Top Philadelphia Holidays in 2026

Join City Sightseeing this holiday season and experience a unique way to view all your favorite parts of our beautiful city on one of our Victorian Style Trolley’s. Our trolleys are all decked out in the holiday spirit ready with lights, holiday decor and music for the ultimate way to see the city’s beautiful light show this season! Our two-hour Holiday Tour (Including Loading and Unloading) will take you to the best decorated streets in the city while you and your friends and family can sing along with us to all your favorite holiday music. City Sightseeing’s Holiday Light Tour is perfect for family, friends, holiday parties and corporate events. We are ready to have you book today and join us for this beautiful holiday experience. Featured sites/neighborhoods include: Smedley Street, where you can get out & stretch your legs Miracle on 13th St. (Beginning November 28th) Christmas Village/Love Park City Hall & Dilworth Plaza Comcast Building Washington Square Franklin Square

Join City Sightseeing this spooky season and experience Philadelphia’s darker side of history. We will take you on an interactive trolley tour. Our tour guide will take you on a 90-minute journey through Old City in a decorated trolley ready for the Halloween season. We have included two surprise stops along the way for you to get off the trolley and walk around while the tour guide tells you the ghostly stories at the sight you are standing on. We start at Independence mall and continue to other sites including The Arch Street Meeting House, Christ Church Burial Ground, Washington Square Park, The Famous Powel House and many more that will have you looking over your shoulder all evening. We include trivia, games and fun on our BYOB Halloween Trolley Experience. We have these available individual timed tickets for you and your friends. This tour is perfect for group events, family get-togethers, and corporate outings. Don’t miss out on the spooktacular event this Halloween.

Soak up the history in Philadelphia’s atmospheric Old City neighborhood—and discover its spooky side as you go—on this haunted pub crawl. Meet your guide in the evening at your first stop, and set off on foot. You’ll visit four historic taverns and learn about their spooky histories as you enjoy snacks and drinks (at your own expense).

See the dark side of Philly during this adult night tour developed by a local university professor. Not for the faint of heart, this tour uncovers Philadelphia’s R-rated sites and stories, from vampires, pirate ghost ships, and haunted attractions to torture, executions, and the red light district. You'll also visit historical attractions and see the sights illuminated at night. This tour is not suitable for children.

Philadelphia is a terrific foodie city, but for visitors, it can be tricky to know where to find the best places to eat and enjoy. This walking tour removes the guesswork: In a small group of no more than 12, you'll eat your way through the city, from Reading Terminal Market to Sansom Street, and experience the best of the Philly food scene.

Avoid having to book separate tours and pair Philadelphia history with delicious brews on this 2-in-1, small-group walking tour. Hosted right in the heart of Old City, this tour introduces you to some of the city’s key landmarks, Founding Fathers, and revolutionary history. As you go, get a taste of Philly’s top-notch drinks scene when you stop at locally beloved bars for pints of beer or cider (own expense).

Get a new perspective on the City of Brotherly Love with this nighttime sightseeing tour. Climb on board a double-decker bus and explore the best that Philadelphia has to offer. Visit 27 of Philly’s top attractions — like the Liberty Bell, Independence Hall, Penn’s Landing and the Rocky Steps at the entrance to the Philadelphia Museum of Art — on a 90-minute loop around this historic city.

Celebrate the holidays in Philadelphia on a festive walking tour filled with delicious donuts, fresh cookies, sparkling lights, and holiday cheer! Your adventure begins at the Comcast Center Concourse, where you'll enjoy sweet treats while learning about Philadelphia's rich history and beloved holiday traditions. Next, stroll through the magical Christmas Village at LOVE Park, where charming holiday stalls, festive decorations, and seasonal celebrations bring the spirit of the season to life. From there, we'll head to the historic Reading Terminal Market, where you'll indulge in fresh, handcrafted donuts featuring delicious flavors and seasonal specialties. The adventure continues with freshly baked cookies, adding another sweet touch to this holiday experience. Along the way, your guide will share fascinating stories about Philadelphia's history, culture, and holiday traditions. It's a fun, family-friendly way to celebrate the season and discover Philly's sweetest side!

Set sail for a magical holiday with a memorable celebration aboard our Signature Philadelphia Christmas Day Cruises. Take in breathtaking views of Philadelphia’s iconic landmarks, such as the Ben Franklin Bridge, from inside or the open-air decks. This fun-filled holiday including a live DJ, dancing, games, a fully stocked cash bar. Revel in merriment and holiday cheer with this unforgettable brunch on the water! Join us December 3 - January 1st for an enchanting and immersive Winter Wonderland experience as City Cruises celebrates the holiday season in style! Step aboard our uniquely decorated yachts, where a whimsical, fun-filled atmosphere awaits. Surround yourself with twinkling lights, snow-covered trees, themed cocktails, seasonal menus, live entertainment, and of course, stunning views of Philadelphia’s skyline, perfectly complementing Philadelphia’s festive mix of holiday-themed attractions and restaurants.

Philadelphia's century-old Italian Market is home to dozens of Italian restaurants and delis, as well as newer eateries that serve its Mexican and Vietnamese communities. Avoid a bad bite and go with a guide to taste the best of the area, learn its history, and soak up its ambiance on this small-group tasting tour. Enjoy enough bites to equal a generous meal, from tacos and bahn mi to cannoli and more.

Visit some of Philadelphia’s spookiest landmarks and drinking dens. on this pub crawl with a twist. Meet your guide in the heart of Center City, then walk around centuries-old cemeteries, macabre colonial landmarks, and other eerie attractions. Then, continue onward to supposedly haunted bars and taverns, where can enjoy light refreshments and drinks (own expense).

Enjoy dinner out in Philadelphia with a difference—and combine your meal with a memorable sightseeing excursion—thanks to this evening dinner cruise. Setting sail along the Delaware River, admire views from the outdoor decks of the Philadelphia skyline and Benjamin Franklin Bridge. Then, enjoy a chef-prepared buffet dinner before hitting the dance floor and making the most of the DJ entertainment.

Discover one of Pennsylvania’s most distinctive regions and communities on this full-day, small-group tour of Lancaster County’s Amish Country. In the morning, meet your guide in Center City Philadelphia and travel via air-conditioned vehicle. You’ll learn all about the region’s Amish history, will see working farmers and visit the Amish Village Museum, can shop for Amish goods from pies to quilts, and otherwise discover this region’s unique heritage.

Explore Philadelphia's vibrant cocktail culture on the Sips of Fishtown tour. Visit some of the city’s top bars and distilleries, where expert mixologists craft unique cocktails and local brews. Enjoy a delightful progression of drinks paired with tasty snacks and munchies while uncovering the fascinating stories behind each creation. Your engaging guide will share insights into Philly’s transformation from a historic warehouse area to a bustling food and drink district. Perfect for cocktail lovers and enthusiasts, this tour includes three curated drink stops and a sweet boozy treat to kickoff your evening strong! - Discover Philadelphia’s cocktail culture in the trendy Fishtown neighborhood - Enjoy three curated drink stops, including local brews and bar snacks to soak up the booze - Learn about the city’s rich history from an engaging guide - Non-alcoholic options available for those who prefer them

Philadelphia is one of the best cities in the country for craft beer fans, and on this tour you’ll get to visit some of the area’s most accomplished producers (and do plenty of tasting). Meet your guide in Center City, and travel via comfortable beer-themed van to three different breweries. Along the way, enjoy generous samples, go on behind-the-scenes tours, and enjoy a snack to accompany those suds.

Step into a modern & fun speakeasy, where the allure of a secret eclectic colorful bar comes alive. Using a secret password for entry, indulge in four expertly crafted cocktails and mocktails featuring premium spirits. Enjoy a fizzy Blueberry Wisconsin Old Fashioned, a refreshing Guava Mojito, a classic Lavender Bees Knees, and a mocktail that serves as a bookend to Prohibition—all while snacking on complimentary treats. Led by an experienced mixologist, making it a perfect outing for both cocktail enthusiasts and casual sippers alike.