Table of Contents
- Introduction
- Top Cities and Places on Long Island
- Tourist Circuits
- Activities and Experiences
- Festivals and Events
- 4 Nights 5 Days Long Island Itinerary
- How to Reach
- Where to Stay
- Estimated Costs
- Food, Shopping, and Culture
- Tips for Different Travelers
- FAQs
- Conclusion
Introduction
Just east of New York City, Long Island stretches along the Atlantic with sweeping beaches, historic lighthouses, vineyard-dotted farmland, and stylish seaside villages. In five days you can blend the Hamptons’ glamorous sands with the North Fork’s wine trail, add a dash of Fire Island’s car-free boardwalks, and step into the Gilded Age on the Gold Coast. This 4 nights 5 days Long Island itinerary balances iconic sights with local favorites, keeping drive times manageable and options flexible year-round.
Top Cities and Places on Long Island
The Hamptons (Southampton, East Hampton, Sag Harbor)
- Pristine Atlantic beaches like Coopers Beach and Main Beach
- Art and architecture at Parrish Art Museum; whaling heritage in Sag Harbor
- Farm stands, historic windmills, and upscale dining
Montauk
- Montauk Point Lighthouse and dramatic bluffs
- Surf at Ditch Plains, hiking at Shadmoor and Hither Hills
- Seafood shacks and harbor sunsets near Gosman’s
North Fork (Greenport, Mattituck, Cutchogue, Orient)
- Over 50 wineries and tasting rooms along Routes 25/48
- Charming Greenport village, maritime vibe, bayside views
- Lavender fields (in bloom late spring–summer) and farm-to-table eateries
Fire Island
- Car-free barrier island with soft beaches and boardwalk communities
- Fire Island Lighthouse, Sunken Forest, Ocean Beach village
- Seasonal ferries from Bay Shore, Sayville, Patchogue
Gold Coast & North Shore (Oyster Bay, Roslyn, Port Washington)
- Gilded Age mansions: Old Westbury Gardens, Sands Point Preserve
- Picturesque harbors, antique shops, and historic museums
Jones Beach & Long Beach
- Classic boardwalks, concerts, and family-friendly sands
- Great for sunrise walks, biking, and birding
Tourist Circuits
- Hamptons–Montauk Coastal Loop: Southampton → East Hampton → Amagansett → Montauk Point → back via Napeague/Hamptons.
- North Fork Wine Trail: Riverhead → Mattituck/Cutchogue → Southold → Greenport → Orient (return or ferry to New England).
- South Shore & Fire Island: Long Beach/Jones Beach → Bay Shore/Sayville ferry → Fire Island communities.
- Gold Coast Mansions: Old Westbury Gardens → Nassau County Museum of Art → Sands Point Preserve.
- Family Fun Route: Jones Beach → Long Island Aquarium (Riverhead) → Splish Splash water park → Tanger Outlets.
Activities and Experiences
- Beach days: Swim, sun, and stroll boardwalks; arrive early in summer for parking.
- Hiking & biking: Hither Hills, Shadmoor, Sunken Forest, Caumsett State Historic Park Preserve.
- On the water: Surfing (Ditch Plains), kayaking/SUP (Peconic Bay), sailing from Greenport/Sag Harbor.
- Wildlife & whale watching: Seasonal tours from Montauk (late spring to early fall).
- History & culture: Montauk Lighthouse, Old Westbury Gardens, Parrish Art Museum, Whaling Museum in Sag Harbor.
- Wine, beer, cider: Tastings along the North Fork; plan a designated driver or use local ride services.
- Fishing & boating: Party boats from Montauk and Captree; charters available.
Festivals and Events
- Jones Beach Air Show: Memorial Day weekend.
- Montauk Music Festival: May.
- Hamptons International Film Festival: October.
- Oyster Bay Oyster Festival: October.
- North Fork Crush / Foodie tours: Summer to early fall.
- Winterfest (music & wine on the East End): Late winter (check annual dates).
- Lavender bloom at Lavender by the Bay: Typically June–July, sometimes again late summer.
4 Nights 5 Days Long Island Itinerary
Overview
This loop minimizes backtracking: start near the western/central South Shore, head through the Hamptons to Montauk, cross via Shelter Island to the North Fork, then return via Riverhead.
Day 1: Gold Coast to South Shore Welcome
- Morning/early afternoon: Arrive via NYC airports or Long Island MacArthur. If driving from NYC, take I-495 (LIE) or Southern State Parkway.
- Explore a mansion: Old Westbury Gardens or Sands Point Preserve for gardens, architecture, and easy trails.
- Late afternoon: Head to Jones Beach or Long Beach for a boardwalk stroll and sunset.
- Dinner: Seafood on the South Shore (Freeport’s Nautical Mile or Long Beach).
- Overnight: Garden City/Rockville Centre for convenient transit and parking.
Day 2: South Shore to the Hamptons (+ Fire Island option)
- Optional morning detour: Fire Island via ferry from Bay Shore/Sayville (Ocean Beach or Sunken Forest). Enjoy a car-free beach walk.
- Drive east along Sunrise Highway (27) to Southampton. Visit Parrish Art Museum and Coopers Beach.
- Evening in Sag Harbor: Harbor promenade, boutique browsing, casual coastal dinner.
- Overnight: Southampton or East Hampton.
Day 3: East Hampton and Montauk
- Breakfast at a local bakery; farm stand stops in Amagansett.
- Hike Shadmoor or Hither Hills for cliff and ocean views.
- Visit Montauk Point Lighthouse; photo stops along the bluffs.
- Beach time at Ditch Plains (surf vibe) or Kirk Park Beach.
- Sunset seafood near Gosman’s Dock.
- Overnight: Montauk (resort or inn) or return to East Hampton.
Day 4: Shelter Island and North Fork Wineries
- Morning: Ferry from Sag Harbor to Shelter Island (South Ferry). Walk Mashomack Preserve trails.
- Midday: Ferry to Greenport (North Ferry). Explore village, maritime history, and harborfront.
- Afternoon: Wine tastings on the North Fork (e.g., Bedell Cellars, Paumanok, Kontokosta). Rotate driver or book a car service.
- Seasonal stop: Lavender by the Bay in bloom.
- Overnight: Greenport/Orient area or Mattituck for central access.
Day 5: Riverhead, Outlets, and Departure
- Family option: Long Island Aquarium in Riverhead.
- Shopping: Tanger Outlets (Riverhead).
- Farm fun: In season, u-pick berries or apples; stop at Harbes Family Farm.
- Lunch in Port Jefferson or Huntington if routing via the North Shore.
- Depart: Return via I-495 to NYC airports or head to Long Island MacArthur (ISP).
Without a Car (Alternative)
- Use LIRR: Montauk Branch (Hamptons/Montauk), Ronkonkoma + Greenport Branch (North Fork).
- Hampton Jitney coaches connect Manhattan with Hamptons/North Fork towns.
- Local taxis/rideshares and seasonal shuttles fill gaps; choose lodgings near stations/villages.
Driving and Timing Notes
- Typical drive times without heavy traffic: NYC → Southampton 2–2.5 hrs; Southampton → Montauk 1 hr; Montauk → Greenport via ferries 1.5–2 hrs; Greenport → NYC 2–2.5 hrs.
- Summer weekends can double these; start early and consider weekday movements.
How to Reach
- By air: JFK and LGA (NYC) serve most flights; Long Island MacArthur (ISP) in Ronkonkoma is closest for central/east LI.
- By train: LIRR from NYC to the Hamptons/Montauk and to Greenport (transfer at Ronkonkoma).
- By coach: Hampton Jitney and Hampton Luxury Liner from Manhattan to Hamptons/North Fork.
- By car: I-495 (LIE), Southern State, and Sunrise Hwy. Expect tolls if crossing bridges/parkways near NYC.
- By ferry: Bridgeport–Port Jefferson and New London–Orient Point car ferries; Fire Island passenger ferries (seasonal).
Where to Stay
- Western/Central base: Garden City, Rockville Centre, Long Beach (good for Day 1/airport access).
- Hamptons: Inns and boutique hotels in Southampton, East Hampton, Sag Harbor; higher summer rates, weekend minimums.
- Montauk: Beach resorts (some year-round), motels, and chic properties with ocean views.
- North Fork: B&Bs and small hotels in Greenport, Southold, Mattituck; quieter vibe.
- Budget-friendly hubs: Riverhead, Islandia, Farmingdale (chain hotels with parking).
Seasonality: Late June–Labor Day is peak (book months ahead). Shoulder seasons (May, Sept–Oct) offer milder crowds and lower rates.
Estimated Costs
- Accommodation (per room/night):
- Budget (central LI/Riverhead): $140–220
- Mid-range (Hamptons/North Fork off-peak): $240–450
- Luxury (peak Hamptons/Montauk): $500–900+
- Food & drinks (per person/day): $40–80 (casual) to $100–180 (fine dining + tastings).
- Transport: Car rental $60–120/day + fuel; parking/fees $10–40/day (state park/municipal). LIRR round trips to East End $30–50+ depending on zone/time.
- Activities: Winery tasting flights $20–50; Montauk Lighthouse ~$15–20; whale watch ~$80–95; Fire Island ferry ~$12–14 one way; Shelter Island car ferries ~$20–30 round-trip.
- Beach access: Some towns require non-resident parking permits/day passes ($20–50). State parks generally $10 vehicle fee (varies by day/season).
Daily rough total (per person): Budget $150–220; Mid-range $250–400; Luxury $450–900+ (season dependent).
Food, Shopping, and Culture
Food
- Seafood staples: lobster rolls, local oysters and clams, fish tacos in Montauk.
- Bagels and delis: classic New York-style breakfasts and heros.
- Farm-to-table: seasonal menus across the Hamptons and North Fork.
- Sweet stops: farm pies, ice cream stands, cider doughnuts (fall).
Drinks
- North Fork wineries (merlot, chardonnay, sparkling)
- Craft breweries and cideries in Riverhead and Peconic region
Shopping
- Hamptons boutiques and design shops
- Greenport galleries and nautical stores
- Tanger Outlets (Riverhead) for deals; Americana Manhasset for luxury
Culture
- Parrish Art Museum, Guild Hall (East Hampton)
- Whaling Museum (Sag Harbor), maritime history in Greenport
- Shinnecock Nation heritage and local history sites
Tips for Different Travelers
Families
- Choose lodgings with parking and kitchenettes (Montauk, Riverhead).
- Plan beach mornings, aquarium or lighthouse midday, outlets/playgrounds late afternoon.
- Pack sun protection, reusable water bottles, lightweight layers; mind rip currents and lifeguard flags.
Honeymooners & Couples
- Time sunset walks at Montauk Point or Shelter Island ferries.
- Book midweek shoulder-season stays for quieter beaches and better rates.
- Reserve winery tastings and chef’s counters ahead in peak months.
Friends & Groups
- Use ride services or hire a driver for wine days; split costs with a vacation rental (respect local noise rules).
- Consider activity mix: surf lesson, charter fishing, brewery crawl.
- Bring insect repellent and do tick checks after hikes in grassy/wooded areas.
General Safety & Practicalities
- Traffic builds Fridays/Sundays in summer; travel early or midweek.
- Some beaches/towns have resident permit rules—verify day-pass options before you go.
- Weather can change rapidly on the coast; carry a light rain/wind jacket.
FAQs
Q: When is the best time for a 5-day Long Island trip?
A: Late May–June and September–October offer warm days, swimmable water (early fall), fewer crowds, and better hotel value. July–August is peak beach season with higher prices and traffic. Winter is quiet with museum, mansion, and food/wine focus.
Q: Do I need a car for this itinerary?
A: A car gives maximum flexibility. Without one, combine the LIRR or Hampton Jitney with walkable bases (Sag Harbor, East Hampton, Montauk, Greenport) and local taxis/rideshares. Ferries and seasonal shuttles help bridge gaps.
Q: Are Long Island beaches free?
A: Many town beaches require non-resident parking permits or day passes. New York State parks (e.g., Jones Beach) typically charge a vehicle fee. Walking in may be free in some places, but check local rules.
Q: Can I visit Fire Island on a day trip?
A: Yes. Take passenger ferries from Bay Shore, Sayville, or Patchogue to Ocean Beach, Cherry Grove, or Sunken Forest. No cars on most of Fire Island—plan to walk or use wagons for gear.
Q: What about wildlife like ticks or jellyfish?
A: Use repellent and check for ticks after hikes, especially in summer. Jellyfish can be present mid–late summer; heed lifeguards and avoid swimming near visible blooms.
Conclusion
In five days, Long Island rewards with a blend of Atlantic beaches, lighthouse views, vineyard afternoons, and historic estates. This route moves smoothly from South Shore icons to Hamptons glamor, Montauk’s wild edge, and the North Fork’s agrarian charm, with flexible options for families, couples, and groups. Time your days to beat traffic, book key stops in advance, and let the coastal rhythm set the pace.
