9 days in Boston & Cape Cod Itinerary

9 days in Boston & Cape Cod Itinerary

Created using Inspirock Massachusetts route planner

Make it your trip
Fly
1
Boston
— 3 nights
Drive
2
Sandwich
— 1 night
Drive
3
Hyannis
— 2 nights
Drive
4
Chatham
— 1 night
Drive
5
Boston
— 1 night
Fly

S M T W T F S
29
30
1
2
3
4
5
6
7
8
9
10
11
12

Boston

— 3 nights

Beantown

Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Boston is known for historic sites, museums, and parks. Your plan includes some of its best attractions: explore the world behind art at Museum of Fine Arts, walk around Boston Common, get curious at Museum of Science, and observe the fascinating underwater world at New England Aquarium.

For maps, photos, other places to visit, and more tourist information, you can read our Boston road trip planning tool.

Orlando to Boston is an approximately 5-hour flight. You can also drive; or take a train. Expect cooler temperatures when traveling from Orlando in December; daily highs in Boston reach 43°F and lows reach 31°F. Wrap up your sightseeing by early afternoon on the 7th (Mon) to allow time for the car ride to Sandwich.

Things to do in Boston

Museums · Parks · Historic Sites · Childrens Museums

Sandwich

— 1 night
Sandwich is a town in Barnstable County, Massachusetts, United States. On the 7th (Mon), see the interesting displays at Heritage Museums & Gardens, view the masterpieces at McDermott Glass Studio, and then contemplate the long history of Plymouth Rock.

To find photos, other places to visit, more things to do, and more tourist information, go to the Sandwich trip itinerary planner.

Getting from Boston to Sandwich by car takes about 1.5 hours. Other options: take a bus. In December, daytime highs in Sandwich are 46°F, while nighttime lows are 30°F. On the 8th (Tue), wrap the sightseeing up by early afternoon so you can drive to Hyannis.

Things to do in Sandwich

Museums · Childrens Museums · Shopping · Historic Sites

Side Trip

Hyannis

— 2 nights

Capital of Cape Cod

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Kick off your visit on the 8th (Tue): take in the spiritual surroundings of St. Francis Xavier Church, examine the collection at John F Kennedy Hyannis Museum, and then see the interesting displays at Cape League Hall of Fame. Here are some ideas for day two: get a new perspective on things with Boat Tours & Water Sports, take a stroll through Main Street Hyannis, then indulge your thirst for a good beer at Devil's Purse Brewing Company, and finally take in the spiritual surroundings of St. Mary's Episcopal Church.

To see ratings, reviews, where to stay, and other tourist information, you can read our Hyannis online visit planner.

Hyannis is just a stone's throw from Sandwich. In December, daily temperatures in Hyannis can reach 45°F, while at night they dip to 31°F. Wrap up your sightseeing by early afternoon on the 10th (Thu) to allow enough time to drive to Chatham.

Things to do in Hyannis

Museums · Historic Sites · Neighborhoods · Parks

Side Trips

Chatham

— 1 night
Chatham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. Start off your visit on the 10th (Thu): tour the pleasant surroundings at Chatham Lighthouse Beach and then relax and rejuvenate at Le Petite Day Spa.

Make your Chatham itinerary with Inspirock to find out what to see and where to go.

Traveling by car from Hyannis to Chatham takes an hour. Alternatively, you can take a bus. In December, plan for daily highs up to 45°F, and evening lows to 33°F. Cap off your sightseeing on the 11th (Fri) early enough to go by car to Boston.

Things to do in Chatham

Parks · Beaches · Outdoors · Spas

Side Trip

Boston

— 1 night

Beantown

For other places to visit, where to stay, ratings, and other tourist information, use the Boston trip builder tool.

Traveling by car from Chatham to Boston takes 2 hours. Alternatively, you can drive; or take a bus. On the 12th (Sat), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Boston

Museums · Historic Sites

Cape Cod travel guide

4.4
Beaches · Dolphin & Whale Watching · Specialty Museums
Located on the southern shore of Massachusetts, Cape Cod contains some 15 towns and two islands. The arm-shaped peninsula is a popular holiday destination throughout the year because of its historical attractions, art galleries, award-winning restaurants, and a scenic coastline dotted by sandy beaches. Start your sightseeing in Provincetown, located at the very tip of the cape and famous for being the site of the first Pilgrims' landing in 1620. From there you can hit up all of the Cape's other small towns, renowned for their comfortable bed and breakfasts and distinctive cuisine of fresh fish and oyster dishes. This maritime community features more than a dozen lighthouses. Part of experiencing the Cape means a trip to its two islands--which showcase several lighthouses and numerous restaurants.