Travel Guide for
Oak Bluffs

Boston Private 3-Hour Tour by Car

This private car tour is the perfect way to orientate yourself to Boston, to see not just the historic sites, but the entire city. On this tour we'll take you into all the city neighborhoods and along the sites of the Freedom Trail. We'll share the history and legends of the city, keep it topical with current day fun facts and light hearted stories. All guides are fully licensed and approved Boston tour guides, driving luxury and livery insured vehicles.

Delicious Donuts of Harvard Square: A Historical Walking Tour

Our tour begins at the Charles Hotel to make sure you get your morning fix before we quickly head over to our first stop, Union Square Donuts. Union Square is featured on both our Harvard Square tour as well as our downtown Boston tour - that’s how good they are! After we get our first fill of donuts, we’re off for a quick walk through Harvard Square and through the university itself. We’ll give you a brief history of Harvard Square, the surrounding area and Harvard University itself. After a short walk through the picturesque campus, we’ll stop at our second shop in the campus center for some unique donut flavors. We can’t tell you what the flavors will be as they change seasonally and we want your input on which ones we pick. All of them are good, we guarantee it. Our last and final stop will be Saloniki, a local Greek restaurant that serves some amazing loukoumades. What are loukoumades you ask? Well, it’s a unique greek twist on donuts. You’re going to love it.

Chatham Bites and Sights Walking Guided Food Tasting Tour

Taste your way through the heart of Cape Cod on a relaxed, flavor-packed food tour through Chatham’s most iconic streets and hidden gems. Led by a local expert, this 3-hour walking tour features multiple tasting stops with hand-picked seasonal bites from beloved local spots. It’s a delicious way to explore the area, whether it’s your first visit or your summer tradition. Along the way, hear the stories behind the food—tales of tradition, local legends, and the people who make Chatham so special.

Private Guided Night Photography Tours on Cape Cod (for one photographer.)

One of the best times to see and and experience Cape Cod is after dark when the landscape is lit by starlight or moonlight. These times also give you the opportunity to visit and travel between destinations during hours that many people are asleep making these places quiet and serene. This tour is available for all experience levels. Night photography is a fantastic way to capture popular or "over shot" subjects in new ways. We'll use long exposure techniques and flashlights to create an immersive art experience. If you've never visited the Cape Cod area and are unsure of where the best subjects are, this tour ensures you get the best locations based on the sky conditions available. Choose between a moonlight or starlight(Milky Way) tour! Contact me for the date range you are available for more information on moon phase and sky information. Please contact me for availability before booking.

A Taste of the Freedom Trail: Boston's Iconic Food & History Tour

Taste Boston’s history with every bite on this flavorful journey through Downtown Boston. Savor Boston classics like creamy New England clam chowder that once fueled sailors and city workers, a classic New England lobster roll from the region’s coastal waters, slow-cooked Boston baked beans with colonial roots, and Boston’s most iconic dessert—the decadent Boston cream pie—enjoyed at the very place it was first created in the 1850s. As you explore historic landmarks along the Freedom Trail, you’ll uncover fascinating food origins that span centuries—from Native American influences and colonial traditions to the beloved local flavors we enjoy today. It’s a fresh (and flavorful!) twist on the city’s most famous walk—experience the Freedom Trail through Boston’s legendary dishes. Don’t miss this one-of-a-kind “Feed ’Em Trail” adventure—where every stop reveals a delicious piece of Boston’s culinary history.

Back Bay Chocolate and Art Galleries Tour

Back Bay is one of Boston's most beautiful neighborhoods and a city-planning masterclass that illustrates American architecture's changing tastes and stylistic evolution from the mid-to-late 19th to the early 20th centuries. It's also home to excellent chocolate vendors and gorgeous art galleries. The group will have chocolate tastings at four locations while visiting two art galleries to see why Back Bay is an essential Boston neighborhood. During this tour, we'll taste the following: -Hot chocolate from one of the pioneers of America's artisanal chocolate industry -Cookies from a legendary New York City bakery that's expanded into Boston -Cupcakes from a delightful Newbury St dessert shop -Chocolate hazelnut cake bites from a three-story Italian goods market We'll also visit two art galleries: -An art gallery representing Old Masters, Impressionists & Modern Masters from the 16th to 21st centuries -A gallery featuring 56 artists, including ceramics, paintings, and mobiles

Private 4-Hour Walking and Driving City Tour

Private tours are priced per GROUP, not per person. This amazing tour is for those who want more than a driving tour but not a ton of walking.(aprox. 90 minute walk) Stroll through the historic North End. Have a snack from a famous North End pastry shop. Go inside the Old North Church and see Paul Revere's house, Explore Copp's Hill Burial Ground and learn about the "Spite House", the "Brink's Job" robbery. and the Great Molasses Flood. Visit the USS Constitution, and go up Bunker Hill where the first organized battle of the Revolutionary war took place. Learn how the Colonists lost that battle but won at the same time. Ride through Downtown, up Beacon Hill, The Back Bay, Fenway and over to Cambridge to see Harvard & MIT. You will see the entire city in half a day. ​Learn all about our history as well as what makes Boston such a great 21st century city. We can confirm tour start time after booking is complete. Weekday tours during the school year tours can only start after 2:30PM

Private North End Neighborhood Tour

Yelp's 2025 pick for Massachusetts #1 food tour! Create food memories with one of Boston's original food tours. Our North End Neighborhood Tour offers a view of Boston's Little Italy from the perspective of our founder, a native Bostonian, with topics ranging from best eats to history to crime to movies, and personal stories that you can't Google! We've included some surprises, too, including FOUR sites that aren't what they appear to be, and two hidden gems in a very unexpected place. And, if you're lucky, you might meet a neighbor or two!

Marthas Vineyard Luxury Tour (2hrs)

Offering private tours of beautiful Marthas' Vineyard Island specifically for small groups of people (5 max) looking for a truly unique experience. Relax and enjoy this narrated tour as we drive along the scenic coast, stop for photos, talk about famous people, learn about local history, all while passing through the 3 down-island towns. For those travelers coming over for the day with limited time, who would like to see the down Island towns, this is the perfect tour.

Private Nantucket Beach Fishing Activity with a Guide

Fish and explore the beaches of beautiful Nantucket Island with your native guide, Steve Tuna. Fish hard or simply explore and enjoy the beach. Steve knows the backroads of his island and will customize your beach adventure based upon wind, tide, beach conditions and your desires. Each area of the Nantucket beach has a different and distinct personality. The south side of the island has the surf. The north side is more protected and much calmer. Great Point, the 7 mile long beach peninsula on the eastern shore, offers the greatest variety - an amazing combination of wildlife, pristine environment and great fishing! Steve is dedicated to helping his guests discover the joys of Nantucket that are hidden away from the vast majority of island visitors. Beginning fishermen are welcomed! Steve will teach his guests how to cast their lures and other necessary techniques. Be prepared to make memories and, perhaps, catch a few fish!