14 days in Boston, New Jersey & Wisconsin Itinerary

14 days in Boston, New Jersey & Wisconsin Itinerary

Created using Inspirock United States itinerary planner

Make it your trip
Fly
1
Boston
— 5 nights
Drive
2
Cape May
— 3 nights
+2
Drive to Philadelphia International Airport, Fly to Austin Straubel International Airport, Drive to Sheboygan
3
Sheboygan
— 1 night
Drive
4
Wisconsin Dells
— 3 nights
Drive
5
Osceola
— 1 night
Drive to Minneapolis-St Paul International/Wold-Chamberlain Airport, Fly to San Francisco International Airport

S M T W T F S
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Boston

— 5 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.
Change things up with these side-trips from Boston: Dolphin & Whale Watching (in Gloucester), Ogunquit (Marginal Way Walkway & Ogunquit Beach) and Fisherman's Walk (in York Harbor). There's lots more to do: admire the natural beauty at Boston Public Garden, get your bearings at John F. Kennedy Presidential Museum & Library, visit North End, and get to know the fascinating history of Freedom Trail.

For reviews, where to stay, other places to visit, and more tourist information, go to the Boston travel tool.

San Francisco to Boston is an approximately 7.5-hour flight. You can also drive; or do a combination of subway, train, and bus. You'll lose 3 hours traveling from San Francisco to Boston due to the time zone difference. In August, Boston is somewhat warmer than San Francisco - with highs of 81°F and lows of 65°F. Cap off your sightseeing on the 7th (Fri) early enough to go by car to Cape May.

Things to do in Boston

Outdoors · Museums · Parks · Historic Sites

Side Trips

Cape May

— 3 nights

The Nation's Oldest Seashore Resort

Cape May represents the other Jersey Shore--the one you don't see on TV--the one with a rich history and a refined, relaxed atmosphere.
Get out of town with these interesting Cape May side-trips: Liberty Escape Rooms (in Ocean City), Atlantic City Boardwalk (in Atlantic City) and Spas & Wellness (in Sea Isle City). On the 10th (Mon), spend a day by the water at Wildwood Boardwalk. The adventure continues: fly like a bird with Atlantic Parasail, kick back and relax at Cape May City Beaches, stroll through Wildwood Beach, and relax in the rural setting at Jersey Shore Alpacas.

To find more things to do, maps, reviews, and tourist information, go to the Cape May day trip site.

Traveling by car from Boston to Cape May takes 7 hours. Alternatively, you can do a combination of flight and bus; or take a bus. Expect a daytime high around 82°F in August, and nighttime lows around 66°F. Finish your sightseeing early on the 10th (Mon) so you can travel to Sheboygan.

Things to do in Cape May

Shopping · Outdoors · Theme Parks · Beaches

Side Trips

Sheboygan

— 1 night
Sheboygan is a city in and the county seat of Sheboygan County, Wisconsin, United States. Kick off your visit on the 11th (Tue): admire the natural beauty at Bookworm Gardens, then join the crowd at Road America, and then tee off at Whistling Straits Golf Course - Straits and Irish.

To find maps, photos, reviews, and tourist information, go to the Sheboygan trip itinerary planner.

The Route module can help you plan travel from Cape May to Sheboygan. Traveling from Cape May to Sheboygan, you'll gain 1 hour due to the time zone difference. Traveling from Cape May in August, Sheboygan is slightly colder at night with lows of 58°F. Cap off your sightseeing on the 11th (Tue) early enough to travel to Wisconsin Dells.

Things to do in Sheboygan

Parks · Golf · Outdoors

Side Trips

Wisconsin Dells

— 3 nights

Waterpark Capital of the World

Named after a nearby scenic gorge famous for its steep sandstone formations, Wisconsin Dells features more than 20 water parks, making it one of the most popular vacation areas in this region.
Venture out of the city with trips to Madison (Owens Conservation Park, Olbrich Botanical Gardens, &more) and Spring Green (Wisconsin Canoe Company & Taliesin Preservation: Frank Lloyd Wright Visitor Center ). There's much more to do: take a memorable tour with Tours, get your game on at Capones Old Time Pic. Studio, and cool off at Noah's Ark Water Park.

To find maps, ratings, and tourist information, go to the Wisconsin Dells day trip website.

Getting from Sheboygan to Wisconsin Dells by car takes about 2.5 hours. In August in Wisconsin Dells, expect temperatures between 79°F during the day and 59°F at night. Wrap up your sightseeing on the 14th (Fri) early enough to travel to Osceola.

Things to do in Wisconsin Dells

Theme Parks · Outdoors · Tours · Adventure

Side Trips

Osceola

— 1 night
Osceola is a village in Polk County, Wisconsin, United States. On the 15th (Sat), whizz through the canopy at Trollhaugen Outdoor Recreation, get a new perspective on things with Riverwood Canoe & Kayak Rental, and then admire the sheer force of Cascade Falls.

For photos, traveler tips, ratings, and tourist information, read our Osceola vacation site.

Getting from Wisconsin Dells to Osceola by car takes about 3.5 hours. Expect a daytime high around 78°F in August, and nighttime lows around 58°F. Finish your sightseeing early on the 15th (Sat) so you can travel back home.

Things to do in Osceola

Outdoors · Tours · Adventure · Parks

Side Trip

New Jersey travel guide

3.9
Casinos · Shopping Malls · Beaches
The Garden State
Often overshadowed by its legendary neighbor, New York, New Jersey holds its own as a land of thriving industrial cities, sprawling farmland, and lively coastal towns. Called the Garden State, New Jersey is a hub of entertainment and cultural attractions for the east coast, from the famous sandy beaches and carnival-like atmosphere of the Jersey Shore to alluring Atlantic City, the Las Vegas of the east. New Jersey also boasts a wealth of historical places to visit, including battle sites and memorials, such as George Washington's Revolutionary War headquarters.

Wisconsin travel guide

4.2
Specialty Museums · Water Parks · Zoos
The Badger State
Wisconsin is known as "America's Dairyland" because of its status as the nation's most famous producer of milk and cheese. A growing favorite with foreign tourists, the state is a perfect holiday destination for nature lovers, offering year-round outdoor activities like fishing, boating, kayaking, and hiking. Dotted with thousands of inland lakes and waterways alongside apple and cherry orchards, Wisconsin also offers numerous urban tourist attractions, its cities hosting renowned beer and art festivals each year.