Luxury Winter Itinerary: Boston and New York with Iconic Hotels and Seasonal Highlights - Part 1

It’s been I think about 7 years since we were last in New York, somewhere I have been quite regularly and often beforehand. We hadn’t been necessarily thinking about a holiday over Christmas again (after I think having been away for the last three, albeit in hot destinations), but when ‘Mrs’ TPT talked about The Plaza and New York at Christmas/Holiday time, an idea for an itinerary started to form. Leaving well before Christmas Day itself and wanting to stay through to at least beyond New Year, it felt like too long a time just to be based in New York, and only one location, so I took the opportunity to fly first to Boston, have a few days there before travelling down to New York for Christmas.

From Boston to New York: A Festive Journey Through Luxury Stays and Unmissable Experiences

As well as staying at The Plaza, I also love to try out new (to us) hotels and locations, so having wanted to visit Hudson Yards for a while now (The Vessel, somewhere on my list opened in 2019) this seemed like the perfect opportunity to go and stay there for a few days at The Equinox Hotel, the first in a chain for the Equinox Company. When I’d been booking flights, the BA agent talked about New York at New Year, and said that if she ever went back at that time she would pick a hotel in Brooklyn with a view of Manhattan, to see all the firework celebrations from there. So that’s exactly what we’ve done, have a quiet local dinner across the water, enjoy the fireworks display from our wraparound balcony, and have a quiet New Year’s Day in Brooklyn. Last stop, being the TWA Hotel at JFK Airport, has also been somewhere I wanted to stay since it opened in 2019. Originally designed by Eero Saarinen in 1962, this has been reimagined by Beyer Blinder Belle (as the architectural firm responsible for the terminal renovation) and Lubrano Ciavarra Architects to design the two new buildings housing all of the accommodations. 

Having been in Palm Springs for Modernism Week in 2020 (just before the COVID wave hit) we were able to go and hear the architect’s team speak at the Annenberg Theater during a presentation of TWA Hotel: Rebirth of a Modern Icon. I did already know about the hotel before that talk, but seeing more images and hearing all about their development process for the two modern extensions (and of course how they are connected to the original terminal using original air tunnels) made it somewhere I had to visit at some point, and this trip seemed the perfect opportunity, with us already scheduled to fly back overnight from JFK.

The hotels featuring in the post are:

• Sofitel London Heathrow

• Four Seasons Boston

• The Plaza New York (a Fairmont Hotel)

• Equinox Hotel Hudson Yards

• The William Vale (Brooklyn)

• The TWA Hotel at New York’s JFK Airport

Explore my comprehensive travel itinerary for this trip, featuring essential tips on:

• The best flights from the UK to Boston.

• Our journey from Boston to New York.

• My top hotel recommendations for Boston.

• Things to do in Boston.

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Flying to Boston USA with British Airways

We’re flying down the previous evening to stay overnight again at the Sofitel London Heathrow Hotel, at Terminal 5, rather than have such an early start with the Edinburgh connection. It will also give us more time in the Concorde Lounge at T5, with a late morning departure direct to Boston’s Logan International Airport.

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Best places to stay in Boston - The Four Seasons Hotel Boston

There was a good choice of five star hotels in Boston, and it was a hard choice for me to whittle down the choice of staying in one of two Four Seasons hotels. There would usually just be one option in a city, but in Boston there was both the Four Seasons Hotel Boston (overlooking Boston Common at one end of Boylston Street) but also Four Seasons Hotel One Dalton at the other, albeit a long street and probably about a 25 minute walk between the two.

Credit @fsboston

Why Book with The Private Traveller in conjunction with Fora Travel

If you book to stay at either Four Seasons Boston or any of the other hotels listed below (as well as more available) with myself (in conjunction with FORA Travel) as well as getting your perfect stay crafted as part of an overall itinerary, you could benefit from a range of additional stay perks by utilising some of the available FORA booking programs.

Typical perks for the Four Seasons Preferred rate booked in this way could include:

• Daily breakfast for 2

• $100 hotel credit for rooms or $200 for suites & private retreats

• Room upgrade to next category (subject to availability)

• Early check-in, late check-out (subject to availability)

Other options that I had considered for Boston

• Mandarin Oriental 

• The Newbury - LHW 

• Boston Harbor Hotel

• The Ritz-Carlton

• Four Seasons Hotel One Dalton

• Raffles Boston

• The Langham
  

It wasn’t an easy choice between the two Four Seasons as I love both older and brand new properties - the original FS Boston opened in 1985, yet the newer One Dalton opened across floors (8-21) of this skyscraper in 2018. In terms of wellness facilities, One Dalton clearly has the edge with a whole wellness floor, but the original FS does have an indoor pool and whirlpool, as well as a gym. FS Boston was higher rated on TripAdvisor, and slightly bigger than the One Dalton’s 215 rooms, but ultimately I went for the older property in the historic downtown Boston area.

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Fast Facts for the Four Seasons Hotel Boston

Address - 200 Boylston Street, Boston, Massachusetts 02116
Website - https://www.fourseasons.com/boston/
Group website - https://www.fourseasons.com
TripAdvisor ranking - #26 of 96 hotels in Boston
Contact - https://www.fourseasons.com/boston/contact-us/
Instagram - @fsboston @fourseasons
Nearest airport - Boston’s Logan Airport (BOS) - 55 km or 34 miles (about a 45 min drive, traffic dependent)
Opened - 1985
Number of rooms / suites - 273 total including 63 executive suites & 12 speciality suites
Number of floors - 16 (the hotel occupies 8 floors)
Bars - 1 (as part of Coterie)
Restaurants - 3 (Aujourd'hui [breakfast], Coterie Brasserie-style lobby lounge [lunch & dinner], & Sottovento Coffee Bar) plus The Sanctuary (outside, so weather-permitting)
Wellbeing - 8th floor indoor pool & whirlpool spa, 24 hour fitness room, treatments available on request in room
Visiting - December 2024

There was a good choice of accommodation, with four different guest rooms, 3 suites, and 5 speciality suites. I didn’t book it for this reason (honest) but a nice touch is The Vault, a complimentary snack pantry on every floor.

Credit @fsboston

Credit @fsboston

Credit @fsboston

Credit @fsboston

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Things to do in Boston

I’ve been to Boston before, but not in the run up to Christmas so I'm looking forward to seeing the city in a different season.

Here are just some of the things I’m planning for our trip:

• Freedom Trail: A 2.5-mile red brick trail that connects key sites from Boston's past. You can explore at your own pace or take a guided walk. 

• Museum of Fine Arts: A diverse art museum with works from ancient to contemporary times, including Egyptian artifacts and American art. 

• Isabella Stewart Gardner Museum: A museum that's a must-see on your first trip to Boston. 

• North End: A historic neighborhood known for its Italian food and pastry shops. You can try cannoli at Mike's Pastry or Modern Pastry, or pizza at Pizzeria Regina. 

• Institute of Contemporary Art (ICA): A world-class art museum in the Seaport District that features contemporary art and multimedia exhibits

• Quincy Market: Since 1826, this Greek Revival style granite structure has been serving the public from daily retail food supply of meat, produce and dairy goods to the wholesale role at a later time.
  

Travelling between Boston & New York by Train

We could have flown, but I do love trains as well, especially when there is something different or special. The Acela Express is Amtrak’s flagship passenger service between Washington D.C. and Boston on the USA’s east coast, with various stops including New York. What caught my eye on this service, which takes under four hours door to door, is their exclusive (to Acela) First Class service. As well as station lounges and all individual seats (in two’s facing), is complimentary food and beverage services.

Staying in New York

If you read the second part of this blog post, you will find out all about the four hotels we’ve chosen in New York, the different locations, and why indeed I’ve chosen four different properties.

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Full Travel Itinerary: Boston & New York, USA

• Day 1   Fly to London’s Heathrow (LHR) with British Airways

• Early evening domestic flight

• Overnight Sofitel London Heathrow

• Day 2  Fly to Boston’s Logan International Airport (BOS) with British Airways

• Morning flight, scheduled 7hr 35mins - Boeing 787-100 Dreamliner

• Hotel transfer with BlackLane

• 3 nights Four Seasons Hotel BlackLane

• Day 3-4  Boston

• Sightseeing

• Day 5  Boston to New York’s Penn Station by Train

• Mid-morning train, Acela First Class with Amtrak

• Train time 3hr 44mins

• 4 nights The Plaza, New York

• Day 6-8  New York

• Sightseeing

• Day 9  Transfer between The Plaza & Hudson Yards

• Drive between hotels

• 3 nights Equinox Hudson Yards

• Dinner at The Peak

• Day 10-11 Hudson Yards, New York

• Sightseeing

• Day 12 Transfer between Hudson Yards & Brooklyn

• Drive between hotels

• 2 nights The William Vale

• Day 13  The William Vale, Brooklyn

• Relaxing day in Brooklyn

• Day 14 Transfer between Brooklyn & JFK’s TWA Terminal Hotel

• An overnight stay (with late check-out) at the TWA Hotel

• Day 15 Leave for home

• Evening flight from New York (JFK) to London’s Heathrow (LHR), with onward domestic flight to Edinburgh the following day

• Flight time scheduled 6hr 45mins - Boeing 777-300

• Day 16  Return home

• Mid-morning arrival back to Edinburgh

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