The Islands of Cape Cod – Deluxe

Martha's Vineyard, Nantucket and Provincetown

5 Days

Starting At $Custom
A high-end tour featuring both Islands, the National Seashore, Provincetown and more. We use wonderful hotels, better restaurants and full time Tour Manager.

The Islands of Cape Cod – Deluxe

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Tour Highlights:

  • A Day on Martha’s Vineyards
  • Island Sights & History
  • Time for Shopping and Lunch
  • Guided Tour of Oak Bluffs
  • Cape Cod Seashore Adventure
  • From Chatham & Provincetown
  • The Cape Cod National Seashore
  • Whale Watching Cruise
  • Dunes Tour with Wine & Cheese
  • A Day on Nantucket
  • Island Sights & History
  • Time for Shopping and Lunch
  • Guided Tour of Hyannisport
  • Group photo stop at JFK Memorial
  • Guided Tour of Historic Sandwich
Tour Inclusions:

  • Four Nights Oceanfront Resort
    • with Cape-Codder Reception
  • Four Hotel Breakfasts
  • Four Dinners including:
    • Cape Cod Lobster Dinner
    • Dinner with Storyteller
    • Wine & Cheese on the Beach
  • Tour Manager from Arrival to Departure
  • All Admissions & Sights as listed
  • All Taxes & Tips on these services
  • Luggage Handling
  • One Free with Every 16 Paid

Prices Per Person

Custom pricing, please contact us for a quote.

Best Rates Spring & Fall

Day 1 – Cape Cod – Cocktail Reception with Local Guide 

Cape Cod, is that hook-shaped peninsula protecting Massachusetts from the Atlantic, and is a popular summertime destination that sell well to group tours in the spring and fall. You’ll see quaint villages, seafood shacks, lighthouses, ponds, bays and ocean beaches.   We utilize the finest beachfront resorts on our trips, like the Red Jacket Beach Resort, where you find an oceanfront lawn, a gorgeous view of Nantucket Sound and a peaceful beach.   When you arrive a reception with tray’s of “Cape-Codder Cocktails will be waiting for your group.

Also on arrival you will your full-time local Guide and historian who will escort you for these next five days.  Dinner is included at a local restaurant.  (D)

Day 2 – A Day on Martha’s Vineyard

Shaped like a triangle and 8 miles off  the coast this island is becoming a secret summer hideaway of the rich and famous. A “Hollywood East” reputation is building thanks to frequent visitors like Pres. Obama, David Letterman and Bill Murray.  But despite the all-star summer lineup, a laid-back lifestyle still rules the island.  While you can find insanely expensive summer cottages and restaurants to match, the reality is this is a summer resort that evolved from an 18th and 19th century whaling heritage.   You may spot a film star in Edgartown, but your guaranteed interesting sights in Oak Bluffs where the Flying Horses Carousel (1876) still spins,  and the Carpenter Gothic Cottages at the Methodist Meeting Grounds where open-air Christian Revivals first started in  1835.

The subtle nuances and diversity of island history, architecture, and culture hide in plain sight — your guide will explain on your morning tour.  You’ll see the stately Greek revival homes built by sea captain of years ago, hear stories of notable residents, religious leaders, and political activists, along with meeting houses, cemeteries, and other points of interest.  You’ll have time to enjoy an Island lunch and find the island’s must-have souvenir — a Black Dog sweatshirt.

Late afternoon, your group will ferry back to the mainland for a delicious group dinner at a local restaurant.  (B,D)


Day 3 – Cape Cod Seashore Adventure – Provincetown – Whale Watch Cruise – Dune Schooners 

Your exciting  day of adventure starts in a charming seaside village beside the Chatham Light (1808) near the elbow of the Cape’s silhouette.  From here you travel along the Cape Cod National Seashore, where spectacular views off the cliffs, overlook the Atlantic Ocean.  You’ll see the horizon as Thoreau saw it when he wrote “There was nothing but that savage ocean between us and Europe.” This great Outer Beach is now a protected national seashore with 40 miles of pristine beach, marshes, ponds, and uplands support a diversity of species with lighthouses and wild cranberry bogs lining the way.

Lunch break is in Provincetown, at the tip of the Cape, a waterfront community filled with eclectic shops and boutiques.

Then a Whale Watching High Seas adventure follows! A naturalist narrates the cruise and describes the whales you may see, their behavior, and some of the other marine life common to the area. It has been said that “To have a huge, friendly whale willingly approach your boat and look you straight in the eye is without doubt one of the most extraordinary experiences on the planet.”

Once your Whaling Ship docks,  you set out on a new adventure, in large four-wheel drive Suburbans, with sand dunes stretching as far as you can see.  It’s a place where beach grass, dark green pine trees and deep red beach plums are nestled in hollows which are brought together by a silhouette of blue sky. As you travel your guide will points out the “dune shacks” where famous artists and writers like Eugene O’Neill and Harry Kemp became inspired to create their work.  Halfway into this experience, we’ll circle the suburbans and enjoy a snack on the beach with Wine & Cheese and wind in your hair.

When you finally return at the end your day, you’ll feast on a traditional Cape Cod lobster dinner at one of the Cape’s most popular seafood restaurants .  And, then completely exhausted from both the day’s experience and the evening’s feast you have a chance to sink gratefully into bed.  (B,D)

Day 4 – A Day on Nantucket – Storyteller & Dinner 

After breakfast, enjoy a brief tour of Hyannisport, home of the Kennedy clan.   You will have a special ‘group photo’ op at the Kennedy Memorial and Korean War Memorial overlooking  Veteran’s Beach, then board the High speed ferry for a cruise to Nantucket. The sight of the island coming into view from the bow is a stirring one, long lines of foaming breakers crash against vast stretches of sands on the south shore, while church steeples dot the downtown horizon to the north.  This Island is 30 miles south and to the east of Martha’s Vineyard.  Fondly known as “The Gray Lady” it is a place of windswept beaches, blinking lighthouses and hosts a charming way of life.

Once the world’s top whaling port it is now designated a National Historic District.  Her downtown architecture has changed little since the 17th century and never fails to captivate visitors with its cobblestone streets, stately facades and quaint wharf cottages intertwined with fragrant roses and dense clusters of colorful hydrangeas. You will have some free time to explore the island, enjoy lunch on our own, and browse among the many charming shops.

Later this afternoon, you cruise back to the mainland, where tonight, you enjoy a delicious dinner and Cape Cod specialty dessert along with an entertaining Storyteller who will share stories of Cape Cod’s mysteries, legends and lore!   (B,D)

Day 5 – Historic Sandwich Tour & Depart for Home 

This morning after breakfast, you journey to the Cape’s oldest town, Sandwich. Enjoy a tour of the village, with views of Shawme Pond, historic Dexter Grist Mill and take a sip out of the ‘fountain of youth’ before you bid farewell and depart for home. (B)

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