Top 27 Places to Visit in 2027 / A Touring Musician's Honest List

I make my living performing at resorts, private charters, and destination weddings around the world, which means I see these places the way travelers never do: off-season, backstage, and at sunrise after the last encore. Here are the 27 places worth your vacation days in 2027, and at the end, the exact tools I use to book my own travel.

The Caribbean & Islands

1. St. Barts — the gold standard for barefoot luxury; go shoulder season (May–June) for half the price.

2. Turks & Caicos, Grace Bay is still the best beach in the hemisphere. Full stop.

3. Aruba, outside the hurricane belt, so it's the safe bet for fall trips.

4. Curaçao, Willemstad's waterfront looks like Amsterdam went on vacation; great diving, fewer crowds.

5. St. Lucia , the Pitons at sunset from a catamaran is a top-five travel moment anywhere.

6. The Exumas, Bahamas ,water so clear it photographs like a rendering; the swimming pigs are overrated, the sandbars are not.

7. Puerto Rico, Old San Juan & more

Europe

1. Seville, Spain, the home of flamenco. As a Spanish guitarist I'm biased, and I'm also right.

2. Amalfi Coast, Italy. Positano is the postcard, Ravello is the secret. Book boats early.

3. Santorini, Greece, stay in Imerovigli for the caldera views without the Oia crowds.

4. Lisbon, Portugal. Europe's best food-per-dollar capital; day-trip to Sintra.

5. Dubrovnik, Croatia, walk the walls at 8am, then island-hop the Elafitis by afternoon.

6. Mallorca, Spain, the Serra de Tramuntana coast road is the drive of your life.

7. The French Riviera . Nice for the light, Èze for the views, Monaco for one unforgettable dinner.

8. Porto & the Douro Valley, Portugal, terraced vineyards, river cruises, and the world's most underrated wine region. Can't get there this year? Bring the Douro to your table via Wine Express.

   
   

The Americas

1. Miami, Florida. Skip South Beach at noon; do the Design District and a sunset sail on Biscayne Bay.

2. Key West, Florida, drive the Overseas Highway; it's the best road trip east of the Rockies.

3. Tulum, Mexico, cenotes at opening time, ruins before 9am, beach club after.

4. Cartagena, Colombia, the walled city at golden hour is pure music; the Rosario Islands are a 45-minute boat away.

5. Napa Valley, California, go midweek in harvest season (September–October).

6. New York Harbor, the skyline is best from the water; City Cruises runs the dinner and sightseeing sailings I recommend to every client visiting NYC.

7. Cabo San Lucas, Mexico, whale season (December–April) turns every sunset cruise into a show.

   
   

Asia & Beyond

1. Dubai, UAE, love it or roll your eyes at it, the desert dinner experiences are world-class.

2. Bali, Indonesia, skip Canggu traffic, base in Ubud or Uluwatu.

3. Tokyo, Japan, the best city on earth for solo travelers; every meal is a concert.

4. Phuket, Thailand, use it as a launchpad for Phang Nga Bay by longtail boat.

5. The Maldives, the overwater villa is worth doing once; splurge on the seaplane window seat.

   
   

How To Actually Book All of This

Flights, hotels, and full itineraries: start here, it's the same tool I use for my own travel between shows. I cross-check For tours and activities in any city on this list: catamarans, cenotes, cooking classes and more

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And for the full story on wine, culture, and more, grab my book The Red Wine Compendium on Amazon.