Looking for some car-free, carefree inspiration? We've got just the ticket for you. Take advantage of LIRR’s discounted escorted tours and spend the day relaxing and taking in Long Island’s most picturesque attractions. No traffic, no aggravation, just a scenic ride and a chance to explore some of our favorite locales. We’ll take you there, back, and everywhere in-between!

Gatsby Mansions

Westbury House at Old Westbury Gardens
The Westbury House at Old Westbury Gardens. (Discover Long Island)

2024 Schedule:
Sunday, July 14
Sunday, August 25
Sunday, September 15

Revisit an era of lavish country mansions, elegant estates, breathtaking architecture, and picturesque landscapes on Long Island’s Gold Coast. Start your tour with a visit to the Vanderbilt Museum, the summer home of William K. Vanderbilt: a Spanish-style mansion named Eagle's Nest, originally built in 1910 as a small English cottage. Next, enjoy lunch on your own at picturesque Huntington Village. Finally, delight in the elegant furnishings and beautifully landscaped gardens at Old Westbury Gardens, the backdrop for several popular movies, such as Age of Innocence, Cruel Intentions and American Gangster.

Cost: $97.75 per person ($85.50 for children 5-11). The tour includes discounted round-trip rail, bus transportation, admission to the Vanderbilt Museum, admission to Old Westbury Gardens, and a stop at Huntington Village for lunch.

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Port Jefferson

Board the rear car of the Huntington train at Jamaica

Plan Trip

Gatsby Mansion and Oyster Fest

2024 Schedule:
Saturday, October 19: The Vanderbilt Museum and the Oyster Fest
Sunday, October 20: Old Westbury Gardens and the Oyster Fest

Revisit an era of lavish country mansions, elegant estates, breathtaking architecture, and picturesque landscapes on Long Island’s Gold Coast, plus visit the East Coast's largest waterfront festival. Start your tour with a visit to either the Vanderbilt Museum, the summer home of William K. Vanderbilt: a Spanish-style mansion named Eagle's Nest, originally built in 1910 as a small English cottage, or Old Westbury Gardens, the backdrop for several popular movies, such as Age of Innocence, Cruel Intentions and American Gangster, where you will delight in the elegant furnishings and beautifully landscaped gardens. Then, enjoy lunch on your own at the Oyster Bay Oyster Festival, where the oyster is celebrated (and served!) in every form: on the half shell, fried, wood-fired and chowder.

Cost: $85.75 per person ($77.50 for children 5-11) for Saturday, October 19th, which includes discounted round-trip rail, bus transportation, admission to the Vanderbilt Museum, and the Oyster Fest; $81.75 per person ($69.50 for children 5-11) for Sunday, October 20th, which includes discounted round-trip rail, bus transportation, admission to Old Westbury Gardens, and the Oyster Fest.

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Port Jefferson

Board the rear car of the Huntington train at Jamaica

Plan Trip

Montauk Lighthouse

MontaukLightGoldLogo JeremyGarretson
The Montauk Lighthouse (Discover Long Island)

2024 Schedule:
Saturday, June 29
Saturday, August 10
Saturday, September 28

Take a trip to Montauk, the ultimate seaside community located at the tip of Long Island, without the stress of a long drive or planning your day. After your train pulls into the station, you will board a bus to “the End,” making stops at three classic sights: Montauk Village, the Montauk Point Lighthouse, and Gosman’s Dock.

Cost: $83.75 per adult ($65.50 per child ages 5-11). The tour includes round-trip rail and bus transportation, a visit to Montauk Village (on your own), admission to Montauk Point Lighthouse Museum, and a stop at Gosman’s Dock to eat and shop (on your own).

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Montauk

Board the rear car of the Montauk train at Jamaica

Plan Trip

LIRR Escorted 190th Anniversary Tour

LIRR 1939 Train Jamaica Queens
A Long Island Rail Road train operating through Jamaica, Queens in 1939.

2024 Schedule:
Saturday, July 27

Take a scenic ride to Greenport and relax while learning about the history of the LIRR and its impact on Long Island from on-board docents. Then, you will head to the Railroad Museum of Long Island to explore the exhibits commemorating both the 190th anniversary of the LIRR and the 180th anniversary of the first LIRR train to Greenport. Once you're finished there, you will board a bus to ride 'The Greenport Express,' an Allen Herschell G-16 park train. After your ride on the mini train, the bus will bring you to the Railroad Museum at Riverhead for some additional exploring.

This tour also includes a stroll through Greenport at your leisure, where you can enjoy some boutique shopping and waterfront dining (not included in the cost) before heading back to the city. And, you’ll get to take home some exclusive LIRR 190th Anniversary commemorative parting gifts to add to your collection!

Cost: $90.00 per adult ($77.75 per child ages 5-11). This escorted tour package includes discounted round-trip rail, bus transportation, admission to the Railroad Museum at Greenport and Riverhead, a ride on a G-16 park train, 'The Greenport Express,' and an LIRR 190th Anniversary commemorative book in addition to some LIRR 190th anniversary merchandise.

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Ronkonkoma

Board the rear car of the Ronkonkoma train at Jamaica

Plan Trip

Sunday Cruise to Fire Island Lighthouse

The Lauren Kristy
(Discover Long Island)

2024 Schedule:
Sunday, July 21
Sunday, September 29

Set sail on the Lauren Kristy, a 65ft turn-of-the-century style riverboat for a cruise along the scenic Great South Bay. Enjoy a buffet-style lunch along the way to the Fire Island Lighthouse, known as the tallest lighthouse on Long Island. You’ll also visit the historic village of Babylon, where you can enjoy a leisurely stroll, local boutique-style shopping, and dining.

Cost: $139.75 per adult ($96.50 per child ages 5-11). This escorted tour package includes discounted round-trip rail, bus transportation, a 3-hour cruise and buffet lunch on the Lauren Kristy, admission to the Fire Island Lighthouse, and a stop at the village of Babylon for shopping and dining.

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Babylon

Board the rear car of the Babylon train at Jamaica

Plan Trip

North Fork Fruit and Hard Cider

North Fork Attractions Farms and Farm Stands 205
(Discover Long Island)

2024 Schedule:
Saturday, July 13 - CANCELLED DUE TO INCLEMENT WEATHER
Saturday, August 24
Saturday, October 5

Visit Long Island’s North Fork for a fun day at the orchards! We will visit Riverhead Ciderhouse for tastings of a wide selection of naturally harvested ciders, local beer and wine, and other treats. Next, enjoy picking fresh fruit at Wickham’s Farms, one of the largest farms on Long Island, offering a delicious variety of freshly baked goods. We will also visit the historic village of Greenport for shopping and local dining.

Cost: This escorted tour package includes discounted round-trip rail, bus transportation, tastings at Riverhead Ciderhouse, fruit picking at Wickham’s Fruit Farms, and a visit to the village of Greenport.

  • $99.75 per adult ($69.50 per child ages 5-11) for Saturday, July 13, 2024

  • $101.75 per adult ($71.50 per child ages 5-11) for Saturday, August 24, 2024

  • $103.75 per adult ($73.50 per child ages 5-11) for Saturday, October 5, 2024

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Montauk

Board the rear car of the Ronkonkoma train at Jamaica

Plan Trip

Greenport Lighthouse Cruise

Bug Lighthouse
The Long Beach Bar "Bug" Lighthouse (Discover Long Island)

2024 Schedule:
Saturday, August 17
Saturday, September 7

Visit Greenport for a memorable cruise to the Long Beach Bar “Bug” Lighthouse. Start by exploring the East End Seaport Museum located on the historic Greenport waterfront offering dynamic exhibits showcasing the rich maritime heritage of Long Island’s East End. Then, set sail on a narrated cruise to “Bug Lighthouse”, an iconic lighthouse and bright beacon welcoming mariners to the protected waters of Peconic Bay. You will also have the opportunity to explore inside the lighthouse originally built in 1870. After the cruise, enjoy your evening in town! Take some time to shop, dine or simply enjoy a scenic stroll around the beautiful Village of Greenport.

Cost: $64.25 per adult ($22.00 per child ages 5-11). This escorted tour package includes discounted round-trip rail, admission to the East End Seaport Museum and Village Blacksmith Shop, and a two-hour narrated cruise and tour of the “Bug Lighthouse."

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Ronkonkoma

Board the rear car of the Ronkonkoma train at Jamaica

Plan Trip

North Fork Vineyards

Photo Oct 10 1 13 21 PM
(Discover Long Island)

2024 Schedule:
Saturday, July 20
Sunday, August 11
Saturday, September 21
Sunday, October 6
Saturday, October 26

Visit Long Island’s North Fork for tastings of the region’s local wines, serene strolls through the vineyards and idyllic scenery at the village of Greenport. On Saturday tours, enjoy wine tastings at Duck Walk Vineyards and Pindar Vineyards, and a visit to the charming seaport village of Greenport for a breezy stroll through boutique-lined streets and endless dining possibilities. On Sunday tours, enjoy wine tastings at Jason’s Vineyard, and a visit to the charming waterside village of Port Jefferson for a breezy stroll through boutique-lined streets and endless dining possibilities.

Cost: For Saturday tours (July 20, September 21, and October 26): $104.75 per person (21+ only). This escorted tour package includes discounted round-trip rail, bus transportation, wine tastings at Duck Walk Vineyards and Pindar Vineyards, and a visit to the village of Greenport.

For Sunday tours (August 11 and October 6): $87.25 per person (21+ only). This escorted tour package includes discounted round-trip rail, bus transportation, wine tastings at Jason's Vineyard, and a visit to the village of Port Jefferson.

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Ronkonkoma

Montauk

Board the rear car of the Montauk train at Jamaica

Plan Trip