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 5: 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.
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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.
Dune: An elegant yet relaxed spot serving seasonal New England-inspired dishes, from fresh seafood to inventive salads, with a charming outdoor patio.
EVENING
Group Dinner at Lola 41
A lively bistro serving inventive sushi, globally-inspired dishes, and creative cocktails just steps from downtown Nantucket.
Overnight Accommodations at one of the following:
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A luxurious harborfront resort with elegant accommodations, top-notch dining, and picturesque views, ideal for a quintessential Nantucket experience.
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This historic inn offers charming accommodations in the heart of Nantucket, blending old-world charm with modern comforts.
Day 6: September 16
MORNING
Golf with Cliff or shop with Carey
Enjoy breakfast on your own at your hotel. Select a morning activity:
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Miacomet Golf Club: Enjoy a day on Nantucket’s only public 18-hole golf course with lush greens and sweeping ocean views.
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Shopping in Downtown Nantucket: Carey Cort will guide you through unique boutiques, art galleries, and local treasures while strolling cobblestone streets.
AFTERNOON
Yours to enjoy. Choose an option:
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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.
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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.
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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.
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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.
EVENING
Dinner on your own
Our travel agent can make recommendations, or enjoy researching options yourself.
Day 7: 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
AFTERNOON
Lunch
TBD—updates soon!
EVENING
Group dinner
Enjoy dinner at the home of Cliff's brother and partner, Glenn Cort.
Day 8: 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 Cape Air or ferry with chartered transportation to Boston.