20 days in Boston, Gloucester & Wellfleet Itinerary

20 days in Boston, Gloucester & Wellfleet Itinerary

Created using Inspirock Massachusetts planner

This plan was created by another user.  Make it your plan

Route & dates

20 days in Boston, Gloucester & Wellfleet Itinerary

Start: Boston
1
Boston
— 14 nights
Drive:  1​h
2
Gloucester
— 2 nights
Drive:  3​h
3
Wellfleet
— 3 nights
Drive:  2​h 15​min
End: Boston

14
nights
Boston

Boston ©
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.
Your day-by-day itinerary now includes Battleship Cove, Classic Harbor Line Boston MA Day Tours, Boston Tea Party Ships & Museum, and other attractions you added. Give yourself a bit of retail therapy at Kittery Trading Post and Thames Street. Discover out-of-the-way places like Fishing Charters & Tours and Herring Cove Beach. Explore Boston's surroundings by going to York Beach (Long Sands Beach & Short Sands Beach), Strawbery Banke Museum (in Portsmouth) and Provincetown (Impulse Art Gallery, Dolphin & Whale Watching, & more). And it doesn't end there: get engrossed in the history at Old Sturbridge Village, visit a coastal fixture at Cape Neddick Nubble Lighthouse, admire the landmark architecture of The Elms, and stroll through Hampton Beach State Park.

To see traveler tips, photos, maps, and tourist information, go to the Boston travel route site .

If you are flying in from United Kingdom, the closest major airports are General Edward Lawrence Logan International Airport, Portsmouth International at Pease Airport and Bradley International Airport. Expect a daytime high around 33°C in July, and nighttime lows around 22°C. Cap off your sightseeing on the 6th (Tue) early enough to go by car to Gloucester.

Things to do in Boston

Museums Outdoors Parks

Side Trips

Provincetown, York Beach, Truro, Plymouth, Sandwich
Highlights from your plan
Lizzie Borden House ©
Lizzie Borden House
Long Sands Beach ©
Long Sands Beach

2
nights
Gloucester

Gloucester ©
The still waters off the Gloucester shore are immortalized in paintings and prints produced by the hundreds of artists who visit this town.
Dolphin & Whale Watching has been added to your itinerary. Kick off your visit on the 7th (Wed): browse the exhibits of The House of the Seven Gables, take an in-depth tour of Salem Witch Museum, and then see majestic marine mammals with a dolphin and whale watching tour. Get ready for a full day of sightseeing on the next day: kick back and relax at Wingaersheek Beach, then kick back and relax at Front Beach, and then see the interesting displays at Beauport, the Sleeper-McCann House.

To find other places to visit, ratings, where to stay, and tourist information, you can read our Gloucester holiday planning website .

Traveling by car from Boston to Gloucester takes an hour. Alternatively, you can take a train. In August, daytime highs in Gloucester are 31°C, while nighttime lows are 19°C. Wrap up your sightseeing on the 8th (Thu) early enough to drive to Wellfleet.

Things to do in Gloucester

Outdoors Beaches Parks

Side Trips

Salem, Front Beach
Highlights from your plan
The House of the Seven Gables ©
The House of the Seven Gables
Wingaersheek Beach ©
Wingaersheek Beach
Dolphin & Whale Watching

3
nights
Wellfleet

Wellfleet ©
Wellfleet is a town in Barnstable County, Massachusetts, United States, and is located halfway between the "tip" and "elbow" of Cape Cod. Your day-by-day itinerary now includes Fishing Charters & Tours. Kick off your visit on the 7th (Wed): enjoy the sand and surf at Mayo Beach and then cast your line with a fishing tour. Get ready for a full day of sightseeing on the 8th (Thu): take in the exciting artwork at Left Bank Art Gallery and then tour the pleasant surroundings at Cape Cod National Seashore.

To see more things to do, where to stay, photos, and more tourist information, you can read our Wellfleet day trip planning site .

You can drive from Boston to Wellfleet in 2.5 hours. Alternatively, you can ride a ferry; or take a bus. In August, daily temperatures in Wellfleet can reach 30°C, while at night they dip to 19°C. On the 9th (Fri), wrap the sightseeing up by early afternoon so you can drive back home.

Things to do in Wellfleet

Outdoors Parks Beaches

Side Trip

Cape Cod National Seashore
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Fishing Charters & Tours
Uncle Tim's Bridge ©
Uncle Tim's Bridge

Similar Plans

21 days in Boston BY A USER FROM BRAZIL May, fast-paced, popular sights PREFERENCES: May ATTRACTION STYLE: Popular sights PACE: Fast-paced 21 days in Boston BY A USER FROM BRAZIL May, culture, outdoors, romantic, beaches, museums, shopping, fast-paced, hidden gems PREFERENCES: May, culture, outdoors, romantic, beaches, museums, shopping ATTRACTION STYLE: Hidden gems PACE: Fast-paced 23 days in Boston BY A USER FROM UNITED STATES March, popular sights PREFERENCES: March ATTRACTION STYLE: Popular sights PACE: Medium 21 days in Boston BY A USER FROM AUSTRIA August, popular & hidden gems PREFERENCES: August ATTRACTION STYLE: Popular & hidden gems PACE: Medium 23 days in Boston BY A USER FROM BRAZIL January, teens, popular sights PREFERENCES: January, teens ATTRACTION STYLE: Popular sights PACE: Medium 22 days in United States BY A USER FROM POLAND August, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: August, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 21 days in United States BY A USER FROM AUSTRALIA May, popular sights PREFERENCES: May ATTRACTION STYLE: Popular sights PACE: Medium 24 days in United States BY A USER FROM IRELAND August, popular sights PREFERENCES: August ATTRACTION STYLE: Popular sights PACE: Medium 23 days in United States BY A USER FROM ROMANIA May, kids, popular & hidden gems PREFERENCES: May, kids ATTRACTION STYLE: Popular & hidden gems PACE: Medium
View more plans