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2027: Boston and Martha's Vineyard with Martha Hall Kelly

September 20 - 25, 2027
2027: Boston and Martha's Vineyard with Martha Hall Kelly image
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Boston and Martha's Vineyard with Martha Hall Kelly

Join New York Times bestselling author Martha Hall Kelly for an unforgettable literary journey through Boston and the picturesque island of Martha's Vineyard.

Best known for her beloved historical novels, including Lilac Girls, Lost Roses, Sunflower Sisters, and The Martha's Vineyard Beach and Book Club, Martha brings history vividly to life through stories of courage, friendship, and resilience.

Our journey begins in historic Boston before traveling to Martha's Vineyard, the enchanting New England island that inspired Martha's most recent novel. Together, we will explore charming harbor towns, colorful seaside cottages, dramatic coastal cliffs, and hidden corners of the island known primarily to locals.

Throughout the tour, guests will enjoy exclusive opportunities to spend time with Martha Hall Kelly as she shares stories from her writing life, discusses her research process, and offers insight into the people and places that inspired her work.

Highlights include exploring the picturesque villages of Edgartown and Oak Bluffs, visiting the breathtaking Aquinnah Cliffs and Gay Head Lighthouse, discovering the fishing village of Menemsha, and sailing aboard the historic Tall Ship Alabama at sunset.

Filled with beautiful scenery, fascinating history, wonderful meals, and meaningful conversations, this intimate journey offers a unique opportunity to experience Martha's Vineyard through the eyes of one of its most celebrated storytellers.

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For More Information:

Please contact Dilya at dilya@johnshorstravel.com. We'd love to have you join this fabulous tour!

Overview

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DAY 1: MONDAY

September 20, 2027
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Arrive at Boston Logan International Airport

Fly into Boston Logan International Airport and take a taxi or rideshare (Uber/Lyft) to the hotel.

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Check in at the Godfrey Hotel Boston.

Nestled in the heart of Downtown Crossing, The Godfrey Hotel Boston seamlessly blends historic charm with modern luxury. Housed in early 20th-century buildings, this boutique hotel offers sleek, contemporary rooms equipped with high-tech amenities. Guests can indulge in Peruvian-Japanese cuisine at the on-site RUKA Restobar or enjoy artisanal coffee at George Howell Coffee. With its prime location, just steps from Boston Common and the Freedom Trail, The Godfrey provides an ideal base for exploring the city's rich history and vibrant culture.

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Welcome Dinner at The Merchant Boston

Time6:30 p.m.

Welcome Dinner at one of the Boston restaurants where guests will meet Martha Hall Kelly and receive an overview of the literary journey ahead.

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DAY 2: TUESDAY

September 21, 2027
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Enjoy breakfast at George Howell's Coffee, which is connected to the Godfrey Hotel

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Depart for Woods Hole

Departure10:00 a.m.

After breakfast, depart Boston by private bus and travel south through coastal Massachusetts toward Cape Cod.

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Lunch

Time12:00 p.m.

Upon arrival in Woods Hole, a charming seaside village known for its maritime history and oceanographic research institutions, we will enjoy lunch before boarding the ferry to Martha's Vineyard.

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Board the ferry to Martha's Vineyard

Departure1:15 p.m.
Destination2:00 p.m.

As we sail across Vineyard Sound, enjoy panoramic ocean views and your first glimpse of Martha's Vineyard—a charming island that has inspired generations of writers, artists, and storytellers.

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Schedule is subject to change

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Arrival in Vineyard Haven

Departure2:00 p.m.

Upon arrival in Vineyard Haven, take a short walk from the ferry terminal to our hotel and check in.

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Check in at the Mansion House Hotel

Check in2:30 p.m.

Relax and enjoy your stay at the Mansion House Hotel, a charming boutique-style hotel ideally located in the center of Vineyard Haven. Within walking distance of the ferry terminal, waterfront, shops, and restaurants, it provides the perfect base for experiencing island life while enjoying comfortable accommodations and modern amenities.

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Literary Conversation with Martha Hall Kelly

Time5:00 p.m.

This evening, gather for a special literary event with Martha Hall Kelly. Depending on availability, this intimate conversation may take place in partnership with a local bookstore, radio station, or community venue, providing guests with a unique opportunity to hear Martha discuss her writing, research, and connection to Martha's Vineyard.

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Dinner at El Barco

Time6:00 p.m.

Following the event, enjoy dinner together at El Barco, a casual Mexican restaurant just a short walk away.

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DAY 3: WEDNESDAY

September 22, 2027
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Enjoy breakfast at the hotel

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Depart for West Tisbury

Departure9:00 a.m.

After breakfast, meet a local guide and depart the hotel on a private bus to begin exploring the western side of Martha's Vineyard. This area is renowned for its scenic landscapes, charming villages, and connections to Martha Hall Kelly's work.

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Explore West Tisbury & Alley's General Store

Time9:30 a.m.

Our first stop is West Tisbury, a peaceful rural community filled with farms, winding country roads, and classic New England charm. Here we will visit historic Alley's General Store, one of the oldest continuously operating general stores in the United States.

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Menemsha Harbor

Time10:45 a.m.

We then continue to Menemsha, a picturesque fishing village famous for its working harbor, lobster boats, and waterfront views. This beloved seaside community offers an authentic glimpse into Martha's Vineyard's maritime heritage and remains one of the island's most treasured destinations.

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Lunch

Time12:00 p.m.

Enjoy your lunch at a local restaurant.

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Drive to Aquinnah Cliffs

Destination1:30 p.m.

Next, travel to Aquinnah, located on the westernmost tip of Martha's Vineyard. Here we will admire the spectacular Aquinnah Cliffs, a National Natural Landmark renowned for its colorful clay formations overlooking the Atlantic Ocean. We will also visit the historic Gay Head Lighthouse, one of the island's most iconic landmarks.

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Return to Vineyard Haven

Departure3:00 p.m.

Return back to the hotel and enjoy your free time.

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Dinner

Time6:30 p.m.

Meet in the hotel lobby and depart for dinner. Tonight, enjoy dinner together at a local restaurant, The Black Dog Restaurant.

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DAY 4: THURSDAY

September 23, 2027
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Enjoy breakfast at the hotel

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Depart for Oak Bluffs

Departure9:00 a.m.

In the morning, meet your local guide in the hotel lobby and depart on a private bus. Today, we will explore two of Martha's Vineyard's most charming and distinctive communities.

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Oak Bluffs, Gingerbread Cottages & Flying Horses Carousel

Time9:20 a.m.

Our morning begins in Oak Bluffs, a colorful seaside town best known for its whimsical Gingerbread Cottages. Originally established as a Methodist camp meeting community in the 19th century, the neighborhood remains one of the island's most recognizable landmarks. We will also visit the Flying Horses Carousel, the oldest continuously operating carousel in the United States.

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Depart for Edgartown

Departure10:45 a.m.

Continue to Edgartown, a picturesque harbor town lined with elegant sea captain's homes and beautifully preserved historic architecture. Once the center of the island's whaling industry, Edgartown remains one of New England's most charming coastal communities.

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Edgartown Walking Tour and Free Time

Time11:00 a.m.

Enjoy a guided walk through town followed by free time for shopping or exploring local galleries.

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Lunch

Time12:30 p.m.

Enjoy a delightful lunch at the seafood restaurant, The Sea Shanty.

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Return to Vineyard Haven

Departure2:30 p.m.

In the afternoon, return to the hotel for some relaxing free time.

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Enjoy a 3-hour sunset cruise aboard the Tall Ship Alabama

Time4:00 p.m.

This evening, we board the historic Tall Ship Alabama for a memorable sunset sail around Martha's Vineyard. As we cruise through Vineyard Sound, enjoy panoramic coastal views and the beauty of the island from the water.

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Duration: 3 Hours

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Dinner

Time7:15 p.m.

Following our voyage, gather for a special Farewell Dinner with Martha Hall Kelly as we celebrate our time together on Martha's Vineyard.

DAY 5: FRIDAY

September 24, 2027
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Enjoy breakfast at the hotel

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Enjoy a relaxed morning before checking out of our hotel

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Check out from the Mansion House Hotel

Check out11:00 a.m.

Meet in the lobby with your packed bags and check out of the hotel. We then make our way to the nearby ferry terminal for our return journey to the mainland.

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Board the Ferry to Woods Hole

Departure11:15 a.m.

After checking out of the hotel, take a short walk to the ferry terminal and board the ferry back to Woods Hole. Enjoy one final look at Martha's Vineyard as we cross Vineyard Sound and return to the mainland.

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Lunch

Time12:15 p.m.

Enjoy lunch at a local restaurant in Woods Hole.

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Depart for Boston

Departure1:30 p.m.

After lunch, head to Boston on a private bus.

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Arrive and check in at the Godfrey Hotel Boston

Check in3:30 p.m.

We will return to the Godfrey Hotel for our last night in Boston. The hotel is just a 20-minute drive from the airport, making for a convenient departure the next day. Enjoy a free afternoon. If time permits, we guests may opt to do a walking tour of the nearby Freedom Trail.

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Farewell Dinner

Time6:30 p.m.

Meet in the hotel lobby and depart for a farewell dinner at Magianno's restaurant.

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DAY 6: SATURDAY

September 25, 2027
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Enjoy breakfast at George Howell's Coffee, which is connected to the Godfrey Hotel

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Check out at the Godfrey Hotel Boston

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Tour with John Shors Travel concludes

Transportation is provided for all guests to Boston Logan International Airport.

Tour Details & Pricing

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All-Inclusive Tour*

(*This is an all-inclusive tour with the exception of alcoholic beverages and hotel incidentals such as laundry, room service, etc.)

Tour Price:

  • $4,995 USD per person, based on double occupancy

  • $6,495 USD per person, based on single occupancy

Price includes: 

  • Hotel accommodations in Boston and Martha's Vineyard

  • All transportation

  • All meals and non-alcoholic drinks

  • Fees (tours, guides, etc.)

  • Excursions 

  • All tips

  • A gift package containing a signed copy of Martha's new novel, The Martha's Vineyard Beach and Book Club, as well as a promotional tote bag

Price does not include: 

  • Airfares 

  • Alcoholic drinks

  • Activities during free times such as golf, spa, etc.

  • Hotel incidentals such as room service, mini bar, phone charges, laundry, etc.

  • Charges incurred if guests arrive a day early or decide to remain in Boston after the tour ends

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Traveler Expectations

Before booking your slot, please ensure that you are physically and mentally fit to travel fully unassisted. This includes being able to:

  • Walk two or more miles per day, including on uneven surfaces

  • Go up and down steps and inclines

  • Stand for periods of time

  • Carry personal bags and luggage independently 

Have a look at our full “Traveler Expectations and Disclaimer” page here.

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Travel Insurance Recommendation

We strongly recommend purchasing travel insurance for your trip. For your convenience, you can explore options from our trusted travel insurance partner here.