Boston Holiday Itinerary

For a stress-free holiday travel experience in Boston, you need a charter bus rental by Ally Charter Bus. When everyone rides together in their own private motorcoach, you can relax knowing you’ll arrive on time and no one will get lost. Call us today at 617-202-9113 to get your free quote!

Book with us for an easy and stress-free experience on your next trip.

Celebrating the Holidays in Boston

During the fall and winter holidays, Boston comes alive with activities and celebrations like no other. You and your friends, family, and colleagues will have plenty to choose from while you visit the city at the most enchanting time of the year.

Instead of relying on crowded public transportation or unscheduled rideshares, book a charter bus that’s outfitted with amenities your fellow passengers will enjoy. We can help you book a bus with features like reclining seats, WiFi, televisions, a climate-controlled cabin, a restroom, and more.

For festive holiday excursions that include adult beverages, a charter bus will ensure that everyone arrives safely to and from their destination. You won’t need to appoint a friend to be your designated driver; with a charter bus or minibus, everyone can join in on the fun.

Need some inspiration for your holiday itinerary? Check out our top recommendations for year-end events in Boston below!


A group of people dressed up in Halloween costumes.

Along with pub crawls, Oktoberfests, and costume parties, Boston has some annual events for ghosts and goblins to look forward to.

Boston Frog Pond Pumpkin Float

Head to the Frog Pond in Boston Common, jack-o’-lantern in hand, for this fun family event. Participants will light their pumpkins and set them afloat on the water. Afterward, you can enjoy music, crafts, and food while you watch the glowing lights float.

Address: 38 Beacon St., Boston, MA 02467

Salem Haunted Happenings

Each year, more than 50,000 people head to Salem for witches’ markets, psychic readings, haunted houses, live music performances, and more.

Address: 81 Washington Street, Salem, MA 01970

Ghosts and Gravestones Tour

For 90 minutes, this walking tour will scare and delight you throughout the city. You’ll hear stories of the dead (and undead) in two of Boston’s oldest burying grounds.

Address: 200 Atlantic Ave, Boston, MA 02110-3615

Phone: (617) 269-3626

Dia de Los Muertos

A table with Day of The Dead holiday food items.

Honor loved ones and celebrate life at some of Boston’s largest Dia de Los Muertos festivals and events.

Peabody Museum Day of the Dead Celebration

Enjoy an evening of festive music, food, and community at the Peabody Museum on Harvard’s campus. Remember loved ones at the Dia de Los Muertos altar, try delicious Mexican food and drinks, and listen to authentic mariachi music with friends and family.

Address: 11 Divinity Avenue, Cambridge, MA 02138

Phone: (617) 496-1027

Block Party at Taza Chocolate

Taza Chocolate Factory hosts a free block party for the community, complete with hot chocolate samples of their own. Head to Somerville for a chocolate-filled night of food, music, face painting, and more.

Address: 561 Windsor St., Somerville, MA 02143

Phone: (617) 623-0804


A spread of Thanksgiving food

Enjoy delicious food and remember everything you have to be thankful for at some of the city’s biggest Thanksgiving events and destinations.

Thanksgiving Dinner in the City

Don’t feel like cooking this year? Opt for a Thanksgiving dinner with friends and family at one of Boston’s top restaurants:

The Industry

Address: 750 Adams Street, Dorchester, MA 02122

Phone: (617) 297-9010

City Table

Address: 3505, 65 Exeter St, Boston, MA 02116

Phone: (617) 933-4800

Beacon Hill Hotel & Bistro

Address: 25 Charles St, Boston, MA 02114

Phone: (617) 723-7575

Home Games at the Garden

In Boston, we have Bruins and Celtics home games to be thankful for in November. Head to TD Garden in a private minibus so you can enjoy food and drinks along the way.

Address: 100 Legends Way, Boston, MA 02114

Phone: (617) 624-1000

Black Friday Shopping

If scoring great deals is your thing, head to shopping hubs like Newberry Street, the Wrentham Outlets, and Assembly Row for the biggest bargains.

Newbury Street

Address: Newbury Street, Boston, MA 02115

Wrentham Village Premium Outlets

Address: 1 Outlet Blvd, Wrentham, MA 02093

Phone: (508) 384-2876

Assembly Row

Address: 355 Artisan Way, Somerville, MA 02145

Phone: (617) 440-5565


A historic street in Boston, decorated for Christmas.

Stay warm on your private charter bus rental and gaze out at Boston’s festive lights and holiday decorations, or join in on one of the city-wide festivals and celebrations.

See the Lights

What’s Christmas without twinkling lights? Ride to Boston Common and Faneuil Hall Marketplace for some of the biggest decorated trees and light shows in the city.

Boston Common

Address: 139 Tremont St, Boston, MA 02111

Phone: (617) 635-4505

Faneuil Hall Marketplace

Address: 4 S Market St, Boston, MA 02109

Phone: (617) 523-1300

See the Arts

Catch a live performance of The Nutcracker at the Boston Opera House or Disney on Ice at the Agganis Arena or TD Garden, or stroll through the Downtown Holiday Market in front of the Smithsonian American Art Museum.

Boston Opera House

Address: 539 Washington St, Boston, MA 02111

Phone: (617) 259-3400

Agganis Arena

Address: 925 Commonwealth Avenue, Boston, MA 02215

Phone: (617) 358-7000

Downtown Holiday Arts Market

Address: 8th St NW & F St NW

Phone: (202) 215-6993

See the Santas

You saw the lights. Now see the…sights! Hundreds of scantily-clad Santas compete each year in the Santa Speedo Run for charity, and you can participate or sit back and enjoy the views.

Book Your Holiday Charter Bus Today

This holiday season, treat your friends and family to some of the best Boston has to offer, including a private charter bus ride to every stop on your itinerary. Our team of reservation specialists is available all day and night to pair you with the right motorcoach and answer any questions you may have. Call us today at 617-202-9113 to get started with a free, no-obligation quote!