Cape Cod and the Islands: Nantucket, Martha's Vineyard and Newport

1. Day 1: Arrive in Boston and walk the Freedom Trail

   Boston Logan International Airport to your hotel, then the Freedom Trail on foot

   • Drive about 15 min
   • Welcome dinner
   • Stay in Boston
   Day 1 details

   Fly into Boston Logan International Airport (BOS), across the harbour from downtown, and a driver meets you for the short drive through the harbour tunnel to a central hotel. We plan the day around flights landing by about 1 pm; that is our working assumption, and the latest arrival time is confirmed with your final itinerary. In mid-afternoon your See Sight Tours guide meets the group in the lobby and we set off on foot along the Freedom Trail, the red line of brick and paint that links the city's revolutionary sites over about 4 km. We start on Boston Common, the oldest public park in the country, pass the gold dome of the Massachusetts State House and the Granary Burying Ground, then the Old South Meeting House, the Old State House and the site of the Boston Massacre, and Faneuil Hall. The walk ends in the North End, the old Italian quarter, at the Paul Revere House and the Old North Church. Dinner is right there: a welcome meal together at a local restaurant.

   Included

   • Pick-up at Boston Logan International Airport (BOS)
   • Guided walk on the Freedom Trail, from Boston Common to the Old North Church
   • Welcome dinner in the North End

   Easier option: Walk the first half, from Boston Common to Faneuil Hall, and take a taxi to meet the group for dinner.

   Free time: Free until the mid-afternoon walk

   Activity: About 4 km on city pavements, with a few short slopes in the North End.

   

2. Day 2: Plymouth, then Chatham on the elbow of the Cape

   Boston to Plymouth, over the Cape Cod Canal to Chatham, then Hyannis

   • Drive about 3 h
   • Breakfast and lunch
   • Stay in Hyannis
   Day 2 details

   We leave Boston at 8:30 and drive about an hour south to Plymouth, reaching the waterfront at about 9:30, before the coaches. Plymouth Rock sits under its granite portico by the harbour, and a few steps away Mayflower II, a reproduction of the 1620 ship that was built in England and sailed over to Plymouth in 1957, shows how 102 passengers lived below deck for more than two months in 1620. A short drive south, Plimoth Patuxet Museums tells both sides of the story: the Historic Patuxet Homesite, where Wampanoag staff talk about their people's life here, and a re-created 17th-century English village; we give it about 90 minutes. Lunch is in Plymouth, and if the museum runs long we shorten the Chatham stop to the lighthouse overlook. In the afternoon we cross the Cape Cod Canal on the Sagamore Bridge and drive out to Chatham. From the lighthouse overlook you see the break in the barrier beach and the open Atlantic beyond; at the Fish Pier the boats unload in the afternoon and grey seals wait in the harbour. Then it is half an hour to Hyannis, our base for three nights.

   Included

   • Plymouth Rock and Mayflower II with your guide
   • Plimoth Patuxet Museums: the Historic Patuxet Homesite and the 17th-century English village
   • Lunch in Plymouth
   • Chatham Lighthouse overlook and Chatham Fish Pier

   Easier option: Skip the English village at Plimoth Patuxet and wait at the visitor centre café, and watch the Chatham harbour from a bench while the group walks to the Fish Pier.

   More active option: At Chatham, take the stairs down from the lighthouse overlook to Lighthouse Beach for a closer look at the break in the barrier beach.

   Free time: Evening free in Hyannis

   Activity: About 90 minutes on foot at Plimoth Patuxet on gravel paths with gentle slopes, plus short walks in Plymouth and Chatham.

   

3. Day 3: Whales off Provincetown and the National Seashore

   Hyannis to Provincetown, out to Stellwagen Bank, then Race Point, Wellfleet and Eastham

   • Drive about 3.5 h
   • Breakfast and lunch
   • Stay in Hyannis
   Day 3 details

   We leave at 8 am and drive about an hour and a half up Route 6, more in summer traffic, to Provincetown, at the tip of the Cape, where the Pilgrims first anchored in November 1620 and signed the Mayflower Compact in the harbour. From MacMillan Pier a mid-morning whale-watch boat runs out to Stellwagen Bank, a marine sanctuary where humpback, fin and minke whales feed through the summer; a naturalist on board explains what you are seeing. The trip takes about three to four hours. Back on shore, lunch is a sit-down meal in town, with time afterwards to walk Commercial Street. Then we head into the dunes of the Province Lands to Race Point Beach, and back down the Cape through the Cape Cod National Seashore: the Marconi Station site in Wellfleet, from which the first wireless message from a US president to a British monarch crossed the Atlantic in 1903, Nauset Light and the view over Nauset Marsh from the Salt Pond Visitor Center. We are back in Hyannis by about 7.

   Included

   • Whale watch from Provincetown to Stellwagen Bank with a naturalist, about 3 to 4 hours
   • Sit-down lunch in Provincetown
   • Race Point Beach in the Province Lands
   • Cape Cod National Seashore: the Marconi Station site, Nauset Light and the Salt Pond Visitor Center

   Optional experiences

   • A dune tour by 4x4 in the Province Lands in place of free time in town (price shown at booking)

   Easier option: Skip the boat if you get seasick: spend the morning in Provincetown at the Pilgrim Monument and Provincetown Museum and on Commercial Street, and meet the group for lunch.

   More active option: After lunch, climb the Pilgrim Monument, about 77 m, by its stairs and ramps for the view over the whole Outer Cape.

   Free time: An hour in Provincetown after lunch; evening free in Hyannis

   Activity: The longest day, about 11 hours out, with about three and a half hours of driving in all. The boat is open water: bring a warm layer and take seasickness tablets beforehand if you need them.

   

4. Day 4: A day on Nantucket

   Hyannis to Nantucket by ferry and back

   • By ferry
   • Breakfast and lunch
   • Stay in Hyannis
   Day 4 details

   Today the vehicle stays parked. We walk from the hotel to the Hyannis harbour for a morning high-speed ferry, about an hour across Nantucket Sound, and come into the harbour past the lighthouse at Brant Point, with grey-shingled houses climbing the hill behind the wharves. We go early so the town walk is done before the day-trip crowds. A local guide takes us up the cobbled Main Street, past the brick and clapboard houses built by whaling captains and merchants when this small island led the world's whaling trade, and explains how the industry rose and fell. Then the Whaling Museum, in a former candle factory, with the skeleton of a sperm whale hanging over the main hall. Lunch is near the wharves. The afternoon is yours: browse the town, walk out to Brant Point Light, or take the island shuttle to Siasconset and its rose-covered cottages. We sail back to Hyannis in the late afternoon, and dinner is your choice.

   Included

   • High-speed ferry from Hyannis to Nantucket and back
   • Guided walk of Nantucket town with a local guide
   • Nantucket Whaling Museum
   • Lunch in Nantucket town

   Optional experiences

   • Bike rental or the island shuttle to Siasconset (price shown at booking)

   Easier option: Stay in town after the museum: the harbour, the shops and Brant Point Light are all within an easy walk.

   More active option: Ride a rented bike about 13 km out to Siasconset on the paved bike path and walk the Bluff Walk towards Sankaty Head Light.

   Free time: Afternoon free on Nantucket; evening free in Hyannis

   Activity: About 3 to 4 km on cobbled and brick streets.

5. Day 5: Martha's Vineyard, from Oak Bluffs to Aquinnah

   Hyannis to Woods Hole, ferry to Vineyard Haven, then Oak Bluffs, Edgartown, Aquinnah and Menemsha

   • Drive about 2.5 h
   • Breakfast, lunch and dinner
   • Stay in Martha's Vineyard
   Day 5 details

   We drive about 40 minutes to Woods Hole and board the ferry to Vineyard Haven with our vehicle, about 45 minutes across Vineyard Sound. First stop is Oak Bluffs and the Methodist camp-meeting grounds, where more than 300 small cottages painted in bright colours and trimmed with wooden gingerbread ring the open iron Tabernacle. Nearby, the Flying Horses Carousel, built in 1876 and one of the oldest working carousels in the country, still gives riders a chance at the brass ring; your ride is included. Then along the beach road to Edgartown for lunch, among the white houses of the whaling captains and the lighthouse at the harbour mouth. In the afternoon we go up-island through the farms and stone walls of West Tisbury and Chilmark to Aquinnah, where coloured clay cliffs fall to the sea below Gay Head Light, on the land of the Wampanoag Tribe of Gay Head (Aquinnah). Dinner is in the fishing village of Menemsha, by the harbour where people gather for the sunset.

   Included

   • Ferry from Woods Hole to Vineyard Haven, with the vehicle
   • Oak Bluffs camp-meeting cottages and the Tabernacle with your guide
   • A ride on the Flying Horses Carousel
   • Edgartown and lunch there
   • The Aquinnah cliffs and Gay Head Light
   • Dinner in Menemsha

   Easier option: Stay at the Aquinnah overlook beside Gay Head Light instead of walking further; every stop today is a few steps from where we park.

   More active option: Walk down to the beach below the Aquinnah cliffs and along the sand while the group stays at the overlook.

   Free time: An hour free in Edgartown after lunch

   Activity: Short walks only; the path down to the beach at Aquinnah is sandy and steep.

   

6. Day 6: Newport: The Breakers and the Cliff Walk

   Vineyard Haven to Woods Hole by ferry, then Newport and Ocean Drive

   • Drive about 2 h
   • Breakfast, lunch and dinner
   • Stay in Newport
   Day 6 details

   A morning ferry takes us back to Woods Hole, and from there it is about an hour and three quarters by road, past New Bedford and Fall River and over the bridge onto Aquidneck Island, to Newport. Lunch is by the harbour. Newport was the summer resort of the richest families of the Gilded Age, and the houses they called cottages line Bellevue Avenue above the sea. In the early afternoon we visit The Breakers, built in 1893 to 1895 for Cornelius Vanderbilt II, a 70-room Italian Renaissance palace with an audio guide, on a timed ticket so we avoid the queue. From its gates we join the Cliff Walk and follow it north towards the Forty Steps, with the mansion lawns on one side and the Atlantic surf on the other. Late in the afternoon we drive Ocean Drive, the coast road past Brenton Point, where the wind usually blows, then come back into town for a farewell dinner together.

   Included

   • Ferry from Vineyard Haven to Woods Hole, with the vehicle
   • Lunch in Newport
   • The Breakers, ticket included
   • The Cliff Walk from The Breakers towards the Forty Steps with your guide
   • Ocean Drive and Brenton Point
   • Farewell dinner in Newport

   Easier option: Ride in the vehicle along Bellevue Avenue to the Forty Steps and look out over the Cliff Walk from there.

   More active option: Walk the Cliff Walk south as well, past Rosecliff and Marble House towards its rocky southern end, where sections are open, and meet the vehicle at the far end.

   Activity: About 2 km on the Cliff Walk; the northern section is paved and level.

7. Day 7: Marble House and back to Boston

   Newport to Marble House, then Boston Logan International Airport

   • Drive about 2 h
   • Breakfast
   Day 7 details

   Breakfast is unhurried. At opening we visit Marble House, a few minutes down Bellevue Avenue, finished in 1892 for William K. Vanderbilt and his wife Alva, and faced with about 500,000 cubic feet of marble. Its gold ballroom and, on the lawn above the sea, the Chinese Tea House that Alva later added are the high points; the visit takes about an hour, before most visitors arrive. We leave Newport around noon and drive about two hours north to Boston Logan International Airport, arriving early to mid-afternoon; your guide sees you to the terminal. If you are staying on in Boston, we drop you downtown instead, and if Rhode Island T. F. Green International Airport (PVD) suits your flight better, it is about 40 minutes from Newport and we can drop you there. Summer Friday and Sunday traffic towards Boston can be heavy, so we allow time for it. Book flights leaving after about 4:30 pm from Boston, or after about 2:30 pm from Providence.

   Included

   • Marble House, ticket included
   • Drop-off at Boston Logan International Airport (BOS), downtown Boston or T. F. Green International Airport (PVD)

   Easier option: See the ground floor of Marble House only and wait in the garden by the Chinese Tea House while the group finishes the visit.

   Activity: Book a flight from Boston leaving after about 4:30 pm, or from Providence after about 2:30 pm.

Wildlife and weather: June to September is warm on the Cape and islands, with fog some mornings and the odd thunderstorm; late August and September can bring tropical storms that cancel ferries for a day. Humpback, fin and minke whales feed on Stellwagen Bank through the summer, and grey seals gather off Chatham, but no sighting is ever guaranteed.

• Boston1 night
• Hyannis3 nights
• Martha's Vineyard1 night
• Newport1 night