Thanksgiving isn’t just a day on the calendar — it’s a feeling. A moment to pause, reconnect, and celebrate the traditions (old or new) that make us grateful.
This week’s Paul’s Picks highlights five destinations that bring Thanksgiving to life in completely different ways: iconic parades, colonial feasts, festive mountain cabins, historic celebrations, and warm-weather escapes that skip the dishes altogether.
Wherever you find gratitude this year, let these ideas inspire a holiday filled with meaning, fun, and a little magic.
Contact me to start a new tradition of traveling.
Macy’s Parade on Thanksgiving morning? Yes, please.
Iconic floats, crisp NYC air, and a big-city holiday buzz like nothing else.
Step back into the 1700s this Thanksgiving.
Colonial feasts, lantern walks, and historic charm everywhere you turn.
Cabin Thanksgiving? Cozy fireplaces, mountain views, and zero stress.
Great for families who want to gather somewhere beautiful.
Thanksgiving where it all began.
Plymouth’s historic celebration is charming, meaningful, and happens before the holiday — perfect for early festivities.
Trade fall chill for island warmth.
Thanksgiving in Maui means golden beaches, fresh island flavors, and the start of whale season—pure holiday bliss.
Macy's Thanksgiving Day Parade
There’s nothing quite like Thanksgiving morning in New York City. From the night-before balloon inflation to the iconic floats gliding down Central Park West, the city practically sparkles with energy. Stay near the parade route for unforgettable views, add in ice skating at Rockefeller Center, and round out the day with a cozy restaurant feast or Broadway show. It’s classic, festive, and perfect for anyone who wants a bit of holiday magic in the world’s most electric city.
From VIP viewing events to fully escorted holiday packages, there are a number of exceptional options available for the Macy’s Thanksgiving Day Parade. One example is this curated offering: 2026 Thanksgiving NYC - Perfect for inspiration or future planning.
Planning a Thanksgiving escape to New York?
I’ll craft a custom itinerary with premium parade access, top hotel recommendations, and holiday experiences tailored to your travel style. Start here: Bespoke Itineraries
Lantern-lit streets, historic taverns, and immersive traditions bring the spirit of Thanksgiving to life.
Step into an 18th-century world where Thanksgiving feels timeless. Colonial Williamsburg elevates the holiday with flickering lantern tours, historic tavern dinners, and immersive reenactments that turn the entire week into a living story.
Guests can enjoy chef-crafted Thanksgiving feasts at the Williamsburg Inn or dine in one of the town’s cozy colonial taverns. It’s warm, atmospheric, and perfect for travelers who want a holiday rich in tradition and charm.
Colonial Williamsburg Dining & Holiday Experiences
I can curate a Williamsburg Thanksgiving with the perfect mix of history, dining, and seasonal experiences, just for you.
Mountain views, warm fireplaces, and family-friendly comfort make this a Thanksgiving retreat to remember.
If “cozy mountain escape” is your Thanksgiving style, Gatlinburg and the Smokies deliver beautifully. Picture a log cabin with scenic views, warm fireplaces, outdoor hot tubs, and the lingering glow of late fall colors in the mountains.
Visitors can enjoy Winterfest lights, craft markets, and plenty of restaurants serving Thanksgiving dinner—ideal for families who want stress-free dining. This is the holiday where everyone gathers under one roof with room to breathe.
Let me plan a mountain cabin Thanksgiving with the right home, views, and activities for your group. Book early for best pricing!
History, heritage, and heartfelt New England charm come together in this cozy, meaningful holiday escape.
Plymouth is the heart of Thanksgiving’s origin story, and its annual “America’s Hometown Thanksgiving Celebration” is one of the country’s most charming holiday traditions. Think costumed reenactors, a historic waterfront parade, candlelit streets, and New England inns wrapped in late-autumn coziness.
Because the celebration happens the weekend before Thanksgiving, travelers can enjoy the festivities and still be home for their own traditions. Perfect for history lovers and families who want meaning woven into every moment. Read more about it here.
Let me build a Thanksgiving getaway to Plymouth with charming inns, historic experiences, and a coastal New England feel.
Golden beaches, gentle breezes, and Hawaiian-inspired holiday flavors create a Thanksgiving unlike any other.
Thanksgiving on Maui feels like a deep exhale. Warm breezes, golden beaches, and the soft start of whale-watching season set a serene backdrop for the holiday.
Many resorts offer Thanksgiving menus with Hawaiian flair—think fresh island seafood, macadamia stuffing, and sunset dinners overlooking the Pacific. Whether travelers want to snorkel, relax at a spa, explore the Road to Hana, or simply rest in the warm glow of aloha, Maui offers a Thanksgiving that’s peaceful, nourishing, and unforgettable. Here are a few specials to dream about:
Fairmont Hawaii
Grand Wailea
Westin Maui
Want Thanksgiving with aloha? I will design a Maui holiday escape—luxury, family friendly resort, boutique hideaway, or beachfront condo—filled with warm island magic.