Great Gatsby Itinerary
- Savvy Single Mama
- Jul 29
- 18 min read
Updated: Oct 10
Get your Roaring 20's experience on while exploring Long Island's Gold Coast, and treating yourself to the Broadway Musical for some extra Gatsby era vibes. Explore old extravagant mansion estates while reminiscing a time long gone, and yet not too far away... This Gatsby Itinerary is a great way to share our milestone birthdays while making amazing memories. To be really honest, we had so much fun with it on our first Gatsby Adventure, we came back for a rerun, adding more speakeasys and a night out on a roof top to top it off! Details below.
We ordered our dresses a couple of weeks prior from Amazon. Our male escort just happened to have an authentic suit from the 1940's to wear! Dressing up definitely made it a little more fun.
The Gilded Age can still be visited any day on the North Shore of Long Island. Lining wooded windy curvy roads allowing just a peek into a time of extravagance and intricate decor, remains some preserved mansion estates for your discovering. They come complete with gardens built to impress nearly 100 years later. View lush Long Island Gardens and experience the Gilded Era with your own eyes. This 4-day adjustable itinerary is for those who appreciate the beauty of excess and being captivated by glittery pretty things that are strictly for your amusement. Let your inner Daisy out to play. Or maybe your inner Nick Carroway. There may even be a Tom, Myrtle, or Jordan in your crew. But Jay Gatsby is the heart of it all. Right where the original story took place, the backdrop is still evident 100 years later!
Now that we are back in the '20's all over again, we have a chance to look through the eyes of time to relive some of its best parts while remembering some of the less favorable moments. And it's fair to say some of us are having fun with it! Grab the proper accessories and let's go!
Places we will visit in our Gatsby Itinerary
Sands Point Preserve - Port Washington 9 – 7 Wed – Sun (closed Monday and Tuesday)
Old Westbury Gardens – Old Westbury10 – 6 Wed – Sun (closed Monday and Tuesday)
Planting Fields Arboretum – Oyster Bay 9 – 5 Daily (Greenhouse closed Tuesday)
Sagamore Hill – Oyster Bay 1:30 – 4:30 Thurs,, 12 – 4:30 Fri – Sun (closed Mon – Wed)
Oheka Castle – Huntington Brunch, Lunch, Happy/ Gatsby Hour and Dinner times Daily
The Vanderbilt Museum – Centerport 10 – 5 pm (closed Mondays)
Broadway Theatre to see the Great Gatsby Musical, NYC
A visual for your itinerary, and some helpful tips for planning each day….
Underlined bolded text links to that site for your convenience.
First of all... Gatsby?
Considered a literary masterpiece, the book penned by F. Scott Fitzgerald in 1925 takes place at a dynamic time in US history emphasizing how the roaring 20's parties on through the bootleg era. Themes of money, influence, sex, and booze overlap into a swirl of night life and escaping reality. Nick Carroway is a young man who has just moved to West Egg where he is trying to become a journalist. He lives in a cottage on the grounds of wealthy host Jay Gatsby, who it turns out has an obsession with Nick's cousin Daisy (his former love). Daisy has since married a spoiled rich brat (maybe that's unfair) Tom, who has a love interest of his own. Jay ironically lives right across the water from Daisy where he's been wishing she'd notice him. The story spirals and the saga continues into today's alignment of the American Dream Vs. reality. If you've never read the book, you're missing out. 100 years later, this book is still telling a story we can all relate to on some level.
Gatsby was the first assigned book at school I actually read! English class in 9th Grade, and it was quiet reading time in class, I was going to "pretend" I was reading, and it actually caught my attention. I took it home and finished the book! I couldn't believe they were letting us read that at school lol.
Great Gatsby Itinerary: Mansions & Gardens
Begins at a Long Island Classic, the Sands Point Preserve.
This location has so many goodies, you could easily spend a full day!
I recommend getting there at opening time and being ready to book a Falaise Tour. There’s a $15.00 entry fee per vehicle, and then the tour will be $15.00 per person. There are no reservations for the tour in advance, they are limited, and they do sell out! A shuttle will pick those with a ticket and drive them across to the Falaise house, which is NOT accessible any other way. The roads along the way are private. This home is not accessible by the beach trails or the wooded trails. The 90-minute tour is filled with art, history, and Long Island local fame. You’ll learn about the connection of Charles Lindburg, the Gould’s and the Guggenheim family. The Falaise is the only home open for tours and kept true to the era. It's famous for many movies and noteworthy accounts, but you may recognize the Dining Room from a scene in the Godfather when the wealthy director wakes up to a horse’s head. That scene was filmed in this room!
Who lived here? Howard Gould and his wife Katherine Clemmons, who was famous for her romance with Buffalo Bill. Later her divorce from Howard was quite the scandal and very public. However, in 1901, Castle Gould was the first of four mansions on the property. Built identical to Ireland’s Kilkenny Castle, with Katherine not approving of the completed product. Howard then built her Hempstead House. Castle Gould served as the stable, carriage house, and servant’s quarters. It’s now the Visitor Center. Howard is the wealthy financier and son of railroad magnate, Jay Gould. In 1917 the Estate was sold to Daniel Guggenheim. The Guggenheim’s usher in their own scandals keeping the allure of the era alive. In 1971, Nassau County took over the property.
Save some time to explore the beautiful grounds. The Hempstead House and Castle photograph well along with the gardens and the beach line. Honestly, I’ve really enjoyed walking the various trails and returned a few times to this scenic location.
Address: 127 Middleneck Rd.
Sands Point, NY 11050
(516) 571-7901
Pay online and show your ticket at the gate. Park. Walk up to the Mansion. And go right in to see for yourself. Feel free to get a tour or wander on your own. While I was wondering I was also listening to a nearby tour which was very helpful. The tour was pretty full, so I opted to do my own thing. But WOW! The Gilded Age shows up in all things Westbury House. Built in 1906 for John S. Phipps, and his wife Margarita Grace Phipps, along with their four children. This mansion is kept on a secluded 200-acre estate. Formal Gardens attract a number of visitors each year, with the Celtic Festival drawing quite the crowd. Listed on the National Register of Historic Places, it’s easy to appreciate the grandeur of a time long gone just by passing through the front door.
How did the Phipps family make their fortune? In 1901 when Andrew Carnegie and steel partner Henry Phipps sold their business to J.P. Morgan, a massive $50 Million dollars was made. John was the inheritor, son, and business executive of Henry. John was a financier, lawyer, polo player, and real estate developer. He died in 1958 in Palm Beach Florida. This massive home serves as a preserve of a prior way of life.
It's worth mentioning this is the home that the musical the Great Gatsby uses as it's backdrop of Daisie's actual home. If this were the East Egg location, which estate would Jay Gatsby's mansion equate to?
Address: 71 Old Westbury Road
Old Westbury NY 11568
(516) 333-0048
Dinner at Gatsby’s on the Ocean will be a great way to end the day and mood.
Address: 2000 Ocean Pkwy, Wantagh NY 11793
Great Gatsby Itinerary Speakeasies & Broadway:
By staying at a centrally located place in Nassau County Long Island you’ll have time for a morning Brunch before getting on the LIRR for your ride into NYC.
Have you ever been to Broadway before?
Oheka Castle is where this exciting day begins. Brunch here will set the tone and these photos are about to be epic so wear something cute! Built in 1919 by Otto Hermann Kahn, with a cost of around 11 million dollars to build (crazy overhead for back in the day). Inspired by the French Chateaus with both European and American flair there’s 127 rooms in this castle. Now an event venue offering high profile weddings and the ability to offer accommodations, the cost for 150 guests comes in at around $70,000. Good thing we are just here for some brunch! If you want o be REALLY fancy your Gatsby weekend could include a night in this extravagant location! A summer special secures rooms at $295/ night.
Oheka’s restaurant offers a variety of menus and options. As a space, you can’t go wrong. Just being here is satisfying. The food really is delicious. The drinks? Made perfectly. All was so well. The new owner Gary Melius came over to our table introducing himself, even took some photos together in the Garden. The garden is only accessible through the Restaurant, so plan to stroll the gardens after eating. On the first level there’s a hallway with some of the stages of restoration and history of the Castle over the years. The Work Developer Gary Melius did on the property and grounds to bring it to it’s current state is impressive and much appreciated by many who have wined, dined, and wedded on these luxurious unique grounds.
Address: 135 W. Gate Dr.
Huntington NY, 11743
(631) 659-1400
Next: Buy your afternoon tickets to the Long Island Railroad which serves 11 branches and 126 stations bringing people to and from either Penn Station or Grand Central around the clock. Use the MTA TrainTime App. This will allow you to see schedules, purchase digital tickets, and chat with customer service. You can link an Apple Pay, Google Pay or credit/ debit card for payment. (This will also be of assistance later when you ride the subway). When boarding the train, watch the gap, expect doors to close suddenly, and know which direction you are going. East is to the further Long Island locations, West will go through Jamaica Ave, or to the City. The busiest commuter railroad is nothing if not a well-oiled machine ready to go, well-labelled, and easy to follow!
Transporting over 300,000 people on any given weekday with more than 700 moving trains this railway is no joke! Penn Station used to be the sole station for all LIRR arrivals. In January 2023, Grand Central’s Madison LIRR Concourse officially opened after MANY years of planning and building. The really cool addition is the lowest laying of the trains in and out of Grand Central Terminal, making the deep corridor an engineering feat. This also makes the escalator up to the concourse a long and steep ride. 182 feet long and 90 feet high, these escalators take 1 minute and 38 seconds to ascend or descend. *You can take a subway from either station up to the Broadway theatre where Gatsby is playing.
Grand Central serves the S train as well as the 4,5,6, and 7 subway lines.
Note: NYC is spread out. The Great Gatsby on Broadway takes place at the Broadway Theatre. With an 8 pm show time, be sure to arrive by 7:30 to ensure smooth arrival. Speakeasies suggested should be contacted for reservations, but plan at least 30 minutes of travel time in-between sites. So you do the math for your stops and adventure. (We undercalculated missing the opening act of the show)
Seeing Gatsby live was an excellent choice for a show. The performance was top tier, with music, dancing and set as perfect as it could have been. It’s fun to get caught up in the romance and glam of all things stage related and just to participate in the moment. There are no “bad” seats in the Broadway theatre, and we were in the back. Getting there early is essential to find your seat, take a few photos and get settled in prior to the opening act. There are absolutely no photos or videos once the curtain lifts. Concessions are very pricey. ($90 for two drinks) so eat and drink prior to the show starting! Dressing comfortably has become more of the vibe. I don’t care. I am a little old school and still like to show up Broadway ready, aka a little fancy. I tend to get cold, but I have never been freezing in a Broadway show, which is how I say it’s nice to have a sweater but also am fine without. The intermission will bring very long lines to the bathroom or concession stand. You can preorder snacks and drinks before the show to make it go faster. 15-minutes doesn’t seem long enough, but the lines move quickly! Doors do not open during an act, only in between, so plan accordingly.
The Gatsby performance nailed the characters portrayed. Music and costumes were fun and the set changes kept true to the whole picture of the roaring 20's. The girl playing Myrtle was the literal embodiment personified. I've enjoyed the movie done with Leonardo DiCaprio as Gatsby, but the show was definitely way more entertaining and as a group activity an awesome choice. Such good energy!
During my summer in NY, I saw a total of three shows. My son and I saw Lion King. My girlfriend Lisa won the lotto for MJ, extending the invitation for me to join her. Each show was unique and wonderful. Broadway really sets the bar for excellence, timing, pitch, and perfection. I have nothing bad to say of any shows I’ve been to. If you’ve never been, it’s time!! Book through The Today Tix App.
Speakeasy options:
Please Don’t Tell – Take the subway down to Astor Place and walk over to Saint Mark’s Square. This is a fun location! Enter through the payphone booth and gather at the dark, private location. Good music, and gets food orders from the neighboring restaurant, Crif Dogs, which is how you’ll know you’re in the right place. Drinks were delicious! Good service and vibes.
Note: I know there are some closer and some farther options, but this one is just the spot. We stayed longer than planned because it felt right. We took the subway here then walked over. Leaving for Broadway, we walked across to catch the subway back uptown, then opted for a taxi due to timing issues.
Address: 113 St. Marks Place
The Back Room – Look for the sign that reads THE LOWER EAST SIDE TOY COMPANY and walk down the alley way. There's graffiti all around and when you feel like you've gone the wrong way, walk up the set of steps and knock on the unlabeled door. You will be ushered into a dimly lit bar. Here, signature cocktails are served in teacups, and bottled beer is brown bagged. One of two speakeasies that was in operation during the Roaring 1920’s. Used to be known as, “The Back of Ratners”. Just the history part adds to the fun.
Note: Pretty far from Broadway, but pairs well with Beauty & Essex (which is closed on Tuesdays) and makes for a fun itinerary
Address: 102 Norfolk St. NY NY 10002
(212) 228 – 5098
Beauty & Essex – Curated as a modern day Pawn Shop with vintage treasures. Known for their dining rooms, and bars, this location will only add to your night life with all the Gatsby Era ritz needed to complete the vibes. Closed on Tuesday! Plan accordingly.
Note: This location is .2 miles from the Back Room and pairs nicely for a two for 1 experience
Address: 146 Essex Street
(212) 614-0146
Madame George’s Cocktail Lounge – Head down the stairs into dark but fun live music vibe with a great atmosphere and art to set the tone. I was disappointed in their version of a pina colada, but the rest of the experience was positive. Meatballs and Oysters were a great late-night bite and our table enjoyed the time together.
Note: This location is closest to Broadway
Address: 45 West 45th Street, NY, NY 10036
(646) 423-9081
Great Gatsby Itinerary Gold Coast & Go
The Vanderbilt Museum & Planting Fields & Sagamore Hill
Centerport & Oyster Bay
While Oyster Bay has two of these locations, Planting Fields, and Sagamore Hill are most likely shorter stops timewise.
Today’s adventure takes us to another Gilded Age Must see – The Vanderbilt Museum and Planetarium in Centerport. Not to be confused with the Vanderbilt Mansion Estate in Hyde Park, upstate NY. This is the same Vanderbilt’s of the Biltmore Estate in Asheville, North Carolina. This family is known for lavish homes that splurge on the details built to impress. This historic gold coast mansion does offer tours daily but the entire estate experience can spend as much time as you have! If your flight is late, take advantage of a morning tour, afternoon trail explore and a late planetarium show. There are Marine life exhibits, a nursery wing, a habitat wing, and Memorial wing featured on the property. What’s really crazy is there is a mummy! Can you imagine being a high price collector at the turn of the century and adding a mummy to your treasures?
The 43-acre waterfront estate was initially constructed in 1910 as the summer home of William K. Vanderbilt II, great grandson of Cornelius Vanderbilt. The Eagle’s Nest started as a small summer cottage. Over 30 years it was grown into the sprawling 24 room Spanish Revival Mansion it is today. Iron work and sparing no expense details highlight property designs that showcase several styles. The rooms today are viewed exactly the way William and Rosamond left them, which does add a flair to visiting.
Be sure to take photos! Dress in your favorite dress to add a nice touch for your photos and your entire Gatsby tour will end once you leave this last home to head back to the airport. I hope you can fly our of Islip Airport (ISP) which will save time and maybe money, but will certainly be a less crazy airport experience!
Planting Fields Arboretum is a personal favorite. Having grown up in Oyster Bay our mom often came here to walk and wander. Now, an extensive botanical garden and Gold Coast estate, check out the 409 acres including the Italian Garden, Cloister Garden and Circular Pool, Children’s Play House, Rose Garden and Perennial Garden, Synoptic Garden, Sensory Garden, Heather Garden, Dwarf Conifer Garden, Hydrangea Collection, Day Lily Garden and Dahlia Garden. This is one of only a few surviving estates on Long Island with its original land intact, as well as its buildings including the Main House, a 65-room Tudor Revival mansion. It took its current form in 1913 when the land was purchased by William Robertson Coe, an English immigrant, and Mai Rogers Coe, heiress and daughter of Standard Oil partner Henry Huttleston Rogers. Born into modest circumstances, W.R. Coe made his fortune in America by climbing the ranks to become chairman of a large marine insurance company. The lavish lifestyle of the Coes included five homes throughout America and associated pastimes such as interior decoration, horse racing, hunting, plant hybridization, animal husbandry, and patronage of the arts. Fun to wander, admire, and be inspired by the timeliness of that era.
9am to 5pm daily
Main House Tours: Learn about tours here!
GREENHOUSES The Main Greenhouse and Camellia House are open 10am – 3:45pm, 6 days a week. Closed to the public on Tuesdays for routine maintenance
info@plantingfields.org or (516) 922-9210.
Sagamore Hill was the home of Teddy Roosevelt from 1885 - 1919. Who is your favorite US President? This should be a stop on everyone's list to get both a little US history and some North Shore beauty into the schedule. No, this isn't on the Gatsby itinerary, but this is a bonus stop along the way! Known as the Summer White House during his Presidency, this Victorian mansion features 23 rooms, woodlands and a museum open to the public. A boardwalk can still be followed down to the marshy long coast. Sagamore is an Algonquian word for "chieftain".
Ahhh the Roosevelt saga, having grown up right up the road from here my family has many stories of their own. Stop and spend a little time, catch a tour if you can, and compare how the old style and newer Gatsby styles steeply contrasted each other. This is another way to appreciate the obnoxious wealth that the Gilded Age represented. By seeing how the rest of the wealthy lived. By walking through the corridors, you can appreciate Teddy Roosevelt's passion for conserving the National Parks and much of his mission is highlighted.
The Old Orchard Museum & Visitor Center is open from 1-4:30 PM Thursday, and 12-4:30 PM Friday-Sunday. The latest tour reservation information is available on recreation.gov. Tickets are $15 Adults, $1 Child, and $7.50 Seniors.
Address: 20 Sagamore Hill Rd, Oyster Bay, NY 11771
Our Gatsby weekend was planned to also take advantage of my favorite NYC Holiday, the 4th of July. I realize not everyone comes during this time of year and that not everyone coming has visited NYC multiple times, so our itinerary may not be the best for all, but this was our version:
Flew in July 3 -✈️✈️✈️
Old Westbury Gardens
Phils Pizza, Massapequa NY, dine in
July 4 – 🎆🎆🎇🎆🎇❤️🤍💙
Morning: Sands Point Preserve
Drove to Brooklyn, Domino Park
Walk across the Williamsburg Bridge
Katz Deli for Dinner
Fireworks! From Domino Park
July 5 – 🚆🥂🍎
Oheka Castle tour & Gardens for Brunch
LIRR to Grand Central
Speakeasies: Please Don’t Tell and the Backroom
Broadway Show: Gatsby
Speakeasy: Madame George’s
July 6 – 🌿🐳🦅
Sagamore Hill
Tour of the Vanderbilt Mansion
Fly out
For reference: Here's a map of the Long Island Gatsby stops recommended, created in Google Maps, and I recommend mapping your plans as traffic and weather can greatly impact timing!
Itinerary Planning:
Adding a day along the Brooklyn Prominade by parking or taking the train to either Domino Park or Brooklyn Bridge Park provides amazing views and opportunities to enjoy NYC in a different light. Feeling adventurous? Walk the Brooklyn Bridge and spend some time exploring the Battery area. OR Walk the Williamsburgh and explore SoHo.
Another Options for one more NYC Day:
Is there a trip to NYC complete without viewing an art collection? Both the Frick Museum and the Morgan Museum and Library align with our Gatsby vibes as both Gilded Era private collections went public later after the passing of the family icon. Some would opt to make this an NYC day with a museum of your choice in the morning followed by the Broadway show at 8! For a day itinerary adding both or either, click HERE.
Need a rooftop bar with music and dancing?
Mr. Purple in the Hotel Indigo on the Lower East Side, this 15th floor roof top bar has both inside and outside views that will make you feel the rush of the skyline's vast contour. DJ will keep the music going, style of play list may vary with time of night. There is a variety of tables, lounge options and seating for all needs. Dancing room. Dress is appreciated at this is defined as an upscale location. There may be a line. Door staff will determine who enters.
180 Orchard Street, 15th Floor
NY NY 10002
(212) 237 - 1790
Central Park mansion estate turned museum, and recently reopened after a five-year refurbishing, this is lovely! Challenging at first to use the app, but great if you search by the ROOM number. Then you can discover the value of everything listed in the room. So much easier!!
If you've ever read the Magnolia Palace this may be on your bucket list. Fiona Davis's books are based around NYC historic places and provide some themed architecture and adventure.
Midtown's very own hidden gem located a few blocks from Bryant Park and just waiting to be discovered. One of my favorite mysterious places, much smaller than most of the museums or galleries, but such a treasure to uncover. In a NYC world, where I often avoid the cafe, this location has an amazing afternoon tea! I highly recommend stopping and staying.
Whatever you do, adjust your mindset and have a great time!!
There will be traffic, navigate
There will be walking, keep your feet supported for the journey
Maps get a bit stressed trying to GPS the city, have a general idea about your route
Stay hydrated
Eat a pretzel, and some other food cart things
Uptown = North of you
Downtown = South of you
All subways indicate Uptown/ Downtown
Download the MTA app, which is your traveling companion on this trip
NYC is a melting pot, which is why we love it. Diversity is appreciated here
Long Island is a land of culture, suburban metro living at its finest
Long Island has it's own vibe and people mostly "stay in their own lane"
Gatsby marries NY and Long Island like peanut butter n jelly, where does one start and the other begin? Does it even matter? It's delicious.
Long Island Fun Facts:
*120 miles Long, 23 miles wide, with 8 million Residents
*The longest island in the 48 contiguous states
*Brooklyn and Queens are technically part of Long Island
*The most populated island in the US and 17th most populated island in the world
in 1927,
*Charles Lindburgh took off from Roosevelt Field on the first nonstop flight across the Atlantic, he also stayed in Sands Point Preserve frequently and his car is still there on display.
*There are over 140 shipwrecks off the coast of Long Island
*Teddy Roosevelt's home from 1885 - 1919 was in Sagamore Hill, Oyster Bay
*I grew up in Long Island and have yet to see and do ALL of the things, this is a destination unto itself with more food and activity options than can be easily expressed
Thank you for taking the time today to plan your adventure with me. I love sharing itineraries we've already used. My website is free, and I go not partner with Google or share your information.
A note from the editor:
The information in this article was accurate when published but may change without notice.
Confirm the prices and times on websites, and use your best judgement.
Confirm details when planning your trip.
Another Great NYC Day - Combine the Museum of Modern Art & Roosevelt Island
If you want to see the most recognizable art in the Western World, stop by the MoMA and check out Starry Night. Vincent Van Gogh's piece lives here along with MANY other amazing works by artists of the era such as Frida Kahlo, Monet, Pollock, and Matisse. This is an amazing collection and the 5th floor rivals NYC top museums, as the 3rd most visited in the city! After a great morning (budget at least 2 hours here) head over to the Roosevelt Tram to go get some amazing views of NYC!
