Curator’s statement
Fall in Boston is like stepping into a cozy storybook—crisp air, vibrant leaves, and historic streets that invite you to wander and explore every charming corner. For Halloween lovers, the city’s spooky spirit comes alive with haunted history, eerie tales, and pumpkin-filled festivities!
The Fora Difference
Book with Angelica to access exclusive perks and experiences on your trip.
Killer perks
Free upgrades, spa credits and more—we got you
Personalized recs
Customized travel planning for your style
Insider knowledge
Expert advice from people who’ve actually been there
Where to stay
Unlock perks by contacting Angelica to book your trip.
Day 1: Sights and local fare

LOBO Rolls from Quincy Market
Start at Boston Common: Take a peaceful stroll through America’s oldest public park, enjoy the fall foliage, or relax by the Frog Pond.
Visit the Boston Public Garden: Walk across the famous Swan Boats and explore the picturesque landscapes.
Grab coffee at Tatte Bakery & Cafe: A popular local spot for delicious pastries and a cozy atmosphere.
Walk the Freedom Trail: Take a short walk to explore iconic landmarks like Faneuil Hall, Paul Revere’s House, and Old North Church.
Lunch at Quincy Market: Enjoy a casual meal at this historic market, known for its variety of food stalls.
Explore Beacon Hill: Wander through the charming cobblestone streets of this iconic neighborhood.
Day 2: Tours and history

Salem Tour
Start your day in Boston with a quick breakfast at Tatte Bakery & Cafe, grabbing a pastry and coffee before heading out to Salem. Once in Salem, dive into the eerie history at the Salem Witch Museum and stroll through Chestnut Street, known for its historic, haunted homes. Visit the Witch Trials Memorial and get a dose of spooky literary history at the House of the Seven Gables. For a truly haunted experience, stay at the Hawthorne Hotel, famously known for its ghostly sightings and eerie charm. Don’t miss booking a guided ghost tour to explore Salem’s darkest secrets, from haunted sites to tales of witches and spirits. End your day exploring the witchy vibes of Salem’s cobblestone streets, with a lingering sense of mystery in the air.
Day 3: Ferry to Martha's Vineyard

Boston Tea Party Tour
For a historical adventure, take the Boston Tea Party Boat Tour, where you can reenact the iconic tea dump, explore the Boston Harborwalk, and follow the Freedom Trail to famous landmarks. Alternatively, for a more relaxed, scenic day, head to Martha’s Vineyard. Enjoy a charming ferry ride to the island, visit the iconic Gingerbread Cottages in Oak Bluffs, and explore the picturesque streets of Edgartown, with plenty of opportunities for shopping, dining, and beachside views. Either way, you’ll experience the best of New England’s history or coastal beauty!
Need to know
Boston is a walkable city with a rich history, vibrant neighborhoods, and delicious seafood. Explore iconic landmarks like Boston Common, the Freedom Trail, and the North End. Take a ride on The T subway for easy access to attractions, and don’t miss a lobster roll or clam chowder. If you’re venturing outside the city, day trips to Harvard University, Cape Cod, or Salem are fantastic options. Fall is perfect for leaf-peeping, while winter offers cozy vibes with beautiful holiday lights. Make sure to check out local craft breweries and enjoy Boston’s diverse culinary scene!

Travel Advisor
Angelica Zureikat

Get in touch with Angelica
Did you like this guide? Reach out to customize and book your own experience. Or, just to chat about travel in general.
You can expect a response from Angelica within 1–2 business days. You’ll also be subscribed to our traveler newsletter (you can unsubscribe at any time).
For more travel inspiration and insider recommendations, check out our Boston page.