Room Cougar

Your AI trip plan for a couple 4 day trip to Boston, MA for ages 18-35 with a high budget - Activities, Attractions, Cost Saving Tips, Hidden Gems, Hotels, Restaurants

Day 1: Discover Historic Boston

  • Morning:

    • Freedom Trail Walk (Begin your trip with a guided walk along Boston's iconic Freedom Trail, exploring 16 historical sites including Paul Revere's House and the Old State House.)
    • Breakfast at Tatte Bakery & Cafe (Enjoy a delightful breakfast with a variety of pastries, coffee, and Mediterranean-inspired dishes in a charming setting.)
  • Afternoon:

    • Boston Tea Party Ships & Museum (Experience an interactive journey through the events of the Boston Tea Party with live reenactments and multimedia exhibits.)
    • Lunch at Union Oyster House (Savor fresh seafood at America's oldest continuously operating restaurant, renowned for its oysters and classic New England fare.)
  • Evening:

    • Sunset Harbor Cruise (Relax on a private boat cruise around Boston Harbor, offering stunning sunset views of the skyline and historic sites.)
    • Dinner at Mamma Maria (Dine in an elegant North End restaurant serving upscale Italian cuisine with a focus on fresh, local ingredients.)

Day 2: Arts and Culture

  • Morning:

    • Museum of Fine Arts (Explore an extensive collection of artwork from around the world, including American, Egyptian, and contemporary pieces.)
    • Breakfast at Flour Bakery & Cafe (Start your day with hearty breakfast sandwiches, house-made pastries, and exceptional coffee in a cozy atmosphere.)
  • Afternoon:

    • Isabella Stewart Gardner Museum (Visit this unique museum housed in a stunning Venetian-style palace, featuring art, gardens, and a rich history.)
    • Lunch at Eataly Boston (Enjoy a variety of Italian dishes and fresh market offerings in a vibrant, upscale food market setting.)
  • Evening:

    • Boston Symphony Orchestra (Experience a world-class performance by the Boston Symphony Orchestra at Symphony Hall.)
    • Dinner at No. 9 Park (Indulge in gourmet French and Italian-inspired cuisine in a refined setting overlooking Boston Common.)

Day 3: Cambridge and Innovation

  • Morning:

    • Harvard University Campus Tour (Take a guided tour of Harvard's historic campus, including Harvard Yard, Memorial Hall, and notable landmarks.)
    • Breakfast at Flour Bakery & Cafe (Cambridge) (Grab a delicious breakfast with a range of baked goods and coffee before exploring Cambridge.)
  • Afternoon:

    • MIT Museum (Discover fascinating exhibits on science, technology, and innovation at the Massachusetts Institute of Technology's museum.)
    • Lunch at Alison's Café (Enjoy modern American cuisine with a creative twist in a trendy Cambridge eatery.)
  • Evening:

    • Charles River Dinner Cruise (Enjoy a romantic evening cruise on the Charles River with panoramic views of both Boston and Cambridge.)
    • Dinner at Oleana (Experience Mediterranean and Middle Eastern-inspired dishes in a beautiful, garden-like setting.)

Day 4: Modern Boston and Relaxation

  • Morning:

    • New England Aquarium (Explore marine life exhibits, including the Giant Ocean Tank and interactive displays at one of Boston's top attractions.)
    • Breakfast at The Friendly Toast (Start your day with eclectic and creative breakfast options in a vibrant, retro-inspired space.)
  • Afternoon:

    • Fenway Park Tour (Take a behind-the-scenes tour of the legendary Fenway Park, home of the Boston Red Sox.)
    • Lunch at Area Four (Enjoy delicious wood-fired pizzas and local brews in a lively, modern setting near Fenway Park.)
  • Evening:

    • Skywalk Observatory (End your trip with breathtaking 360-degree views of Boston from the Skywalk Observatory at the Prudential Center.)
    • Dinner at Top of the Hub (Celebrate your final night with upscale dining and panoramic city views from the 52nd floor of the Prudential Tower.)
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