September 15 - 18, 2025

Nantucket Extension

Experience the perfect blend of relaxation and adventure on Nantucket with a three-day itinerary that includes a harborfront dinner, a guided island tour, and plenty of free time to explore beaches, shops, and local cuisine at your own pace. With a relaxed schedule, each day promises a balance of planned activities and moments to unwind amid Nantucket’s coastal beauty.

Day 1: September 15

Nestled 30 miles off the Cape Cod coast, the island Town of Nantucket is a premier summer retreat with a unique blend of cosmopolitan allure and small-town charm.

MORNING

Nantucket Guests leave for the island via chartered transportation to Hyannis & ferry to Nantucket . Begin your island escape with a scenic ferry ride across Nantucket Sound, offering comfortable amenities and beautiful views.

AFTERNOON

Downtown Nantucket—a 5-minute stroll from the hotels— is the island’s hub for entertainment, rich island history, beautiful architecture, secret gardens, and waterfront dining.

Walk to Town/Lunch on your own: Wander through Nantucket’s charming, historic downtown filled with cobblestone streets, unique shops, and centuries-old architecture.

The following lunch options, along with the other fine restaurants, make downtown Nantucket a fun place to enjoy a meal with friends.

  • Provisions: Known for its famous turkey sandwiches and fresh ingredients, this cozy deli is perfect for a quick, satisfying lunch right near the harbor.

    Something Natural: A beloved spot offering generously-sized sandwiches, fresh-baked breads, and salads, all set in a peaceful, garden-like setting.

    The Nautilus: Enjoy creative, globally-inspired small plates and fresh seafood in a lively atmosphere, just steps from Nantucket’s main shopping area.

EVENING

Group Dinner at Brant Point Grill
Featuring regionally inspired New England fare in a relaxing setting overlooking the harbor, our quintessential Nantucket eatery offers exceptional seafood, steaks, handcrafted cocktails, and choice selections from an award-winning wine cellar

Overnight Accommodations at one of the following:

  • A luxurious harborfront resort with elegant accommodations, top-notch dining, and picturesque views, ideal for a quintessential Nantucket experience.

  • This historic inn offers charming accommodations in the heart of Nantucket, blending old-world charm with modern comforts.

Day 2: September 16

MORNING

Shop with Carey or explore on your own

Enjoy breakfast on your own at your hotel. Select a morning activity:

  • Shopping in Downtown Nantucket: Carey Cort will guide you through unique boutiques, art galleries, and local treasures while strolling cobblestone streets.

  • A short walk from the hotel: Established in 1746, America's second oldest lighthouse has been in service more than 250 years.

  • An 8-minute ride; beach with snack bar

  • A 30-minute bike ride or go by taxi; beach with crashing waves

AFTERNOON

Lunch on your own

Group Nantucket Island Tour

Friendly island tour guides take you away from downtown by coach, and allow you to enjoy the natural beauty Nantucket has to offer!

During the tour you will enjoy the Old Mill, Sconset Village, Sankaty Head Lighthouse, the Oldest House, or the Jethro Coffin house, and much more. Visit sites on the west end of the island as well. These are places you really cannot walk to, such as beautiful Madaket, Mr Rogers history on Nantucket, the famed “Madaket Millie”, and stops at Bartlett Farm and Cisco Brewers.

The following dinner options, along with the other fine restaurants, make downtown Nantucket a fun place to enjoy a meal with friends.

EVENING

Dinner on your own

  • Cru: iconic waterfront location in the heart of Nantucket harbor offers the ideal back drop to enjoy a glass of champagne, indulge in caviar and perfectly-shucked oysters or sip on a glass of rosé at sunset.

    Nautilus: a cornerstone of Nantucket's dining scene, offering a unique blend of New England coastal cuisine with Asian and global street food influences—the restaurant emphasizes a shared social dining experience in a lively atmosphere.

    Ship’s Inn: American bistro located in an historic whaling captain's mansion built in 1831, with an updated colonial atmosphere.

Day 3: September 17

MORNING

Quintessential Nantucket

Enjoy breakfast on your own at your hotel.

Visit the Nantucket Whaling Museum:
Dive into the island’s whaling history with fascinating exhibits, artifacts, and a full-sized whale skeleton. Hear the Island's fascinating stories over four centuries

  • Explore the Nantucket’s scenic paths and beaches at your own pace with a self-guided bike tour. Enjoy 35 miles of bike paths around the island, $50 per person, optional.

  • Embark on a fishing adventure for striped bass, bluefish, and false albacore as the waters are teeming with fall species. Experience a quintessential Nantucket adventure, $200 per person (5 people), optional.

  • Get a local’s perspective on Nantucket’s history, lighthouses, and iconic landscapes on a guided island tour. See parts of the island not accessible on foot, $45 per person, optional.

  • Experience the freedom to explore the island’s secluded beaches, scenic trails, and picturesque lighthouses at your own pace, making for an adventurous and memorable day.

AFTERNOON

Lunch on your own

Yours to enjoy. Choose an option:

EVENING

Group dinner

Enjoy dinner at the home of Cliff's brother and partner, Glenn Cort.

Day 4: September 18

MORNING

A fond farewell, until we meet again!

Following breakfast on your own, guests depart back to Boston or destinations of their choosing.

Return via ferry with chartered transportation to Boston.

Download an overview and schedule here: