Cornelius Amann
October 06, 2026
5/5
Cape Cod and the Islands: Nantucket, Martha's Vineyard and Newport
7 days from Boston: Plymouth, three nights on Cape Cod with Chatham, Provincetown and a whale watch, a day on Nantucket, a night on Martha's Vineyard and the Newport mansions.
7 days · Round trip from Boston · up to 12 guests
Nantucket town and harbour, with the gold-domed tower of the Unitarian church Photo: John Phelan, CC BY 3.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Nantucket_Skyline,_Nantucket_MA.jpg)
The facts
At a glance
- Length
- 7 days, 6 nights
- Start and end
- Round trip from Boston
- Group size
- 7 to 12 guests
- Activity level
Easy
Easy walking on most days: about 4 km on city pavements on the Freedom Trail, town walks on cobbles in Nantucket and Edgartown, sand paths at the National Seashore and up to about 2 km of the Cliff Walk in Newport. Three to four hours on an open-water whale-watch boat and four ferry crossings. You can sit any walk or the boat out.
- Meals included
- 6 breakfasts, 5 lunches, 2 dinners
- Room of your own
- + CAD 1,060 (estimated price)
- Season
- June to September
Highlights
Why this trip
- The Freedom Trail on foot with your guide on the afternoon you land, and a welcome dinner in the North End
- Plymouth Rock, Mayflower II and Plimoth Patuxet, then the seals at Chatham Fish Pier
- A whale watch from Provincetown to Stellwagen Bank, included, with Race Point and the National Seashore on the way back
- A whole day on Nantucket by ferry, with a guided walk of the old whaling town and the Whaling Museum
- A night on Martha's Vineyard: the gingerbread cottages of Oak Bluffs, Edgartown, the Aquinnah cliffs and dinner in Menemsha
- The Breakers, Marble House and the Cliff Walk in Newport, with a farewell dinner by the harbour
- Three nights in one Cape Cod base, a short walk from the Nantucket ferry
What makes this trip different
Free time is part of the plan
Free time and choices are marked on the days they fall.
Solo without the penalty
A room of your own is + CAD 1,060 (estimated price).
Day by day
Itinerary
Tap any stop on the map to open that dayClick any stop on the map to open that day
Arrive in Boston and walk the Freedom Trail
Boston Logan International Airport to your hotel, then the Freedom Trail on foot
- Welcome dinner
- Stay in Boston
- Drive about 15 min
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.
Afternoon
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.
Evening
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.
Plymouth, then Chatham on the elbow of the Cape
Boston to Plymouth, over the Cape Cod Canal to Chatham, then Hyannis
- Breakfast and lunch
- Stay in Hyannis
- Drive about 3 h
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.
Afternoon
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.
Whales off Provincetown and the National Seashore
Hyannis to Provincetown, out to Stellwagen Bank, then Race Point, Wellfleet and Eastham
- Breakfast and lunch
- Stay in Hyannis
- Drive about 3.5 h
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.
Morning
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.
Afternoon
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.
A day on Nantucket
Hyannis to Nantucket by ferry and back
- Breakfast and lunch
- Stay in Hyannis
- By ferry
Today the vehicle stays parked.
Morning
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.
Afternoon
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.
Evening
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.
Martha's Vineyard, from Oak Bluffs to Aquinnah
Hyannis to Woods Hole, ferry to Vineyard Haven, then Oak Bluffs, Edgartown, Aquinnah and Menemsha
- Breakfast, lunch and dinner
- Stay in Martha's Vineyard
- Drive about 2.5 h
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.
Afternoon
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).
Evening
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.
Newport: The Breakers and the Cliff Walk
Vineyard Haven to Woods Hole by ferry, then Newport and Ocean Drive
- Breakfast, lunch and dinner
- Stay in Newport
- Drive about 2 h
Morning
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.
Afternoon
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.
Evening
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.
Marble House and back to Boston
Newport to Marble House, then Boston Logan International Airport
- Breakfast
- Drive about 2 h
Morning
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.
Afternoon
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.
- Boston1 night
- Hyannis3 nights
- Martha's Vineyard1 night
- Newport1 night
- Bostonend
- Overnight stop
- Day trip
- By boat or train
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.
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Before you book
Right for you?
Good for you if you want
- Travellers who want Cape Cod, both islands and Newport in one summer week without driving or booking ferries themselves
- First-time visitors to New England who like history, harbours and lighthouses
- Couples and solo travellers who want a small table and the same guide all week
- Anyone who wants the whale watch and the mansion tickets in the price, not sold on the day
Not for you if you want
- Beach holidays: there is time by the sea, but every day has a plan
- Travellers who want two nights everywhere: the Vineyard and Newport get one night each
- Fall foliage: this is a summer trip; our New England Fall Colours and Acadia trip runs in autumn
- Anyone who cannot face a three-to-four-hour boat trip, unless you take the easy option on the whale-watch day
Book flights after we confirm your seat.
6 nights
Where you'll stay
Your hotels are named in your trip confirmation.
- Boston1 night
- Hyannis3 nights
- Martha's Vineyard1 night
- Newport1 night
One price
What's in the price
Included
Accommodation
- 6 nights in central hotels of at least 3-star-plus standard: 1 in Boston, 3 in Hyannis within walking distance of the Nantucket ferry, 1 on Martha's Vineyard, 1 in Newport
- Rooms shared, or your own for a supplement
Transport
- Pick-up at Boston Logan International Airport (BOS) on day 1 and drop-off there, downtown or at T. F. Green (PVD) on day 7
- Our own vehicle and driver for the whole trip
- High-speed ferry from Hyannis to Nantucket and back
- Ferry from Woods Hole to Vineyard Haven and back, with the vehicle
- The whale-watch boat from Provincetown
Your guide
- A See Sight Tours guide for the whole trip, with a local guide on Nantucket and a naturalist on the whale-watch boat
Activities
- Boston: guided walk on the Freedom Trail
- Plymouth: Plymouth Rock and Mayflower II
- Plymouth: Plimoth Patuxet Museums
- Chatham: the lighthouse overlook and the Fish Pier
- Provincetown: whale watch to Stellwagen Bank
- Cape Cod National Seashore: Race Point Beach, the Marconi Station site, Nauset Light and the Salt Pond Visitor Center
- Nantucket: guided town walk and the Whaling Museum
- Martha's Vineyard: the Oak Bluffs cottages, a Flying Horses Carousel ride, Edgartown, the Aquinnah cliffs and Menemsha
- Newport: The Breakers, the Cliff Walk and Ocean Drive
- Newport: Marble House
Meals
- Breakfast daily (6)
- 5 lunches: Plymouth, Provincetown, Nantucket, Edgartown and Newport
- 3 dinners: welcome dinner in Boston's North End, dinner in Menemsha, farewell dinner in Newport
Not included
- International flights to and from Boston
- An ESTA or US visa, if you need one
- Travel insurance
- Meals not listed: dinners on days 2, 3 and 4 in Hyannis, lunch on days 1 and 7
- Drinks
- Tips
- Optional activities: the Province Lands dune tour, bike rental or the shuttle on Nantucket
- Personal expenses
- Extra nights before or after the trip
Extras
- Room of your own
- CAD 1,060 (estimated price)
When you can go
Dates and prices
Pick your start date when you request to book. We check that date and confirm it in your quote.
Prefer to travel without a group or guide? Ask us about arranging hotels, transport and city tours for you to travel independently.
Before you book
Booking terms
Nothing is charged now. Full terms and the cancellation schedule come with your quote, before you accept.
Business addresses
See Sight Tours Trips (USA): 3172 N Rainbow Blvd, Las Vegas, NV 89108, United StatesSee Sight Tours Trips (Canada): 5305 50 Avenue, #1091, Red Deer, AB T4N 4B6, Canada+1-888-961-6584Guest reviews
What guests say
Reviews from guests on our day tours.
Jane
October 06, 2026
5/5
Susan
October 06, 2026
5/5
Tom L
October 05, 2026
5/5
MandL83
October 05, 2026
5/5
Darren O
October 05, 2026
5/5
Good to know
Questions
What does the price include?
Six nights in central hotels, breakfast daily, five lunches and three dinners, airport transfers, our own vehicle and driver, all four ferry legs, your See Sight Tours guide throughout, and every visit in the day plan: the Freedom Trail walk, Plimoth Patuxet and Mayflower II, the Provincetown whale watch, the Nantucket Whaling Museum, The Breakers and Marble House.
How big is the group?
The small-group trip runs with 7 to 12 guests, never more. That means one table at lunch, everyone hears the guide on the Freedom Trail and in Nantucket, and we board ferries and the whale-watch boat without waiting behind a coach load.
Who leads the trip?
A See Sight Tours guide travels with the group from the Boston airport on day 1 to the airport on day 7, with a professional driver in our own vehicle. On Nantucket a local guide leads the town walk, and a naturalist explains the whales on the boat.
How fit do I need to be?
Not very. The longest walk is about 4 km on the Freedom Trail on city pavements; elsewhere it is town walks on cobbles, short sandy paths and about 2 km of the Cliff Walk. The whale watch is three to four hours on open water. Every day has an easier option, and you can sit any walk out.
I am travelling solo. What will I pay?
A room of your own is CAD 1,060 on top of the shared-room price, shown up front with nothing added at checkout. Solo travellers share the same table, walks, ferries and boats as everyone else, and the guide looks after the group as one.
When is the best time to go?
June to September. Ferries run their full summer schedules, the whale-watch boats are in season, and the water is at its warmest. July and August are the busiest and dearest months on the islands; June and September are a little quieter. Expect fog some mornings and the chance of a tropical storm in late summer.
Will we see whales?
Very likely in summer, but no one can promise it. Humpback, fin and minke whales feed on Stellwagen Bank, a few miles off Provincetown, and the captain goes where the latest sightings are. If you get seasick, you can stay in Provincetown that morning and meet the group for lunch.
Why only one night on Martha's Vineyard and in Newport?
To fit both islands and Newport into a week. We give the Cape three nights in one base and visit Nantucket as a day trip from there, so the Vineyard and Newport get one night each. Each still has a full afternoon and evening, and your bags travel with our vehicle, so the moves are easy.
How is this different from your fall foliage trip?
New England Fall Colours and Acadia is our autumn trip: the White Mountains, the Mount Washington Cog Railway, Acadia National Park and the Maine coast. This one is the summer coast: Plymouth, Cape Cod, Nantucket, Martha's Vineyard and Newport. Only the Boston start is shared, so the two work well in different seasons.
How does booking work?
Pick a start date and request to book. We confirm your place within 24 hours, and nothing is charged until then. The small group starts from CAD 5,895 per person sharing, taxes included, and the private trip from CAD 10,610 per person.
Can we travel privately or on our own dates?
Yes. Besides the small group, the trip comes as a private trip for your party only, on a date you choose, with your own guide and vehicle. If you would rather travel independently on your own dates, ask us from the dates section and we will quote the same hotels, ferries and visits.
Do I need a visa for the United States?
Canadian citizens need only a valid passport. Travellers from Visa Waiver Program countries, such as the United Kingdom, Australia and most of the European Union, need an approved ESTA before flying. Others need a US visa. Check the US government rules for your nationality before you book flights.
See Sight Tours has been providing travel services across North America since 2006. Operating in 20 cities across Canada and the USA, the company specializes in small group tours that offer personalized, high-quality experiences for travelers.
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