Scroll down for a full 4-day itinerary and my gluten-free finds.
Day 1: Drive from Boston, sunset on the beach, Lanyards Bar and Grille
To start our long girl’s weekend, we flew into Boston Airport since it was cheaper than flying directly into Cape Cod, Massachusetts. We then rented a car and drove the 2-3 hours to our cute Airbnb in Harwich, which was down the coast of Cape Cod.
Tips on places to stay: Cape Cod is very big, and you’ll definitely want to rent a car. If you’re looking for a cute, relaxing, slow beach weekend, Harwich is a great place to stay! If you want to be closer to things to do (although not as cute), Hyannis is a great place to stay. If you’re looking to shop and go out at night, Provincetown is the place to stay. Harwich was about an hour from Provincetown.
Once we got to our Airbnb, we walked down to one of the best Cape Cod beaches, only a couple of blocks away, to watch the sunset, which was the perfect way to start the trip. We then went to dinner at Lanyards, a local bar and grill. They had an extensive gluten-free menu and I got the baked Cod!
Day 2: Nantucket, Provincetown
We took a high-speed 1-hour ferry from Hyannis to Nantucket through the Steamship Authority. We bought the tickets there for the 8:15 am ferry. Since it was a Friday in October, we could experience the island without the summer crowd, and it felt like we had the whole island to ourselves. After we got off the ferry, we went straight to Lemon Press for breakfast, which had a lot of gluten-free options. The coffee was excellent, and the eggs benedict with gluten-free bread was a delicious way to start the day.
Since Nantucket is walkable, we leisurely wandered through the gorgeous streets, admiring the fall foliage and charming houses. We shopped at local businesses, took a photo with Mr. Rogers on a bench outside the movie theater, and visited the 1871 lighthouse, a monument to nautical history, on the tranquil shoreline.
After a full day in Nantucket, we returned to the Cape and headed to Provincetown (P-Town) for a delicious meal at Mews, a restaurant renowned for its amazing food, views, and gluten-free options. We both had the Lobster Rosotto, which was absolutely delicious! After dinner, we walked down Commercial Street, looked at all the Halloween decorations and costumes, did a little shopping for souvenirs, and then returned to our Airbnb.
Day 3: Whale Watching, Hyannis, Cape Cod Photo at Cape Cod Potato Chip Facility
On day 3, we had reservations to go Whale Watching through the Hyannis Whale Watching Company. It was the last tour of the season (since Whales migrate to the Caribbean in the winter), and boy, did the Whales put on a show! The Whale Watching experience was about 3-4 hours long and worth very penny. We were absolutely amazed by the whales, and a 10-month-old whale even stayed next to our boat for an amazing 15 minutes, making it an experience of a lifetime. I would highly recommend booking this and making sure you book in advance. I would also recommend you pack snacks or lunch since the tour is right in the middle of the day.
Following the Whale Watching experience, we shopped for souvenirs in Hyannis and enjoyed snacks and drinks at Kkatie’s Burger Bar. We also stopped at the Cape Cod Potato Chip Facility to take a photo with a Cape Cod sign.
Since it was our last night, we returned to our Airbnb in Harwich to enjoy a perfect sunset on the beach to finish the night. When it got dark, we split a pizza at Harwich Pizza Company for dinner and packed up our things to leave in the morning.
Day 4: Drive back to Boston, Breakfast in Sandwich, Plymouth Rock, Mayflower II
Since the drive from Cape Cod to Boston was about 2 hours away, we decided to break it up and stop at a few more places along the way. Our first stop was Marshland Restaurants & Bakeries in Sandwich, MA, which was an old diner right next to a gas station. It was delicious and one of the coolest diners I have been to!
After that, we traveled to Plymouth, where we saw the famous Plymouth Rock and the Mayflower II, two historical sites that offered insights into the early history of the United States.
The trip had the perfect mix of history, delicious food, and natural beauty, made even better by the mild October weather and beautiful fall foliage. If you want to enjoy the beauty of Cape Cod, October might be the best month to go.
4-Day Weekend Itinerary
Things to Do in Cape Cod:
- Day 1: Fly into Boston Logan Airport, rent a car, drive the 2 hours to Cape Cod, and enjoy a sunset walk on the nearby beach. If staying in Harwich, dine at Lanyards Bar and Grille and have the gluten-free baked cod.
- Day 2: Take a day trip to Nantucket on a high-speed ferry (1 hour) from Hyannis, have breakfast at Lemon Press (so many gluten-free options), stroll the picturesque streets, enjoy the fall foliage and quaint houses, shop at local businesses, take a photo, Mr. Rogers, visit the 1871 lighthouse on the beach. Return to Cape Cod, drive to Provincetown, have dinner at Mews with delicious Lobster Risotto, and walk down Commercial Street.
- Day 3: Go whale watching with Hyannis Whale Watching Company (open from May – October make sure you book your tickets in advance), a souvenir shop in Hyannis on Main Street, and visit the Cape Cod Potato Chip Facility for a photo (they weren’t doing tours when we went). Walk the sunset on the beach, grab a pizza from Harwich Pizza Company for dinner.
- Day 4: Begin the drive back to Boston (about 2 hours), have breakfast at Marshland Restaurants & Bakeries in Sandwich, MA. Stop in Plymouth to see Plymouth Rock and the Mayflower II and finish the trip at the airport
My Gluten-Free Finds:
- Lanyard Bar & Grille: (Harwich) – Extensive gluten-free dinner options (I had the baked Cod)
- Lemon Press: (Nantucket) – Gluten-free breakfast and great coffee (I had eggs benedict)
- Mews: (Provincetown) – Nicer dinner with gluten-free options (I had the Lobester Rositto)
- KKatie’s Burger Bar (Hyannis) – Gluten-free buns for burgers
- Harwich Pizza Company (Harwich) – Gluten-free crust for pizzas
- Marshland Restaurants & Bakeries (Sandwich, MA) – Easy breakfast, no gf bread or substitutes