Arrive at Logan Airport, pick up your rental car, and settle into a centrally located hotel in Back Bay or the North End—consider the Lenox or The Godfrey for comfort and walkability. Start with a relaxed brunch at Tatte Bakery & Cafe on Charles Street or Mike’s Pastry in the North End if you crave a classic cannoli, then stroll the nearby Boston Common and Public Garden to stretch your legs and admire the historic parkland.
Wander the cobblestone streets of Beacon Hill, popping into antique shops and boutique stores on Charles Street, then walk the Freedom Trail’s first few stops — Massachusetts State House and Park Street Church — to get an early taste of Boston’s history. If you prefer museums, spend the afternoon at the Museum of Fine Arts or the Isabella Stewart Gardner Museum; both offer world-class collections and a cozy respite from winter weather.
For dinner, savor New England seafood at Neptune Oyster or enjoy contemporary bistronomy at SRV in the South End—reserve ahead for peak times. Afterward, take an evening walk along the waterfront at Christopher Columbus Park or catch a cocktail at a rooftop bar like Yvonne’s to toast the start of your trip and plan the scenic drives and culinary stops ahead.
Begin your day with a hearty New England breakfast at Flour Bakery + Cafe or a classic diner meal at South Street Diner, then pick up the Freedom Trail where you left off — follow the red brick or painted line from Park Street to Granary Burying Ground and King’s Chapel to connect with revolutionary-era stories and famous resting places. Pause for a coffee at Thinking Cup in the nearby North End before continuing toward Faneuil Hall to hear lively street performers and browse Quincy Market’s artisan stalls.
Spend the afternoon diving into culture: choose the expansive collections at the Museum of Fine Arts or for a more intimate and atmospheric visit, the Isabella Stewart Gardner Museum — both are a short drive or T accessible from the downtown core. If history still calls, visit the Boston Tea Party Ships & Museum for an interactive, family-friendly retelling of the events that shaped the nation, then warm up with clam chowder at Legal Sea Foods or a lobster roll at James Hook & Co.
For dinner, reserve a table at a celebrated spot like Mistral for refined bistro cuisine, O Ya for inventive sushi, or the oyster-forward Neptune Oyster in the North End for an unpretentious treat; cap the night with a cocktail at Backbar in Somerville or a riverside drink at Lookout Rooftop Bar for skyline views. If you’d like a mellow cultural finish, check the schedule at the Boston Symphony Orchestra or see a play in the Theatre District to end the day on a distinctly Bostonian note.
Leave Boston after breakfast and enjoy a roughly 30-45 minute coastal drive along I-95/Route 1A to historic Salem. Start with a coffee and pastry at Bob’s Return on Derby Street before exploring the Peabody Essex Museum’s remarkable maritime and Asian art collections and wandering the cobblestone streets of the McIntire Historic District to admire Federal-era homes and decorative trim.
For lunch, sample fresh seafood at Turner’s Seafood (or the popular Lobster Shanty for a casual roll) then stroll the Salem Harbor waterfront and Derby Wharf—stop by the Salem Maritime National Historic Site to learn about the port’s trading past. In the afternoon, take the self-guided Salem Witch Trials walking tour to visit the Witch House and Old Burying Point, or opt for a guided walking tour if you’d like richer storytelling; finish with a quiet drive along the scenic Marblehead neck for postcard coastal views.
Dine in downtown Salem at Cultivar or Ledger for a seasonally driven meal, then enjoy a relaxed evening drink at Gulu-Gulu Cafe or the cozy tavern vibe of the Red’s Sandwich Shop (open late for a local bite). If you’re up for a bit of local atmosphere, check if the Salem Theatre or The Merchant offers evening performances, otherwise return to your Portsmouth-bound route or a nearby inn to rest before tomorrow’s drive to New Hampshire.
Head north after breakfast in Salem for the roughly 1-1.5 hour coastal drive to Portsmouth, taking Route 1 for scenic shoreline views. On arrival, park near Market Square and begin with a stroll along the waterfront to Strawbery Banke Museum, where costumed interpreters and restored historic houses bring colonial and 19th-century seaport life to vivid life; grab a coffee and a pastry at Ceres Bakery to warm up before exploring.
For lunch, savor local seafood at the Waterfront’s Row 34 for oysters and a warm chowder or try Jumpin’ Jay’s Fish Café for creative New England bites, then browse boutiques and galleries around Market Square and the charming side streets of the South End. Spend the afternoon touring the Music Hall (check for midday tours or performances), visiting the USS Albacore Museum if you’re interested in naval history, or taking a short drive to Prescott Park to enjoy harbor views and public art installations.
Dine at one of Portsmouth’s excellent farm-to-table spots—The Black Birch or The Franklin for seasonal menus—or choose a more relaxed meal at Portsmouth Brewery with a local brew. After dinner, soak up the town’s cozy evening vibe with a nightcap at The Bistro at Strawbery Banke or a craft cocktail at The Green Monkey, and finish with a moonlit walk along the Piscataqua River to admire the historic bridges and lights of the waterfront.
After a scenic 2-2.5 hour drive from Portsmouth along I-95/I-295 and Route 1, arrive in Portland and warm up with breakfast at Standard Baking Co. or the cozy Tandem Coffee + Bakery in the West End. Spend the morning wandering the Old Port’s cobblestone streets, popping into specialty shops, and visiting the Portland Head Light in nearby Fort Williams Park for iconic Maine coastal views and easy, bracing walks along the shoreline.
For lunch, dive into Portland’s celebrated seafood scene with a lobster roll at Eventide Oyster Co. or a raw bar experience at Portland Lobster Company on the waterfront, then explore the Portland Museum of Art’s collection or browse the galleries and artisan shops along Congress Street. If weather permits, take a short harbor cruise or a guided food tour to sample local cheeses, craft brews, and seasonal specialties while learning about Portland’s maritime and culinary history.
Dine at one of Portland’s acclaimed restaurants — consider Fore Street for rustic, wood-fired fare or Hugo’s for refined, seasonally driven cuisine — and pair the meal with a local craft beer or Maine cider. After dinner, enjoy a relaxed stroll along the waterfront or a nightcap at Novare Res Bier Café, then return to your accommodation in the Old Port or West End to rest up for tomorrow’s golf or spa day in Greater Portland.
Start the day with a relaxed breakfast at The Great Lost Bear or Standard Baking Co., then head out for a morning on the links at one of Greater Portland’s best courses — consider seaside views at Cape Arundel Golf Club (Kennebunkport) or the well-maintained greens at Sable Oaks Golf Club in South Portland for a shorter drive. If you prefer pampering to playing, book a morning spa block at The Spa at The Westin Portland Harborview or the White Barn Inn & Spa in Kennebunk for a signature massage and sauna to unwind after several travel-filled days.
Continue your golf round or spa treatments after lunch — grab a clubhouse sandwich or lobster roll on-site if golfing, or enjoy the spa’s light seasonal lunch service and relaxation lounge before a facial or body wrap; for a golf alternative with scenic walking, stroll the trails at Fort Williams Park and visit Portland Head Light for iconic coastal views. If energy allows, stop by a local brewery like Allagash or Rising Tide for a tasting flight to sample Maine craft beers and chat with brewers about local ingredients and pairings.
Dine back in Portland’s Old Port at a cozy, celebratory spot such as Fore Street for wood-fired comfort or Eventide Oyster Co. for a casual yet outstanding seafood meal, then finish the evening with a cocktail at The Honey Paw or a pint at Novare Res Bier Café. If you’ve had a full spa day and prefer low-key plans, opt for a quiet dessert and coffee at Bard Coffee before turning in early to rest up for the scenic drive south to Providence on Christmas Eve.
Leave Portland after a leisurely breakfast—try Standard Baking Co. or Tandem for one last coffee—then enjoy the roughly 2-hour coastal drive south to Providence, taking I-95 for the most direct route or Route 1 for more shoreline scenery. On arrival, stretch your legs with a walk through the historic College Hill neighborhood: stroll Brown Universityʼs campus, admire the colonial and Federal architecture along Benefit Street, and pop into the John Brown House Museum to get a compact dose of Rhode Island mercantile history.
For lunch, head to the revitalized downtown and sample innovative small plates at North or the acclaimed seafood and seasonal dishes at Hemenway's, then wander the Waterplace Park and Riverwalk to see the cityʼs canals and arched pedestrian bridges. Spend the afternoon browsing the RISD Museum for its surprising and well-curated collections or duck into local boutiques and galleries on Thayer Street; if the weather allows, consider a short Providence River boat tour or a drive to the nearby Colt State Park in Bristol for sweeping waterfront views.
Celebrate Christmas Eve with a memorable dinner—reserve a table at Al Forno for its legendary grilled pizza and Italian-American fare or choose the modern American tasting at Persimmon for a seasonally focused meal—then enjoy a moonlit stroll along the Riverwalk to see the city lights reflected on the water. If youʼre in the mood for a relaxed nightcap, stop by The Avery for craft cocktails or grab dessert and coffee at Seven Stars Bakery before settling into a centrally located hotel to rest up for your return to Boston on Christmas Day.
Drive back from Providence after a leisurely breakfast and aim to arrive in Boston mid-morning; return your rental car at Logan or a downtown pick-up location depending on your departure plans. If you have time before a flight or late check-out, enjoy a calm stroll through the Public Garden and Back Bay — pick up a warm pastry and coffee at Tatte Bakery on Charles Street or a classic New England breakfast at The Paramount to savor one last taste of the city.
If your travel schedule allows a relaxed afternoon in town, tuck into a cozy lobster roll or clam chowder at James Hook & Co. on the waterfront and wander the historic North End for last-minute pastries at Mike’s Pastry or Modern Pastry. For a quieter cultural option, spend an hour at the Isabella Stewart Gardner Museum or the Boston Public Library to soak up art and architecture before heading to the airport, otherwise keep plans flexible and allow extra time for traffic and security on this holiday.
If you’re staying an extra night or have a late flight, celebrate the trip’s end with a final New England meal—reserve a table at Mamma Maria in the North End for Italian comfort or Legal Sea Foods near the waterfront for reliable seafood—and enjoy a nightcap at Yvonne’s or Lookout Rooftop Bar if open; otherwise, head to Logan with plenty of time to spare, return home with relaxed memories of coastal drives, historic towns, and great food.