Long Island Itineraries. 3 Days, 1 Week, Budget Travel

-hour layover highlights from JFK/LGA

Morning: Take the LIRR to A Very long beach for a boardwalk stroll and the sea views, or head to Garden City for a suburban, upscale atmosphere.

Afternoon: Visit Old Westbury Gardens for its beautiful grounds, or explore Roosevelt Field Mall for shopping.

Quick Visit Ideas

LIRR access is quick from NYC airports.
Long Beach boardwalk access.
Buying things or garden visits.

Weekend & Longer Stays

Tailored plans for 2-3 day and week-long explorations.

Weekend Getaway 2-3 days - North Fork Wine & Culture

Focus on Greenport village and its access to wineries.

Suggested Plan

Day 1: Get to Greenport, explore village, East End Seaport Museum, local seafood dinner.
Day 2: North Fork Winery Tour by bicycle or car service, lunch at vineyard.
Day 3: Relaxed breakfast, quiet local beach, then return travel.
Consider GetYourGuide for easy booking of North Fork experiences.

Consider seasonal pick-your-own experiences at farms.

One-Week Comprehensive Experience 7 days

A journey across Nassau and Suffolk Counties.

Weekly Highlights

Days 1-2: Nassau County - Old Westbury, Jones Beach, Sands Point Preserve.
Days 3-4: Western Suffolk & North Fork - Huntington, Vanderbilt Museum, wineries.
Days 5-6: Hamptons & Montauk - Southampton, East Hampton, Montauk Point Lighthouse.

Two-Week In-Depth Exploration 14 days

Combine the one-week itinerary with dives into particular areas.

Expanded Journey

Allocate more time: 3-4 days each in the Hamptons/Montauk and North Fork.
Include a day trip to Fire Island (Ocean Beach, Fire Island Lighthouse).
Add a day trip or overnight stay on Shelter Island for tranquility.
Consider a 2-3 day extension to New York City at the start or end.

Long-Term Stay Recommendations

For prolonged visits, immerse yourself in local life.

Living Like a Local

Consider vacation rentals via platforms like Airbnb or Vrbo for monthly rates.
Frequent fresh markets for fresh, local produce.
Explore local parks and community classes.
Experience the rhythm of Long Island living.

Tailoring Your Long Island Journey

Adjust your travel pace and focus based on your available time and interests.

Short Trips

Focus on one region to avoid excessive travel time.

Mid-Length

Balance sightseeing with relaxation in areas.

Extended Stays

Dive into local culture and hidden gems.

Efficient Planning

For short trips, concentrate on a single Long Island region to maximize your time without extended travel.

Interest-Based Routes

Tailor your Long Island itinerary to your specific passions, whether history, food, adventure, or art.

Historical and Heritage Focus

Explore the past through significant sites.

Historical Sites

Nassau County: Sagamore Hill (Theodore Roosevelt's "Summer White House"), Old Westbury Gardens, Planting Fields Arboretum.
Suffolk County: Stony Brook Village, Long Island Museum, Raynham Hall, Sag Harbor Whaling & Museum Of history.
Conclude with the Montauk Point Lighthouse.
Consider local guided tours for historical insights.

Many historical sites have special events; check calendars.

Food and Culinary Experiences

Savor Long Island's diverse gastronomic landscape.

Taste of Long Island

North Fork: Wineries, farm stands, oyster farms; farm-to-table restaurants.
Hamptons/Montauk: High-end dining, fresh seafood, lively bar scenes.
Local diners and casual eateries also offer authentic flavors.
Explore diverse ethnic cuisines in the west of Long Island.

Adventure and Outdoor Activities

For active travelers, Long Island has much to offer.

Outdoor Pursuits

Beaches: Surfing at Ditch Plains, swimming at Jones Beach and Coopers Beach.
Hiking: Trails at Camp Hero State Park, Caumsett State Historic Park Preserve, Mashomack Preserve.
Boating/Fishing: Charters from Montauk, Port Jefferson, or Freeport.
Cycling: North Fork Wine Trail or Bethpage Bikeway.

Check local regulations for outdoor gear rentals.

Family-Friendly Itinerary

Activities for all ages to enjoy.

Fun for Everyone

Splish Splash Water Park (Riverhead) for water fun.
Long Island Children's Museum, Cradle of Aviation Museum (Garden City).
Rides at Adventureland (Farmingdale).
Farm visits for apple/pumpkin picking, corn mazes at Harbes Family Farm.

Art and Architecture Emphasis

Appreciate aesthetic beauty and design.

Artistic Explorations

Parrish Art Museum (Water Mill), Heckscher Museum of Art (Huntington).
Guild Hall (East Hampton), various art galleries in Hamptons/Sag Harbor.
Grandeur of the Gold Coast Mansions for architectural significance.
Discover unique local artist studios.

Spiritual and Wellness Journey

Recharge mind, body, and spirit.

Tranquil Experiences

Quiet beach walks, especially during the off-season.
Yoga classes at local studios.
Spa treatments, like those at Gurney's Montauk.
Contemplation in nature preserves.

Personalized Paths

Curating an itinerary around your specific passions enriches your Long Island experience.

Budget-Based Plans

Long Island provides choices for different budgets, allowing you to tailor your trip expenses.

Backpacker's Guide

Maximize savings while experiencing Long Island.

Budget Travel Tips

Accommodation: Camping in state parks or budget motels in western Long Island.
Food: Buy groceries, cook your own meals, casual diners, pizza by the slice.
Transportation: LIRR, local buses, walking. Hitchhiking is not recommended.
Activities: Free attractions like public beaches, state parks, self-guided town walks.

Free concerts and events in summer.

Mid-Range Traveler's Itinerary

A balance of comfort and value.

Balanced Planning

Accommodation: Mid-range hotels, B&Bs, or modest vacation rentals.
Food: Mix of casual and mid-range restaurants, occasional fine dining.
Transportation: Rental car for flexibility, LIRR for NYC trips.
Activities: Paid museum admissions, one or two winery tours, beach parking fees.

Luxury Experience Plan

Indulge in premium services and comfort.

High-End Travel

Accommodation: High-end resorts, boutique hotels, luxury vacation rentals (especially Hamptons).
Food: Fine dining, private chef experiences, exclusive beach club access.
Transportation: Private car services or luxury rental cars.
Activities: Private boat charters, exclusive art tours, luxurious spa treatments, high-end shopping.

Value-Focused Recommendations

Intelligent options for a rewarding trip within budget.

Cost-Saving Tips

Travel during the shoulder season for lower prices and fewer crowds.
Utilize LIRR off-peak fares (cheaper weekends/non-commuter hours).
Pack picnics for spending time on the sand to save on dining costs.
Look for restaurant week deals in spring and fall.

Planning Your Spending

Accommodation First

Your largest expense. Choose wisely to match your budget.

Transport Costs

Rental car, LIRR, or buses have different cost implications.

Activities & Food

Free attractions and self-catering reduce daily expenses.

Budgeting Insight

Flexible spending options for every traveler. Careful planning allows you to match your trip with your financial goals.

Seasonal Specialties

Long Island's seasons transform the island, offering unique experiences depending on your visit time.

Summer June-August

This season is beach-focused, ideal for swimming, surfing, and sunbathing.

Summer Fun

Enjoy outdoor concerts.
Fishing opportunities.
Whale watching tours are popular.
All major beaches are fully operational.

Book accommodations well in advance for summer.

Fall September-November

A season of harvest and colors.

Autumn Charm

North Fork wine harvest time of year with vineyard events.
Farm festivals, apple picking, pumpkin patches.
Spectacular fall foliage viewing.
Oyster season begins, offering fresh shellfish.

Winter & Spring

Each season gives a distinct character and appeal.

Winter December-March

Cozy B&B stays in quiet towns.
Seasonal seal watching tours.
Indoor attractions for cold weather.

Spring April-May

Gardens burst into bloom (Old Westbury, Planting Fields).
Early winery visits for intimate experience.
Birdwatching is popular when animals are migrating.

Festival or Event-Centered Visits

Plan your trip around specific events for an unique local experience.

Event Highlights

The Shinnecock Powwow (Labor Day weekend).
Li Restaurant Week.
Local craft fairs throughout the year.
Summer concerts and folk performances.

Off-Season Exploration Strategies

Discover the tranquil beauty of Li with fewer crowds.

Off-Peak Advantages

Benefit from lower prices on accommodation and a few activities.
Fewer crowds for a more serene experience.
A more local feel in many communities.
East End businesses may have altered hours or closures; verify in advance.

Seasonal Reminders

Check Ahead

Always confirm opening times and availability, especially during shoulder and off-seasons.

Weather Preparedness

Pack appropriate clothing; Long Island weather varies considerably by season.

Seasonal Planning

Aligning your visit with Li's seasonal offerings truly deepens your travel experience.

Long Island Itineraries