14-Day Family-Friendly Itinerary to Orleans, Massachusetts

  • Day 1: Visit Nauset Beach
    10 minutes (5 miles) from Orleans

    Enjoy a scenic drive along the Atlantic Ocean to Nauset Beach, known for its beautiful dunes and great waves for surfing. Spend the day relaxing on the beach and taking in the stunning views.

  • Day 2: Explore Chatham
    20 minutes (12 miles) from Orleans

    Discover the charming town of Chatham, home to lighthouses, historic homes, and quaint shops. Be sure to take a tour of the Chatham Lighthouse, located on the picturesque Monomoy Island.

  • Day 3: Visit Provincetown
    45 minutes (29 miles) from Orleans

    Take a day trip to Provincetown, home to a thriving LGBTQ+ community, numerous art galleries, and unique shops. Visit the famous Pilgrim Monument, a towering granite structure that commemorates the landing of the Mayflower Pilgrims.

  • Day 4: Whale Watching Tour
    10 minutes (8 miles) from Orleans

    Embark on a whale watching tour from Barnstable Harbor and witness humpback whales, dolphins, and seals in their natural habitat. Be sure to bring a camera and rain jacket!

  • Day 5: Visit Martha's Vineyard
    1.5 hours by ferry from Woods Hole

    Take a ferry from Woods Hole to Martha's Vineyard for a day trip! Explore the charming town of Edgartown, visit the Gingerbread Houses, and relax on the beach.

  • Day 6: Cape Cod Rail Trail Bike Ride
    5 minutes (2 miles) from Orleans

    Experience the scenic Cape Cod Rail Trail by bike, starting near Orleans and ending in Wellfleet. Take a break along the way to explore the numerous shops and restaurants in each town.

  • Day 7: Visit Skaket Beach
    10 minutes (5 miles) from Orleans

    Enjoy a day at Skaket Beach, known for its calm and warm waters. Walk along the sand bars during low tide and catch a stunning sunset over the water.

  • Day 8: Go Fishing in Rock Harbor
    15 minutes (6 miles) from Orleans

    Charter a fishing boat at Rock Harbor for a day of deep sea fishing. Catch striped bass, bluefish, and tuna while enjoying the scenic views of Cape Cod Bay.

  • Day 9: Visit Nantucket
    2 hours by ferry from Hyannis

    Take a ferry from Hyannis to Nantucket for a day trip! Explore the charming cobblestone streets, visit the Whaling Museum, and enjoy the beaches.

  • Day 10: Go Mini Golfing at Cape Escape Mini Golf
    5 minutes (2 miles) from Orleans

    Enjoy a family-friendly activity at Cape Escape Mini Golf. Challenge each other to a round or two of mini golf and enjoy the playful theme of the course.

  • Day 11: Visit Monomoy National Wildlife Refuge
    30 minutes (18 miles) from Orleans

    Explore the natural beauty of Monomoy National Wildlife Refuge, home to numerous species of birds and seals. Take a guided tour or venture on your own along the trails and boardwalks.

  • Day 12: Visit Wellfleet Drive-In Theatre
    15 minutes (8 miles) from Orleans

    Experience a classic drive-in movie at Wellfleet Drive-In Theatre. Grab some snacks from the concession stand and enjoy a movie under the stars with your family.

  • Day 13: Visit Cape Cod National Seashore
    20 minutes (13 miles) from Orleans

    Take a scenic drive along the Cape Cod National Seashore, home to numerous beaches, hiking trails, and historic sites. Be sure to visit the iconic Cape Cod Light and explore the trails around the lighthouse.

  • Day 14: Visit Nickerson State Park
    15 minutes (7 miles) from Orleans

    End your trip with a visit to Nickerson State Park, known for its numerous freshwater ponds and woodland trails. Take a dip in one of the crystal-clear ponds or hike one of the scenic trails.

Time and Costs Estimates

  • Nauset Beach (free)
  • Chatham Lighthouse ($6 admission fee, $1 for children under 12)
  • Pilgrim Monument ($18 admission fee, $10 for children 4-12)
  • Whale Watching Tour ($59-$85/adult, $39-$55/child)
  • Martha's Vineyard Ferry ($17/adult, $9/child)
  • Bike Rental for Cape Cod Rail Trail ($20+)
  • Wellfleet Drive-In Theatre ($12/adult, $9/child)
  • Cape Cod National Seashore (free)
  • Nickerson State Park ($14/day parking fee, cash or check only)
  • Total Estimated Costs: $126+ per adult, $70+ per child

Useful Tips

If you have more time, consider visiting nearby towns such as Hyannis or Sandwich. If you have less time, consider skipping Nantucket or Martha's Vineyard, or condensing your itinerary to a shorter timeframe. Be sure to check opening and closing times for all locations before planning your trip!

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