September is my favorite month to hit the road—or more accurately, the water. still remember standing on Waiʻānapanapa’s black-sand beach in Maui during a breezy September afternoon. After the 2023 wildfires, visiting Maui in 2026 requires respectful tourism, but September remains magical. There was no jostling for space to set down my camera gear, and the island felt incredibly peaceful. If you are looking for the best islands to visit in september, this shoulder season is an absolute goldmine.
After visiting islands across the U.S., I’ve found that September is the absolute best time for an American island getaway. The chaotic summer crowds completely disperse after Labor Day, resort rates hit their sweet spot with significant shoulder-season discounts, and the ocean water holds onto its summer warmth, especially along the East Coast and Caribbean.
However—and this is a crucial point—not every island is a great choice in September. September is the absolute peak of the Atlantic hurricane season, meaning parts of the Caribbean and Florida Keys carry weather risks. On the flip side, destinations like New England or the Pacific Northwest are at their absolute prime. I’ve personally navigated these weather shifts so you don’t book the wrong island. Timing is everything. I’ve made the mistakes so you don’t have to.
Drawing on my experience visiting islands from Hawaii to the U.S. Virgin Islands and the Florida Keys, I’m sharing a list of the 15 best U.S. islands to visit in September—complete with rankings, details, and the insider tips I wish I’d had myself.
Let’s get started.
1. Maui, Hawaii
When I first drove the ‘Road to Hana’ in August, I spent more time in traffic than actually driving. The ‘Road to Hana’ is a 64-mile route featuring 620 curves and some of the most spectacular coastal scenery in the United States. In July, long lines of cars form at every waterfall viewpoint. However, when I returned to Maui the following September, I found parking immediately at the Twin Falls trailhead, the Wailua Valley Lookout, and even the Garden of Eden Arboretum. At Waiʻānapanapa Black Sand Beach—usually a very crowded spot—I saw only 50 to 60 people on a Tuesday morning.
Watching the sunrise from Haleakalā Volcano is on everyone’s bucket list, yet parking reservations (which are mandatory) are easy to secure in September While peak summer slots sell out within minutes of opening 60 days in advance, September offers a massive relief. I easily snagged a ticket through Recreation.gov’s last-minute 48-hour release window at 7:00 AM HST without any stress.The view of the sunrise from an altitude of 10,023 feet—clouds below and stars above gradually giving way to an orange glow—is the closest I have ever come to a spiritual experience in nature.
Things to do:
- Go snorkeling at Molokini Crater (book an early morning tour for good visibility)
- Go hiking in Haleakalā National Park — the trails remain open and aren’t too crowded
- Support West Maui’s local economy by dining at reopened spots in north Front Street or the Cannery Mall in Lahaina. (Note: Keep a respectful distance from the historic commercial core which is fenced for rebuilding).
- Drive the ‘Road to Hana’ without the summer crowds
- Take advantage of flat ocean conditions for a clear-water kayak tour along the Makena Coastline (since the official Humpback whale season doesn’t start until November).
Where to stay: Stay in West Maui areas like Kaanapali or South Maui areas like Wailea for premier beach access. If you love nature, stay in Haiku or Paia—these places are quiet and affordable, and offer a better experience of the “real” Maui.
My honest advice: September is the ‘shoulder season’ (neither too crowded nor completely empty). Since Maui is one of the best islands to visit in september, book your Molokini snorkel boat tours and Road to Hana rental cars 2 weeks in advance to lock in those low shoulder-season prices.
2. Key West, Florida
Let me be clear in terms of weather, September isn’t the best time for Key West. It’s hot (around 86°F) and humid, and most afternoons bring storms and rain. But here’s the trade-off: if you embrace the humidity, early September brings incredible events like the annual ‘Just a Few Friends’ festival celebrating Jimmy Buffett’s legacy. It’s a period where you get amazing resort deals, cheap flights, and a vibrant local vibe without the suffocating winter pricing.
Most people visit Key West in winter or spring, when the place is packed with cruise ship crowds and the famous sunset celebration at Mallory Square feels like Times Square on New Year’s Eve. I made that mistake once, too.
Then, I visited in September.
The sunset scene at Mallory Square in September: maybe 50 people, a juggler, a man with his trained cats, and a spectacular Gulf of Mexico sunset beyond your wildest imagination—all in complete tranquility. In February, that same spot is packed with 800 people, and you have to watch the sunset over the tops of other people’s heads.
Things to do:
- Watch the sunset at Mallory Square (without fighting for a spot)
- Kayak through the backcountry mangroves
- Go snorkeling or diving at Looe Key Reef (one of the best reefs in the Florida Keys)
- Visit Hemingway’s house (six-toed cats and all)
- Attend the ‘Just a Few Friends’ street parade or join a clothing-optional snorkel trip during Womenfest if visiting during early September.
Where to stay:
- Duval Street: Ideal if you want to be steps away from the famous nightlife.
- Old Town: Best for a classic, walkable historic district lifestyle.
Weather tip: Plan outdoor activities for mornings. Afternoon thunderstorms are common and usually intense but brief. The evenings are warm and clear — perfect for outdoor bars and restaurants.
3.Mount Desert Island, Maine
Mount Desert Island is home to Acadia National Park—New England’s only national park—and September brings something special here: the first glimpses of autumn colors appear on the mountains, while the ocean water remains warm enough for kayaking. It is like enjoying two seasons at once.
Bar Harbor, the island’s main town, is a quintessential example of New England charm, featuring lobster shacks, whale-watching boats, and Victorian-style inns overlooking a harbor filled with sailboats. Bar Harbor gets very crowded in July and August, but things quiet down a bit after Labor Day.
I have driven along the Park Loop Road in both July and September. In July, you have to arrive by 5:00 AM to find a parking spot at the summit of Cadillac Mountain—the first place on the U.S. mainland to see the sunrise. In contrast, when I visited in September, I simply logged onto the Recreation.gov Acadia Page two days prior at 10:00 AM ET to snag one of the 70% re-released vehicle passes. Arriving at 6:30 AM with my pass, the summit was blissfully quiet compared to the summer madness.
Unforgettable Things I Did Here in September:
- Hiked the Precipice Trail—climbing up the vertical rock face using iron rungs. Since the seasonal falcon nesting closures on the Acadia National Park Alerts usually lift by late August, September is the perfect window to safely conquer this adrenaline-pumping climb.
- Biked along the 45-mile carriage road network, passing through forests and over stone bridges—it was the best biking experience I’ve ever had.
- Cracked open a whole wood-fired, seawater-boiled lobster at the historic Trenton Bridge Lobster Pound just before the causeway. Market prices fluctuate, but paying around $28 for a fresh 1.5-pound catch on a scenic waterfront picnic table felt like a steal.
Where to stay:
- Bar Harbor: The best location for walking access to fantastic waterfront restaurants, shops, and harbor tours.
- Southwest Harbor (quiet area): An excellent spot for budget-friendly coastal cabins and a peaceful atmosphere reminiscent of a local fishing village.
My honest advice: September mornings in Maine are very cold (temperatures often drop to the low 40s°F). When you head to Cadillac Mountain at sunrise, make sure to bring a thick windbreaker, a beanie, and some hot coffee. Believe me, the wind at an elevation of 1,000 feet cuts right through a standard summer hoodie!
4. Hilton Head Island, South Carolina
Hilton Head has a reputation as a golf resort destination—and yes, there are 24 championship golf courses here. But Hilton Head also boasts 12 miles of beach, 60 miles of paved bike paths, opportunities for dolphin watching and kayaking, and a food scene that punches well above its weight for a resort town.
The island’s development has been thoughtfully executed: trees were preserved, building heights were kept low, and resort areas are tucked away beneath a canopy of live oaks and Spanish moss—making it feel more like a natural barrier island than a typical resort strip.
I took a kayak tour through the marshes of the Back River in September and watched a pod of bottlenose dolphins hunting fish in the shallows, less than 30 feet from our kayaks. That is Hilton Head in September—wildlife encounters, open beaches, and plenty of space to truly enjoy the island.
Things to do:
- Kayak through the back marshes to spot dolphins (guided tours are excellent, and prices are lower in September)
- Cycle along the trails of ‘Sea Pines Forest Reserve’ at sunrise
- Dine at Hudson’s Seafood House on the Docks—operating out of a 1910s oyster factory, they serve incredible local shrimp shucked straight from the incoming boats.
- Play a round of golf at a course where it was impossible to get a weekend tee time during the summer
Where to stay:
- Sea Pines Resort:Best if you want direct access to championship golf courses, bike trails, and the iconic Harbour Town Lighthouse.
- Coligny Beach Area: Ideal for budget-friendly beach rentals and walking-distance access to public beach parks and local dining shops.
My honest advice: September marks the end of the hatching season for ‘Loggerhead’ sea turtles. If your beachfront rental property faces the ocean, please turn off all balcony lights and close the curtains or blinds after 10:00 PM. Local beach patrol teams strictly enforce this so that the hatchlings can safely make their way toward the sea, guided by the moonlight. It is a wonderful local initiative that you can be a part of, too.
5. Kauai, Hawaii
There is a place called ‘Kalalau Lookout’ nestled deep within Kōkeʻe State Park on Kauai’s rugged western side.You drive through a forest shrouded in clouds to get there, step out of your car, and suddenly find yourself 4,000 feet above the Na Pali Coast—where lush green cliffs, 3,000 feet high, plunge straight into the blue ocean. The view is so magnificent that the moment you see it, you feel compelled to take a photograph.
September is the best month for hiking in Kauai, a major highlight of the island. The Kalalau Trail—which runs along the Na Pali Coast and is, in my honest opinion, the most spectacular coastal hike in America—requires navigating through forests, and these trails are much more accessible in September compared to the summer months. I hiked to Hanakapiai Beach (the initial two-mile stretch of the Kalalau Trail) on a Wednesday in September and crossed paths with perhaps only eight other hikers the entire time.
The island’s waterfalls—Wailua Falls, Opaeka’a Falls, and Secret Falls—flow vigorously in September following the intermittent summer rains; furthermore, the kayaking trip up the Wailua River to Secret Falls ranks among the most enjoyable half-days I have ever spent on any island.
Things to do:
- Kayaking up the Wailua River to a hidden waterfall—in September, you can paddle leisurely without bumping into other kayaks.
- Snorkeling at Tunnels Beach (Makua) on the North Shore—featuring massive lava tubes, green sea turtles, and stunning underwater visibility. Always check the daily safety updates on the local Kauai Beach Guide before heading out.
- Watching the sunset from Poipu Beach—be sure to bring a blanket, as you won’t want to leave.
- Eating a “plate lunch” from a roadside truck in Hanapepe—my favorite “local” meal on Kauai, which cost me $11.
Where to stay:
- Poipu—the best spot for plenty of sunshine, swimmable beaches, and resort dining.
- Princeville—an excellent location for spectacular cliff views and premium luxury resorts (though the North Shore experiences more tropical rain).
My honest advice: If you rent a Jeep or 4WD to drive on the rugged, unpaved roads leading to Polihale State Park, read the rental terms carefully. Major corporate rental companies often void your insurance coverage if you drive there. To protect yourself, book a vehicle through specialized local companies like ‘Island Cars Kauai,’ which explicitly permits driving their 4WD vehicles to Polihale.
6. Mackinac Island, Michigan
Mackinac Island is situated in the Straits of Mackinac, between Michigan’s Upper and Lower Peninsulas; the moment I stepped off the ferry and heard the clip-clop of horse-drawn carriages on Main Street, I understood why people return here time and again. Cars have been banned on the island since 1898—there are no Ubers or rental cars here. The only ways to get around are by walking, cycling, or taking a horse-drawn carriage ride. If you are researching the best islands to visit in september for pure relaxation, this vehicle-free sanctuary tops the list.
Being on Mackinac feels like stepping back in time, yet the island also boasts stunning natural beauty, a well-preserved historic fort, and the iconic Grand Hotel, which features a spectacular 660-foot Victorian front porch—the longest in the world.
By this time, the summer crowds visiting the fudge shops have departed, the weather remains pleasant (with highs around 60–65°F), and the colors of autumn begin to appear along the shoreline. Cycling the 8-mile perimeter road is one of the most enjoyable and effortless rides I have ever experienced.
Things to do:
- Rent a bicycle and circumnavigate the island (8-mile paved road around the perimeter)
- Try the famous Mackinac Island fudge (the island literally perfected it)
- Visit Fort Mackinac (1780s British fort with military demonstrations)
Where to stay:
- The Grand Hotel: Best for a memorable, luxurious, and historic experience with superb hospitality.
- Main Street Hotels: Excellent for a comfortable and affordable boutique stay, just steps away from the docks and fudge shops.
My honest advice: Although Shepler’s Ferry and Arnold Transit operate convenient routes from Mackinaw City and St. Ignace, their schedules change significantly after Labor Day. Be sure to check the “last boat departure time” at the dock each day so you don’t accidentally get stranded! Plan to stay for at least two nights to truly enjoy the island after the day-trippers have headed home.
7. Lanai, Hawaii
Let me be upfront about Lanai: it isn’t for everyone. There are virtually no chain restaurants, the main town (Lanai City) has just one main street,and getting there requires a small plane or the official Expeditions Passenger Ferry operating out of Maalaea Harbor on Maui. The island is 98% owned by billionaire Larry Ellison, who transformed it into an ultra-luxury eco-sanctuary. While peak winter rates at the two legendary Four Seasons resorts easily soar past $2,200 a night, September introduces their baseline shoulder-season pricing. It’s still a splurge at around $1,200–$1,400, but you get world-class luxury wrapped in absolute, uninterrupted silence.
Hulopoe Beach is the kind of beach that makes you resent every other beach you’ve ever visited. White sand, clear water, spinner dolphins visiting the bay in the morning, and—in September—hardly anyone else around. I spent three hours on that beach in September and saw perhaps only 15 people in total.
Things to do:
• Snorkeling in the tide pools at Hulopo’e—encountering octopuses and reef fish, and the feeling of being the only person to have discovered this place
• Having a sunset dinner at Nobu Lanai (at the Four Seasons)—which cost less than the same meal would in Tokyo
• Hiking to Pu’u Pehe (Sweetheart Rock)—a rock formation in the middle of the ocean with a story so heartbreaking that I immediately had to Google the full tale
Where to Stay:
- Four Seasons Resort Lanai: Best for seaside luxury, a golf course set against red-dirt cliffs, and easy walking access to Hulopoe Bay.
- Hotel Lanai (Lanai City): A great spot to experience a historic 1920s plantation-style lodge on a budget, amidst the cool mountain air.
My honest advice: There are no ride-sharing services like Uber or Lyft on Lanai. If you are visiting for a day trip via ferry, you should book a local shuttle (cash only) or rent a 4WD vehicle in advance. Don’t arrive at Manele Harbor assuming a taxi will be waiting for you, or you’ll end up stranded at the dock.
8. Marco Island, Florida
Marco Island sits at the edge of the ‘Ten Thousand Islands’—a 2,500-square-mile network of mangroves and waterways that forms the western boundary of Everglades National Park. Most tourists never venture beyond the resort beaches. That is their loss and your gain.
In September, Marco Island’s luxury resorts slash their rates by 30–40%. A world-class room that easily clears $950 during the peak winter rush drops closer to $450 during the early autumn dip.By September, the Gulf waters reach temperatures of 88°F—warmer than most backyard pools—and the water remains perfectly calm in the mornings.
September is a truly spectacular time in Marco for those who love wildlife and the water. The surrounding waters teem with dolphins; I have been on boat trips where bottlenose dolphins surfed in our boat’s wake for a full 20 minutes. The area is renowned for having some of the best shelling in Florida, and the afternoon storms common in September actually improve the quality of the shells found the next morning by churning up fresh ones to the surface.
Things to do:
- Join the ‘Paddle Marco Mangrove Tour‘ and spot hidden tree crabs and manatees as you navigate through spectacular saltwater tunnels.
- Search for rare calico scallops and lightning whelks in the tidal lagoons of the famous Tigertail Beach.
- Rent a two-seater catamaran from ‘Craig’s Cat Tours’ and cruise through the pristine waters of the ‘Ten Thousand Islands’.
Where to stay:
- JW Marriott Marco Island Beach Resort: Best for ultimate luxury, an adults-only Balinese-style private zone, and direct beach access.
- Hilton Marco Island Beach Resort: Excellent for a premium boutique experience and easy access to beachfront dining options.
My honest advice: Even if the resort room rate is very low, don’t overlook the necessary local extra costs. At large beachfront hotels here, a hefty resort fee of $60 per day and parking fees of up to $48 per day can be added to your final bill. Budget for these fixed extra expenses in advance so you aren’t hit with a shocking bill at check-out when you were expecting an affordable trip.
9. Sanibel Island, Florida
Sanibel Island has a unique shape—because it curves from east to west in the Gulf of Mexico, it creates a spot where vast quantities of seashells accumulate; there is nowhere else quite like it in North America. After a September storm (and such storms occur frequently), the beach turns truly white—not from sand, but from shells.
I have visited beaches in about eight different countries, yet I have never bent down to pick things up as often as I did while strolling along Sanibel’s Lighthouse Beach at low tide one morning after a storm. I filled a mesh bag in just 45 minutes, having walked fewer than 200 steps.
The “Sanibel Stoop” is a real thing—that is what locals call the posture of shell-hunters who are constantly bending over as they walk. In September, you will find yourself doing the same thing within ten minutes of arriving.
Things to do:
- Go kayaking among the mangroves
- Tour the newly expanded Bailey-Matthews National Shell Museum & Aquarium—the only museum in North America dedicated purely to malacology, now featuring a world-class living gallery of aquariums.
- While exploring the famous J.N. ‘Ding’ Darling National Wildlife Refuge by car, bicycle, or tram, you can spot roseate spoonbills and migratory waterbirds within its pristine mangrove ecosystem.
Where to stay:
- Periwinkle Way Corridor: The best spot for cozy historic cottages, boutique coastal inns, and easy access to bike trails.
- South Seas Island Resort: Perfect if you are looking for premium luxury by the sea; it is located on nearby Captiva Island, just a short, scenic drive away.
My honest advice: The Sanibel Causeway is fully restored and operational, but the toll system is now completely cashless. You need a local prepaid transponder (costing $6) to drive across; otherwise, a ‘Toll-by-Plate’ photo bill will arrive in your mailbox at the higher rate of $9. Since afternoon storms are common in September, head to the beach to collect seashells and conchs exactly one hour after low tide following a heavy downpour—that is when the rarest treasures wash ashore.
10. Nantucket, Massachusetts
Nantucket lies 30 miles off the coast, accessible only by ferry or small plane. It boasts the best-preserved 19th-century downtown of any island in America. With its cobblestone Main Street, grey-shingled houses featuring white trim, and hydrangeas blooming through September, the place looks as though it were designed by someone who loved New England so much they simply didn’t want to change a thing.
Visiting Nantucket during the peak summer season is a real challenge. Ferries fill up weeks in advance, restaurant reservations must be made months ahead, and the compact downtown feels like an obstacle course. In September, however, you arrive on a half-empty ferry, walk straight into a restaurant, and feel as though you’ve discovered a secret that 30,000 other people have somehow forgotten.
Things to do:
- See the 46-foot-long sperm whale skeleton at the historic Nantucket Whaling Museum and enjoy a stunning view of the harbor from the rooftop deck.
- Rent a beach cruiser bike and cycle along scenic paths to the pristine, quiet sands of Madaket Beach.
- Take an evening stroll around the famous Brant Point Lighthouse and watch the yachts entering through the narrow harbor channel.
Where to Stay:
- Downtown Historic District – Offers easy walking access to boutiques along cobblestone streets, fine dining, and the high-speed ferry dock.
- Siasconset (Sconset Village) – An excellent spot for seaside peace and seclusion, featuring historic rose-covered fishing cottages and stunning views directly from the cliff’s edge.
My honest advice: September is a wonderful month, but after Labor Day, many seasonal restaurants and boutique ice cream shops either reduce their operating hours or close completely for the winter. Book your spot on the Hy-Line Cruises or the Steamship Authority high-speed passenger ferry in advance, as their daily trip frequency drops significantly as the month progresses. high-speed passenger ferry in advance, as their daily trip frequency drops significantly as the month progresses.
11. Amelia Island, Florida
Amelia Island is the northernmost barrier island on Florida’s Atlantic coast, and its character is distinct from any other island in the state.
The island’s main town, Fernandina Beach, features a historic Victorian-era district—comprising 50 blocks of beautifully preserved 19th-century architecture—which has earned a place on the National Register of Historic Places. Watching the sunset at the end of Centre Street while enjoying a dinner of local shrimp is one of the simple pleasures I cherish most during my travels in America.
Amelia Island is quiet and affordable in September. The beach—stretching 13 miles along the Atlantic coastline—is wide, flat, and largely free from crowds. During sea turtle nesting season (which runs through October), sections of the beach are roped off at night, but this also offers the chance to see hatchlings making their way to the ocean—one of the most memorable and heartwarming wildlife experiences I have ever had.
Things to do:
- Stroll through the historic district of Fernandina Beach on a quiet weekday morning
- Book an experience to see sea turtle hatchlings through the local naturalist program
- Paddle through the saltwater marsh creeks in the island’s interior—where ospreys and herons can be seen all around
- Visit ‘Fort Clinch State Park,’ one of the best-preserved 19th-century brick forts in the United States. Here, you can hike through maritime hammocks (coastal forests) and search for prehistoric shark teeth on the beach.
Where to stay:
- Fernandina Beach Historic District: The best area to stay in cozy, Victorian-era bed-and-breakfasts located within walking distance of local dining spots on Centre Street.
- South Island Coastline (Summer Beach/Omni Resort area): The best area for magnificent oceanfront luxury villas, excellent golf courses, and direct access to a private beach.
My honest advice: if you are planning your trip for mid-to-late September, be sure to check the schedule for the annual ‘Amelia Island Jazz Festival.’ It features world-class musical performances at unique, intimate local venues. Also, since storm activity in the Atlantic peaks in September, opt for morning slots for boat tours or marsh kayaking trips—as stormy clouds can build up rapidly along the coast in the afternoon.
12. Catalina Island, California
Here is the lowdown on Catalina Island in September: it lies 22 miles off the Los Angeles coast—a 75-minute ferry ride away—boasts water temperatures of 70°F, has absolutely no cars, and sees far fewer crowds than in July or August.
It is one of the best and most affordable places to visit in California.
Avalon, the island’s only city, has the atmosphere of a Mediterranean port—waterfront restaurants, colorful buildings dotting the hillside, and the famous Catalina Casino (which, incidentally, never actually hosted gambling) situated near the bay. Golf carts are the fastest vehicles on most of the island’s roads, and even they are restricted to specific areas.
For me, the highlight is snorkeling at Casino Point Marine Park. This underwater park, located right off the shore, is a kelp forest reserve. In September, visibility in the water reaches 30 to 40 feet; the kelp sways gently with the currents, and the Garibaldi—California’s state marine fish, with its brilliant orange hue—darts through the kelp fronds like a flickering flame. I have snorkeled in many places, but the experience at Casino Point in September is truly extraordinary.
Things to do:
- Go snorkeling or diving at Casino Point Marine Park — here, you can see kelp forests, Garibaldi fish, and spectacular underwater scenery in September.
- Enjoy a zip-line tour over the canyon.
- Go kayaking in the sea caves located on the other side of the island.
Where to Stay:
- Avalon Waterfront Corridor: The best spot for direct beach access, walking distance to Green Pleasure Pier, and excellent outdoor dining options.
- Two Harbors (West End): Perfect if you prefer secluded camping, simple cabins, and a completely peaceful atmosphere away from the main tourist area.
My honest advice: a round-trip ferry ticket costs around $99 per adult, so book your weekend slots online in advance. If you wish to rent a golf cart to explore the beautiful hills of Avalon, keep in mind that local regulations limit tourist rentals to a maximum of two consecutive hours (rates typically range from $65 to $80 per hour). Vehicles are not available for overnight or full-day rental on the island, so wear comfortable walking shoes for getting around.
13. Big Island of Hawaii
The ‘Big Island’ is the only place in the world where, in a single day, you can swim with manta rays at night, witness flowing lava in the early morning, and gaze at the stars from above the clouds. I did exactly this during my trip in September, and I still find it hard to comprehend how all of this can exist on a single island.
Technically, the ‘Big Island’ is a blend of ten distinct climate zones all on one landmass. Within just a 30-minute drive, you can travel from lush tropical rainforests to barren lava fields and then to snow-capped mountain peaks. It might sound strange, but it is absolutely true.
Hawaii Volcanoes National Park is the main attraction here, and September is one of the best times to visit. The park’s ‘Chain of Craters Road’ winds its way down to the coast through miles of solidified lava fields. While Kīlauea’s summit inside Hawaiʻi Volcanoes National Park is currently in a highly dynamic, episodic fountaining phase, you need to track the live updates. If you catch an active eruptive episode—which has been bursting from the vents inside Halemaʻumaʻu Crater every few weeks—the sight of 500-foot lava fountains illuminating the sky is an unearthly experience. Between episodes, you will witness massive volcanic steam vents reshaping the caldera floor.
Things to do:
- Book a night snorkeling boat tour off the Kona Coast and swim alongside massive, magnificent manta rays as they feed beneath illuminated boards.
- Drive along the scenic Chain of Craters Road to the spot where ancient lava flows completely swallowed the historic coastal highway.
- Take a guided sunset tour to the Mauna Kea Visitor Center or the summit to stargaze and enjoy world-famous views from above the cloud layer.
- Where to stay: Kailua-Kona Coast—the best spot for sunny beach days, luxurious oceanfront resorts, and easy access to docks for manta ray boat tours.
- Volcano Village or Hilo side—great locations for historic rainforest lodges, early morning access to the national park, and viewing tropical waterfalls.
My honest advice: don’t underestimate the sheer size of the ‘Big Island.’ Driving from the Kona resort area to the volcano’s crater (caldera) takes a full 2 to 2.5 hours each way. Since bookings are easy to secure in September, rent a reliable car and split your stay: spend three nights in the sunny Kona area for ocean-related activities, and two nights in ‘Volcano Village’ or ‘Hilo’ to explore the rainforest without the exhausting daily trek across the island.
14. Kiawah Island
Kiawah Island is a perfect example of coexistence—it is a private resort island that is also a genuine wildlife sanctuary. Its 10-mile-long beach serves as a nesting ground for loggerhead sea turtles, while the coastal forests are home to deer, bobcats, and alligators. Yet, amidst this wild landscape, you’ll find five-star spa resorts and world-class dining. If you are curating a bucket list of the best islands to visit in september where pristine luxury meets untouched nature, this low-country escape deserves your attention.
In September, loggerhead sea turtle hatchlings emerge from their eggs; no bigger than a child’s palm, they crawl across the beach toward the ocean under the cover of darkness. Kiawah’s “Turtle Patrol” volunteers check the nests every morning, and if you are lucky enough to witness the hatchlings emerging, it is a sight that makes time seem to stand still.
Things to do:
- Cycle along the island’s 30 miles of paved trails that wind through maritime forests.
- Go kayaking in the lagoons of Night Heron Park and spot waterfowl and the occasional alligator.
- Visit the spectacular Kiawah Beachwalker Park early in the morning to enjoy wide sand flats before the vehicle parking lot hits capacity.
Where to Stay:
- The Sanctuary at Kiawah Island Golf Resort: Best for ultimate five-star oceanfront luxury, world-class spa facilities, and premium Atlantic views.
- East Beach Village: Ideal for renting mid-range private coastal villas, cozy townhomes, and securing quick bike-path access to night lagoon trails.
My honest advice: Kiawah Beachwalker Park is the only public beach access point on this private island, and parking costs $15 on weekdays and $20 on weekends. To save money and avoid long morning lines, rent a bicycle near Freshfields Village—entry to the park is completely free for pedestrians and cyclists! Also, please follow the Kiawah Island Turtle Patrol’s guidelines: completely flatten any sandcastles and fill in any holes you’ve dug before leaving the beach so that baby turtles don’t get trapped in them at night.
15. Oahu, Hawaii
Most people think of Oahu as a crowded place—with throngs of people in Waikiki, traffic at Diamond Head, and jams caused by tour buses on the North Shore.While this is true during the chaotic summer months, those crowds vanish almost entirely by the fall. If you are trying to map out the absolute best islands to visit in september, Oahu during this breezy shoulder season is an incredible choice.
I once spent ten days on Oahu in September, and it was my best experience on the island. We hiked the iconic Diamond Head (Lēʻahi) Summit Trail. Thanks to the out-of-state tourist reservation system managed through the Hawaii State Parks Portal, the crowd flow is strictly controlled. By locking in our time slot online, we conquered the historic bunker stairs in 45 minutes without fighting massive bottlenecks. The North Shore, famous for winter surfing, is calm in September and ideal for swimming; the gentle, quiet waves are perfect for beginners.
The atmosphere in Waikiki is completely different in September. Yes, there is still a buzz—after all, it is Waikiki—but there is plenty of space between the beach chairs. ABC Stores aren’t overcrowded, either. You can get a table at Duke’s without waiting two hours.
Beyond the lack of crowds, what truly makes Oahu special in September is the water. The Pacific Ocean temperature reaches around 80°F, water clarity at Hanauma Bay is at its peak for the year, and afternoon breezes ensure you don’t feel stifled or uncomfortable, even when the temperature hits 83°F.
Things to do:
- Hike Diamond Head (arrive before 7 AM—trails fill up early, even in September)
- Snorkel the crystal waters of the Hanauma Bay Online Booking System window exactly 2 days in advance at 7:00 AM HST (Note: The preserve is strictly closed every Monday and Tuesday for ecosystem rest).
- Drive along the Windward Coast—stop at Lanikai Beach, the Kailua Pillbox Hike, and Waimanalo Beach
- Try a ‘plate lunch’ at a local spot (like Zippy’s or Rainbow Drive-In)—it gives you a taste of authentic Hawaiian food
Where to stay:
- Waikiki Beach Corridor – Here, you can enjoy magnificent resort towers, walkable access to great restaurants and shops, and a vibrant nightlife.
- Kailua (Windward Side) – Here, you will find quiet and comfortable rental homes near world-famous soft-sand beaches.
- My honest advice: the ocean surface remains calm during the summer, but by late September, the first winter swells begin to arrive at the North Shore beaches. It is a great time for visitors because swimming is easier, and you can also sense the shifting ocean currents. Before entering the water, be sure to pay attention to the ocean warning flags posted at Waimea Bay.
Frequently Asked Questions
Q1 Do I really need to make advance reservations for Hawaii and the islands of New England in September?
Ans: Absolutely. Even though the heavy summer crowds thin out after Labor Day, many major natural tourist destinations now enforce strict rules regarding visitor numbers. You are required to make online vehicle reservations for Cadillac Mountain in Acadia National Park and Diamond Head State Monument on Oahu. Furthermore, tickets for snorkeling spots like Hanauma Bay sell out within minutes of online booking opening.
Q2 Can I combine an island getaway with a visit to a US national park in September?
Absolutely—many of the fantastic islands on this list are either located within or right next to magnificent protected areas. For instance, Mount Desert Island encompasses the entirety of Acadia National Park, and you can easily visit Hawaii Volcanoes National Park from Hawaii’s Big Island. If you want to take your autumn trip beyond just the beach, exploring destinations on the mainland is a great idea. For comprehensive information on the best places to visit on the mainland, check out my detailed guide: ‘20 Best National Parks to Visit in September.’ It covers locations across the country that offer great weather, wildlife viewing opportunities, and uncrowded trails.