Top Boston Day Trips

Boston to New Hampshire Fall Foliage White Mountains Day Trip

12 hoursFree Cancellation

4.9

(251)

from $150

Leave Boston behind and set out on a full-day journey to Martha's Vineyard, one of New England's most beloved islands. This experience blends a scenic ferry crossing, historic seaside villages, and the laid-back charm of island life. Board the Island Queen ferry in Falmouth and cruise across Nantucket Sound to Oak Bluffs, where colorful gingerbread cottages surround the historic Tabernacle at the Martha's Vineyard Camp Meeting Association. Enjoy time to explore the island's most iconic spots, with an optional sightseeing bus tour covering the Flying Horses Carousel, the refined harbor town of Edgartown, Gay Head Light atop the dramatic Aquinnah cliffs, and Nobska Point Lighthouse. Return via the Steamship Authority ferry from Woods Hole, rounding out a full day of coastal views, ocean breezes, and authentic New England island character.

Boston: Martha's Vineyard ICONIC Small Group Day Escape w/Ferry

Boston: Martha's Vineyard ICONIC Small Group Day Escape w/Ferry

12 hoursFree Cancellation

Explore Newport in a single day without planning or driving from Boston. This small-group tour includes pre-booked mansion admissions, guided transport with hotel pickup, and free time in the historic waterfront district to help you use your time efficiently. Visit iconic mansions, enjoy a scenic coastal walk, and discover additional historic landmarks along the way. With logistics handled in advance, you can focus on architecture, scenery, and independent exploring.

Newport Small-Group Day Tour: The Breakers & Marble House

8 to 10 hoursFree Cancellation

Visit Martha’s Vineyard on a day trip from Boston to experience the island beauty without the hassle of booking ground and ferry transport. From hotel pickup and drop-off to included ferry tickets, snacks, water, and sightseeing maps, this Martha’s Vineyard excursion is designed for maximum time exploring, with the option to upgrade and include a guided tour of the entire island aboard a high-top, small-group van and explore all six towns on the island, indulge in lunch, and spend more time learning about scenic New England.

Martha's Vineyard Day Trip with Optional Island Tour from Boston

13 hoursFree Cancellation

4.5

(457)

from $130

Enjoy one of the simplest ways to discover Martha's Vineyard, and leave all the planning and logistics to someone else, on this hassle-free day trip from Boston. Following pickup directly from your centrally located hotel, take a short ferry ride to Martha's Vineyard. Upon arrival, enjoy free time to explore—or upgrade to add on an island tour that visits its highlights. Complimentary snacks, bottled water, and guidebooks are provided during the drive.

Boston to Martha's Vineyard Day Trip with Optional Island Tour

12 hoursFree Cancellation

Experience the best of New England’s marine wildlife on this guided whale-watching cruise around the Stellwagen Bank National Marine Sanctuary. Hop on a high-speed boat in Boston that gets to and from the whales in the least amount of time possible. Look out for humpback and fin whales, plus Atlantic white-sided dolphins, with the help of a naturalist guide. The on-board galley offers food and beverages for purchase during the trip.

City Cruises Boston Whale Watching Cruise by High-Speed Boat

City Cruises Boston Whale Watching Cruise by High-Speed Boat

3 hours 30 minutesFree Cancellation

4.5

(3,363)

from $86

New York One Day Tour-One World Trade&Liberty Cruise From NY/BOS

New York City is a huge city, so it can be hard to know where to start exploring alone. Instead, get the help of a guide who knows the Big Apple’s secrets on this group guided day tour from Boston or New York City. Spend the whole day getting a well-rounded picture of New York, with the option to include a cruise to the Statue of Liberty or entry to the One World Trade Center Observatory.

New York One Day Tour-One World Trade&Liberty Cruise From NY/BOS

8 hours

4.5

(2)

from $119

Escape Boston for a full day along the southern Maine coast, blending scenic seaside walks, historic harbor towns, and iconic lighthouse views. Begin at Marginal Way in Ogunquit, a cliffside coastal path that winds along the Atlantic with uninterrupted ocean views and classic New England scenery. Continue to Kennebunkport, a postcard-perfect harbor town known for its historic homes, local boutiques, and working waterfront. Arrive in Portland in time for lunch in the Old Port district, where cobblestone streets, 19th-century brick buildings, and fishing piers set the scene for some of Maine's best seafood — this is the spot to try fresh, locally caught lobster on your own. Finish at Portland Head Light, Maine's oldest and most iconic lighthouse, perched dramatically above the rocky shoreline within Fort Williams Park, with sweeping Atlantic views to close out the day.

Portland: Lighthouse, Old Port and Park 1-Day Tour from Boston

Portland: Lighthouse, Old Port and Park 1-Day Tour from Boston

7 to 9 hoursFree Cancellation

Discover the best of historic Plymouth in just one day—and enjoy a hassle-free way to explore—on this full-day trip from Boston. Check off several key Plymouth sights, including Plymouth Rock, the Mayflower II, and Plimoth Patuxet Museums, all while benefitting from skip-the-line admission tickets. Plus, have bonus free time to explore the 400-year-old town's harbor, enjoy lunch (own expense), and sightsee at your own pace.

Boston to Plymouth Day-Trip including Quincy, Plimoth Patuxet and Mayflower II

11 hoursFree Cancellation

4.8

(423)

from $159

Boston to Kennebunkport with Optional Lobster Tour

Discover the New Hampshire and Maine coasts, plus the highlights of Kennebunkport, all in one day: this private, full-day tour from Boston makes exploring easy. Meet your guide in the morning at your departure point, and hop aboard your private van. You'll stop in the historic town of Portsmouth, will discover the Cape Neddick Nubble Lighthouse, can tour the President Bush Compound at Kennebunkport, and upgrade to add on a lobster tour.

Boston to Kennebunkport with Optional Lobster Tour

8 to 10 hoursFree Cancellation

4.8

(47)

from $125

Day Trip from Boston To Salem Witch Exhibits

8 to 9 hoursFree Cancellation

4.7

(96)

from $190

Spend a day away from Boston and experience southern Maine's picture-perfect coastline without transportation headaches and the benefit of a guide to provide insights and history on the region you'd miss otherwise. Drink in the ocean views as you head north to the Nubble Light lighthouse and Ogunquit's Marginal Way before visiting idyllic Kennebunkport. Here, enjoy a narrated trolley tour and time to shop and eat (own expense) before your return trip. Hotel pickup and drop-off are included for ease.

Boston to Kennebunkport Day Trip with Optional Trolley Tour

11 hoursFree Cancellation

Private Day Tour of Salem and Boston

7 hours 30 minutesFree Cancellation

(30)

from $475

This private car tour is comprehensive enough for any history buff, but as interesting in other ways for non history nerds. It's a unique combination of the Revolutionary War sites in Boston and Cambridge that you won't have seen. Then onto Lexington and Concord to see the towns where the "shot heard round the world" was fired. We'll take the same route as Paul Revere, stopping at the most significant, and lesser known sites along the way giving a detailed account of events in April 1775. For those less interested in the details of the battles, there's the option to visit the home of Louisa May Alcott or just take some time to enjoy the pretty main street of Concord. The itinerary gives the list of sites we'll visit, but timings are flexible to let us spend time at the places you're most interested in. We'll also stop for lunch (not included in price of tour) and there's plenty of photo opportunities.

Boston, Lexington and Concord Revolutionary War Car Tour

(14)

from $995

Per group

Take a break from your Boston city break with this scenic private tour. There's lots of ocean views, rocky coastline, a bit of shopping and even some witch history. We keep this full day itinerary flexible to let you customize the tour but here's a feel for what we'll see. Pick up in Downtown Boston, taking the 60 minute highway drive to Manchester-by-the-Sea, where we pick up the scenic back roads. We'll take a picturesque country road to Gloucester, where we stop to walk along the waters edge to the Fisherman's memorial statue. We'll continue the scenic drive to Rockport, where there's a great collection of cute stores to browse and views to admire. Then drive to Salem, where we have time for a short walking tour around the main sites and historic spots. To finish out the day we'll squeeze in a few more ocean views on our drive back to Boston. We'll stop along the way for lunch (not included in price of tour).

Salem & North Shore Full Day Private Tour from Boston

(15)

from $995

Per group

Take a semi-private day trip you'll never forget! Start the day with a pickup at your door, then ride up the North Shore to Hammond Castle, located on the ocean cliffs of Gloucester. Take a guided tour of the castle, learning about the history of the eccentric millionaire inventor who built it. Enjoy free time to explore the castle and gardens with plenty of opportunities for stunning photos. Drive to Salem, where you will have free time for lunch. Choose from a wide variety of dining options in the historic downtown. After lunch, your guide will take you on a tour of Salem. Learn about the infamous witch trials of 1692, see the real places where the victims were hanged. Learn the story of the "Corwin Curse" as you take a picture in front of the historic Witch House. See the locations where Hocus Pocus was filmed. Take a drive through one of the most beautiful streets in North America, lined with mansions built on the city's maritime fortune.

Top Left: Hammond Castle
Top Right: Witch House
Bottom Left: Witch Museum
Bottom Right: Hammond Castle Arches

Small Group Day Trip to Salem and Hammond Castle from Boston

7 to 9 hoursFree Cancellation

This private day tour is the perfect way to get to know Boston & Cambridge at a leisurely pace. It's a combination of walking and driving (although can be driving only if you prefer). We start with a walking tour of parts of the Freedom Trail, stopping at some of the city's most significant sites. We'll then drive in and out of the other city neighborhoods, Beacon Hill, Back Bay and Seaport and finish out the Freedom Trail with a stop at Bunker Hill. Then it's across the Charles River to Cambridge, where we drive around the MIT campus, and onto Harvard for a walking tour of the oldest college in the country. We'll share lots of history and legends but also keep it topical with current day fun facts and light hearted stories. After the walk you'll need some lunch and we know some great spots (not included in price of tour). All guides are fully licensed and approved Boston tour guides, driving luxury and livery insured vehicles.

Boston and Cambridge walking and driving private tour

Plymouth Colony comes to life in our recreation of early Plymouth, complete with timber-framed houses furnished with reproductions of the types of objects that the Pilgrims owned, aromatic kitchen gardens, and heritage breeds livestock. At The Patuxet Homesite, learn about the Indigenous heritage of the 17th-century lifeways of a culture that continues to thrive today. At the Craft Center, located in close proximity to the 17th-Century English Village, you will learn from a variety of skilled artisans and museum historians. Mayflower is an iconic symbol of freedom. Of the hundreds of ships that made the transatlantic crossing in the 1600s, she is the ship we remember. At our reproduction of the Plymouth Colonists’ original 1636 grain mill on Town Brook, take a fascinating look at the mill’s history and workings, from the 200-year-old millstones grinding corn to the ecology of the brook that has powered mills throughout the centuries.

(9)

from $995

Per group

Tour to Plymouth including Plimoth Patuxet Museum and Mayflower

Tour to Plymouth including Plimoth Patuxet Museum and Mayflower

6 to 8 hoursFree Cancellation

Boston Private Day Trip with Salem & Cape Ann’s North Shore

(4)

from $279

6 hours

4.8

(4)

from $615

Make exploring beyond Boston city limits seamless—and discover the history and highlights of Newport, Rhode Island, long a summer retreat for the city's upper crust—on this full-day tour from Boston. Visit the Breakers Mansion (owned by the Vanderbilts) and the Marble House (a "Great Gatsby" filming location), and go for a bus tour of Newport's other highlights before enjoying free time for some independent sightseeing.

Boston to Newport Small-Group Day Trip with Breakers & Marble House Admission

11 hoursFree Cancellation

4.7

(289)

from $155

Lost River Gorge and White Mountains Day Tour

7 to 8 hoursFree Cancellation

4.0

(4)

from $190

Full-Day Private Tour of Boston with Pick Up

(1)

from $1,507

New York City Day Tour from Boston

15 hours 30 minutesFree Cancellation

4.0

(36)

from $184

Highlights of Boston Private Tour

5 hours 30 minutesFree Cancellation

4.9

(34)

from $393

Boston: Underground Railroad History Tour of Beacon Hill

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Top Attractions in Boston

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Attractions

What are people saying about Boston

Wanda_B, Aug 2026

This tour was so informative and enlightening! I would recommend anyone visiting, or living, in Boston to experience it!

This tour was so informative and taught a bit on the lives of enslaved people and their plight for freedom. Megan did a wonderful job educating us on some of the more famous, and those not as famous, abolitionists who had their hands in helping dissolve the abysmal and dreadful institution of slavery. Since the tour is a walking tour of Beacon Hill, she allowed many breaks so that we were not so physically overwhelmed. I think this educational tour would be a wonderful learning experience for the young and old, as well as Boston natives or those just visiting Boston. It allowed the tourist to understand a bit about the importance Boston played in the fortification of the Underground Railroad. It was definitely a side of Boston I would not have gotten to enjoy and experience if I had not done the tour.

Boston to Newport Small-Group Day Trip with Breakers & Marble House Admission

C_D, Aug 2026

You should really book it! You won’t be disappointed.

We had an absolutely wonderful experience on the Newport Small Group Tour from Boston! Two days before the trip, I received a call with detailed information about exactly where we would meet, and everything went exactly as promised. We were greeted at the designated location right on time, given our itinerary, and from there, the entire day ran like clockwork. A few days earlier, I had taken a small-group tour to Maine that I thought was great—until I took this trip with Chris! Chris was training another guide on the day of our tour, so we essentially got a two-for-one experience when it came to the tour guides. Both were fantastic! From the historic buildings in Boston to the entire drive into Rhode Island, we learned interesting facts and stories about the landmarks along the way. The trip was incredibly well organized and completely seamless. Although the tour was about 11 hours long, it never felt overwhelming or too long. The time really flew by because there was always something interesting to see or learn about. I would highly recommend this tour to anyone staying in Boston who wants to take a day trip to Newport and experience the beautiful Rhode Island mansions. Chris and the team did an outstanding job!

Newport Small-Group Day Tour: The Breakers & Marble House

Courtney_R, Aug 2026

Willy was a great guide! ...

Willy was a great guide! His communication with the group via text was very helpful including giving us the itinerary the day before. We had ample time at each stop. The 15 person van has strong AC which was good for the hot day. I would definitely recommend this tour.

Martha's Vineyard Day Trip with Optional Island Tour from Boston

Patti_O, Aug 2026

Fantastic experience. ...

Fantastic experience. Picked up right at the hotel we were staying at and had a smooth ride to Cape Cod. Everything was well organized to take the ferry and then catch the bus tour around the island. John was an awesome guide and shared some great perspective that only a local like him would know. We got a great tour of the island and still had time to do some wandering on our own before heading back. Thank you all for the great time!

Boston to Kennebunkport Day Trip with Optional Trolley Tour

London_J, Jul 2026

A five star must do trip and guide!

Jennifer was the best tour guide we have experienced through our travels. She made sure that it was a stress free day even before it started. She listened to our requests and made us feel that we were here number one priority. She made us feel safe throughout the day and she went out of her way to provide a 5-star service. This tour was beautiful, relaxing, fun, and so much more. I’d give this tour (especially our guide) more stars if I could! It was the best part of our trip! Thank you!

Portland: Lighthouse, Old Port and Park 1-Day Tour from Boston

David_C, Jul 2026

Great lobster trip

Sam was an excellent tour guide and driver. Easy to hear and good information. I only wish the vehicle would have been bigger or fewer people. It was a minivan designed for a family with children not 7 adults. My wife was cramped in the middle of the middle seat which is actually not a seat. There was a couple in the back seat and I don’t know how he managed to sit. The overall trip was good and the lobster meal was wonderful and very reasonable. The really sweet thing that Sam did was drop us off at our hotel so we didn’t have to get an uber.

Boston: Martha's Vineyard ICONIC Small Group Day Escape w/Ferry

Roseanne_H, Jul 2026

Great Martha’s Vineyard trip.

This tour was very informative, not rushed, very enjoyable. Having a guide that was born and raised on Martha’s Vineyard, made the tour more personal. Along the route people would recognize John and wave. Both John, our guide, and Paco our van driver from Boston, were courteous and friendly.

Boston to Plymouth Day-Trip including Quincy, Plimoth Patuxet and Mayflower II

Lauren_M, Jul 2026

Thatch was fantastic! He...

Thatch was fantastic! He was engaging the entire time & provided a lot of information. He made the experience light and fun even though it was a very long day. When it came time to explore on our own, the time alloted was adequate. The transport bus was comfortable and spacious even though it was almost filled. Great experience!

Day Trip from Boston To Salem Witch Exhibits

Debra_Y, Jul 2026

Great Trip to Salem

It was a great day learning about the history of the Salem Witch Trial. We had a trolley tour and the tour guide on the trolley was excellent driving around the city and listening to the history of Salem. After the trolley we went to the Witch's Museum and learned interesting facts. If you have time, you need to visit the Witch's house too. We had approximately 2 hours for lunch and shopping. I wished we had 2 1/2 hours instead of 2 hours. Afterwards we proceeded to the oldest candy shop in the US. Then we headed to the House of the Seven Gables guided by a tour guide. This was very interesting, especially the hidden staircase in the house! The tour was excellent to learn about the history of the house. I would highly recommend this tour. We were back in Boston by 5:00pm.

Best Boston Small Group Tour: I Know the Secrets Others Don't!

Trish_T, Feb 2026

Awesome

This is the best tour to take if your limited on time . Stevie our tour guid was kind, funny , and very knowledgeable!!!! He is like and encyclopedia…. Stevie is great on sharing the little details ….. We had a great time !!!! I would recommend this tour to my family and friends 🙂