The third-oldest city in the country boasts an enviable waterfront setting, grand architecture, a booming arts and theater scene, and vibrant community spirit. Meander its worn brick streets, flanked by 18th-century homes and historic sites, pretty gardens, and galleries showcasing local and national artists.
MODERN DIGS: The Ale House Inn (121 Bow St., 603-431-7760, www.alehouseinn.com, $139.99-$299.99) is located in a historic brick building, once home to the Portsmouth Brewing Co. Inside the 10-room inn is sleek and contemporary, more urban boutique than country inn. Modern, loft-like rooms have private baths, luxurious linens, and iPads. Guests have free use of Trek cruiser bikes, but the property is within easy walking distance of shops and restaurants.
WATERSIDE DINING: The large outdoor deck at Martingale Wharf (99 Bow St., 603-431-0901, www.martingalewharf.com, sandwiches $9-$18), overlooking the Piscataqua River and Portsmouth Harbor, is the best place for drinks and casual fare on a hot summer night. Try the watermelon martini with steamed mussels and truffle french fries.
ROMANCE IS IN THE AIR: Walk up narrow stairs to the tiny wine bar at Black Trumpet (29 Ceres St., 603-431-0887, www.blacktrumpetbistro.com, small plates $6-$14, entrees $18-$26), where you’ll find brick walls, wood flooring, low lights, and a handful of tables. There’s a smart wine list and small imaginative dishes, like the pan-seared foie gras pancake with marrow butter and smoked salmon on blue corn blini with nettle puree, created by award-winning chef Evan Mallett, a 2011 and 2013 James Beard Best Chef Northeast nominee. Ristorante Massimo (59 Penhallow, 603-436-4000, www.ristorantemassimo.com, entrees $22-$36) is a romantic Italian eatery housed in a former bank building. The brick and stone dining room, with linen-topped tables, fresh flowers, and original, world-class artwork, is elegant and enchanting, and the made-from-scratch dishes are consistently delicious. Splurge on lobster two ways, served side-by-side: grilled lobster with rosemary butter and lobster risotto with butter-poached lobster claws.
HISTORY IN THE MAKING: Stroll award-winning gardens and visit historic homes, dating from the early 1600s through the 1950s, at the 10-acre Strawbery Banke Museum (14 Hancock St., 603-433-1100, www.strawberybanke.org, daily May-October, adults $17.50, ages 5-17 $10). Portsmouth is loaded with historic buildings and landmarks, including the 1763 Moffatt-Ladd House and Gardens (154 Market St., 603-436-8221, www.moffattladd.org, June-mid-October, Mon-Sat 11 a.m.-5 p.m., Sun 1-5, adults $6, children $2.50), the 42-room Wentworth-Coolidge Mansion State Historic Site (375 Little Harbor Road, 603-436-6607, www.nhstateparks.org, mid-June-Sept. 2, daily 10-4, Sept. 7-mid-October Sat-Sun 10-4, N.H. residents adults $4, under 18 free, nonresidents adults $5, 6-17 $3), the 1784 Governor John Langdon House (143 Pleasant St., 603-436-3205, www.historicnewengland.org, June-October, Fri-Sun 11-5, adults $6, students $3), and the John Paul Jones House (43 Middle St., 603-436-8420, www.portsmouthhistory.org, May-October daily 11-5, adults $6, 12 and under free). The Portsmouth Chamber of Commerce offers guided tours along the Portsmouth Harbour Trail, visiting several historic sites and landmarks (late June-early October, Tue-Thu and Sat 10:30 a.m., meet at Market Square information kiosk, no reservations required, adults $12, 8-14 $8).
WATER ADVENTURES: Sail the Piscataqua River on a replica gundalow (60 Marcy St., 603-433-9505, www.gundalow.org, one- to two-hour sails, $15-$35), or take a guided kayaking tour with Portsmouth Kayak (187 Wentworth Road, 603-559-1000, www.portsmouthkayak.com). Choose from a variety of excursions, including kayaking in Great Bay and Portsmouth Harbor, and full-moon tours.
LET US ENTERTAIN YOU: Watch first-rate, professional musicals and plays at the intimate Seacoast Repertory Theatre (125 Bow St., 603-433-4472, www.seacoastrep.org). The Players’ Ring (105 Marcy St., 603-436-8123, www.playersring.org), with a small, 75-seat venue located in a historic 19th-century building, showcases local artists and original works. Top-name musicians, authors, dance troupes, and comedians appear at the beautifully restored, 1878 Victorian-style Music Hall (28 Chestnut St., 603-436-2400, www.themusichall.org). Watch free outdoor movies on a giant screen and live plays at pretty Prescott Park, surrounded by 10 acres of lawns, gardens, walkways along the Piscataqua River (Prescott Park Arts Festival, 603-436-2848, www.prescottpark.org, July-mid-September, suggested donation $5-$10).