Spend a relaxing week on the Cape with this road trip getaway. Start with a few days on Martha's Vineyard to help you quickly adjust to the pace of the Cape. Relax on windswept beaches, bike along island trails, and enjoy warm evening nights. Then it's back to the mainland Cape, where you will explore the more sparsely populated areas of the Lower and Outer Cape. Hike marsh-side trails, top massive sand dunes, climb local lighthouses, and refuel at weathered roadside clam shacks.The drive is only 2 hours from Boston to Provincetown (without traffic), and you can easily split this itinerary in two as well, with a long weekend in Martha's Vineyard or a few days in the Outer Cape.


  • Bike to remote beaches on Martha's Vineyard
  • Hike along sand bars on the outer edges of Cape Cod
  • Enjoy delicious fresh seafood in local restaurants and seafood shacks

Brief Itinerary

Day Highlights Overnight
Day 1 Woods Hole & Martha's Vineyard Martha's Vineyard
Day 2 Bike Ride to Chappaquiddick Martha's Vineyard
Day 3 Island Alpaca Company & Aquinnah Cliffs Martha's Vineyard
Day 4 Nauset March & Lighthouse Wellfleet
Day 5 Great Island Trail & Provincetown Provincetown
Day 6 Exploring Provincetown Provincetown
Day 7 Drive back from Provincetown  

Detailed Itinerary

Day 1: Woods Hole & Martha's Vineyard

Martha's Vineyard
Martha's Vineyard

Drive south to Woods Hole on the southwestern point of Cape Cod. Here, you'll catch a ferry to Martha's Vineyard to spend a couple of days. You can take your car on the ferry (for additional cost), or leave it on the mainland and rent a bike to explore the island, or take advantage of the bus network.

Woods Hole
Start the day in Woods Hole. This small, quintessential Cape Cod town is home to several world-famous research institutions focused on Marine Biology, climate change and more. With extra time to pass before your ferry, you can walk around the main street, climb up Nobska Light (a beautiful lighthouse added to the National Register of Historic Places in 1987), or enjoy a delicious meal at one of the many top-notch restaurants.

Stop by Pie in the Sky for delicious, freshly baked pastries and popovers, or head to Coffee Obsession for (usually) shorter lines and inexpensive-yet-delicious breakfast sandwiches. Grab your coffee and enjoy the 30-45 minute ferry ride across the Vineyard Sound. Enjoy the views looking back over the cape and Nobska Light.

Ferries depart Woods Hole every 30-60 minutes, taking passengers to either Vineyard Haven or Oak Bluffs.  Either option works, and there are nice places to eat and nearby local beaches in each location. 

Depending on your arrival time, you may want to spend the rest of the afternoon at the beach, or check out some of the small local shops in the towns of Vineyard Haven, Oak Bluffs, or Edgartown.

Day 2: Bike Ride to Chappaquiddick

Bikes in Edgardown
Bikes in Edgardown

Today, you'll ride from Oak Bluffs to Chappaquiddick Island, to relax on a remote beach made famous by the Kennedys. The total ride is about 18 miles (9 miles each way), but you can also hitch your bike to a bus and relax for the ride back if you like.

In the morning, head to  Anderson's Bike Rentals in Oak Bluffs to pick up your rental bikes for the day. If you spent the night closer to Vineyard Haven, there are bike rental options there as well.

The first ride is 6 miles to Edgartown, where you can pick up some sandwiches for lunch. Ride along Seaview Ave. the whole way, which offers breathtaking views of the coastline, and several soft sand beaches if you want to take a break. Three and a half miles into the ride you'll come across Jaws Bridge, made famous by the movie Jaws, which was filmed here. You'll often see kids jumping off the bridge into the water below.

Follow the curvy path as it turns to Beach Road, and then Main Street as you arrive into quaint Edgartown, much quieter than Oak Bluffs. Spend some time exploring the various shops and art galleries, or head over to Lighthouse Beach for a short walk to the Edgartown Harbor Light

Before crossing over to Chappaquiddick, stop at the Rosewater Market to pick up a picnic of fresh sandwiches, salads, or other delicious sides, then hop on the Chappy Ferry with your bike for an extremely quick ride over the Chappaquiddick.

Once on Chappy, you have 3 miles to go before you arrive at East Beach (stay on Chappaquiddick Road, which turns into Dike Road). The last bit is unpaved before you arrive at the infamous Dike Bridge, where Ted Kennedy crashed his car into the water in 1969.

Once on East Beach, find a spot to call home for the next couple hours as you enjoy the warm, fine sand and the sound of the waves. Stay as long as you like, you can walk for miles on the sand in either direction. 

More things to do
Back in Oak Bluffs, you can explore the Gingerbread Cottages, a small village of brightly-colored, cookie-cutter cottages. Or, relax on the grass in Ocean Park- you'll often hear music played from the Gazebo. 

Treat yourself to a much-deserved (jumbo) ice cream cone from one of the many shops, such as Mad Martha's Homemade Ice Cream. Or enjoy a heartier meal at one of the many restaurants in town.

Day 3: Island Alpaca Company & Aquinnah Cliffs

Colorful Aquinnah Cliffs
Colorful Aquinnah Cliffs

Today, you'll explore the southwestern part of the island at Chilmark and Aquinnah. You can get around by car, bike, or by the public bus system (get a day pass and check time tables, as you will need to transfer).

Start in Tinsbury/Vineyard Haven with breakfast at the Waterside Market, and order some sandwiches to take with you to enjoy later in the day.

If you're a fan of fluffy alpacas (and who isn't?), head to the Island Alpaca Company (a short walk from the 1, 7, or 9 Island Transit Bus Routes), and meet some of the four-legged locals. In the shop you can purchase a number of items made from the Alpaca wool, and you can even experience an alpaca yoga session.

Continue towards Chilmark and Aquinnah for a taste of remote, slow-paced island life.

Menemsha Hill offers some nice hiking trails to the western cliffside and Squibnocket Beach is a nice place to walk along the shore. However, most day-trippers to this part of the island come to see the colorful Aquinnah Cliffs.

We recommend finding a spot on the beach to enjoy your lunch, float in the waves, walk along the windswept sandy shores, and forget what time it is. On the road above, you can see the cliffs from the overlook and head over to the Gay Head Lighthouse.

Nearby, Lobsterville Beach is another nice place to spend some time.

For dinner, consider Larsen's Fish Market in Menemsha (by car, you'll have to approach from the eastern side, but a small boat can ferry bikers). Enjoy some clams or a lobster roll by the water to end the day before driving back to the north side of the island. 

Spend another night here, or catch a late afternoon ferry back to Woods Hole and overnight on mainland Cape.

Day 4: Nauset March & Lighthouse

Nauset Lighthouse
Nauset Lighthouse

Catch the morning ferry from Martha's Vineyard back to Woods Hole to collect your car and drive about 75 minutes to Nauset Marsh on the east side of the Cape.  Along the drive, Snowy Owl Coffee Roasters (Brewster) is a great place to stop for coffee and a snack.

Enjoy the leisurely walk along the Nauset Marsh Trail. The loop is about 1.3 miles and you can extend the hike with an out and back to the Coast Guard Station at Nauset Beach (about 2.8 miles round trip for the combined hike).

For lunch, taste some local oysters at Wicked Oyster, or head a bit further up the road to the BYOB Moby Dick's Restaurant.

In the afternoon, relax on Nauset Light Beach near the lighthouse before continuing north to nearby Wellfleet and Marconi Beach.

Wellfleet is home to a small, quiet community, which many local artists call home. It's also known for its oysters, so be sure to try some. Stroll the small streets admiring the local architecture & boutique shops, or head out to the marsh area in the late afternoon for some local bird watching and a sunset over the harbor. One of the best places for spotting wildlife is the Wellfleet Bay Wildlife Sanctuary.

For dinner, enjoy the delicious local American fare at Winslow's Tavern.

Day 5: Great Island Trail & Provincetown

Great Island
Great Island

Start the day at Great Island, which offers remote hiking along the trails and sand dunes. Hike as long as you like along the marsh side, or all the way out to Jeremy Point (8 miles out and back). Along this trail, you'll feel worlds away from the busier Cape Cod scene on Martha's Vineyard and Provincetown.

In the afternoon, continue north to the tip of the Cape to Provincetown where you can spend some time exploring the local boutiques, art galleries, and great restaurants along Commercial Street. Visit the Pilgrim Monument (commemorating the Pilgrims' first New World landing in Provincetown in November 1620), or grab a drink and a snack by the water.

For dinner, make a reservation at The Pointe Restaurant & Wine Bar which offers delicious local cuisine in a lovely New England house setting.

Day 6: Exploring Provincetown

Race Point Lighthouse, Provincetown
Race Point Lighthouse, Provincetown

Fuel up for the day with a delicious breakfast at Liz's Cafe Anybody's Bar, where they make great eggs benedict, french toast, and more.

You have a few options for how to spend the day.

For a more active day, rent a bike and ride around the Province Lands Bike Trail and other smaller roads of the Outer Cape.

You can also drive out to the beaches at Race Point or Herring Cove and spend the day on the remote windswept sandy beaches at the furthest tip of Cape Cod.

Another great option- walk across the Provincetown Causeway to Wood End where you can stroll along the shores to Wood End Lighthouse, Long Point Beach, and Long Point Light Station.

Or, join a whale watching tour for the day and head out on the open water.

You can drive back along the Cape in the afternoon (2 hours to Boston without Traffic), or stay another night to peruse more of the art galleries and unique local shops, slowly making your way home the next day.

Day 7: Drive back from Provincetown

Walking among the giant dunes
Walking among the giant dunes

Slowly make your way back along the Cape today (it's 2 hours to Boston without traffic).

Start the day with a walk along the giant sand dunes along the Dune Shacks Trail, and spend some time dreaming of owning one of the small, quaint, and quintessentially-Cape Cod beach shacks that dot the shoreline between the dunes.

Some shorter/flat walks to stretch your legs on the drive back:
- White Cedar Swamp Trail (Wellfleet)
- Fort Hill Trail (Eastham)
- Cliff Pond Trail (Brewster)

Consider a stop in Brewster at Snowy Owl Coffee Roasters as well for a coffee and snack.