Where to Go in April & May + Smart PTO Trips
April and May are some of the smartest months to travel: longer daylight hours, fewer crowds, shoulder-season pricing, and just enough warmth across Europe, the U.K., and beyond to make cities and countryside shine.
It’s also one of the easiest windows to stretch PTO thanks to Easter weekend, Memorial Day, and spring Fridays that practically beg for long weekends.
Below are destinations I recommend most often to clients during this window, and why they work especially well this time of year.
Lisbon & Porto, Portugal
Why April–May works
Sunny but not hot (60s–70s°F)
Wildflowers bloom in the Douro Valley
Ideal walking weather for Lisbon’s hills
Fewer cruise crowds than summer
Best PTO strategy
Pair Easter week with a long weekend → 9 days off using 4 PTO days.
Special spring moments
Semana Santa processions
Douro wine season reopening
Coastal seafood peak season
Trip Whisperer tip
Portugal is one of the easiest first Europe trips post-winter thanks to nonstop flights from the East Coast and relaxed pacing.
Check my Portugal itinerary in 10 Nights/11 Days for inspiration.
United Kingdom Countryside + London
Why April–May works
Garden season begins
Countryside is lush and green
Shoulder-season hotel availability improves
Perfect time for manor-house stays
Best PTO strategy
Stack Easter + one extra Friday → effortless 5-night escape.
Special spring moments
RHS Chelsea Flower Show (May)
Lambing season in the countryside
Early festival calendar begins
Trip Whisperer tip
Clients who think they “don’t want Europe yet” almost always love a spring England trip or a ideal road trip to iconic luxury properties.
Mexico City
Why April–May works
Jacaranda trees bloom purple across the city
Dry season means ideal walking weather
Museums and restaurants shine without summer rain
Best PTO strategy
Long weekend destination (3–4 nights)
Special spring moments
Peak culinary season
Art fairs + gallery programming
Outdoor terrace dining returns
Trip Whisperer tip
One of the easiest international trips from the East Coast with huge cultural payoff.
Here’s my recent visit and guide to Mexico City here.
India (Rajasthan or the Himalayas)
Why April–May works
Depends on region:
Rajasthan
End of peak season = fewer crowds at major sites
Himalayan foothills
Prime travel window begins
Best PTO strategy
Use Memorial Day weekend to anchor a longer cultural itinerary.
Special spring moments
Shoulder-season palace hotel pricing
Wildlife safaris still strong
Himalayan trekking season opens
Check out my fantastic trip to India for my 40th birthday recently to draw some insight.
Italy (Rome + Umbria + Lake Como)
Why April–May works
Ideal walking temperatures
Garden villas open around Lake Como
Pre-summer pricing window
Best PTO strategy
Memorial Day → 9-day itinerary using 4 PTO days
Special spring moments
Easter in Rome
Spring produce season begins
Lakes reopen before peak crowds
Trip Whisperer tip
May is my favorite Italy month for first-time visitors.
Morocco
Why April–May works
Warm but not scorching
Atlas Mountains are green
Desert camps are comfortable at night
Best PTO strategy
Ideal 7–9 day cultural trip anchored to Easter or Memorial Day
Special spring moments
Rose Valley bloom season
Excellent trekking conditions
Market season in full swing
Trip Whisperer tip
Spring is the single best time of year for Morocco overall.
Costa Rica (Rainforest, Volcanoes & Beaches in One Easy Trip)
Why April–May works
April marks the tail end of Costa Rica’s dry season, with warm sunny weather across most of the country. By May, the landscape shifts into the start of the “green season,” when rain typically arrives in short afternoon bursts, bringing lush jungle scenery, fewer crowds, and softer hotel rates.
It’s one of the best-value windows of the year to visit.
Best PTO strategy
Memorial Day weekend makes Costa Rica especially easy:
Take 4 PTO days → enjoy a 9-day rainforest + beach itinerary
Or plan a quick 4–5 night escape combining Arenal and the Central Valley.
Special spring moments
Excellent wildlife viewing between seasonal transitions
Waterfalls at their fullest by mid-May
Lower hotel pricing after Easter travel ends
Comfortable temperatures before peak summer humidity
Trip Whisperer tip
Costa Rica is one of my favorite recommendations for travelers who want something adventurous without committing to a long-haul itinerary. With easy nonstop flights from the East Coast and straightforward routing between regions, it’s ideal for a relaxed road-trip-style getaway.
I typically suggest renting a car through Vamos Rent-A-Car, which makes it simple to move between volcanoes, cloud forest, and the coast at your own pace, turning the trip into a true rainforest-to-beach journey rather than a transfer-heavy itinerary.
Ideal spring routing
San José → Arenal → Monteverde → Manuel Antonio
or
Liberia → Guanacaste beaches → Rio Celeste → cloud forest
Charleston or Savannah (Closer-to-home option)
Why April–May works
Azaleas and magnolias bloom
Warm but not humid yet
Ideal walking weather
Best PTO strategy
Perfect 3-night long weekend
Special spring moments
Historic garden tours
Food festivals
Outdoor dining season begins
Check out my long-weekend Charleston recap for inspiration.
How to Maximize PTO in April & May
Best spring travel windows based on my full PTO optimizing calendar:
Easter week → Europe sweet spot
Late April shoulder season value for your money
Memorial Day → easiest 9-day trip stretch of the year
Not sure how to stretch your vacation days? See my guide on how to turn a long weekend into a 9-day trip using strategic PTO timing.
