Day 1:  Chatham for 3 nights
Pick up car in Boston at the airport
Drive to the Cape Cod peninsula where America hides some of its most beautiful beaches (about 1 hour and 30 minutes)

Accommodation at Chatham Bars Inn *****
Offering views of the Atlantic Ocean, this oceanfront inn in Chatham, Massachusetts features 4 restaurants and a full-service spa. Each spacious accommodation provides a fully stocked minibar and flat-screen TV.
An oceanfront heated pool with surrounding cabanas and the private beach area are available at Chatham Bars Inn. A 24-hour gym, tennis and croquet courts are on site as well.
Decorated in New England design, each accommodation offers air conditioning, a state-of-the-art sound system and coffee facilities. The bathrooms include deluxe bath amenities, bathrobes and slippers.
Chatham Inn offers local tours which leave from the private boat dock and travel to Martha’s Vineyard and Nantucket. Deep sea fishing, barrier beach walks and antique car tours can be arranged.
The elegant Main Dining Room features panoramic views of the ocean. Local seasonal cuisine is offered. Guests can have a casual meal at the Sacred Cod Tavern or afternoon tea in the South Lounge.
https://www.chathambarsinn.com/

Day 2
Day at leisure to relax
Or you could also
Bike on the Cape Cod Rail Trail, an old railway line that has been converted into a bike path
Visit Cape Cod natural history museum
Visit Cape Cod crisps factory in Hyannis, yum!
Do some bird watching:  blue herons, peregrine falcons and bald eagles
Try the famous sea salt caramels, Salt water taffy
Spot the rich and famous in Hyannis, where the Kennedys had their second home
Take a kayak or paddle board out for the day. This is a wonderful manner to explore the bay.  

Day 3
3h 30 minutes Private Whale Watch Charter at 9:45 am
Your captain will be take you in the area out of Provincetown, MA., off the waters of Cape Cod.
He will try to find the best spot for seeing whales.
Since 1986, hunting has been prohibited and whales have stopped here for several months on their way to the Caribbean and South America. Off Cape Cod, you can come across dozens of whales – humpback whales, right whales … – in a single trip.

Have lunch in Provincetown, go for a clam chowder and a lobster roll.

Then explore this typical New England sea side resort.  The first settlers stayed only three months, as they thought that the land was too wild and difficult to cultivate.  It then expanded in the 19th century with the whaling industry.
Immerse yourself in history just by reading plaques on buildings. Blue plaques contain the dates.

Day 4:  Nantucket for 2 nights
Drive to Hyannis and leave car at ferry parking
Take the ferry and cross to Nantucket tickets included
Departure at 9:30 am, arrival at 10:30 am
Shuttle from the ferry to the hotel
1 double queen, taxes included at The Wauwinet Nantucket*****
This luxurious Nantucket hotel boasts private beach access, as well as an on-site restaurant. Sailing and fishing opportunities are also offered. Nantucket town centre is 16.1 km away.
A flat-screen cable TV, free Wi-Fi, and an iPod docking station are offered at The Wauwinet Nantucket. Each guest room is decorated in bright colours and beach decor. Select rooms offer views of the Bay.
Guests can relax in the lounge chairs or visit the tennis courts at the Nantucket Wauwinet Hotel.
Topper’s Restaurant serves fine cuisine overlooking Nantucket Bay. Al fresco dining is available for lunch and dinner on Topper’s Deck.
No resort fee, Wi-Fi access, concierge, ferry shuttle, early risers’ coffee, tea and baked goods continental breakfast, afternoon port and cheese,  bicycles, kayaks, sunfish, paddleboards, tennis, van and watershuttles, movie DVD library and popcorn, daily newspaper, beach chairs, towels, umbrellas
https://www.wauwinet.com/?utm_source=google%20my%20business&utm_medium=listing&utm_campaign=visit%20website

Day 5
Day at leisure
Walk to breathtaking beaches on the Atlantic Ocean to swim, surf, and soak up the sunshine.
Explore historic lighthouses, enjoy shopping, dining and sightseeing in Nantucket Town, or tour unique Nantucket attractions like the Whaling Museum. The history, charm, and natural beauty of Nantucket is all around us.
The famous seals are often seen out at Great Point Beach, a heavily secluded beach near Great Point Lighthouse on the very tip of Nantucket’s farthest peninsula. This beach is a part of the Coskata-Coatue Wildlife Refuge, which has special restrictions to minimize disturbances to Nantucket’s growing colony of seals.

Day 6  Martha’s Vineyard for 2 nights
Shuttle to the ferry
Ferry tickets from Nantucket to Hyannis
Departure at 9:55 am, arrival at 10:55 am

Drive to Falmouth
Park your car at the ferry terminal
Visit Falmouth and have lunch
Designated a Preserve America community in 2013 by former First Lady Michelle Obama, Falmouth is iconic.
Explore the pedestrian-friendly, tree-lined streets that lead to a picturesque Village Green surrounded by majestic homes showcasing Colonial and Federalist-inspired architecture, once owned by sea captains and other legends of local lore. On the hour, a bell cast by Paul Revere rings from atop the First Congregational Church.
Historic Falmouth Village, which spans Main Street to Queens Buyway, is packed with an array of authentic ethnic offerings, from Indian to Thai, along with American gastropub comfort food, sure to please every age and every palate.
Mom and Pop shops offering Cape Cod fashion to souvenir keepsakes mingle with iconic modern favorites like Lilly Pulitzer and The Black Dog. Bring home a piece of the Cape at one of the local galleries showcasing stunning oils and watercolors inspired by the local palette of sea and sky.

Ferry tickets from Falmouth to Edgartown
Departure at 4 pm, arrival at 5 pm

1 double king room, breakfast & taxes included at The Christopher
Featuring free WiFi and a terrace, The Christopher offers accommodation in Edgartown. Free private parking is available on site.
The rooms include a flat-screen TV. Certain units have a seating area where you can relax. Each room is fitted with a private bathroom equipped with a shower. For your comfort, you will find bath robes and free toiletries.
Complimentary breakfast and afternoon treats are offered.
Falmouth is 20 km from The Christopher, while Hyannis is 35 km from the property. Martha’s Vineyard Airport is 8 km away.
https://www.thechristophermv.com/

Dinner reservation at Detente
Situated in downtown Edgartown, Détente is a charming restaurant and bar that serves seasonal, creative dishes. Its setting features two floors for guests to dine, as well as a garden patio. Détente uses ingredients that are sourced from local farmers and fishermen. This eatery also offers a tasting menu with optional wine pairings. 

Day 7
Day at leisure
Edgartown was a major whaling port in the late 1700’s and early 1800’s and the charm of that era is evident around every corner. Picturesque and chic, it’s the perfect home base for discovering a variety of Martha’s Vineyard activities during your island vacation.
Stroll left out our front door, meander through town and on through the neighborhood of historic captain’s homes to Edgartown Lighthouse. You’ll love the beach scene surrounding the structure, but for the best experience, pay for a tour and climb to the top for panoramic views of Edgartown Harbor.

Sunset paddle tour with picnic at 6 pm for 2 hours
This romantic tour departs an hour before sunset. With your guide paddle out in the calm, colorful waters of dusk, enjoy the wildlife and beauty of the watery coast. Land for a beach picnic as the sun sets and the moon rises! Use the light of the moon or our glow sticks to explore the pond on your return trip, listening and watching for nocturnal animals! Equipment, guides & beach picnic provided!

Day 8
Ferry tickets from Edgartown to Falmouth
Departure at 9:30 am, arrival at 10:30 am
Drop off car at Boston airport