten buildings on the National Register of Historic Buildings and will guide you through the South End, North End, and Downtown Portsmouth. Check out sites like the North Church, the Moffatt-Ladd House (home of one of the signers of the Declaration of Independence) and the Memorial Bridge.
Evening
There’s no better way to unwind after a day exploring historic Portsmouth than with a sunset sail on the Piscataqua River aboard the Gundalow Company’s gundalow boat. Take in the sights as you cruise on a flat-bottomed cargo barge and learn about the region’s history from maritime experts. You’ll even help the crew with steering the ship!
Afterward, enjoy a relaxing dinner on the outdoor patio at Jumpin’ Jay’s Fish Cafe. Known for its trendy and casual atmosphere, you can sample oysters and their signature haddock piccata.
Day 4: Mansions, Breweries and Comedy Clubs
Morning
Start your morning with coffee and pastries while people watching on the streetside patio at Popovers on the Square. This bakery serves freshly baked bread, popovers, and eclairs and even has gluten-free items.
Next, journey through time at the Wentworth-Coolidge Mansion, named after Benning Wentworth, New Hampshire’s first royal governor. Built in the 1700s, this 40-room mansion is one of the last remaining homes of the colonial era. During the tour, you’ll explore the dining room, kitchens and more – all furnished with 18th-century woodwork, curtains and art. After the tour, walk on the Little Harbor Loop Trail – a charming waterside pathway connecting the mansion grounds to Creek Farm and Portsmouth Conversation Land.
Afternoon
Sit down for lunch at The District, a chic restaurant and bar with patio seating. This gastropub features craft beers and creative pub fares like poutine, crab cakes, burgers and pad Thai.
Next, enjoy a laid-back afternoon with a brewery tour and tasting at Smuttynose Brewing Company in nearby Hampton or Great Rhythm Brewing Company right here in Portsmouth. Both joints have refreshing IPAs, lagers, stouts, and sour ales with picturesque tasting rooms. Great Rhythm’s tasting room overlooks the beautiful North Mill Pond, while Smuttynose has an indoor tasting bar and beer garden.
Evening
Head to downtown Portsmouth for dinner at Franklin Oyster House. This seafood restaurant specializes in raw bar items and entrees like oysters, mussels, calamari, and fish tacos.
Ready for a night of laugh-out-loud entertainment? Check out a comedy show at The Stone Church Music Club. Located in a historic building built in 1832, this venue has a lovely beer garden and a main club with live music.
Day 5: Birdwatching, Naval History & the Sweet Sounds of Jazz
Morning
Your final day in Portsmouth begins with breakfast at Roundabout Diner & Lounge, a dose of nostalgia with an extensive menu of classic staples such as eggs, pancakes and french toast – all in an atmosphere that mirrors the 1950s, complete with checkered floors and neon signs.
Next, take a scenic drive 15 minutes south of Portsmouth to Rye Harbor State Park, a breathtaking nature area featuring views of the Atlantic and the Isle of Shoals. Bird watchers flock to this area due to the abundance of fowl in the region, from ducks to gulls, loons and egrets.
Afternoon
While near Rye Harbor, lunch at Ray’s Seafood Restaurant is a must-do. This classic New England seafood spot boasts fresh catches and a homey vibe with friendly staff. Enjoy house-caught lobster, fantastic rolls, fried clams, and fresh chowder.
After lunch, take a whale watching tour with Granite State Whale Watch. You’ll travel to Jeffrey’s Ledge, where you’ll have the opportunity to spot Humpback whales, Finback whales and possibly catch a glimpse of the endangered Right whale. Sightings of dolphins, sharks and harbor seals are also possible on your tour.
Evening
For your final meal in Portsmouth, savor the flavor of modern Mexican cuisine at Vida Cantina. With a menu featuring pork belly tacos, goat cheese queso and fried avocado, this fun and funky restaurant is a never-ending party. There’s also an extensive margarita menu.
Finally, wrap up the evening with easy listening at Jimmy Jazz & Blues Club. Located in a historic landmark built in 1905, this multi-level venue has been meticulously restored, offering incredible acoustics for its nightly shows. Dance the night away to the sounds of musicians like Early Times & the High Rollers or Kenny Garrett on his sax while toasting to an incredible five days in Portsmouth.
