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Getaways from Boston · Winter 2026–27

Winter getaways from Boston

Fifteen ways out of Boston between December and February, from a 36-minute Acela to Providence to a Saturday nonstop to Turks and Caicos. Each lists how long it takes, the dates worth timing it for, where to stay and one thing to know before you go.

  • 15trips
  • 8by car
  • 3by train
  • 4by air
  • Facts checked 24 October 2026

15 winter trips from Boston, sorted by how you get there: 8 by car, 3 by train and 4 by air. The quickest to reach is Providence, 36 min away; the longest trip is Anguilla, 4 hr 40 min. Each one lists the travel time, the dates worth timing it for and where to stay.

At a glance

GetawayFrom BostonBest forTime it for
Portsmouth 1 hr Culture, Festival, Family Candlelight Stroll, 4–20 Dec 2026
Newport 1 hr 30 min Romantic, Culture, Festival Holidays at the Newport Mansions, 21 Nov 2026 – 3 Jan 2027
Kennebunkport 1 hr 30 min Romantic, Festival, Family Christmas Prelude, 3–13 Dec 2026
Chatham, Cape Cod 1 hr 45 min Romantic, Outdoors, Food & wine January and February, when the Cape is at its quietest
Woodstock, Vermont 2 hr 15 min Romantic, Ski, Festival Wassail Weekend, 11–13 Dec 2026
The Berkshires 2 hr 30 min Spa, Culture, Outdoors January to March, when the Clark is free on the first Sunday of the month and Notchview's trails are groomed
Bretton Woods, White Mountains 2 hr 30 min Ski, Family, Outdoors Mid-December to early April, when the Nordic trails are groomed
Stowe 3 hr 30 min Ski, Romantic, Spa January to March, for the deepest snow
Providence 36 min City break, Food & wine, Culture WaterFire Holiday Basin Lighting, 11 Dec 2026
Portland, Maine 2 hr 31 min City break, Food & wine, Culture Any winter Friday, when the Portland Museum of Art is free
New York City 4 hr City break, Culture, Food & wine NYC Restaurant Week (winter), 19 Jan – 11 Feb 2027
Montréal Passport 1 hr 30 min City break, Festival, Food & wine Montréal en Lumière, 18–28 Feb 2027
Bermuda Passport 2 hr 15 min Romantic, Food & wine, Spa Bermuda Restaurant Weeks (2027 dates TBA)
Turks and Caicos Passport 3 hr 45 min Romantic, Outdoors, Food & wine Any Saturday-to-Saturday week from 19 December 2026, matching the weekly flight
Anguilla Passport 4 hr 40 min Romantic, Food & wine, Outdoors 18 December 2026 to 12 March 2027, while the twice-weekly nonstop runs

By car 8 trips

1 hr
Photograph · Strawbery Banke Museum
New Hampshire, USA

Portsmouth

Less than an hour from Boston, per Go PortsmouthC&J buses link Logan Airport and South Station with Portsmouth, per Go Portsmouth.

Portsmouth is the closest coastal town on this list, and in December Strawbery Banke Museum lights its historic Puddle Dock neighborhood for three weekends of Candlelight Strolls. The same grounds become an outdoor rink in winter, a short walk from Market Square.

Time it for Candlelight Stroll 4–20 Dec 2026

Strawbery Banke Museum's evening tours of decorated historic houses in the Puddle Dock neighborhood.

Do
  • Candlelight Stroll Decorated historic houses and candlelit streets at Strawbery Banke Museum; this year's theme is "Welcome, Neighbor." Timed arrival windows; no on-site parking.
  • Labrie Skate, Puddle Dock Pond Outdoor rink at Strawbery Banke with daily public skating, rentals and sharpening, run on a chilling system.
  • Vintage Christmas Go Portsmouth's holiday season with a parade, the candlelight stroll and a gingerbread house exhibit.
Stay
  • The Hotel Portsmouth 32 rooms in an 1881 Queen Anne Victorian mansion at 40 Court Street, within a 10-minute walk of Market Square, with a complimentary small-plates breakfast.
  • Martin Hill Inn Main House and Guest House rooms and the Athens Suite at 404 Islington Street, about 10 minutes' walk from Market Square, with gardens and free parking.

Map by Stay22. If you book through it we may earn a commission, at no cost to you. It never decides what we write.

Winter tip Candlelight Stroll tickets carry a timed arrival window, and there is no parking on site; the trolley runs on Saturdays and Sundays.

On Not An Atlas: Saga’s No-Fly Premium

1 hr 30 min
Photograph · The Preservation Society of Newport County
Rhode Island, USA

Newport

About 90 minutes (70 miles) from Boston, per Discover NewportWithout a car, Discover Newport points to Amtrak to Kingston, then a van, ride-share or RIPTA bus 64 (no service on Sundays or holidays).

The Preservation Society decorates The Breakers, Marble House and Chateau-sur-Mer with nearly 30 Christmas trees, and on select evenings a half-mile path of lights runs through The Breakers' grounds. Castle Hill Inn and The Chanler make it a winter weekend on the water.

Time it for Holidays at the Newport Mansions 21 Nov 2026 – 3 Jan 2027

The Breakers and Marble House open daily and Chateau-sur-Mer on weekends, all decorated for the season.

Do
  • Holidays at the Newport Mansions Nearly 30 decorated trees across three houses, including a 15-foot poinsettia tree of 150 plants in The Breakers' Great Hall; The Breakers needs a dated, timed ticket.
  • Sparkling Lights at The Breakers Select evenings 21 November to 27 December 2026, 4 to 8 p.m., with timed entry every half hour to 6 p.m.; adults $45, ages 6 to 12 $18, and the ticket includes the decorated interior.
  • A Christmas Carol at The Breakers A musical retelling of "A Christmas Carol" on Thursday 17 December 2026 at 7 p.m.; public tickets on sale 29 October.
Stay
  • Castle Hill Inn Set on its own 40-acre peninsula where Narragansett Bay meets the Atlantic, run as a year-round retreat since its rooms were winterized after the war; Rhode Island's first Relais & Châteaux member (2008).
  • The Chanler at Cliff Walk Twenty rooms and villas on the Cliff Walk at 117 Memorial Boulevard, each drawn from a different period or place, with the Atlantic-view Cara restaurant.

Map by Stay22. If you book through it we may earn a commission, at no cost to you. It never decides what we write.

Winter tip Regular Breakers tickets are not accepted after 3 p.m. on Sparkling Lights nights, so a single evening ticket covers both the lights and the decorated house.

1 hr 30 min
Maine, USA

Kennebunkport

About 90 minutes by car from Boston, per the White Barn InnBy train, the Downeaster reaches Wells in about 1 hr 46 min from North Station, and the Kennebunkport tourism site puts the onward ride at about 10 minutes.

Christmas Prelude turns Kennebunkport into a ten-day holiday village in early December, with a tree lighting in Dock Square, a hat parade and Santa arriving by lobster boat. The White Barn Inn's Five Star dining room makes it a romantic weekend.

Time it for Christmas Prelude 3–13 Dec 2026

The 45th annual Kennebunkport Christmas Prelude, with tree lightings, parades and Santa's lobster-boat arrival.

Do
  • Dock Square tree lighting Caroling from 5:30 p.m. and the tree lit at 6 p.m. on Friday 4 December 2026; a second lighting follows on Friday 11 December.
  • Santa arrives by lobster boat Sunday 6 December 2026 at 1 p.m. at The Nonantum Resort, with viewing from 12:30 p.m.
  • Hat Parade The 21st annual parade on Saturday 5 December 2026 at 3 p.m., rain or shine.
Stay
  • White Barn Inn & Spa 23 rooms and four stand-alone cottages at 37 Beach Avenue, with a Forbes Five Star and AAA Five Diamond dining room and a spa with a couples suite.
  • Cape Arundel Inn & Resort Overlooking the Atlantic on Ocean Avenue, with the Ocean restaurant; the Tree Spa winter pop-up opens there on 13 November 2026 and a shuttle runs Fridays and Saturdays during Prelude.

Map by Stay22. If you book through it we may earn a commission, at no cost to you. It never decides what we write.

Winter tip Kennebunkport Resort Collection waives its pet fee during Prelude, and the Pooch Parade is on Sunday 13 December, the festival's last day.

1 hr 45 min
Photograph · Chatham Bars Inn
Massachusetts, USA

Chatham, Cape Cod

About 90 minutes to 2 hours (87 miles) by car from Boston, per the Chatham Chamber of CommerceThe chamber puts the Sagamore Bridge to Chatham center at 30 to 35 miles, 45 minutes to an hour in normal traffic.

Chatham in winter is the Cape without the traffic: beach walks at Lighthouse Beach, seals on the Monomoy sandbars and a Main Street with room to browse. Chatham Bars Inn keeps its restaurants open year-round and runs a winter art series and cooking classes.

Do
  • Monomoy National Wildlife Refuge About 6 miles from Chatham Bars Inn, for birdwatching and seals on the sandbars.
  • Chatham Lighthouse and Lighthouse Beach Quiet winter beach walks and the lighthouse, recommended by Chatham Bars Inn for the off-season.
  • Winter classes at Chatham Bars Inn Cooking, mixology, oyster-shucking and painting classes, plus a monthly Winter Art Series of local and regional artists.
Stay
  • Chatham Bars Inn Forbes Five Star resort founded in 1914, with 217 rooms on 25 acres over Chatham Harbor, a full-service spa with an adults-only pool, and STARS and the Sacred Cod Tavern open year-round.
  • Chatham Inn 18 rooms on Main Street, continuously operating since 1830 and Cape Cod's only Relais & Châteaux property (since 2019), with Cuvée Bistro and The Wine Bar.

Map by Stay22. If you book through it we may earn a commission, at no cost to you. It never decides what we write.

Winter tip Chatham Bars Inn gives overnight guests a complimentary Lexus for up to four hours, which covers a winter run to the Cape Cod National Seashore.

2 hr 15 min
Photograph · Woodstock Inn & Resort
Vermont, USA

Woodstock, Vermont

About 2 hr 15 min from Boston, per the Woodstock Area Chamber of Commerce

Woodstock is two and a quarter hours from Boston, and its Wassail Weekend brings a horse parade, a Yule log bonfire and luminaries on the green. After the holidays, the Woodstock Inn's own ski hill and Nordic center, and Twin Farms in Barnard, carry the season.

Time it for Wassail Weekend 11–13 Dec 2026

Woodstock's holiday weekend: a ticketed welcome party, the Wassail Horse Parade around the green, a Yule log bonfire and the Rotary lighting of the luminaries.

Do
  • Saskadena Six The Woodstock Inn's alpine ski area on Standing Mountain, operating since 1936.
  • Woodstock Nordic Center Cross-country skiing and snowshoeing on what the inn calls an extensive trail network, moments from the inn.
  • Wassail at Billings Farm Wassailing the orchard, a Victorian-decorated farmhouse, candle dipping and horse-drawn sleigh or wagon rides, 11 to 13 December 2026, 10 a.m. to 4 p.m.
Stay
  • Woodstock Inn & Resort Village resort with its own ski area, Nordic center and a LEED-certified spa using organic products.
  • Twin Farms All-inclusive retreat in Barnard for adults (14 and over): meals, drinks and on-site activities including skiing, with equipment and instruction, are included.

Map by Stay22. If you book through it we may earn a commission, at no cost to you. It never decides what we write.

Winter tip The chamber's Wassail welcome party at Peace Field Farm (Friday 11 December, 3 to 6 p.m.) is ticketed with limited seating, so book it with the room.

2 hr 30 min
Photograph · Canyon Ranch
Western Massachusetts, USA

The Berkshires

About 2 hr 30 min (135 miles) by car from Boston Logan, per the Berkshires visitors bureauAmtrak's Lake Shore Limited runs from Boston to Pittsfield, per the visitors bureau; take I-90 to Exit 2 (Lee) for Lenox.

The Berkshires pair two all-season wellness resorts in Lenox, Canyon Ranch and Miraval, with serious art at the Clark and MASS MoCA and 25 miles of groomed ski trails at Notchview. It is quiet between the summer festivals.

Do
  • Clark Art Institute, Williamstown Galleries open Tuesday to Sunday, 10 a.m. to 5 p.m., September to June, plus Martin Luther King Jr. Day and Presidents' Day; adults $22, free on the first Sunday of each month from October to May.
  • Notchview, Windsor The Trustees' 3,108-acre reservation, mostly above 2,000 feet, with 25 miles of groomed ski trails, open early December to early April, conditions permitting.
  • MASS MoCA, North Adams Open 10 a.m. to 5 p.m. daily except Tuesdays in fall and winter, with some Tuesdays during school breaks; adults $25.
Stay
  • Canyon Ranch Lenox All-inclusive wellness resort and spa built around the Bellefontaine Mansion, with unlimited meals and 35-plus optional daily activities.
  • Miraval Berkshires Resort & Spa 380 acres in Lenox with grounds by Frederick Law Olmsted and an 1894 mansion at its center.

Map by Stay22. If you book through it we may earn a commission, at no cost to you. It never decides what we write.

Winter tip The Clark opens on Martin Luther King Jr. Day (18 January 2027) and Presidents' Day (15 February 2027), both Mondays it would otherwise be closed.

2 hr 30 min
Photograph · Bretton Woods
New Hampshire, USA

Bretton Woods, White Mountains

About 2 hr 30 min (160 miles) by car from Boston, per Omni Mount Washington ResortTake I-93 north through Franconia Notch to Exit 35, then Route 3 to Twin Mountain and Route 302 east to Bretton Woods.

Bretton Woods puts New Hampshire's largest ski area, more than 84 km of Nordic trails and the Cog Railway's winter trains at the foot of Mount Washington. The Omni Mount Washington Resort and its 25,000-square-foot spa anchor the stay.

Do
  • Bretton Woods alpine 63 trails and 36 glades on 464 acres, with nine lifts including a high-speed gondola; no night skiing.
  • Bretton Woods Nordic Groomed cross-country and snowshoe trails at the base of Mount Washington, about half in the White Mountain National Forest, open mid-December to early April.
  • Mount Washington Cog Railway in winter Trains run to Waumbek Station, at about 4,000 feet, from November to early May; the round trip takes about an hour with 25 minutes at the top.
Stay
  • Omni Mount Washington Resort The grand hotel at the base of Mount Washington, with a 25,000-square-foot spa, heated indoor and outdoor pools and its own Nordic center.
  • Omni Bretton Arms Inn The smaller inn on the same resort at 173 Mount Washington Road, sharing the spa and pools, with 1896 Bretton Arms Dining.

Map by Stay22. If you book through it we may earn a commission, at no cost to you. It never decides what we write.

Winter tip The resort also runs sleigh rides and what it calls New England's longest zip-line canopy tour in winter, which fills a non-ski afternoon.

3 hr 30 min
Photograph · Stowe Mountain Resort
Vermont, USA

Stowe

About 3 hr 30 min by car from Boston, per Go StoweBurlington International Airport is about 40 minutes away, and Amtrak and buses serve Waterbury, about 15 minutes from Stowe.

Stowe pairs Vermont's highest peak, Mt. Mansfield, with Spruce Peak's village, linked by an inter-mountain gondola. At three and a half hours, it is the big-mountain ski weekend within driving range of Boston.

Do
  • Stowe Mountain Resort Summit elevation 4,395 feet, with 485 skiable acres, 116 trails and 12 lifts.
  • Inter-mountain gondola Links Mt. Mansfield and Spruce Peak, so skiers can move between the two without a car.
  • Topnotch Spa Spa with a solarium pool and hot tub at Topnotch Resort, near Mount Mansfield.
Stay
  • The Lodge at Spruce Peak Guestrooms, suites and penthouses at 7412 Mountain Road, with the Spa at Spruce Peak, a fitness center and a salon.
  • Topnotch Resort Rooms, suites and one- to three-bedroom resort homes near Mount Mansfield, with Topnotch Spa, a solarium pool and The Roost.

Map by Stay22. If you book through it we may earn a commission, at no cost to you. It never decides what we write.

Winter tip Stowe's 2026-27 opening date is not posted yet; the resort's stats page still refers to winter 2025-26.

On Not An Atlas: Vermont Skiing, 90 Minutes From Montréal, at Par

By train 3 trips

36 min
Photograph · Erin Cuddigan / WaterFire Providence
Rhode Island, USA

Providence

About 36 min by Amtrak Acela, Boston South Station to Providence (Amtrak timetable)Every Acela from South Station reaches Providence in 36 to 40 minutes, from the 6:05 a.m. to the 6:05 p.m. on weekdays and the 6:15 p.m. on weekends.

Providence is the shortest trip on this list, under 40 minutes by Acela and walkable from the station. WaterFire lights the downtown basin for the holidays on 11 December and the Van Leesten bridge on New Year's Eve, and winter adds a downtown rink with ice bumper cars.

Time it for WaterFire Holiday Basin Lighting 11 Dec 2026

WaterFire's holiday lighting of the basin at Waterplace Park, a winter version of the May-to-November fire installations.

Do
  • WaterFire Holiday Basin Lighting Basin lighting at Waterplace Park on Friday 11 December 2026, 4 to 9 p.m.
  • WaterFire on New Year's Eve "Starts at Sunset" lighting on the Michael S. Van Leesten Memorial Bridge, Thursday 31 December 2026, 5 to 9 p.m.
  • The Providence Rink Outdoor winter skating downtown, listed by Go Providence; season dates and bumper-car sessions are posted on the rink's own site.
Stay
  • The Beatrice Downtown hotel at 90 Westminster Street with Matouk linens, heated towel racks in every room, Bellini Providence and the Bellini Rooftop bar.
  • Hotel Providence Three connected buildings in the Downtown Providence Historic District, the oldest the 1882 Westminster Building, with Backstage Kitchen & Bar.

Map by Stay22. If you book through it we may earn a commission, at no cost to you. It never decides what we write.

Winter tip Go Providence says Restaurant Weeks runs for two weeks of lunch and dinner specials but has not posted 2027 dates; check before booking a late-winter visit.

2 hr 31 min
Maine, USA

Portland, Maine

About 2 hr 31 min by Amtrak Downeaster, Boston North Station to Portland (Downeaster timetable effective 19 October 2026)Weekday Downeasters leave North Station at 8:50 a.m., 12:00 p.m., 4:10 p.m. and 5:15 p.m.; weekend trains take about 2 hr 35 min. Portland station is at Thompson's Point, and METRO Route 1 runs to the Old Port.

Portland is the car-free coastal weekend: the Downeaster runs from North Station in about two and a half hours and arrives beside the Thompson's Point rink. The Old Port, the free-on-Fridays Portland Museum of Art and Portland Head Light in snow fill two days.

Do
  • Portland Museum of Art Free to the public on Fridays, per Visit Maine.
  • Thompson's Point rink Outdoor skating with views of the city and the Fore River, plus a beer garden and warming areas, next to the Downeaster station.
  • Portland Head Light The lighthouse just outside the city, with snow and ice along the rocky shore around the keeper's house in winter.
Stay
  • The Press Hotel In the former Gannett Building, the Portland Press Herald's headquarters, at 119 Exchange Street in the Old Port, with the UNION restaurant, Inkwell bar and a lower-level gallery of Maine artists.
  • Canopy by Hilton Portland Waterfront On the working waterfront at 9 Center Street, with Salt Yard Cafe & Bar and the Luna Rooftop Bar over Casco Bay.

Map by Stay22. If you book through it we may earn a commission, at no cost to you. It never decides what we write.

Winter tip The last northbound Downeaster leaves Boston at 9:00 p.m., 10:30 p.m. or 11:25 p.m. depending on TD Garden events, so a Friday-night departure after work is possible.

4 hr
Photograph · Colin Miller / Bryant Park Corporation
New York, USA

New York City

About 4 hours by Amtrak Acela, Boston South Station to Moynihan Train Hall (Amtrak timetable)Most weekday Acelas take 3 hr 58 min to 4 hr 2 min; the weekday 6:05 p.m. is the fastest at 3 hr 41 min, and the Saturday and Sunday 6:15 p.m. takes 3 hr 51 min.

New York's slow season is when NYC Tourism + Conventions runs Restaurant Week and Broadway Week, and Bryant Park's free-admission rink runs to the end of February. The Acela from South Station puts Midtown about four hours away.

Time it for NYC Restaurant Week (winter) 19 Jan – 11 Feb 2027

Two-course lunches and three-course dinners at $30, $45 or $60, Monday to Friday plus optional Sundays, run by NYC Tourism + Conventions.

Do
  • The Rink at Bank of America Winter Village A 17,000-square-foot rink in Bryant Park, free admission (skate rental $18.72 to $64.48), open 28 October 2026 to 28 February 2027, weather permitting.
  • NYC Broadway Week Half off each ticket when you buy two or more; the program returns in winter 2027, with dates and shows posted about two weeks ahead.
  • Winter Jazzfest A multi-venue marathon with a Friday night across Manhattan venues and a Saturday across eight venues in Williamsburg and Bushwick; 2027 dates not confirmed on its site.
Stay
  • The Whitby Hotel Firmdale's Kit Kemp-designed hotel at 18 West 56th Street, with a pewter-topped bar at The Whitby Bar & Restaurant and an orangery for private dinners.
  • The Beekman, A Thompson Hotel In Temple Court, completed in 1883 as one of Manhattan's first skyscrapers, built around a nine-story atrium.

Map by Stay22. If you book through it we may earn a commission, at no cost to you. It never decides what we write.

Winter tip Restaurant Week excludes Saturdays, so a Sunday-to-Monday Acela trip catches more participating dining rooms than a classic weekend.

On Not An Atlas: Explora III Arrives in New York

A short flight 4 trips

1 hr 30 min
Photograph · Victor Diaz Lamich / Montréal en Lumière
Montréal, Québec, Canada Passport needed

Montréal

About 1 hr 30 min nonstop from Boston, per Tourisme MontréalMontréal-Trudeau is 12 miles (20 km) from downtown, and the 747 express bus runs 24/7, taking 45 to 70 minutes. Air Canada and Porter list Boston fares for December to February.

Montréal runs two winter festivals back to back: Igloofest's outdoor electronic music nights in the Old Port, then Montréal en Lumière's free outdoor site with a skating trail and light works. Bota Bota, a floating spa in the Old Port, is the warm counterweight.

Time it for Montréal en Lumière 18–28 Feb 2027

Late-winter festival with a free outdoor site, a skating trail, light works, food and shows, and an all-night Nuit blanche.

Do
  • Igloofest Outdoor electronic music festival with an igloo village at the Old Port, 14 January to 6 February 2027.
  • Mount Royal in winter Free skating on the refrigerated Beaver Lake rink, snow tubing, snowshoe rentals and 16 km of cross-country trails.
  • Bota Bota, spa-sur-l'eau Floating spa in the Old Port since 2010, adding a second boat designed by Sid Lee Architecture in winter 2026.
Stay
  • The Ritz-Carlton, Montréal On Sherbrooke Street West since 1912, with Daniel Boulud's Maison Boulud and Spa St. James's indoor saltwater pool.
  • Hôtel William Gray Old Montréal hotel at 421 rue Saint-Vincent near Place Jacques-Cartier, with Spa William Gray and its pool, Maggie Oakes and an eighth-floor terrace.

Map by Stay22. If you book through it we may earn a commission, at no cost to you. It never decides what we write.

Winter tip Bring a valid US passport. With one, Immigration, Refugees and Citizenship Canada says Americans need no visa or eTA to enter.

On Not An Atlas: Air Canada Keeps Copenhagen and Manchester Flying All Winter · Air Canada Adds Montréal–Seville

2 hr 15 min
Photograph · Bermuda Tourism Authority
Bermuda Passport needed

Bermuda

About 2 hr 15 min nonstop from Logan on BermudAir, per the airline's published winter scheduleFrom 20 December 2026 BermudAir leaves Logan on Thursdays and Sundays at 7:30 a.m. (arriving 10:45 a.m. local), Fridays at 6:30 p.m. (from 18 December) and Tuesdays at 10:00 a.m. (from 22 December).

Bermuda is the closest warm-weather escape from Boston, about two and a quarter hours on BermudAir, with winter highs around 70°F (21°C). Winter is its quiet season, built around Restaurant Weeks, February's Spa Month and the UNESCO town of St. George's.

Time it for Bermuda Restaurant Weeks 2027 dates still to be announced; ran 16 January to 16 February in 2026

The island's winter dining promotion, listed by the Bermuda Tourism Authority.

Do
  • St. George's bus tour Three-hour guided tour of the UNESCO World Heritage town, including St. Peter's Church, the Old State House and Fort St. Catherine.
  • Bermuda Spa Month February program with up to 50 percent off at participating spas; 2027 details not yet posted.
  • Verdmont Museum A 325-year-old house with a 45-minute guided tour and a free shuttle from Hamilton.
Stay
  • Rosewood Bermuda 88 rooms and suites on 240 coastal acres, with the par-70 Tucker's Point course, SENSE spa and what it calls the largest private pink-sand beach on the island.
  • The St. Regis Bermuda Resort Oceanfront in the UNESCO town of St. George's, steps from St. Catherine's Beach and about 8 minutes from the airport, with the Five Forts Golf Club.

Map by Stay22. If you book through it we may earn a commission, at no cost to you. It never decides what we write.

Winter tip Visitors arriving by air need a valid passport and the free Bermuda Arrival Card, completed before or on arrival on the Government of Bermuda site only; third-party sites charge for it.

3 hr 45 min
Photograph · Turks & Caicos Islands Tourist Board
Providenciales, Turks and Caicos Islands Passport needed

Turks and Caicos

About 3 hr 45 min nonstop from Logan to Providenciales on BermudAir, per the airline's published scheduleBermudAir flight 2T 201 leaves Boston on Saturdays at 3:25 p.m. and lands at 7:10 p.m., 19 December 2026 to 1 May 2027. Amanyara is about 25 minutes from Providenciales International Airport.

A weekly Saturday nonstop puts Providenciales under four hours from Logan, with Grace Bay's beaches, Chalk Sound's turquoise water and reefs for diving. It is the longest flight on this list and best as a full week.

Do
  • Chalk Sound National Park Kayak or paddleboard a protected sound scattered with small islets.
  • Reef diving Dive Providenciales' reefs or kayak through its mangroves; Amanyara borders Northwest Point Marine National Park, known for wall and reef diving.
  • Thursday Night Fish Fry Weekly evening in Providenciales with seafood, live rake and scrape music and island crafts.
Stay
  • Amanyara 36 pavilions and 20 villas on Northwest Point, on an 800-meter beach beside the marine national park, with four double spa treatment pavilions.
  • Grace Bay Club About 1,100 feet of Grace Bay Beach, with an adults-only Hotel Building of 22 oceanfront suites and Infiniti among six restaurants and bars.

Map by Stay22. If you book through it we may earn a commission, at no cost to you. It never decides what we write.

Winter tip US citizens need no visa, but the Turks and Caicos Border Force asks for a passport valid for the whole stay and at least six months overall; the officer on arrival decides entry.

On Not An Atlas: Turks and Caicos: New Flights From Canada and Up to 35% Off

4 hr 40 min
Anguilla Passport needed

Anguilla

About 4 hr 40 min nonstop from Logan on BermudAir, per the airline's published scheduleBermudAir flight 2T 101 leaves Boston on Mondays and Fridays at 7:30 a.m., arriving 1:10 p.m. local, 18 December 2026 to 12 March 2027 (12:10 p.m. from 15 March).

BermudAir's seasonal nonstop makes Anguilla a same-day Caribbean trip from Boston, with no connection. The island has 33 beaches, calls itself the Culinary Capital of the Caribbean, and averages about 80°F all year.

Do
  • Shoal Bay East Beach at the island's eastern end with restaurants, beach bars and a day spa.
  • Sandy Island Offshore cay a five-minute boat ride from Sandy Ground.
  • Wallblake House Built in 1785 in The Valley, alongside Ebenezer's Methodist Church and the Old Valley architecture.
Stay

Map by Stay22. If you book through it we may earn a commission, at no cost to you. It never decides what we write.

Winter tip The Anguilla Tourist Board requires a passport valid beyond your departure date and a return or onward ticket; check the eVisa list before you fly.

On Not An Atlas: Anguilla, Without the Crowds · Anguilla’s Fall Offers, by the Night

The season

The winter calendar

The dates that make a winter trip, as the organizers have announced them. Events still waiting on 2027 dates are listed with their trip, not here.

November 2026

  • 21 Nov 2026 – 3 Jan 2027Holidays at the Newport MansionsNewport

December 2026

January 2027

  • 19 Jan – 11 Feb 2027NYC Restaurant Week (winter)New York City

February 2027

  • 18–28 Feb 2027Montréal en LumièreMontréal

Massachusetts observes Martin Luther King Jr. Day on Monday 18 January 2027 and Washington's Birthday on Monday 15 February 2027, per the Secretary of the Commonwealth. Boston Public Schools publishes its 2026–27 recess dates in its district calendar; check it before booking a February trip. School holidays in Boston →

Questions

Quick answers

What are the best winter getaways from Boston without a car?

Providence is about 36 minutes by Acela from South Station, New York about 4 hours, and Portland, Maine about 2 hours 31 minutes on the Downeaster from North Station. Kennebunkport is about 10 minutes by road from the Downeaster's Wells stop.

Where can you ski within a drive of Boston?

Woodstock, Vermont is about 2 hours 15 minutes away, with the Woodstock Inn's Saskadena Six. Bretton Woods, New Hampshire's largest ski area, is about 2 hours 30 minutes, and Stowe about 3 hours 30 minutes.

Can you fly nonstop from Boston to the Caribbean or Bermuda this winter?

Yes. BermudAir's published schedule has Boston nonstops to Bermuda (about 2 hours 15 minutes) from 18 December 2026, to Providenciales, Turks and Caicos on Saturdays from 19 December, and to Anguilla on Mondays and Fridays from 18 December 2026 to 12 March 2027.

What are the best holiday events near Boston in December 2026?

Kennebunkport's Christmas Prelude runs 3 to 13 December, Strawbery Banke's Candlelight Stroll in Portsmouth runs three weekends from 4 December, Woodstock's Wassail Weekend is 11 to 13 December, and the Newport Mansions are decorated from 21 November 2026 to 3 January 2027.

When are Montréal's winter festivals in 2027?

Igloofest runs 14 January to 6 February 2027 and Montréal en Lumière 18 to 28 February 2027. The flight from Boston is about 1 hour 30 minutes, and Americans need a valid passport.

What are the best winter getaways from Boston by car?

The closest are Portsmouth (1 hr), Newport (1 hr 30 min), Kennebunkport (1 hr 30 min), Chatham, Cape Cod (1 hr 45 min). Times are the tourism boards' own figures from downtown in normal conditions; allow more in snow.

Where can you go from Boston by train in winter?

By train: Providence (36 min), Portland, Maine (2 hr 31 min), New York City (4 hr). Rail skips winter driving entirely; book early for school-holiday weeks, when trains sell out.

Do I need a passport for these trips?

Only for the trips that cross a border: Montréal, Bermuda, Turks and Caicos, Anguilla. Check passport and entry rules for your nationality before booking; everything else on this list is domestic.

Sources (92)

Checked 24 October 2026. Dates change: confirm with the event or hotel before you book. Spot something out of date? Tell us via our corrections policy.

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