Exploring Portsmouth, New Hampshire: A 2-Day Itinerary

Hello again, fellow wanderers! (And if you’re new here, welcome to the adventure!) As I’ve shared before, my international escapades are on hold this year while I take a deep dive into exploring the wonders of the USA. Over on 50 at 60, I’m documenting my ambitious quest to visit all 50 states during my 60th year, with plenty of stories, photos, and probably some questionable road trip snacks along the way.

While I’m busy capturing all that state-to-state action, I’m also popping in here to start laying the groundwork for my next adventure—New England, here I come! Armed with AI and a love for good planning, I’ll be mapping out my journey and sharing the details soon. Stay tuned for more posts as I prepare to hit the road (again)!


Portsmouth, NH

Located on the picturesque Seacoast of New Hampshire, Portsmouth is a historic maritime city with a vibrant cultural scene, charming streets, and beautiful waterfront views. Known for its rich history, eclectic mix of shops and restaurants, and vibrant arts community, Portsmouth offers a delightful escape for those looking to experience New England charm. This two-day itinerary will guide you through the best of Portsmouth, from its historic landmarks and scenic waterfront to local dining and artistic treasures. Prepare to explore the unique character and beauty of this charming coastal town.

Day 1: Arrival and Evening Exploration

  • Arrival and Check-In: Arrive in Portsmouth by late afternoon and check into a charming accommodation like The Hotel Portsmouth, known for its historic charm and central location, or Wentworth by the Sea, a luxurious waterfront resort with stunning views and elegant rooms.
  • Evening Stroll: After checking in, take a leisurely walk through Market Square, the heart of downtown Portsmouth. Explore the historic architecture, boutique shops, and enjoy the vibrant atmosphere of this charming area.
  • Dinner: Dine at Mamma Marias, a local favorite offering delicious Italian cuisine in a cozy setting. Their menu features fresh ingredients and traditional recipes that highlight local flavors.

Day 2: Exploring Portsmouth

  • Breakfast: Start your day with breakfast at The Friendly Toast, known for its inventive breakfast dishes and eclectic decor. Enjoy a hearty meal to fuel your exploration of Portsmouth.
  • Morning Exploration: Visit the Strawbery Banke Museum, a living history museum showcasing Portsmouth’s past through historic buildings, gardens, and costumed interpreters. The museum offers a fascinating look at life in the 17th through 19th centuries and provides excellent photo opportunities.
  • Lunch: Enjoy a casual lunch at The River House, offering fresh seafood and waterfront views in a relaxed, friendly atmosphere.
  • Scenic Drive: Take a scenic drive along Route 1A, known as the Ocean Boulevard, which provides stunning coastal views and picturesque landscapes. This drive offers a great way to experience the beauty of New Hampshire’s coastline.
  • Afternoon Activity: Explore the Portsmouth Harbor Lighthouse and the surrounding area. The lighthouse offers a glimpse into the region’s maritime history and provides excellent photo opportunities.
  • Dinner: For dinner, try Black Trumpet Bistro, known for its creative menu featuring locally sourced ingredients and a cozy, intimate atmosphere.

Day 3: Morning Farewell

  • Breakfast: If time permits, enjoy a final breakfast at Café Mediterraneo, offering delicious Mediterranean-inspired dishes and a welcoming atmosphere.
  • Morning Stroll: Take one last walk along the Prescott Park, a lovely waterfront park with beautiful gardens and views of the harbor. It’s a peaceful way to wrap up your visit to Portsmouth.

As your visit to Portsmouth comes to an end, consider taking a short drive to explore the nearby New Castle. This small island town offers additional scenic views, historic sites, and charming coastal landscapes. It’s a wonderful way to extend your exploration and enjoy a bit more of New Hampshire’s coastal beauty before heading home.

“This post, it’s itineraries, and the accompanying artistic images were crafted with the assistance of AI technology, blending human creativity with artificial intelligence to explore new possibilities in travel and visual storytelling. While these images evoke the essence of their real-world counterparts, they are the result of artistic imagination, designed to transport you to places both familiar and fantastical. For a deeper understanding of our use of AI in creating these elements and its implications, please refer to our comprehensive AI statement linked here.”