Long Island Tours & Activities

Plan your trip to Long Island, New York — handpicked tours and activities, the best time to visit, where to stay and eat, how to get there, and a sample itinerary.

Top things to do in Long Island

• Jones Beach State Park. Six and a half miles of white-sand Atlantic Ocean beach spread across 2,400 acres on the South Shore, drawing roughly 8 million visitors a year. Beyond swimming, the boardwalk, fishing piers, and the Northwell Health at Jones Beach Theater for summer concerts make this the quintessential Long Island day out.
• Montauk Point Lighthouse. Commissioned by George Washington in 1792 and completed in 1797, this is the oldest lighthouse in New York State and the fourth oldest active lighthouse in the United States. Perched dramatically at the far eastern tip of Long Island, it is a National Historic Landmark with a museum inside and sweeping Atlantic views…
• North Fork Wine Country. More than 40 wineries dot a 30-mile stretch of farmland between the Long Island Sound and Peconic Bay, producing acclaimed Merlot, Cabernet Franc, and Chardonnay from the region's maritime climate. Iconic producers like Bedell Cellars and Lenz Winery welcome tasting-room visitors along Route 25, making the North Fork…
• Fire Island National Seashore. A 26-mile car-free barrier island reached only by ferry, Fire Island preserves pristine Atlantic beaches, the wild Otis Pike Wilderness, and the boardwalk-threaded Sunken Forest at Sailors Haven. A third of all North American bird species pass through during migration, making it a world-class birding site alongside…
• Sagamore Hill National Historic Site. Theodore Roosevelt's beloved 23-room Victorian home in Oyster Bay served as the Summer White House from 1901 to 1909, hosting foreign dignitaries and peace talks that helped end the Russo-Japanese War. Sitting on 95 acres of forest and salt marsh, the house retains nearly all original furnishings and is viewable by…
• The Hamptons. A collection of about 20 villages across the South Fork — including Southampton, East Hampton, Sag Harbor, and Amagansett — the Hamptons deliver world-class ocean beaches, grand Gilded Age estates, acclaimed restaurants, and gallery-lined Main Streets. Coopers Beach in Southampton and Ditch Plains surf break in…
• Greenport Village. The North Fork's most charming waterfront village packs over 40 eateries, boutique shops, a restored antique carousel at Mitchell Park, and the Greenport Harbor Brewing Co. into barely one square mile of walkable streets beside a working marina. It is the natural base for exploring the surrounding wine country and…
• Parrish Art Museum. Designed by the Pritzker Prize-winning architects Herzog and de Meuron and set in Water Mill amid open farmland, the Parrish holds more than 2,600 works with particular strength in Long Island-connected artists including Jackson Pollock, Lee Krasner, Roy Lichtenstein, and Eric Fischl. Rotating exhibitions make every…

Best time to visit Long Island

Late May through June, or September through mid-October. Shoulder seasons offer warm weather (70s-80s F), fewer crowds than July-August peak, and major events: the Montauk Music Festival (May), Hampton Classic (late August), Hamptons Film Festival (October), and North Fork wine harvest (September-October). Fall brings crisp air, foliage, and vineyard harvest events without summer congestion

Long Island weather by month

Getting to Long Island

The Long Island Rail Road (LIRR) connects Penn Station and Grand Central in Manhattan to over 124 Long Island stops. Buy tickets in advance via the MTA TrainTime app — on-board purchases cost more. Off-peak travel (outside weekday 6-10am arrivals into NYC and 4-8pm departures) costs significantly less. A car is still essential for reaching wineries, state parks, and most Hamptons beaches.

• JFK John F. Kennedy International Airport — 30 min drive
• LGA LaGuardia Airport — 45 min drive
• ISP Long Island MacArthur Airport — 20 min drive

Where to stay in Long Island

Where to base yourself, by neighborhood.

• The Hamptons (East Hampton and Southampton). The South Fork's iconic cluster of villages is the premier address on Long Island — luxury inns, boutique hotels, and high-end rentals set among ocean beaches, celebrity restaurants, and gallery-lined Main Streets. Prices are steep, especially in July and… Good for: Romance, upscale beach holidays, food and wine lovers, culture seekers.
• Montauk. At the far eastern tip of Long Island, Montauk delivers a more relaxed, surf-town energy than the Hamptons proper — hotels and motels cluster near the famous surf break at Ditch Plains Beach, and the lighthouse is a short drive away. It suits visitors who… Good for: Surfers, outdoor adventurers, couples seeking a low-key beach escape.
• Greenport and North Fork. Greenport is the most walkable and family-friendly base on Long Island's North Fork, with a compact waterfront village, ferry access to Shelter Island, and dozens of wineries within a 20-minute drive. Boutique inns and B&Bs outnumber chain hotels here, and… Good for: Wine country explorers, families, cyclists, weekend getaways from New York City.
• Garden City and Nassau County (Mid-Island, South Shore). Garden City anchors the Nassau County interior with well-located hotels that put visitors within easy reach of Jones Beach, the Nautical Mile in Freeport, and the Long Island Rail Road into Manhattan. It is the most practical base for travelers who want to… Good for: Budget-conscious travelers, day-trippers to NYC, families visiting multiple areas.
• Oyster Bay and the North Shore Gold Coast. The North Shore's Oyster Bay area blends historic grandeur with nature, placing visitors near Sagamore Hill, Planting Fields Arboretum, Cold Spring Harbor, and a string of charming waterfront villages. Inns and small hotels here cater to history lovers and… Good for: History buffs, garden and architecture lovers, nature hikers, romantic getaways.

Where to eat in Long Island

A curated set of standout tables and local favorites.

Local favorites & classics

• Nick and Toni's. East Hampton · Italian-Mediterranean — The gold standard of Hamptons dining since 1988, Nick and Toni's is celebrated for its wood-burning oven whole fish, handmade pasta, and a seasonal menu that…
• Claudio's Waterfront. Greenport, North Fork · Seafood — Widely cited as the oldest restaurant continuously owned by the same family in the United States, Claudio's has anchored Greenport's waterfront since 1870, serving…
• Akbar Restaurant. Garden City, Nassau County · Northern Indian (Mughlai) — The first Indian restaurant on Long Island and still its finest, Akbar has served aromatic biryanis, rich kormas, and properly spiced tandoor…
• Vespa Italian Kitchen and Cocktails. Long Island (Nassau County) · Italian — Named Best New Restaurant on Long Island in 2025, Vespa earned rapid acclaim for its baked clams oreganata, calamari fritti, bucatini with sardines, and…
• Pasta Pasta. Port Jefferson Village · Italian — A North Shore fixture since 1991, Pasta Pasta is Port Jefferson Village's beloved neighborhood Italian, named Best Italian Restaurant on Long Island in 2025. The…
• Catcher's Fish House and Grille. Freeport Nautical Mile, South Shore · Seafood — One of the standout restaurants on Freeport's famous Nautical Mile strip, Catcher's focuses on locally caught fish, fresh shellfish, and waterfront…
• Bedell Cellars Tasting Room. Cutchogue, North Fork · Wine Tasting / Local Fare — Producing wine on the North Fork since 1980, Bedell Cellars is one of the region's most respected estates, known for bright-acid, saline-mineral…
• Vincent's Clam Bar. 179 Old Country Rd · 4.5★ (5,237 reviews)

Cafés, bakeries & casual

• Jordan Lobster Farms. Island Park, Nassau County · Seafood / Lobster — Part wholesale market, part clam bar, part restaurant — Jordan Lobster Farms is a South Shore institution where visitors pick live lobsters from the…
• Veniero's Pasticceria & Caffe. 342 E 11th St · 4.5★ (5,478 reviews)
• Supermoon Bakehouse. 120 Rivington St · 4.6★ (1,799 reviews)
• The Dirty Cheesecake AKA Made by Lilis. 1160 Deer Park Ave · 4.8★ (838 reviews)
• Krispy Mango Café & Bakeshop. 21 Wall St · 4.9★ (654 reviews)
• St. Rocco's Bakery. 4 St Rocco Pl · 4.7★ (828 reviews)
• Copenhagen Bakery. 75 Woodbine Ave A · 4.6★ (907 reviews)
• Buttercooky Bakery & Cafe. 495 New York Ave · 4.3★ (1,047 reviews)

Fine dining & Michelin

• George Martin's Strip Steak. Great River · American Steakhouse — Named Best Fine Dining on Long Island in the 2025 Daily Voice Readers' Choice Awards, this Great River steakhouse is the marquee venue of the George Martin Group,…
• Louie's Prime Steak & Seafood. 395 Main St · 4.5★ (4,421 reviews)
• Blackstone Steakhouse. 10 Pinelawn Rd · 4.5★ (2,895 reviews)
• The Capital Grille. 630 Old Country Rd · 4.6★ (2,090 reviews)
• Insignia Prime Steak & Sushi. 610 Smithtown Bypass · 4.5★ (2,437 reviews)
• Tellers: An American Chophouse. 605 E Main St · 4.6★ (1,927 reviews)
• Prime: An American Kitchen & Bar. 117 North New York Ave · 4.4★ (2,295 reviews)
• Maiella. 46-10 Center Blvd · 4.4★ (2,108 reviews)

A 7-Day Long Island Plan

1. Day 1 — Gold Coast Grandeur. Begin your Long Island journey on the North Shore with a visit to Sagamore Hill National Historic Site in Oyster Bay, touring Theodore Roosevelt's beloved home and the surrounding estate grounds. Pick up a ranger-led tour to fully appreciate the presidential history and Victorian…
2. Day 2 — Beaches, Boardwalks & Barrier Islands. Drive south to Jones Beach State Park, one of the world's great urban beaches, arriving early to walk the two-mile boardwalk before the crowds gather. Explore the grand Art Deco bathhouses and the wide Atlantic shoreline stretching nearly seven miles. Take the ferry from…
3. Day 3 — Art, Culture & the Hamptons. Head east on the South Fork to Water Mill, stopping at the Parrish Art Museum in Southampton, a stunning Herzog & de Meuron–designed building housing an exceptional collection of Long Island–connected artists including William Merritt Chase and Fairfield Porter. Continue east into…
4. Day 4 — Whaling History & Harbor Village Life. Spend the morning at the Sag Harbor Whaling and Historical Museum, housed in an 1845 Greek Revival mansion that vividly recounts Long Island's seafaring past through artifacts, scrimshaw, and ship models. The surrounding streets of Sag Harbor are among the best-preserved…
5. Day 5 — Wine Country & Farm Roads. Dedicate this day to the North Fork Wine Country, one of the fastest-rising wine regions on the East Coast. Start at Bedell Cellars or Wolffer Estate's North Fork outpost for a morning tasting, learning how the maritime climate produces distinctive Merlot and Cabernet Franc. Work…
6. Day 6 — Aquarium, Wildlife & South Shore Nature. Head to Riverhead and spend the morning at the Long Island Aquarium, home to a massive shark exhibit, touch tanks, and a butterfly atrium. It's an excellent all-ages stop and one of the premier aquariums in the Northeast. Drive south to the barrier beaches of the South…
7. Day 7 — Land's End at Montauk. Make the scenic drive all the way to the eastern tip of Long Island to Montauk Point Lighthouse, the oldest lighthouse in New York State, perched dramatically above the Atlantic. Climb the tower for sweeping ocean views and tour the keeper's quarters museum below. Spend the afternoon in…

Events & festivals in Long Island

• Montauk Music Festival (Mid-May (2026: May 14-17)). 15th annual free festival in 2026; 100+ acts across 40 Montauk venues with 400+ performances including the Main Stage at Montauk Lighthouse.
• Invasion of the Pines (Fire Island) (July 4 (annually)). Annual Fourth of July celebration in which hundreds of drag queens from Cherry Grove sail to Fire Island Pines Harbor, drawing thousands of spectators. Tradition began 1976.
• Hampton Classic Horse Show (Late August (annually, Bridgehampton)). One of the largest outdoor horse shows in the USA; approximately 1,500 horses and 200+ competitions. Held at 240 Snake Hollow Road, Bridgehampton.
• Greenport Maritime Festival (Late September (annually, Greenport Village)). Annual celebration of the North Fork's maritime heritage at the East End Seaport Museum; includes a Merfolk parade, cardboard boat regatta, live sea shanties, and street fair.
• North Fork Wine Harvest Season (September-October). Long Island Wine Country vineyards host barrel tastings, vineyard walks, harvest dinners, and oyster showcases throughout fall across the North Fork AVA.
• Hamptons International Film Festival (Early October (2026: October 2-12)). 34th annual festival in 2026; screenings and events across the East End Hamptons communities.

Top-rated tours & activities in Long Island

• Bermuda Island Tour — 4.8★ (20 reviews)
• Luxury Beach Bonfire and Picnic Dinner at Town Line Beach — 4.8★ (19 reviews)
• JFK AIRPORT LIMO | JFK To Manhattan Transfer With a Stretch Limo — 4.6★ (78 reviews)
• Private Beach Fire Montauk — 4.7★ (13 reviews)
• Captain Steve's Sailing Experience on Long Island — 5.0★ (11 reviews)
• Big Apple Transport: Premier Transportation Services in NYC — 4.4★ (70 reviews)
• Bermuda Aquarium and Crystal Caves Admission — 4.4★ (69 reviews)
• Skip the Lines Reliable Comfortable and stress free Rides — 5.0★ (68 reviews)

Long Island travel FAQ

When is the best time to visit Long Island?

Late May through June, or September through mid-October.

What are the top things to do in Long Island?

Top experiences include Jones Beach State Park, Montauk Point Lighthouse, North Fork Wine Country, Fire Island National Seashore, Sagamore Hill National Historic Site.

Which airport is closest to Long Island?

Long Island MacArthur Airport (ISP) is the nearest, about 20 minutes away.

Where should I stay in Long Island?

Popular areas to base yourself include The Hamptons (East Hampton and Southampton), Montauk, Greenport and North Fork, Garden City and Nassau County (Mid-Island, South Shore).

How do I get around Long Island?

The Long Island Rail Road (LIRR) connects Penn Station and Grand Central in Manhattan to over 124 Long Island stops.