29 days in Long Island Itinerary

29 days in Long Island Itinerary

Created using Inspirock Long Island itinerary maker

©
Plan created by another user. Make it yours
1
Fire Island
— 6 nights
2
Southold
— 7 nights
3
Montauk
— 8 nights
4
Bohemia
— 7 nights

S M T W T F S
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22

6
nights
Fire Island

Fire Island ©
Fire Island is the large center island of the outer barrier islands parallel to the south shore of Long Island, New York. Appreciate the collections at Parrish Art Museum and Southampton History Museum. Escape the urban bustle at Long Beach and Ocean Beach. Get out of town with these interesting Fire Island side-trips: Southampton (Shinnecock East County Park, Cooper's Beach, &more), Lido Beach (in Lido Beach) and Hampton Bays (Ponquogue Beach, Church of St. Rosalie, &more). There's still lots to do: delve into the lush surroundings at The Sunken Forest, stroll around Robert Moses State Park, identify plant and animal life at Norman J. Levy Park & Preserve, and enjoy the sand and surf at Kismet Beach.

To see more things to do, ratings, maps, and more tourist information, read our Fire Island trip itinerary builder app.

New York City to Fire Island is an approximately 2-hour travel. In July, daily temperatures in Fire Island can reach 84°F, while at night they dip to 69°F. Cap off your sightseeing on the 28th (Tue) early enough to travel to Southold.

Things to do in Fire Island

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Highlights from your plan
Ponquogue Beach ©
Ponquogue Beach
Meschutt Beach ©
Meschutt Beach
Fire Island Lighthouse ©
Fire Island Lighthouse

7
nights
Southold

Southold ©
The Town of Southold is one of ten towns in Suffolk County, New York, United States. Popular historic sites such as Horton Point Lighthouse Nautical Museum and Oysterponds Historical Society are in your itinerary. Sannino Bella Vita Vineyard and Macari Vineyards are good opportunities to explore the local culture. Explore the numerous day-trip ideas around Southold: Quogue Wildlife Refuge (in Quogue) and Woodside Orchards (in Aquebogue). Next up on the itinerary: learn about winemaking at Raphael Winery, identify plant and animal life at Elizabeth A. Morton National Wildlife Refuge, and tour the pleasant surroundings at Orient Beach State Park.

For reviews, where to stay, other places to visit, and tourist information, you can read our Southold journey planner.

Traveling by journey from Fire Island to Southold takes 2 hours. When traveling from Fire Island in July, plan for little chillier days in Southold, with highs around 79°F, while nights are about the same with lows around 67°F. Cap off your sightseeing on the 4th (Tue) early enough to go by car to Montauk.

Things to do in Southold

Wineries · Parks · Museums · Wildlife

Side Trips

Highlights from your plan
Osprey's Dominion Vineyards ©
Osprey's Dominion Vineyards
Orient Beach State Park ©
Orient Beach State Park
Sannino Bella Vita Vineyard ©
Sannino Bella Vita Vineyard

8
nights
Montauk

Montauk is a census-designated place (CDP) that includes the hamlet with the same name located in the town of East Hampton in Suffolk County, New York, on the eastern end of the South Shore of Long Island. Deepen your sense of the past at sights like Montauk Point Lighthouse and St. Therese of Lisieux Catholic Church. For shopping fun, head to Main Beach or Round Swamp Farm. Change things up with these side-trips from Montauk: Bridgehampton (Children's Museum of The East End, Channing Daughters Winery, &more), Sag Harbor (Havens Beach, Foster Memorial Beach, &more) and East Hampton (Home Sweet Home Museum & Guild Hall). There's still lots to do: enjoy the sand and surf at Gin Beach, admire the majestic nature at Montauk Point State Park, cast your line with a fishing tour, and steep yourself in history at Pollock-Krasner House and Study Center.

To find other places to visit, where to stay, photos, and tourist information, use the Montauk online sightseeing planner.

Traveling by car from Southold to Montauk takes 1.5 hours. Expect a daytime high around 79°F in August, and nighttime lows around 66°F. Wrap up your sightseeing on the 12th (Wed) early enough to travel to Bohemia.

Things to do in Montauk

Outdoors · Parks · Museums · Beaches

Side Trips

Highlights from your plan
Fishing Charters & Tours
Main Beach ©
Main Beach
The Leiber Collection ©
The Leiber Collection

7
nights
Bohemia

Bohemia ©
Bohemia is a hamlet (and census-designated place) in Suffolk County, New York, United States. Take a break from the city and head to Fire Island National Seashore and Tobay Beach. Your inner history buff will appreciate Sagamore Hill National Historic Site and William Floyd Estate. Venture out of the city with trips to Gilgo Beach (in Babylon), Calverton National Cemetery (in Calverton) and Westhampton Beach (Pike's Beach & Cupsogue Beach County Park). There's lots more to do: look for all kinds of wild species at Avalon Park & Preserve, admire the majestic nature at Connetquot River State Park Preserve, tour the pleasant surroundings at Corey Beach, and stroll around Joel L. Lefkowitz Park at West Meadow Beach.

To see more things to do, photos, traveler tips, and more tourist information, you can read our Bohemia trip planner.

Drive from Montauk to Bohemia in 1.5 hours. Expect a daytime high around 82°F in August, and nighttime lows around 66°F. Finish your sightseeing early on the 19th (Wed) to allow enough time to travel back home.

Things to do in Bohemia

Parks · Outdoors · Beaches · Nature

Side Trips

Highlights from your plan
William Floyd Estate ©
William Floyd Estate
Cupsogue Beach County Park ©
Cupsogue Beach County Park
Fire Island National Seashore ©
Fire Island National Seashore

Similar plans

36 days in United States BY A USER FROM UNITED STATES June, slow & easy, popular sights Preferences: June Attraction style: Popular sights Pace: Slow & easy 4 days in Long Island BY A USER FROM UNITED STATES July, slow & easy, popular sights Preferences: July Attraction style: Popular sights Pace: Slow & easy 2 days in Long Island BY A USER FROM UNITED STATES July, popular sights Preferences: July Attraction style: Popular sights Pace: Medium 4 days in Long Island BY A USER FROM UNITED STATES July, popular sights Preferences: July Attraction style: Popular sights Pace: Medium 14 days in Long Island BY A USER FROM UNITED STATES July, popular sights Preferences: July Attraction style: Popular sights Pace: Medium 2 days in Long Island BY A USER FROM UNITED STATES June, popular sights Preferences: June Attraction style: Popular sights Pace: Medium 3 days in Long Island BY A USER FROM UNITED STATES June, popular sights Preferences: June Attraction style: Popular sights Pace: Medium 3 days in Long Island BY A USER FROM UNITED STATES July, popular sights Preferences: July Attraction style: Popular sights Pace: Medium 4 days in Long Island BY A USER FROM UNITED STATES June, popular sights Preferences: June Attraction style: Popular sights Pace: Medium 2 days in Long Island BY A USER FROM UNITED STATES June, popular sights Preferences: June Attraction style: Popular sights Pace: Medium 1 day in Long Island BY A USER FROM UNITED STATES July, popular sights Preferences: July Attraction style: Popular sights Pace: Medium 1 day in Long Island BY A USER FROM UNITED STATES June, kids, popular sights Preferences: June, kids Attraction style: Popular sights Pace: Medium
See more plans