Romantic Holidays: A Month-by-Month Guide to Warm Spots & Perfect Destinations for 2020

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Warm Romantic Holiday at a Palm Desert Resort, CaliforniaWarm Romantic Holidays by the Pool at the Marriott Shadow Ridge Resort, Palm Desert, California

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By: Greg Mattson, ERV Editor - Updated: Aug 7, 2019   

Have you got time off together in January? Need ideas for that romantic getaway in May? Know your month but not your destination?

We've collected a list of some of the best vacation spots for winter, spring, summer and fall...because knowing when to go is just as important as knowing where to go! Just pick the month you would like to get away, and you'll find a listing of different romantic vacation destinations particularly good for travel to that month.

Each page includes:

  • What to expect for weather at various places and holiday resorts
  • What the travel season is (high or low) and what the crowds are usually like
  • When you can expect to find the cheapest deals

Best Romantic Holidays for Winter 2019-20

Christmas & New Years 2019-20 Travel Rush - Dates to Avoid: The Christmas Travel Season will probably begin to get very busy around Friday, December 20, and stay busy until Christmas Day. So for this time period (and especially the period from Dec 21 to 24), expect to see airports very crowded. You should also brace for flight delays at most airports, but especially in hubs like Chicago, NYC, Charlotte NC, Miami, Dallas, Houston, Denver, Los Angeles and San Francisco.

For New Years, expect heavy travel loads from Wednesday January 1 to Sunday January 5. After that, things rapidly return to normal, which is why many couples will plan and book their 2019-20 winter getaways from Dec 1 to 15 and anytime after January 5, 2020. 

Caribbean Resorts - 50% Off Romantic Hotels in Puerto Rico, Aruba, Grand Cayman

November 2019
Late Autumn usually brings wet weather and cool temperatures to most of the northern part of the country, but we did our research and can recommend these destinations in the U.S. for warmth and good beaches. Plus, see areas still peak for romantic foliage tours, and the best place to visit in Canada in November.   

December 2019 
Winter arrives in North America, and you can either escape it with one of our suggestions for hot December beach destinations, or embrace it with a romantic winter holiday in the snow at one of our top 5 best ski resorts for couples. 

January 2020 
If warm weather is your quest, we've got some opportunities here, including 2 very exotic January vacation spots. You'll find out more on temperatures in some of the best beach vacation destinations in Mexico, and a city in Texas which has very comfortable January weather for exploring all of it's quirky and romantic spots.     

February 2020
Lots of romantic travel ideas for the month which includes Valentines day. See our video embedded here, "Top 10 Best February Vacation Spots". We look at the best places to travel in February for hot beaches in the Caribbean and mild weather in the U.S. We've also got a fun suggestion for a great couples getaway in the snow to a cozy and romantic winter carnival just north of the border in Canada.

Romantic Winter Getaway - February in Punta Cana, DRRomantic Getaway in February on the Beach in the Dominican Republic

Mexico All-Inclusives: Rock-Bottom Rates & Best Deals for Winter / Spring 2020

Spring Getaways for 2020

Spring Break Alert: The actual dates of Spring Break 2020 vary from state to state, but for travel purposes, anytime between March 8 to March 26, 2020 can see heavy travel and sold-out hotels in many places.

The following are destinations that get loads of Spring Break visitors, so if you want to steer clear of parties and crowds, you might want to avoid these places in March and visit another time of the year:

  • USA: South Padre Island, Texas, Panama City Beach, Florida.
  • Caribbean: Nassau & Freeport, Bahamas, Cancun & Puerto Vallarta, Mexico, Punta Cana, Dominican Republic.

March 2020 
Thinking about where to vacation in March? Our suggestions will keep you away from all the spring break crowds and help you relax in a warm, sunny destination. Included is our video "Top 10 Best March Vacation Destinations", which now has over 11,000 views on YouTube! 

April 2020
Spring is a terrific time in many places for couples to get away - check out these tips for romantic April destinations and places to honeymoon. You'll find good reasons why this is a good month to travel to Florida and Hawaii, and why we absolutely love the South Island of New Zealand in April.  

May 2020
For suggestions on destinations and holidays in May, we've come up with a cruise, a European getaway and a city in Canada ideal for a late spring visit. Plus, romantic golf getaways and an affordable beach getaway in the Southwest.

Romantic Summer 2020 Getaways

June 2020
Our ideas for romantic summer destinations and cheap holidays in June include Prague, Canada and some hot weather spots in the American Southwest like Arizona and Las Vegas where you can getaway for very cheap if you love holidaying in the heat.

Romantic Hotels Perfect Any Time of Year

New York

Hotel 50 Bowery NYC

Hotel 50 Bowery


Hotel Palomar Chicago

Hotel Palomar

Los Angeles

Shade Hotel Manhattan Beach CA

Shade Hotel


Hotel Granduca


Hyatt Regency

San Francisco

The Alise Hotel

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