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They say timing is everything, and when it comes to travel, that couldn’t be more true. Between now and Memorial Day, there’s a sweet spot where you can enjoy amazing destinations before peak season prices and crowds hit. Whether you’re looking for the perfect beach escape, a European getaway, or an adventure in the U.S., here are some of my top picks for the best times to travel between now and Memorial Day:
1. Japan – Cherry Blossom Season (Late March – Early April)
Why Now? Springtime in Japan is incredible, with cherry blossoms (sakura) painting the landscapes pink. The weather is mild, and cultural festivals are in full swing. Tokyo, Kyoto, and Osaka all offer excellent viewing spots, and hanami (cherry blossom viewing) is a cultural experience you shouldn’t miss.
Pro tip: Book your accommodations early—this is one of Japan’s busiest travel seasons, and hotels fill up fast. If you want fewer crowds, consider visiting smaller cities like Kanazawa or Fukuoka instead of the major hotspots.
2. Portugal – Shoulder Season Perfection (April – Early May)
Why Now? Portugal’s golden beaches, historic cities, and amazing wine are best enjoyed before the summer heat and tourist rush. Lisbon and Porto are bustling with energy, while the coastline remains peaceful in April. Plus, flights and accommodations are significantly cheaper compared to peak summer months.
Pro tip: If you’re visiting Lisbon, grab a Viva Viagem card for easy access to metro, buses, trams, and ferries—load it with a 24-hour unlimited pass or pay-as-you-go credit. In Porto, the Andante card is your best bet for getting around; opt for the Andante Tour (1-day or 3-day) for unlimited travel.
3. The Netherlands – Tulip Bloom & King’s Day (Mid-April)
Why Now? Mid-April is prime time for tulip fields in full bloom. Keukenhof Gardens is a must-see, and a short bike ride through the countryside will take you past stunning flower fields. At the end of April, King’s Day (April 27) transforms the country into a massive orange-clad party—one of the most exciting celebrations in Europe.
Pro tip: Rent a bike, but learn the biking rules first! The Dutch take cycling seriously, and there are dedicated lanes, traffic signals, and unwritten rules. Always stay to the right, use hand signals, and don’t walk in bike lanes (you’ll hear the bell if you do!).
Bonus tip: If you’re visiting Keukenhof for tulip season (March–May), go early in the morning or late in the afternoon to avoid peak crowds. Better yet, explore the surrounding tulip fields by bike for a more scenic and less touristy experience!
4. Costa Rica – Green Season Beginnings (May)
Why Now? May marks the start of Costa Rica’s green season, meaning lush landscapes, fewer crowds, and lower prices. Rain showers are brief and mostly in the afternoon, so mornings are perfect for exploring cloud forests, volcanoes, and pristine beaches. It’s the ideal time for eco-tourism, from wildlife spotting to rainforest hikes.
Pro tip: Rent a car to get around Costa Rica and see as much as you can during your trip! Each region has its own unique feel, its own environment, and different things to do. You can drive around the country to get a fun combination of cloud forests, adventure, and beach.
5. Greece – Samos & Athens Before the Crowds (April – Early May)
Why Now? The Greek Islands are dreamy, but summer brings cruise ship chaos. Visiting in April or early May means you’ll have those whitewashed streets and historical sites practically to yourself. The weather is pleasant, ferries are running, and local tavernas are open—but without the peak-season price tag.
Plan at least 1 full day in Athens if you’ve never been, to see the Acropolis (book your ticket in advance and download Rick Steves’ audio tour), walk the Plaka, and eat amazing moussaka before you head to the port.
Pro tip: Do your research before you go! Santorini is beautiful, but it can be packed with tourists and higher prices. Take a ferry or short flight to lesser-visited islands. We loved Samos and Icaria (both different in their own right), but Naxos, Paros, and even Mykonos are amazing places without the crowds of Santorini.
6. Washington, D.C. – Cherry Blossoms & Spring Festivals (Late March – Mid-April)
Why Now? The National Cherry Blossom Festival is a must-see, with D.C. covered in pink blooms. The Fiesta Asian Street Fair brings amazing food, entertainment, and a sense of community to your visit. Spring is also an ideal time to explore the National Mall and museums without the sweltering summer heat or massive crowds. If you love history and culture, this is the perfect window to visit before school vacations start.
Pro tip: Reach out to your state representatives before you leave to get tickets for tours of the Capitol. They often accept requests on their websites and/or by email and the tickets are free.
7. New Orleans – Jazz Fest & Mild Weather (April – Early May)
Why Now? New Orleans in the spring is unbeatable—before the sticky summer heat settles in. The New Orleans Jazz & Heritage Festival (late April–early May) is a music lover’s dream, featuring top-tier acts and incredible local cuisine. Plus, the city’s vibrant streets, historic neighborhoods, and energy make it a fantastic pre-summer getaway.
Pro tip: Whenever I visit a new city, I start with a hop-on, hop-off bus tour (or equivalent) to get a lay of the land and usually the tour drivers will give you some good recommendations for local restaurants – not just the popular tourist spots.
8. St. Augustine, FL – History, Beaches & Festivals (March – May)
Why Now? Spring is the best time to visit St. Augustine before the summer humidity kicks in. The city’s cobblestone streets, centuries-old forts, and beautiful beaches are perfect for exploring in the mild weather. Plus, springtime brings lively festivals like the St. Augustine Lions Seafood Festival (March) and the Gamble Rogers Folk Festival (May). Whether you’re a history buff, foodie, or beach lover, this Florida gem offers something for everyone—without the summer crowds.
St. Augustine has a great hop on/hop off trolley that gives you a history of the town. The St. Augustine Distillery is one of my favorite stops with the Ice Plant Bar upstairs! The building itself is ripe with history (it used to be the ice house for the city), the craft cocktails are amazing, and the staff is dressed in old-timey outfits (circa the Roaring Twenties!).
Pro tip: If you’re into ghost stories, book a haunted tour—St. Augustine is one of the most haunted cities in the U.S.!
Final Thoughts
Timing your trip right can mean the difference between an overcrowded, expensive trip and a relaxed getaway. Whether you’re chasing cherry blossoms, exploring Europe without the summer surge, or enjoying the best of the U.S. before peak season, now is the perfect time to pack your bags (check out my packing tips before you hit the road).
Which of these is on your bucket list? Drop your dream destination in the comments!