Winter Packages | Traveling Wahoo

Winter 2026–27 · Flights from New York included

Warm-weather packages, planned by a real person

Nine winter escapes, each a hand-picked resort plus the experience that makes the trip. Flights, stay and taxes in one price. Pick one as-is or let me tailor it to you. Planning ahead? The Mediterranean for spring through fall 2027 is below.

Winter 2026–27

Nine ways to skip winter

Palm trees leaning over a white-sand beach in Punta CanaMost popular

Dominican Republic

Punta Cana Beach Escape

Soft white sand, all-inclusive ease and the most nonstop flights from New York.

  • Round-trip nonstop flights from JFK
  • 7 nights, all-inclusive, at Riu Republica
  • Add-on: Catamaran snorkel and sunset cruise
  • Add-on: Private airport transfers

From, per person

$1,310

Based on 2 adults sharing a room. 7 nights, Jan 23–30, 2027, departing JFK. Taxes and fees included. Checked bags and seat selection extra. Details

See the trip: Punta Cana Beach Escape
Kites over the bay at Cabarete on the Dominican Republic’s North CoastOff the beaten path

Dominican Republic

Puerto Plata North Coast

Mountains meet the sea on the quieter North Coast, with real local flavor.

  • Round-trip nonstop flights from JFK
  • 7 nights, all-inclusive, at Viva Heavens
  • Add-on: 27 Waterfalls of Damajagua day trip
  • Add-on: Cable car up Mount Isabel de Torres

From, per person

$1,400

Based on 2 adults sharing a room. 7 nights, Jan 23–30, 2027, departing JFK. Taxes and fees included. Checked bags and seat selection extra. Details

See the trip: Puerto Plata North Coast
A humpback whale’s tail rising out of Samaná Bay, photographed by TroySeasonal

Dominican Republic · Jan–Mar

Samaná Whale Week

Thousands of humpbacks gather in Samaná Bay each winter. Our signature trip. Fly into Puerto Plata (about 3 hours away) or Santo Domingo (about 2½).

  • Round-trip nonstop flights from JFK to Puerto Plata
  • 7 nights, all-inclusive, at Bahia Principe Escape Samaná
  • Add-on: Whale-watching boat trip
  • Add-on: Cayo Levantado island day

From, per person

$1,710

Based on 2 adults sharing a room. 7 nights, Jan 23–30, 2027, departing JFK. Taxes and fees included. Checked bags and seat selection extra. Details

See the trip: Samaná Whale Week
Aerial view of a beachfront resort on turquoise water near CancúnEasy getaway

Mexico

Cancún Sun & Ruins

Turquoise water, big resorts and Maya history a day trip away.

  • Round-trip nonstop flights from Newark (EWR)
  • 7 nights, all-inclusive, at Riu Ventura
  • Add-on: Isla Mujeres catamaran
  • Add-on: Chichén Itzá day tour

From, per person

$1,470

Based on 2 adults sharing a room. 7 nights, Jan 23–30, 2027, departing Newark. Taxes and fees included. Checked bags and seat selection extra. Details

See the trip: Cancún Sun & Ruins
Aerial view of the beaches at Tamarindo, GuanacasteAdventure

Guanacaste, Costa Rica

Costa Rica Pura Vida

Beach mornings, rainforest afternoons and wildlife everywhere you look.

  • Round-trip nonstop flights from JFK
  • 7 nights, all-inclusive, at Occidental Papagayo
  • Add-on: Canopy zipline tour
  • Add-on: National park guided hike

From, per person

$2,050

Based on 2 adults sharing a room. 7 nights, Jan 23–30, 2027, departing JFK. Taxes and fees included. Checked bags and seat selection extra. Details

See the trip: Costa Rica Pura Vida
Turquoise water and a long sand beach at Bloody Bay, NegrilRomance

Montego Bay · Negril

Jamaica Island Vibes

Reggae, jerk and the famous Negril sunsets from the cliffs.

  • Round-trip nonstop flights from JFK
  • 7 nights, all-inclusive, at Grand Palladium Jamaica
  • Add-on: Dunn’s River Falls climb
  • Add-on: Negril sunset catamaran

From, per person

$1,790

Based on 2 adults sharing a room. 7 nights, Jan 23–30, 2027, departing JFK. Taxes and fees included. Checked bags and seat selection extra. Details

See the trip: Jamaica Island Vibes
A wind-bent tree on the white sand of Eagle Beach, ArubaSunniest pick

Aruba

Aruba One Happy Island

Dry, breezy and sunny all winter, with some of the Caribbean’s best beaches.

  • Round-trip nonstop flights from JFK
  • 7 nights, all-inclusive, at Tamarijn Aruba
  • Add-on: Snorkel and sail cruise
  • Add-on: Island jeep tour

From, per person

$3,280

Based on 2 adults sharing a room. 7 nights, Jan 23–30, 2027, departing JFK. Taxes and fees included. Checked bags and seat selection extra. Details

See the trip: Aruba One Happy Island
Palm trees and calm water on Dickinson Bay beach, AntiguaHidden gem

Antigua

Antigua 365 Beaches

A beach for every day of the year, calm turquoise coves and real British-Caribbean charm.

  • Round-trip nonstop flights from JFK
  • 7 nights, all-inclusive, at Jolly Beach Resort
  • Add-on: Catamaran sail and snorkel
  • Add-on: Nelson’s Dockyard and Shirley Heights sunset

From, per person

$2,010

Based on 2 adults sharing a room. 7 nights, Jan 23–30, 2027, departing JFK. Taxes and fees included. Checked bags and seat selection extra. Details

See the trip: Antigua 365 Beaches
The twin Pitons rising from the sea on St. LuciaBucket list

St. Lucia

St. Lucia Pitons & Romance

Twin volcanic peaks, rainforest and the most romantic views in the Caribbean.

  • Round-trip nonstop flights from JFK
  • 7 nights, all-inclusive, at Royalton Saint Lucia
  • Add-on: Sulphur Springs mud bath and waterfall
  • Add-on: Sunset cruise beneath the Pitons

From, per person

$2,050

Based on 2 adults sharing a room. 7 nights, Jan 23–30, 2027, departing JFK. Taxes and fees included. Checked bags and seat selection extra. Details

See the trip: St. Lucia Pitons & Romance

What’s included, and the fine print

  • Included in the winter prices: round-trip nonstop economy flights from the airport shown (basic-economy fares), 7 nights at the resort named for 2 adults sharing a standard room on its all-inclusive plan, and all government taxes and supplier fees charged at booking.
  • Not included: airport transfers, travel protection, checked bags, seat selection and other optional airline fees, the add-on experiences listed on each trip, gratuities, and any taxes or fees collected locally at the destination (for example, Mexico’s Quintana Roo visitor fee). I quote transfers and travel protection with your trip, and I recommend protection on every trip.
  • Prices and availability: “From” prices are the lowest per-person price I found for the sample dates (Saturday, January 23 to Saturday, January 30, 2027), as listed by my suppliers on October 20, 2026. Prices change daily, are subject to availability and aren’t guaranteed until your trip is booked and paid. Other dates, airports, rooms and resorts will cost more or less. Single travelers and families are priced differently.
  • Flights: basic-economy fares are the most restrictive: no seat choice, boarding last, and generally no changes or refunds. I’ll show you the cost to upgrade. Airlines set their own bag fees.
  • Payment and cancellation: trips are paid in full at booking. Cancellation and change penalties are set by each airline, resort and package supplier and are shown before you pay.
  • Travel documents: a passport valid for your whole trip is required for every destination on this page, and each traveler is responsible for meeting entry requirements (like the Dominican Republic’s free e-Ticket).
  • Samaná: flights land in Puerto Plata, about 3 hours by road from Samaná (Santo Domingo is about 2½ hours, Punta Cana about 4). Your driver is quoted separately.
  • Mediterranean trips are sample itineraries and aren’t priced yet.
  • Who you’re booking with: Traveling Wahoo LLC is an independent, veteran-owned travel advisor. Travel is booked through our host agency, Fora Travel, Inc. (California seller of travel No. 2151995-50, Florida No. ST43973, Washington UBI 605329242), with airlines, resorts and package suppliers such as Travel Impressions and Apple Vacations. Photos are representative.

Plan ahead · Spring, summer & fall 2027

The Mediterranean, done right

Europe’s best summer trips book up a year out. Lock in flights and the best rooms now for April through October 2027.

Dubrovnik’s red rooftops and Lokrum Island in the Adriatic, photographed by TroyFrom April 2027

Dubrovnik · Split · Hvar

Croatia Coast & Islands

Walled medieval towns, crystal-clear Adriatic water and island hopping by boat. Mikki and I have walked these walls, and I’ll plan it the way we’d do it again.

  • Flights from New York, quoted with your trip
  • 8 nights: Dubrovnik, then Split or Hvar
  • Dubrovnik city walls guided walk
  • Island-hopping boat day

Price

Quoted for your dates

Sample 8-night itinerary. Not yet priced; I’ll send real prices for your dates and airport.

See the trip: Croatia Coast & Islands
The Bay of Kotor and its old town seen from the fortress aboveHidden gem

Kotor · Budva

Montenegro’s Bay of Kotor

A fjord-like bay, mountain views and old stone towns, an easy add-on from Dubrovnik.

  • Flights from New York, quoted with your trip
  • 8 nights on the Bay of Kotor and the coast
  • Boat to Our Lady of the Rocks
  • Kotor old town and fortress hike

Price

Quoted for your dates

Sample 8-night itinerary. Not yet priced; I’ll send real prices for your dates and airport.

See the trip: Montenegro’s Bay of Kotor
White and blue buildings of Oia, Santorini, above the calderaBucket list

Athens · Santorini · Mykonos

Greece: Athens & the Islands

Ancient history in Athens, then whitewashed villages and caldera sunsets on the islands.

  • Flights from New York, quoted with your trip
  • 8 nights: Athens and the islands
  • Acropolis guided tour
  • Santorini caldera sunset sail

Price

Quoted for your dates

Sample 8-night itinerary. Not yet priced; I’ll send real prices for your dates and airport.

See the trip: Greece: Athens & the Islands

Don’t see your trip? I’ll build it.

“From” prices are for sample dates. Tell me when and who’s coming, and I’ll send real prices within a day.

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Photos: Traveling Wahoo, except Wikimedia Commons: Bloody Bay, Negril by wardyboy400 (CC BY 2.0); Dickinson Bay, Antigua by Paul Kowalow (CC BY-SA 3.0); Tamarindo, Costa Rica by Tamarindowiki (CC BY-SA 3.0); the Pitons, St. Lucia by Gruepig (CC BY-SA 4.0); Eagle Beach, Aruba by SIryn (CC BY-SA 4.0); Kotor Bay by miketnorton (CC BY 2.0); Oia, Santorini by bongo vongo (CC BY-SA 2.0); Druif Beach and “Aruba bliss” by Jason Boldero (CC BY 2.0); Arikok National Park by Misty Johnson (CC BY 2.0); Our Lady of the Rocks by Alexey Komarov (CC BY 3.0); Kotor old town by Gzzz (CC BY-SA 4.0); Budva beach by Miomir Magdevski (CC BY-SA 4.0); Athens from Philopappos Hill by A.Savin (CC BY-SA 3.0); Little Venice, Mykonos by Zde (CC BY-SA 4.0); Santorini caldera boat by Gozitano (CC BY-SA 4.0). Resort photos on trip pages: Expedia listings.