September 19th - September 25th, 2027

Classic Cape Cod

Cape Cod, MA

Experience the best of coastal New England on this Cape Cod getaway, featuring a beachfront stay at the Red Jacket Beach Resort and memorable day trips to the region’s most iconic destinations. Fly into Boston and enjoy the relaxed rhythm of the Cape as you explore seaside towns, scenic coastal routes, and historic landmarks, including Provincetown with your choice of whale watching or a guided dune tour, full-day visits to Martha’s Vineyard and Nantucket, the Kennedy legacy in Hyannis, and the grandeur of Newport’s Gilded Age mansions. With included meals, expert local guides, and a balanced mix of guided touring and free time, this journey captures the classic charm and coastal beauty that define Cape Cod and New England.

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Tour Inclusions:

Air

Group roundtrip air included when booked by September 1, 2026

Transportation

Deluxe motorcoach transportation

Meals

12 Meals

Gratuities

Gratuities for guides & driver

Activity Level

Physical activity rating based on 1 of 5 levels.

Activity Level 3 (Out of 5)

Moderate

For active travelers with good mobility and balance.

Walkers, rollators, wheelchairs, or canes are not recommended.

Walking distance: 1.5 to 3 miles per day.
Pace: Moderate with limited rest opportunities.
Terrain: Uneven surfaces may include cobblestones, light hills, or stairs without handrails.
Elevation: Includes stairs, occasional steep areas, or boarding transportation without ramps.
Suitable for: Travelers who are independently mobile and can comfortably walk and stand for extended periods.
Typical activities: Walking tours in historic districts, visits to outdoor markets, scenic paths with inclines.

What You'll Do

Highlights

Six-night beachfront stay on Cape Cod at the Red Jacket Beach Resort….Unpack once!
Full-day guided visit to Martha’s Vineyard, including Edgartown and Oak Bluffs
Guided island tour and free time on picturesque Nantucket
Choice of adventure: whale watching cruise or guided dune tour in Provincetown
Gilded Age elegance in Newport, featuring Marble House and The Breakers
Free time to explore Provincetown’s shops, galleries, and waterfront
Classic New England lobster dinner with alternate entrées available
Insight into the Kennedy legacy in Hyannis with museum visits
12 Meals

Pricing

*Group roundtrip air included if you book by September 1, 2026

$3,595 Per Person Double

$4,595 Per Person Single

Your Itinerary

Day One

Arrive in historic Boston and travel south to the relaxed seaside charm of Cape Cod. Settle in at the beachfront Red Jacket Beach Resort, your home for the week, and enjoy a welcome dinner overlooking the Atlantic. A perfect start to your Cape Cod escape. (D)

Day Two

Explore the scenic beauty of Cape Cod along historic Route 6A, passing classic windmills, lighthouses, and sweeping ocean views. Visit the Cape Cod National Seashore and travel to the colorful harbor town of Provincetown. Choose between an unforgettable whale watching cruise with onboard naturalists or a guided dune tour through protected coastal landscapes. (B,D)

Day Three

Travel to Woods Hole and ferry to iconic Martha’s Vineyard. Enjoy a guided Down Island tour highlighting the island’s history, charming villages, and coastal scenery. Free time allows you to explore Edgartown and stroll through the colorful cottages of Oak Bluffs before returning to the Cape for dinner. (B,D)

Day Four

Discover Hyannis and its deep ties to the Kennedy family with visits to local memorials and museums dedicated to President John F. Kennedy’s time on Cape Cod. Enjoy free time for shopping and lunch along Main Street, then relax with a leisurely afternoon back at the resort and time on the beach.(B,D)

Day Five

Journey to elegant Newport, America’s first resort town. Enjoy a narrated tour through Gilded Age neighborhoods, along Ocean Drive, and past the grand estates lining Bellevue Avenue. Step inside two of Newport’s most famous mansions, Marble House and The Breakers, before enjoying dinner in Newport and returning to Cape Cod. (B,D)

Day Six

Cruise to storybook Nantucket, where cobblestone streets, whaling history, and seaside charm await. Take a guided island tour, then enjoy free time for lunch, shopping, and exploration near the harbor. Return to the Cape for a classic lobster dinner, with alternate entrées available. (B,D)

Day Seven

Travel through historic Sandwich, the oldest town on Cape Cod, known for its village green, salt marshes, and cranberry bogs. Continue to Plymouth, America’s Hometown, with photo stops at Plymouth Rock, the Forefathers Monument, and the Mayflower II. Enjoy free time along the waterfront before returning to Boston for your flight home. (B)