Hear Me Out—Instead of Island-Hopping, Limit Your Vacation to Exactly One

Image of La Residencia Belmond Hotel is Deia Mallorca, The Northern Lights above Eleven Delpar Farm in Iceland, A red ladder at Rockhouse Hotel in Jamaica, and Manshausen hotel with a rainbow in the background — (Image credit: Courtesy of Belmond, Eleven, Rockhouse, and Adrien Giret)

Visiting a new place can be overwhelming. Agendas start feeling like checklists and FOMO kicks in trying to squeeze in every stop. While many travelers enjoy a high-energy approach, I find it hard to keep up with, and would take a more low-key approach when planning a trip.

To ground my plans, I build my itinerary around an island. I find a perimeter relaxing, knowing I can only go so far, and the horizon a subtle reminder to slow down. It's easy to go from a bustling downtown to a secluded shore in an afternoon, and with water on all sides, my itineraries become more intentional and personal. Less time in transit, no pressure to “maximize,” no frantic zigzags across a region. Just slow mornings, micro-adventures, and evenings that almost always end on a beach.

A recent trip to Crete crystallized this approach. A quiet swim in a rocky cove to start the day, a hike and then pottery class in town, a late mezze lunch, and an evening that dissolved by the sea. Nothing required more than a few hours, yet everything felt within reach. I felt my senses honed and observations clear—the hue of golden hour, the salt in the wind, the tangy flavor of feta. The isolation helped me focus.

Below, I’ve pulled together five island itineraries that embody this philosophy of locality and activities to structure your day around, where you can craft simple agendas that lean into authenticity, immersion, and lightly structured days. You’ll leave feeling like you really got to know a place.

Crete, Greece

The vibe: microclimates, secluded coves, volcanic wine, and winding old towns by the sea. The island is vast, with intimate inlets and a range of casual, toes-in-the-sand dining, to a budding luxury scene.

Stay: The JW Marriott Crete is only 20 minutes from Chania International Airport, the island's major airport. The resort has a private coastline for snorkeling and is a great jumping-off point for other adventures.

What to do:

areal view of the JW Marriott Crete on a sunny day showing a turquoise blue sea and a speed boat.

The mornings are the best for leisurely swims, as sea-life is more active earlier in the day. And obviously, there's no need to rush a beach day if the vibe is right.
Plan a meal or two in town. I suggest Chania, where tavernas covered in bougainvillea are abundant. Take in a long lunch or low-lit dinner between shopping for olive wood goods at the local boutiques.
Visit a boutique winery in the foothills (look for Vidiano or Assyrtiko grapes) and discover how much personality Cretan wines possess.
Try a pottery class to get in touch with Greece's history of ceramics.
Rent or charter a boat for easy access to secluded beaches and archaeological sites. This is usually a half- or full-day activity so pack a lunch. Take in the varying rock faces from the water, then ease into tiny coves normally accessed by long treks.

the author walking in Chania, the bow of a boat in an inlet on the sea, an archeological site

Iceland

The vibe: Geothermal pools, volcanic drama, moody coast. Iceland remains on my bucket list, and since I can't speak from experience here, I asked the experts at Black Tomato for some tips.

Stay: Eleven Deplar Farm, one of the best lodges in the world, is surrounded by rugged mountains and rivers. If you're looking for an urban vibe, check out the Reykjavik EDITION.

How to plan your time: Plan lightly structured days around pockets of landscapes like lagoons, cliffs, and waterfalls.

What to do:

a whale jumps out of the water in dark bay in iceland with mountains in the background

After landing in Reykjavik, get your IG pics in town and at the Blue Lagoon, then head north—it's far less touristy and more authentic than the south. Remember to check for local travel alerts before heading to the Reykjanes Peninsula—the area has experienced closures due to recent volcanic activity.
Head to Akureyri, a charming small city with colorful houses, great coffee shops, and a thriving arts scene. It's surrounded by low-key fishing villages that feel frozen in time. You won't find many other tourists here and it's a great place to see the Northern Lights.
Go whale watching from Húsavík in Skjálfandi Bay, where humpback whales, blue whales, minke whales, and dolphins frequent. The coastal town itself radiates genuine Icelandic coastal charm.
The Tröllaskagi Peninsula (Troll Peninsula) includes Lake Mývatn, a geothermal wonderland with lava formations that look like trolls. Relax in hot springs and the Mývatn Nature Baths.

full waterfalls flowing in iceland in the fall

Mallorca, Spain

The vibe: quiet rocky coves, luscious green mountains with winding roads, a vibrant cultural center, and stone hillside towns. Mallorca's got range. One afternoon you could be strolling in the charming inlet of Deia and dining on seafood paella in vibrant Palma by evening.

Stay: Ca's Xorc Luxury Retreat & Restaurant: Nestled within an ancient olive grove near Sóller, a charming seaside town. It's a short drive from the water and offers insane views of the mountains and horizon. If budget allows, splurge on the legendary La Residencia, A Belmond Hotel, Mallorca, located in Deià, or at least stop by Bar Miro for sunset spritzes.

What to do:

Plan a mini roadtrip from Palma to Deià (or the other way), stopping in Valldemossa for lunch. Spend some time on Cala de Deià, one of the island's most popular beaches. It's intimate with a dramatic mountainous backdrop, and the town itself looks like a storybook with green shutters and tiers of olive groves.
Rent a boat on the south side of the island and check out the island's most iconic inlets from the water. Make sure S'Almonia, Cala Llombards, and Caló del Moro are on the itinerary.
Spend an evening in bustling Palma. Grab drinks (or even stay at!) the Hotel Cappuccino, a centrally located and design-forward boutique hotel. Enjoy a seafood dinner by the water and end the night with cocktails on the cobblestone streets.
Explore the center of the island. Mallorca has a huge cycling scene. Rent a bike (or ebike) and find a loop from a local guide. Alternatively, hike in the central valley for views of farmland and luxury fincas.

Jamaica

The vibe: Clear water, volcanic cliffs, quiet mornings, and an easy pace that makes it simple to unwind. Aim for Negril. It's warm, unhurried, and focused on good food, good company, and the sea.

Stay: Rockhouse Hotel. A 40-room boutique property on Pristine Cove with stone and thatch villas, a spa, and three restaurants serving Jamaican dishes and fresh drinks.

What to do:

The Rockhouse Hotel in Jamaica pictured from an areal view. Pictured is a bright blue clear sea with little huts dotted along the cliff side with red ladders that dip into the sea. A few blue umbrellas and lounge chairs are along the edge as well.

Start the day with a swim. If you're staying at Rockhouse, climb down one of the iconic red ladders directly to the sea. The water is calmest in the morning and great for snorkeling or paddleboarding.
Take a glass-bottom boat trip with Famous Vincent to the reef. Check out a beach club, like Skylark Negril, for something more high-key during the day.
Get involved with the community and join a volunteer activity. The hotel's outreach collective, the Rockhouse Foundation, helps support local schools in Negril, like the Savanna-la-Mar Inclusive Academy, built by the Foundation for children with and without disabilities. It also provided direct support to students, families, and teachers most affected by Hurricane Melissa.
Negril's art scene is found on the streets instead of in museums. Take in unique pieces and installations on Seven Mile Beach made by local legends like Michael aka "Sandman." Just a short drive outside of Negril is the Jamaica Giants Sculpture Park and Art Gallery, which will deliver on both extraordinary art and views.
End your day with a Red Stripe or rum without straying far from Seven Mile. Nightlife unfolds in the afternoon at bars like the laidback Tony's Hut, Woodstock, and Roots Bamboo with live music. On Negril's most western tip, Rick's Cafe is the spot to watch the sunset.

Stone steps leading down to the sea at the Rockhouse Hotel in Jamaica. A red ladder is pictured that dips into the water. A woman in a red bikini is lounging on the stones.

Lofoten Islands, Norway

The vibe: Wild, dramatic beauty that feels otherworldly. Perfect for adventurers and lovers of Scandinavian coziness. I'd love to get to the Lofoten Islands soon. While I wait for my chance, Black Tomato put together a few ideas for a well-rounded trip.

Stay: Manshausen is made up of individual cabins and a main house. Think modular glass boxes on pillars over the sea, surrounded by snowy mountains. The hotel has won 40 architectural awards and focuses on comfort and immersive views.

How to plan your time: The summer is great for hiking and experiencing the midnight sun. In the winter you can see the Northern Lights and more dramatic weather. Make sure you take into account plenty of time to travel between destinations because the archipelago is wide, and distances may seem shorter on a map.

What to do:

View of a modular room at the the hotel Manshausen at night with the Northern Lights above in the sky in green and blue. A tree with red blooms is in the foreground.

View of the nose of a kayak in a fjord in Lofoten Island in blue/green crystal clear water with snowy mountains in the background in a sunny day with a few clouds in the sky.

The best way to see the archipelago may be by water. Take a boat from Hopen to the secluded island of Manshausen where you'll get to marvel at the Arctic Trollfjord. This narrow waterway between towering mountains is ripe with Norwegian folklore and history.
Explore Lofoten's fishing villages through its food with a local tasting while taking in the captivating landscapes. Learn about the historical significance of Kabelvåg, the charm of Lyngvær, and the artistic allure of Henningsvær.
In the winter months (September-March) you can take advantage of the archipelago's position above the Arctic Circle for prime Northern Lights viewing. Watch them dance above the dramatic mountains and sparkle in the reflection of the fjords.

A room at hotel Manshausen in Lofoten Islands with the Northern Lights in the sky at night. Streaks of green light spread across the sky with stars. A ladder is pictured in the foreground leading up to the modular hotel room that is cantilevered over a small cliff.

Katie is a New York City-based art director and writer, covering luxury hotels and bucket-list experiences. She's currently serving as Marie Claire's Contributing Senior Designer and travel contributor.