American Bucket List: Cape Cod to Boston
This 6-night, 7-day journey is the kind of experience you’ve always said you’d do someday—exploring Cape Cod’s quiet luxury, walking Boston’s Freedom Trail, and savoring the best of New England in style. With five-star stays, meaningful history, and unforgettable moments, it’s the perfect blend of heritage and indulgence—designed for those who want to finally check this one off the bucket list, and do it beautifully.
Travel Deeper, Experience More
Marshall and Jessica Pennell, your Tour Hosts have traveled, researched, and dreamed to curate a marvelous experience for you. Every aspect of these days has been custom curated by these discriminating travel experts.
The group is carefully limited in size for a more personal experience. The small group allows your hosts to serve as your personal concierge. Need something extra, want to spend a day doing something different, just say the word!
Expert local guides will enrich your knowledge of each location—from the coastal charm of Cape Cod to the Revolutionary spark that ignited a nation. You will be enriched by immersive, interactive experiences—just the right blend of luxury, learning, and fun for discerning travelers.
Itinerary
Day 1 | September 30, 2026
Arrival & Welcome to Cape Cod
- Arrival at Wequassett Resort and Golf Club, a Forbes Five-Star haven on Pleasant Bay. Champagne check-in and time to relax on the waterfront terrace or stroll the manicured gardens.
- First Gathering: We’ll gather for a welcome reception this evening followed by Welcome Dinner at the resort’s Twenty-Eight Atlantic, one of Cape Cod’s premier fine dining destinations.
Day 2 | October 1, 2026
Revolutionary Heritage on the Cape
- Step back in time with a tour through key Revolutionary War-era sites including Sandwich, Barnstable, and the Cape Cod Canal region.
- Afternoon at leisure to relax by the pool, play a round of golf, or book a spa treatment – let us know what you’d like and we’ll book it for you!
- End the day with a classic clam bake on the beach while taking in the view of the marina and watching the sunset.
Day 3 | October 2, 2026
Nantucket Excursion
- Depart by high-speed ferry for a day trip to Nantucket, a storybook island known for its cobblestone streets, whaling heritage, and boutique charm.
- Discover local shops, visit the Whaling Museum if that’s your thing, explore historic lighthouses—and yes, savor that iconic lobster roll.
- Return to Cape Cod in the late afternoon and gather for a relaxed farewell dinner on the Cape.
Day 4 | October 3, 2026
From Coast to Cradle of Liberty
- Check out and transfer in comfort to Boston.
- En route, explore Lexington & Concord, where the American Revolution began and visit Buckman Tavern and the Old North Bridge.
- Arrive in Boston and check in at the legendary Boston Harbor Hotel, offering waterfront elegance and exceptional service.
Day 5 | October 4, 2026
Walking through the Revolution
- Embark on the Freedom Trail walking tour, including Paul Revere’s House, Old North Church, Faneuil Hall, and the Granary Burying Ground.
- See the Old State House or USS Constitution.
- Enjoy a meal at Union Oyster House, the oldest continuously operating restaurant in America.
- Time for leisure for shopping or relaxing at the hotel spa.
- Optional evening performance at the Boston Symphony or Emerson Colonial Theatre.
Day 6 | October 5, 2026
Harvard, Art & Afternoon Tea
- Cross the Charles River to Harvard University for a private campus tour and visit to the Harvard Art Museums.
- Afternoon Tea because what’s Boston without a nod to the tea party?
- Time for final shopping or museum visits.
- Celebrate the journey with a farewell dinner at a Michelin-rated restaurant, crafted for elegance and reflection.
Departure | October 6, 2026
- Breakfast at leisure.
- Departure with new friendships, elevated memories, and a deeper appreciation for the cradle of American liberty.
- Travel in style back to the airport (Boston Logan) by water taxi from the hotel if you so desire! Let us know!
Details and Limitations
Pricing and Availability
- Per Person, Double Occupancy Price: $10,500
- $500 per person deposit due now to reserve your space
- $2,500 per person due March 30,2026
- $4,200 per person due April 16, 2026
- Final balance of $3300 per person due by June 30, 2026
- If you will be traveling alone and require single occupancy for hotel rooms you’ll be invoiced for an additional $3355.
- If you are registering after any of these due dates you’ll be invoiced the total due.
- Reserve your spot today! While there’s no set deadline to register, space is limited, and once the tour fills, registration will close automatically. If the tour reaches capacity before the scheduled deposit date, we will contact registered guests and offer the opportunity to secure their place with a per person advance deposit. This amount is not an additional charge. It is simply an early portion of your tour payment and will be fully applied toward the total tour price. We’d love to have you with us!
Tour Includes
- 7 days on ground
- 6 nights in 5-star deluxe hotels
- Porterage at each hotel
- Full breakfast at each hotel
- Some lunches during tour
- Dinners for most days during tour
- Ferry fees if applicable
- Deluxe motor coach and driver
- Expert local guides
- All entrance fees on itinerary
- Tips to drivers, restaurants, hotel staff, etc.
Note
- Please refer to the terms & conditions for a list of items not included.
- For any requests outside of the tour package, please email: [email protected]
- This tour includes walking tours and visits to historic sites. Guests should be comfortable walking at a steady group pace for up to an hour at a time and navigating stairs, cobblestones, inclines, and uneven surfaces. There is plenty of opportunity to rest throughout the tour, and if you occasionally prefer to skip a walk or activity, we’re happy to help arrange an alternative when reasonably possible. If there is ever a need for mobility related assistance the traveler must have a companion who can accomplish that purpose. If you have mobility concerns, please contact us before registering. We’re happy to talk through the itinerary with you and discuss how we may be able to help. Read our terms and conditions for more information.
Register Now!
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