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Who’s going?

The right resort depends more on who’s traveling than on the brochure. Here’s where I’d start.

Couples & honeymoons

Adults-only resorts, quieter beaches and a few special dinners. Saint Lucia and Antigua are classic honeymoon picks, and Jamaica and Mexico have plenty of adults-only choices.

Saint Lucia · Antigua · Jamaica · Riviera Maya

Plan a getaway for two

Families & multigenerational

Kids’ clubs, family suites, calm water and short flights, with something for every age. Big resort areas give you the most choice.

Punta Cana · Cancun · Riviera Maya · Jamaica

Plan a family getaway

Friends & celebrations

Lively resorts with pools, nightlife and room blocks for a group, from milestone birthdays to girls’ trips.

Cancun · Punta Cana · Montego Bay

Plan a group trip

Worth the splurge

Smaller luxury resorts, suites with plunge pools and butler service, on beaches that feel far from the crowds.

Turks & Caicos · Saint Lucia · Los Cabos

Plan a luxury stay

Destinations

Where to go

A turquoise bay in Jamaica with a catamaran and a beach lined with palm trees and resort buildings

Jamaica

Best December to April

Best for: couples, families, groups

Montego Bay, Negril and Ocho Rios, with all-inclusives from adults-only to family-friendly.

Plan a Jamaica trip
A small white-sand beach below the cliffs at Tulum on Mexico’s Caribbean coast

Mexico’s Caribbean coast

Best December to April

Best for: every kind of traveler

Cancun, the Riviera Maya, Tulum and Playa Mujeres, with the widest choice of resorts and easy flights.

Plan a Mexico trip
An aerial view of a white-sand beach with palm trees and lounge chairs

Dominican Republic

Best December to April

Best for: families, groups, value

Punta Cana’s long beaches and large all-inclusive resorts, with plenty for kids.

Plan a Dominican Republic trip
Bright blue water and colorful buildings on Paradise Island in Nassau, the Bahamas

The Bahamas

Best December to May

Best for: long weekends, families

Clear water and a short flight from the East Coast. There are fewer all-inclusives here, so picking the right resort matters more.

Plan a Bahamas trip
A white-sand beach in Aruba with beach cabanas over clear turquoise water

Aruba & Curaçao

Good year-round

Best for: fall trips, reliable sunshine

Dry and sunny, and south of the main storm track, which makes them a smart pick from August to November.

Plan an Aruba or Curaçao trip
An aerial view of Marigot Bay, Saint Lucia, with a palm-covered sandbar and forested hills

Saint Lucia & Antigua

Best December to May

Best for: honeymoons, couples

Mountains, rainforest and quiet coves on smaller islands, usually reached with one connection.

Plan an island trip
A waterfall dropping into a turquoise pool in the Costa Rican rainforest

Costa Rica

Best December to April

Best for: adventure plus beach

Pacific beaches with rainforest, waterfalls and wildlife close by, for travelers who want more than a lounge chair.

Plan a Costa Rica trip
An aerial view of green mountains meeting the coast and a reef on Kauai, Hawaii

Hawaii

Good year-round

Best for: island-hopping, no passport needed

Each island has its own pace. Resorts are usually not all-inclusive, so I help you budget for meals.

Plan a Hawaii trip

Also ask me about Turks & Caicos, Barbados, Grenada, Belize, Los Cabos, Puerto Vallarta and Cozumel. If you have a beach in mind, I can find you a place on it.

Timing

When to go

The beach you pick and the month you go matter as much as the resort.

Peak season

December to April

Driest, sunniest weather and the highest prices. Holidays and spring break book up first.

Sweet spot

Late April to May

Warm water, fewer crowds and better prices before hurricane season starts.

Hurricane season

June to November

Most storms come from August to October. Prices drop, and travel insurance matters more.

Seaweed

Late spring and summer

Sargassum seaweed can wash up on Mexico’s Caribbean coast and some east-facing beaches. I steer you toward beaches that tend to stay clearer.

How I help

How I match you to the right resort

  • Size and atmosphereA small, quiet resort or a big one with something always going on.
  • Beach and waterCalm, swimmable water or waves, sand or rocky entry, and where seaweed tends to land.
  • FoodHow many restaurants, which ones need reservations, and whether the food is worth the trip.
  • Your roomOcean view, swim-up or family suite, and where it sits in the resort, so you’re not a long walk from everything.
  • Adults-only or kids’ clubsThe right crowd for the trip you’re planning.
  • What’s really includedPremium drinks, specialty dining, airport transfers and tips vary by resort, and I spell it out before you book.
“We ran into several snags on our FL trip and Libby took care of all of them. All I had to do was enjoy myself – a real treat for me. She also found the perfect hotel – I would never have found it on my own.”
Marsha · Florida

Read more client stories

All-inclusive, explained

What’s included, and what isn’t

Usually included

  • Your room
  • Meals, snacks and most drinks, including alcohol
  • Pools, beach and non-motorized water sports
  • Evening entertainment
  • Kids’ clubs at family resorts

Often extra

  • Airport transfers, at some resorts
  • Top-shelf drinks and some specialty restaurants
  • Spa treatments
  • Excursions and motorized water sports
  • Tips, at resorts that don’t include them
  • Flights and travel insurance

When I send you options, each one shows its total price with taxes and fees included, so you can compare them side by side. Prices are subject to change until booked.

First beach vacation?

Beach trip questions

Do I need a passport?

Yes, for flights to Mexico, the Caribbean islands and Costa Rica. Make sure it’s valid well past your return date, since some countries require six months. Hawaii, Puerto Rico and the U.S. Virgin Islands don’t need a passport for U.S. citizens.

Is all-inclusive worth it?

For most beach trips, yes. You know most of your cost up front and don’t have to think about every meal and drink. If you plan to eat out in town most nights, a regular hotel can make more sense, and I’ll tell you if that’s the case.

Should I tip at an all-inclusive?

Some resorts include tips and some don’t. Even where they’re included, many guests bring small bills for standout service. I’ll tell you the policy at your resort.

Are airport transfers included?

Sometimes. When they aren’t, I arrange a private or shared transfer so you’re not sorting it out at the airport.

How far ahead should I book?

For holidays, spring break and the best rooms at popular resorts, 6 to 12 months ahead. Quieter times of year can work closer in.

What about hurricane season?

Most trips from June to November go smoothly, and prices are lower. I recommend travel insurance for every trip and especially these months, and I can suggest islands south of the main storm track.

A tropical beach with palm trees

Not sure where to begin?

Let the Matchmaker Tool narrow it down

Tell the tool who’s coming and what kind of week you want, and it’ll suggest beaches and resort areas to start with. Send me your matches and I’ll price them.