Skip to main content

A Travel Guide to the Luxurious Side of Boston

Boston isn’t all about sports and beer. Sure, we love our Red Sox, Pats, and Sam Adams, but Beantown is also packed with lavish hotels, swanky speakeasies, and laboratory cocktail bars that give Paris and New York City a run for their money.

Contents

Next time you’re planning an extravagant guy’s weekend or lavish getaway with the boo, skip overdone destinations and head to Boston. Here’s your full itinerary for the most luxurious trip to Massachusett’s capital city.

Stay

XV Beacon

XV Beacon
Image used with permission by copyright holder

With only seven rooms per floor, XV Beacon is the epitome of a boutique hotel, as evident by the elegance, charm, and killer sound system and fireplace in every suite. Settled in the heart of Boston, XV Beacon blends modern sensibilities with an aura of cozy hominess emphasized by the handsome décor and strictly taupe, cream, and espresso pallet. Each room was also custom-designed and curated with art specifically commissioned for the hotel. Ask the complimentary driver to take you to dinner and skip the smelly Uber.

The Boston Harbor Hotel

Boston Harbor Hotel
Image used with permission by copyright holder

If you and your old frat buddies have evolved into golfing financiers, The Boston Harbor Hotel will be your haven for the weekend. The Forbes 5-Star hotel sits directly off the harbor with opulent, classic rooms with maritime hints (and two TVs so you can watch both games at once). Go big and rent the 4,800-square-foot John Adams Presidential Suite ($15,000 a night) with private elevator entrance, massive smoking terrace, and floor-to-ceiling windows overlooking the water. Grab oysters downstairs at the Sea Grille before catching a seaplane to the cape.

Drink

ArtScience Culture Lab & Café

Titi Mokey at ArtScience Culture Lab & Café
Bostonfoodie

Hidden amid futuristic research labs is ArtScience Culture Lab & Café, a minimalist bar and restaurant that looks like a Scandinavian art museum. This is a must-visit in Boston. Applying experimental, lab-inspired techniques to French fare and cocktails, ArtScience is one of the coolest places you’ll ever drink. The rotating cocktail menu can be themed anything from “endangered species” to “aquatic,” and the presentations seem straight from Blade Runner. This bar began as a food lab and subterranean club in Paris and moved to Boston in 2014. Order a Titi Monkey and ask to try the crème de menthe vapor. Stay for art-inspired concept dishes if you’re up for the wild ride.

Yvonne’s

Yvonnes
Yvonnes/Facebook

Three words: marble, mahogany speakeasy. Only a quick walk from XV Beacon, Yvonne’s is a playful yet handsome hideaway tucked into an alley (and very easy to miss). Look for the glowing red sign and enter this swanky two-bar spot for an elevated social drink. The space itself has been around over 150 years and expands to separate drink and eat areas backed by raw unvarnished brick, antique crystal chandeliers, grand library shelving, and — best of all — large format drinks in crystal chalices.

Eat

Ruka

An exploration in Peruvian-Japanese culture, food, and spirits, Ruka sits at the corner of The Godfrey and features dishes and sake meant to be shared. Moody yet elevated, Ruka’s dishes and vibe blends the “bold flavors of Nikkei cuisine while expressing the harmony of South America’s dramatic landscapes and vibrant cities,” says the restaurant. It’s intimate yet lively, so trust your knowledgeable server, bring all your friends, and order a mix of delicious sushi, hot pork belly, Peruvian pepper curry, and Japanese fried chicken.

Shop

Ball and Buck

ball and buck
Image used with permission by copyright holder

Gentlemanly hunting-inspired menswear is hard to get perfect unless you’re Ball and Buck. Their Boston brick-and-mortar features made-in-the-USA apparel with the perfect notes of class and outdoor ruggedness. You’ll want handsome high-performing threads in the wet and cold Boston winter. Grab a few essentials like a $1,300 Shooting Jacket and Bison Wool Knit Hat before taking a chair at the on-site barber.

Mr. Sid

Image used with permission by copyright holder

Nothing says luxury vacation like a made-to-measure suit. The custom tailors at Mr. Sid offer nearly incomparable service and will even give you a wardrobe consultation and recommend the right groomer to get your beard looking noble and fine again after No Shave November. Mr. Sid also carries the highest-end suit and menswear brands without the cold superclub vibe of a department store.

Swoon

Winston Flowers

winston flower shop
Image used with permission by copyright holder

Family-owned for more than 75 years, Winston Flowers’ first shop in Boston still stocks some of the most rare and interesting flowers and plants on the planet. Entering the underground shop is like entering a curated organic gallery, with rare Italian ranunculus, South African proteas, and fragrant greenery. Winston’s flowers are flown in fresh almost daily from Holland and Italy, and may arrangements are housed in European-designed vessels hand-picked by owner David Winston. Visiting Boston with a crush? Stop in for a bouquet.

Beacon Hill Chocolates

beacon hill chocolate
Beacon Hill Chocolate/Facebook

With imported chocolates from around the globe, Beacon Hill Chocolates is a sweet and lavish pit-stop to make during your grand weekend in Boston. Owner and chocolatier Paula Barth travels personally to source and procure the finest and rarest treats and ingredients from chocolate masters around the world. Plan a private tasting and enter elegant chocolate bliss. During the holidays, opt for a dark chocolate hot cocoa truffle and rum-infused eggnog chocolate.

Sweat

EverybodyFights

everybody's flight
Image used with permission by copyright holder

You’ve never seen a gym like this. Centered around boxing, EverybodyFights is a luxe sweat cave with modern street style design and an absolutely killer staff of fighters/trainers. The exclusive training center boasts two featured rings, a massive red-light bag room, live DJ, cardio and weight divisions, and juice bar and physical therapist next door. Yes, you could jog around the city dodging dog poop, or you could clock in for a private session or group class, hear that beautiful punch slap, and get inspiration from a throwback fight projected on the wall. We pick the latter.

Play

Boston Common Frog Pond

Image used with permission by copyright holder

Ice skating isn’t “extravagant” but there’s something luxurious and refined about lacing up skates and swirling in circles around the Boston Common Frog Pond. This seasonal rink in the center of the park is illuminated with sparkling lights and gives you a chance to be a kid again. Our advice: Have a glass of bourbon at Avery Bar in the The Ritz Carlton to loosen up before heading onto the ice, then skate your heart out.

Before you go, invest in a sturdy weekender so you never have to check your bag. Our suggestion: Dagne Dover’s XL Landon. Seriously slick, solid padded material, and great size. For more great picks, here are our favorite travel bags and weekenders.

Editors' Recommendations

Jahla Seppanen
Former Digital Trends Contributor
Born and raised off-the-grid in New Mexico, Jahla Seppanen is currently a sports, fitness, spirits, and culture writer in…
A complete breakdown of airline loyalty programs: American Airlines, Southwest Airlines, United Airlines, and more
All the airline rewards programs, reviewed and ranked
American Airlines over the beach

 

American Airlines started the first loyalty program in 1981, which is still running today. Since then, most companies offer some form of frequent flyer rewards program. Loyalty programs are wonderful, but each airline has its own rules and its own style.

Read more
Travel to these 5 countries is more difficult because they don’t have an airport
Spoiler alert: They're all in Europe
A shot of an outside airport with the sun shining in the background

Unless you count hot air balloons and hang gliders, there's really only one way to fly from one country to another — an airplane. And to travel successfully to your destination via airplane, that plane will need an airport to land. Air travel has become such an integral part of our lives that it's difficult to imagine an entire country without at least one airport for foreign travelers to fly into. But believe it or not, there are actually five such places in Europe that lack this modern convenience. Nestled amidst stunning landscapes and historic cityscapes, travel to these destinations often requires a multi-leg journey. While it's not necessarily hard to get to these European countries, flying directly there is out of the question.

1. Andorra
A country no bigger than the average city, Andorra faces a unique challenge due to its mountainous terrain. Situated between Spain and France and encircled by the Pyrenees mountains, the country's high peaks, reaching almost 10,000 feet, make it quite inhospitable for air travel, especially in adverse weather conditions. In short, building an airport, let alone trying to land a plane among the mountaintops, would be incredibly difficult. 

Read more
Travel tips: It will be more expensive than ever to visit Amsterdam next year — here’s why
Amsterdam has a plan to curb the tourist crowd - it just means a visit there will cost you more than before
The Amsterdam sign in Amsterdam

The reality of trying to see a sight like the Mona Lisa or the Eiffel Tower is not what you see on an influencer's Instagram. It's overcrowded, loud, and you'll be stuck in line forever. From Barcelona to Venice, places are struggling with overtourism, but there is one particular city having a hard time reigning in the visitors, and it's going to make you pay big time if you want to go there. Amsterdam is trying to control its visiting population with a hike in its tourism tax in hopes of evening out the numbers for the locals.

The tax it takes to travel
A little travel tip — the tourism tax is already a part of travel no matter where you go, from hotel fares to airline fees. The tourism tax helps the place you visit in several ways, from keeping the buildings and other structures in good condition to protecting the gorgeous environment you want to see.
A few ways the tourism tax is collected

Read more