Punta Cana & Dominican Republic Getaways | Traveling Wahoo

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Dominican Republic Winter Getaways

Trade the snow for the Caribbean. We plan Punta Cana and Cap Cana all-inclusives, private villas on the North Coast, Samaná whale watching and group trips, one-on-one, from first call to the flight home.

  • Best timeDecember to April
  • Whale seasonJan 15 – Mar 31
  • Flight timeAbout 4 hours from New York
  • Planning feeNone on most bookings

Three Ways to Spend Winter in the DR All places we’ve stayed ourselves

Tell us your dates and we’ll send 3 hand-picked options with real prices within 24 hours. Free, with no obligation.

A white-sand beach in Punta Cana with umbrellas, loungers and tall palm trees
Most popular

Punta Cana & Cap Cana All-Inclusives

Bávaro · Punta Cana · Cap Cana

Adults-only or family-friendly, laid-back or high-end. We match you to the right resort, then handle the airport transfers and excursions. Troy has stayed at Meliá Caribe Beach and ZEL Punta Cana more than once.

Best for: Couples, families, friends and first-timers

Get Punta Cana prices →
A private villa pool surrounded by palm trees in Cabarete, on the Dominican Republic’s North Coast
Troy’s favorite

North Coast Private Villas

Cabarete · Sosúa · Puerto Plata · Las Terrenas

A pool of your own, beach cafés, horseback rides on the sand, the Cabarete caves and the La Aurora cigar factory. We book villas through partners and stay at them ourselves.

Best for: Families, friend groups and longer stays

Read our North Coast villa guide → Get villa prices →
A humpback whale surfacing in Samaná Bay, with green hills on the shore behind it
Winter only

Samaná Whale Season

Samaná Bay · Las Terrenas

Every winter, thousands of humpback whales gather in Samaná Bay to mate and give birth. We set up the boat tour and a villa with a view of the bay. Book early, since the best villas fill up fast.

Season: January 15 to March 31

Get whale-season prices →
Group Trips

Bringing the Whole Crew?

Family reunions, milestone birthdays, clubs, company retreats and veteran organizations. You get one point of contact for the whole group, and we handle the room blocks, payments, airport transfers and group excursions, so you don’t have to.

See How Group Trips Work
  • One-on-one planning with a real person, not a call center
  • Partner perks at many hotels and resorts through Fora Travel
  • Help with the free Dominican Republic e-Ticket entry form
  • Veteran-owned, with 23 years of military service behind the planning
From our travelers

What Our DR Travelers Say

Photo from Vicky Marks, Punta Cana with friends

★★★★★

From start to finish this was an exceptional getaway. Dealing with Troy was a breeze. He's the only way to travel. Smart, concise, quick, professional just a few words to describe my experience. The resort was hands-down amazing. The food was exceptional. The spa was incomparable. The views are breathtaking. The staff at the resort, professional kind, courteous, and quick. I can't wait to go back.

Vicky MarksSchenectady, NYPunta Cana with friends, February 2025
Photo from Tanya Johnson, Cabarete, Dominican Republic

★★★★★

Everything from the house, horseback riding, hiking the national park, walking the beach, kayaking to Wilson's, the food! Such an amazing trip! Thank you!!

Tanya JohnsonClarksville, TNCabarete, Dominican Republic, July 2025 and 2026
Photo from Jodee O., Punta Cana with family and friends

★★★★★

What a blast!! My first time out of the country and Troy really made it an amazing experience. Went with family and friends. I can't wait to go back again February 2027. Troy made it possible for us to have another fun, amazing and enjoyable trip at an affordable price. From the resort, restaurants, pool bar, the beach and our excursion to an island with an amazing boat trip I could not have asked for a better trip.

Jodee O.Tivoli, NYPunta Cana with family and friends, January 2025
Good to know

Dominican Republic Trip Questions

When is the best time to visit the Dominican Republic?

December through April is the driest, most comfortable stretch, and it lines up with whale season in Samaná Bay (January 15 to March 31). Hurricane season runs June through November, so we recommend travel insurance for trips in those months.

All-inclusive or private villa: which is right for us?

All-inclusives are easy: food, drinks, pools and entertainment in one place, which is great for couples, families and first-timers. A villa on the North Coast gives you more space, privacy and a taste of local life, which works well for families, friend groups and longer stays. We book both and can help you decide on a free call.

What do I need to enter the Dominican Republic?

U.S. citizens need a valid passport, and every traveler fills out the free Dominican Republic e-Ticket before the trip. Watch out for lookalike sites that charge a fee. Read our e-Ticket guide.

Do you charge a planning fee?

There’s no planning fee on most bookings, since we’re paid by the travel suppliers. Here’s how it works.

More DR reading: North Coast villas and Samaná whale watching · The free DR e-Ticket · How to plan a group trip

Get in Touch

Let’s Plan Your DR Winter Trip

Tell us where you'd like to go, when, and who's coming, and we'll start planning a trip built around you.

Every message comes straight to me, not a call center. I'll personally get back to you within one business day, and there's never any pressure.

Troy Haley, Founder
Prefer to talk? Book a free, no-pressure 15-minute call at a time that suits you. Book a free call (opens in a new tab)
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