Two weeks on the Cape and islands will give you ample time for a relaxing family vacation that takes in a number of the sites. You'll get to take a leisurely drive down the Old King's Highway, explore art galleries in Provincetown, listen to a town band concert in Chatham, and even take a kayak trip in Barnstable's Great Marsh.
Day 1: Falmouth
Start your tour of the Cape and islands in Falmouth, where you'll need a couple of days to see all the sites. Bike down the Shining Sea Bikeway to the village of Woods Hole, a fishing village and world-renowned science center. Visit the aquarium and take a 90-minute discovery cruise with OceanQuest, a fun, science-filled boat ride. Wander through the free Spohr Gardens, in Quissett, near Woods Hole.
Day 2: Sailing in Vineyard Sound
Spend the morning at Falmouth Heights Beach, and then head to Grews Pond, a freshwater pond in Goodwill Park, for swimming and a picnic lunch. Take a sunset cruise around Vineyard Sound on the Liberte, a 74-foot, three-masted schooner out of Falmouth Inner Harbor.
Day 3: Sandwich
Spend several hours exploring the Heritage Museums and Gardens, in Sandwich. Check out Sandy Neck Beach, one of the Cape's best beaches. On the way home, stop for ice cream at Twin Acres Ice Cream Shoppe, an ice-cream shop out of another century.
Day 4: Kayak Trip to Sandy Neck
Exploring estuaries of the Cape by kayak is a great way to get away from the crowds. A trip around the Great Marsh in Barnstable and over to Sandy Neck, the 7-mile peninsula that extends from Sandwich, can take a couple of hours or most of a day, depending on how much you want to do. Experienced kayakers will want to paddle out to the tip of Sandy Neck, where there's an isolated 19th-century summer community, complete with a lighthouse and a couple dozen simple cottages.
Day 5: A Drive up Route 6A, a Trip to Hyannis
The John F. Kennedy Hyannis Museum is one of the most popular attractions on the Cape. Visit it first thing in the morning, and then walk around Hyannis Harbor, which, as part of a new renovation, has a number of small crafts shacks where artists demonstrate and sell their wares. Drive over to the north side of the Cape to explore the Old King's Highway/Route 6A, which stretches from Sandwich to Orleans. The road hasn't changed much since the 19th century, when it was a stagecoach route. There's great shopping, especially antiquing, on Route 6A, as well as restaurants in all price ranges.
Day 6: Chatham
Spend the day in Chatham, one of the Cape's most charming towns. Stroll down Main Street to check out the shops. Stop at the Chatham Fish Pier to watch the fishermen bring in the daily catch. Drive to Morris Island, part of the Monomoy National Wildlife Refuge, to hike trails and do some bird-watching. Have a drink on the porch of the Chatham Bars Inn, and then head over for a band concert (every Fri night in summer) at Kate Gould Park.
Day 7: Cape Cod National Seashore
A visit to Cape Cod National Seashore is not just a day on the beach. There are visitor centers, numerous trails, and several historic sites. The first stop is Fort Hill, which has one of the best scenic vistas on the Cape. Your next stop is the Salt Pond Visitor Center, in Eastham. In Truro you can visit the Highland House Museum and Highland Lighthouse. A climb to the top of the lighthouse will give you a great view of the coastline. Continue on to Provincetown for a visit to the Province Lands Visitor Center and the Old Harbor Lifesaving Museum.
Day 8: Whale-Watching Off Provincetown
You'll need several days in Provincetown to take in all that this unique place has to offer. A trip to Stellwagen Bank on a whale watch takes half a day, but it's an experience you'll always remember.
Day 9: Provincetown History & Arts
The Pilgrim Monument & Provincetown Museum are musts for an overview of the history of the town and a bird's-eye view of the geography from the top of the monument. You'll want to leave yourself plenty of time for strolling along Commercial Street and stopping at galleries, especially the Provincetown Art Association & Museum. For those who enjoy biking, pedaling through the Provincetown dunes on the Province Lands Trail is heaven.
Day 10: A Sail Off the Coast of Provincetown
A hike along the West End breakwater is a temptation for most visitors, but only the heartiest hikers make it all the way out to Long Point at the tip of the Cape Cod peninsula. A less vigorous way to get there is by boat; Flyer's Boatyard runs frequent shuttles. End your day with a sunset sail on the Bay Lady II, a 73-foot schooner.
Day 11: Exploring Nantucket
It's worth it to spend a couple of nights on Nantucket to see the whole island and to have time to try out some of the fabulous fine-dining restaurants. The island is perfect for casual bikers. You can crisscross the entire island on well-maintained bike paths. You may want to try all the major paths -- to 'Sconset, to Madaket, and to Surfside Beach. For history buffs, the first stop is the Whaling Museum. A Nantucket Historical Association ticket will get you into several other interesting historic sites. Leave plenty of time to wander the cobbled streets of Nantucket for shopping.
Day 12: Nantucket Tours
Two terrific tours on Nantucket will give you special insight on the island: around the harbor and out to Great Point. Several companies offer a cruise around the harbor, including Endeavor Sailing Excursions, or you can rent your own motorboat to check it out. The Trustees of Reservations offers tours through the Coskata-Coatue Wildlife Refuge and out to Great Point Lighthouse.
Day 13: Arrive on Martha's Vineyard
Whether you decide to explore by shuttle bus, by guided bus tour, or by bicycle, you'll have time to see the major sites on the island of Martha's Vineyard in a couple of days. Start your visit in Vineyard Haven, which has, arguably, the best shopping on the island. With your gift shopping completed, you can head over to Oak Bluffs to check out the "gingerbread houses," the turn-of-the-20th-century Victorian cottages clustered around the Trinity Park Tabernacle. Before leaving Oak Bluffs, take a ride on the Flying Horses Carousel.
Day 14: Edgartown & Aquinnah
Next head to Edgartown, a quintessential New England town of sea captains' houses and white picket fences. Take the 5-minute ferry over to Chappaquiddick to stroll through Mytoi, a 14-acre Japanese garden. Head "up-island," by bike or shuttle bus, to West Tisbury, and check out the interesting art galleries. In Chilmark you'll want to stop in Menemsha, a traditional, weathered fishing village. In Aquinnah you'll visit the red-clay Gay Head Cliffs.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.