(32 Reviews)
100% Recommended

Tory Gilligan

Vail, CO
Vail Travel Agent Expert

Vail, Colorado, a winter wonderland nestled in the heart of the Rocky Mountains. Known for its world-class ski resorts, breathtaking alpine scenery, and vibrant outdoor culture, Vail is a premier destination for adventure enthusiasts and nature lo...
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Massachusetts Travel Agent Expert

The coast of Marblehead
The coast of Marblehead

As a Massachusetts native, Cape Cod and Martha's Vineyard have always held a special place in my heart. Returning to these coastal havens felt like coming home. The pristine beaches, iconic lighthouses, and vibrant streets of Provincetown filled me with nostalgia. Pedaling along Martha's Vineyard's scenic paths, I rediscovered cherished childhood memories. From the whimsical gingerbread cottages of Oak Bluffs to the captivating sunsets on Menemsha Beach, these coastal gems forever embody the spirit of my Massachusetts upbringing.


Taking a trip to Martha's Vineyard promises a serene escape to a picturesque island paradise off the coast of Massachusetts. Renowned for its pristine beaches, charming seaside villages, and rich maritime heritage, Martha's Vineyard offers a perfect blend of relaxation, outdoor adventure, and cultural exploration for visitors of all ages.Scenic Beauty and Outdoor Recreation Begin your journey by exploring the island's stunning natural landscapes and scenic beauty. Discover miles of pristine coastline dotted with sandy beaches, tranquil harbors, and rugged cliffs, perfect for swimming, sunbathing, and beachcombing. Explore the island's lush forests, rolling hills, and scenic trails, ideal for hiking, biking, and nature walks amidst breathtaking scenery and abundant wildlife.Historic Landmarks and Cultural Attractions Delve into Martha's Vineyard's rich history and cultural heritage with a visit to its historic landmarks and cultural attractions. Explore the charming seaside village of Edgartown, with its cobblestone streets, historic homes, and picturesque harbor. Visit the iconic Edgartown Lighthouse, a beloved symbol of the island, and learn about the island's maritime history at the Martha's Vineyard Museum.Art Galleries and Boutique Shopping Discover Martha's Vineyard's vibrant arts scene and eclectic shopping districts, where you can browse local galleries, boutiques, and artisan shops showcasing the work of talented artists and craftsmen. Explore the historic town of Oak Bluffs, known for its colorful gingerbread cottages, lively waterfront promenade, and eclectic shops and eateries.Farmers Markets and Culinary DelightsIndulge your senses with the flavors of Martha's Vineyard's farm-to-table cuisine and culinary delights. Visit the island's farmers markets and roadside stands, where you can sample fresh produce, artisanal cheeses, and gourmet specialties from local farmers and food producers. Enjoy waterfront dining at one of the island's seafood restaurants, where you can savor fresh-caught seafood, lobster rolls, and New England clam chowder overlooking the harbor.Vineyard Tours and Wine Tasting Explore Martha's Vineyard's burgeoning wine industry with a vineyard tour and wine tasting experience at one of the island's wineries and vineyards. Sample award-winning wines made from locally grown grapes, learn about the winemaking process, and enjoy panoramic views of the vineyards and surrounding countryside.Beachside Relaxation and Water Sports Unwind and recharge with a day of beachside relaxation and water sports along Martha's Vineyard's scenic coastline. Lounge on the sandy shores of South Beach or Joseph Sylvia State Beach, where you can swim, surf, paddleboard, or kayak in the pristine waters of the Atlantic Ocean. Charter a fishing boat or sailboat and explore the island's scenic bays and harbors, or embark on a whale-watching excursion to catch a glimpse of these magnificent creatures in their natural habitat.Planning Your TripWhen planning your trip to Martha's Vineyard, consider the time of year and the activities you'd like to enjoy. Summer is the most popular time to visit for warm weather and outdoor activities, while spring and fall offer milder temperatures and fewer crowds. Be sure to book accommodations in advance, especially during peak seasons, and check the local events calendar for festivals, concerts, and other special events happening during your visit. Whether you're seeking relaxation, outdoor adventure, or cultural exploration, Martha's Vineyard offers an idyllic island getaway that's sure to leave you enchanted and inspired.    

My Travel Albums

Massachusetts & Cape Cod

My Reviews

2 of 2 people found this review helpful
Outstanding Expertise, Unparalleled Service!
Tory's outstanding expertise and dedication made my travel experience exceptional. From understanding my preferences to flawless planning and personalized suggestions, Tory's attention to detail was impressive. Her prompt responses, top-notch arrangements, and local connections enhanced my journey. The level of customer service was unmatched. I highly recommend Tory for their expertise, meticulous planning, and genuine care.
By  John  from  West Hartford, CT
Traveled to  Chamonix ~ France ~ Europe
I would recommend this agent to my family and friends
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2 of 3 people found this review helpful
The Best Travel Decision I Ever Made
I consider myself lucky to have found Tory to plan my vacation. Her knowledge, expertise, and attention to detail made my trip absolutely amazing. From the moment I reached out to her, she was responsive, professional, and eager to make my dream vacation a reality. Tory's ability to understand my travel style and preferences was remarkable. She meticulously curated an itinerary that exceeded my expectations, taking into account every little detail that mattered to me. Thanks to Tory, I discovered hidden gems, experienced local culture, and made memories that will last a lifetime. I can't recommend her enough!
By  Ethan  from  Houston, TX
Traveled to  Vail/Eagle ~ Colorado ~ USA
I would recommend this agent to my family and friends
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1 of 1 people found this review helpful
A Travel Experience to Cherish Forever
Working with Tory was an absolute delight. Her passion for travel and commitment to creating memorable experiences shines through in everything she does. From our initial conversation to the final day of my trip, Tory was there every step of the way, ensuring every detail was taken care of. She curated a one-of-a-kind itinerary that perfectly matched my interests and provided insider tips that made the journey truly special. Her dedication and personalized service made me feel like I was her only client. I highly recommend Tory to anyone seeking a travel agent who genuinely cares about creating unforgettable memories.
By  Barbara  from  Colorado Springs, CO
Traveled to  Athens ~ Greece ~ Europe
I would recommend this agent to my family and friends
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1 of 1 people found this review helpful
A Traveler's Dream Come True!
Tory is an absolute gem of a travel agent! I had the pleasure of working with her recently, and I must say, she made my dream vacation a reality. Her attention to detail and personalized approach were unparalleled. Every aspect of my trip was meticulously planned, from the breathtaking accommodations to the handpicked activities that perfectly suited my interests. Tory's insider knowledge and connections ensured I experienced the true essence of the destination. I am forever grateful for her expertise and highly recommend her services to anyone seeking an extraordinary travel experience.
By  Grace  from  Boston, MA
Traveled to  Aspen ~ Colorado ~ USA
I would recommend this agent to my family and friends
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2 of 3 people found this review helpful
Travel Goals Achieved, Thanks to Tory!
I'm still on cloud nine from the mind-blowing adventure Tory planned for me. This girl knows how to make dreams come true! She took the time to understand exactly what I wanted, and then she made it happen. Her dedication and passion for travel are contagious, and I couldn't have asked for a better guide.
By  Duke  from  Salt Lake City, UT
Traveled to  Vail/Eagle ~ Colorado ~ USA
I would recommend this agent to my family and friends
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Destination Expert:

  • Marthas Vineyard
  • Hyannis
  • Cape Cod
  • Nantucket
  • Massachusetts

Travel Specialist:

  • Beach Vacations
  • Family Vacations
  • Villas
  • Nightlife
  • Outdoor Activities & Sports

Industry Affiliations:

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