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TBH Land > Blog > Islands > Island Lifestyle > The Best Island Getaways in the US: A Traveler’s Guide
Island Lifestyle

The Best Island Getaways in the US: A Traveler’s Guide

TBH LAND
Last updated: September 19, 2026 12:05 am
TBH LAND Published September 19, 2026
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The Best Island Getaways in the US: A Traveler’s Guide

1. Maui, Hawaii

Maui, known as “The Valley Isle,” is the second-largest Hawaiian island and offers a unique blend of adventure and relaxation. Visitors can explore the scenic Road to Hana, where cascading waterfalls and black sand beaches captivate the senses. Snorkel at Molokini Crater, an underwater volcanic caldera teeming with marine life. Also, don’t miss the sunrise at Haleakalā National Park, where you can witness a breathtaking view above the clouds.

Contents
The Best Island Getaways in the US: A Traveler’s Guide1. Maui, Hawaii2. San Juan, Puerto Rico3. Nantucket, Massachusetts4. Key West, Florida5. Catalina Island, California6. Hilton Head Island, South Carolina7. Block Island, Rhode Island8. Orcas Island, Washington9. Amelia Island, Florida10. Galveston Island, Texas

Must-Do Activities:

  • Snorkeling at Turtle Town
  • Exploring the lush Iao Valley
  • Attending a traditional Hawaiian lua or feast

Best Time to Visit: April to June and September to November for mild weather and fewer crowds.

2. San Juan, Puerto Rico

San Juan combines rich history with stunning beaches, making it a perfect getaway. The historic Old San Juan features colorful colonial architecture, cobblestone streets, and the formidable El Morro fortress. Explore the vibrant local culture through its art and music, and taste authentic Puerto Rican dishes at local eateries. The nearby beaches like Isla Verde and Condado offer relaxation or water sports.

Must-Do Activities:

  • Visit El Yunque National Forest for hiking
  • Explore the Bacardí Rum Distillery
  • Lounge on the pristine beaches of Luquillo

Best Time to Visit: December to April when the weather is dry and more pleasant.

3. Nantucket, Massachusetts

Nantucket is an idyllic island renowned for its charming cobblestone streets and historic whaling culture. Rent a bicycle to tour the island’s picturesque lighthouses, pristine beaches, and whale-watching opportunities offshore. Visit the Nantucket Whaling Museum for a glimpse into the island’s maritime history. The dining scene boasts fresh seafood, with many eateries showcasing local lobsters and scallops.

Must-Do Activities:

  • Visit Brant Point Lighthouse
  • Enjoy the sunset at Jetties Beach
  • Explore the quaint shops and boutiques

Best Time to Visit: Late spring (May to June) for blooming flowers and pleasant weather.

4. Key West, Florida

Key West is the southernmost point of the continental U.S. and offers a laid-back atmosphere with a vibrant nightlife scene. Explore the rich history at the Ernest Hemingway Home and Museum, dive into the blue waters for snorkeling, or take a sunset sail for an unforgettable view. The famous Duval Street is lined with bars, restaurants, and art galleries.

Must-Do Activities:

  • Visit the Dry Tortugas National Park
  • Take a ghost tour exploring the island’s haunted history
  • Enjoy water activities like jet-skiing and parasailing

Best Time to Visit: December to April, avoiding the hurricane season and enjoying cooler temperatures.

5. Catalina Island, California

Catalina Island is a stunning getaway just off the coast of Southern California. Accessible by ferry or helicopter, it’s known for its rugged beauty and quaint towns. In Avalon, enjoy a leisurely stroll along the waterfront or rent a golf cart to explore the island. Snorkeling at Lover’s Cove, lush hiking trails, and the Catalina Island Casino are must-visits.

Must-Do Activities:

  • Dive or snorkel at the Underwater Park
  • Hike to the Catalina Island Conservancy
  • Participate in the annual Catalina Island JazzTrax Festival

Best Time to Visit: May to October for warm weather and vibrant local festivals.

6. Hilton Head Island, South Carolina

Hilton Head Island is a golfer’s paradise with over 30 championship golf courses. However, its allure extends beyond golf to beautiful beaches, stunning wildlife, and outdoor activities. The island is famous for its ecotourism, providing opportunities to explore nature trails and wildlife refuges. Don’t miss the Harbour Town Lighthouse and the picturesque views from Sea Pines Resort.

Must-Do Activities:

  • Kayaking or paddleboarding in the marshes
  • Enjoying fresh seafood at local restaurants
  • Cycling along the island’s extensive bike trails

Best Time to Visit: March to May and September to November, allowing visitors to sidestep summer heat and winter chill.

7. Block Island, Rhode Island

Block Island is a serene escape, only a short ferry ride from the mainland. Known for its rugged cliffs, sandy beaches, and wildlife, the island offers biking, hiking, and beach-going opportunities. Explore the scenic Mohegan Bluffs for stunning views and enjoy the tranquility of the island’s North Lighthouse.

Must-Do Activities:

  • Climb the Southeast Lighthouse
  • Relax at the Great Salt Pond
  • Visit the Block Island Historical Society Museum

Best Time to Visit: Late spring through early fall (May to September), when the island’s flora is vibrant and local shops and restaurants are open.

8. Orcas Island, Washington

Part of the San Juan Islands, Orcas Island is known for its stunning vistas and outdoor activities. At Moran State Park, hikers can trek to the top of Mount Constitution for panoramic views of the surrounding islands. The quaint village of Eastsound provides local shops, dining, and cultural experiences. Orcas Island is particularly famous for its whale-watching opportunities.

Must-Do Activities:

  • Kayaking through the peaceful waters
  • Participating in the annual Orcas Island Film Festival
  • Exploring Orcas Island Artworks for local art

Best Time to Visit: Late spring to early fall (May to September) for ideal weather and outdoor exploration.

9. Amelia Island, Florida

Amelia Island is a charming coastal destination known for its historic sites and beautiful beaches. Visit Fort Clinch State Park for its preserved 19th-century fort and scenic trails. St. Marys and Fernandina Beach provide a glimpse into local history with Victorian architecture and quaint shops. You might also indulge in the island’s rich culinary scene.

Must-Do Activities:

  • Explore Historic Downtown Fernandina Beach
  • Take a horseback ride on the beach
  • Enjoy local seafood at the historic Crab Trap restaurant

Best Time to Visit: March to May offers mild weather and avoids the summer crowds.

10. Galveston Island, Texas

Galveston Island combines historical charm and beach fun. Visit the Strand Historic District for unique shops and eateries. The island’s beaches are perfect for sunbathing and swimming. Discover the Moody Gardens, featuring an aquarium, rainforest, and 3D theater. Galveston is also home to various festivals throughout the year, adding to its allure.

Must-Do Activities:

  • Visit the Galveston Island Historic Pleasure Pier
  • Explore the Texas Seaport Museum
  • Relax at Stewart Beach

Best Time to Visit: September to November after the peak summer season and before the chill of winter.


These island getaways across the U.S. offer a rich tapestry of experiences, culture, and natural beauty. Each destination presents unique opportunities to immerse in local traditions, activities, and scenic views, making them perfect for both adventure seekers and those in need of a peaceful retreat.

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