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Here are this week’s travel contests. You can win trips to Italy; Florida; Santa Barbara, California; London, England; Antarctica; Monterey, California; Jamaica; Puerto Rico; Las Vegas, Nevada; and more.

Good luck & be sure to subscribe to my weekly newsletter so you don’t miss any sweepstakes, and please share this post with friends who might take you along if they win!

Win a trip to Italy

  • One (1) Prize: There will be one (1) Prize awarded. The prize winner (“Winner”) will receive the following prize package (“Prize”): a Five (5) nights’ trip for two (2) people to Capri, Italy (“Trip”). Trip will include:
    • Hotel accommodations
    • Roundtrip airline transportation for two (2)
    • Should the trip total be less than $18,000 after hotel and transportation, the balance will be awarded to the winner (by check) as expense cash. For the purpose of clarity, the total prize package may not exceed $18,000.
  • open only to legal residents of the 50 United States and the District of Columbia, twenty-one (21) years of age or older
  • Enter by April 30, 2023

Win a trip to Florida

  • 3-night/4-day stay for 1-4 guests at Osprey Pointe by Sandestin Golf & Beach Resort in Miramar Beach on Florida’s emerald coast ($1,300)
    50 year celebration of Sandestin Golf & Beach Resort
    High-end amenities, award-winning dining, and unique shopping experiences
    $1,250 cash to put toward airfare and travel expenses
    Dollar Flight Club Lifetime Premium Membership ($600)
    Classic 6-piece Sozy Mystery Bag ($516)
  • open to anyone who is at least eighteen (18) years of age and has reached the age of majority in their jurisdiction of residence at the time of opt-in (19 in Alabama and Nebraska; 21 in Mississippi) and a resident of the United States of America and the District of Columbia (excluding residents of Alaska, Hawaii, Rhode Island, overseas military installations, Puerto Rico, and other U.S. Territories)
  • Enter by March 9, 2023

Win a trip to Santa Barbara, California

  • – 3 nights at the Drift Santa Barbara with accommodations for two
    – $500 AMEX gift card for travel
    – $100 hotel credit for food & beverages
    – 2 tickets to the Santa Barbara Wine Country Group Tour
    -2 tickets to the Downtown Santa Barbara Food Tour
  • open to anyone who is at least eighteen (18) years of age and has reached the age of majority in their jurisdiction of residence at the time of opt-in (19 in Alabama and Nebraska; 21 in Mississippi) and a resident of the United States of America and the District of Columbia (excluding residents of Alaska, Hawaii, Rhode Island, overseas military installations, Puerto Rico, and other U.S. Territories)
  • Read about craft beer in Carpinteria
  • Enter by March 10, 2023

Win a trip to London

Win a trip to Antarctica (does not include airfare)

  • Prize: The prize has a commercial value of USD
    $17,795 and consists of participation for one
    person in Antarctica21’s December 7-14, 2023,
    Classic Antarctica Air-Cruise (trip code: OCN05-
    CA_2023-24), in a Single Cabin on board Ocean
    Nova.
    The official expedition language of the trip is
    English.
    The trip’s itinerary is the following:
    Classic Antarctica Air-Cruise
    8 days / 7 nights
    Day 1, December 7, 2023 / Start of the Air-Cruise
    Arrive in Punta Arenas, Chile, before 2 PM, where
    you are welcomed by Antarctica21 staff and
    transferred to your hotel. In the afternoon, you
    are welcomed at Explorers House to attend a
    mandatory briefing that provides important
    information about your air-cruise and reviews the
    essential guidelines for Antarctic visitors. Later,
    gather for a welcome dinner and meet your fellow
    adventurers while enjoying a typical regional
    menu.
    Day 2, December 8, 2023 / Scheduled flight to
    Antarctica
    Your Antarctic adventure begins with a two-hour
    flight from Punta Arenas to King George Island, in
    the South Shetland Islands. As you exit the
    airplane, the clear Antarctic air fills your lungs for
    the first time. You then walk 2-km (1.25-miles),
    passing Chile’s Frei Station and Russia’s
    Bellingshausen Station to reach the shore and
    board a Zodiac that will take you to your boutique
    expedition vessel.
    Day 3-6, December 9-12, 2023 / Exploring
    Antarctica
    Cruise between the South Shetland Islands and
    the western coast of the Antarctic Peninsula,
    sailing along ice-filled fjords and among
    spectacular icebergs, while enjoying the company
    of seabirds, penguins, seals, and whales. Each day
    disembark by Zodiac and explore the landscape
    together with expert polar guides. On board the
    ship, attend an engaging program of educational
    presentations, and enjoy spectacular views from
    the lounge while sharing your daily adventures
    with fellow guests.
    No journey is the same and flexibility is the key to
    success in Antarctica. The Expedition Team plans
    the voyage route to take advantage of the everchanging opportunities provided by nature,
    crafting a unique and extraordinary experience
    every time. While the exact itinerary changes with
    each expedition, you will explore several sites that
    offer the best possible overview of the varied
    Antarctic environment. Your voyage may include
    visits to sites in the South Shetland Islands, the4
    Antarctic Sound, the Gerlache Strait, and the
    Penola Strait.
    Day 7, December 13, 2023 / Scheduled return
    flight from Antarctica
    Return to King George Island and bid farewell to
    Antarctica before boarding the flight back to
    Punta Arenas. Upon arrival, transfer to your hotel
    for the night. (Note: Meals in Punta Arenas are at
    your leisure and not included in the program).
    Day 8, December 14, 2023 / End of the Air-Cruise
    After breakfast, transfer to the Punta Arenas
    airport for your onward flight.
    Included in the prize:
    · Group transfers airport/hotel on Day 1.
    · One overnight with breakfast in Punta Arenas at
    the Cabo de Hornos Hotel or similar, with a
    welcome dinner including drinks on Day 1.
    · 1 overnight with breakfast in Punta Arenas at the
    Cabo de Hornos Hotel or similar on the Day of the
    Scheduled Return Flight from Antarctica.
    · Access to Explorers House in Punta Arenas.
    · Group transfers airport/hotel on the Day of the
    Scheduled Return Flight from Antarctica, and
    group transfers hotel/airport on the last day of
    the air-cruise.
    · Flight from Punta Arenas to Frei Station on King
    George Island and vice versa as indicated in the
    program.
    · Ship cruise as indicated in the program.
    · Daily buffet breakfast and lunch on board ship
    offering a wide choice of dishes.
    · Daily served dinner on board ship offering a
    choice of three main courses.
    · Wine, beer, juice, and soft drinks served with
    lunch and dinner on board.
    · Coffee, tea, chocolate, cappuccino, water, and
    snacks on board ship throughout the expedition.
    · All guided shore excursions.
    · Lectures and entertainment on board.
    · Comprehensive pre- and post-voyage
    information material.
    · Loan of waterproof boots for landing in
    Antarctica.
  • Worldwide, Anyone over 18 years old who
    completes the participation form, answers the
    knowledge questions correctly, and meets the
    requirements outlined
  • Enter by March 17, 2023

Win a trip to Monterey, California

  • – 3-night stay at The Sanctuary Beach Resort, a Kind Traveler Hotel, in a Premium King
    – Food & beverage credit with The Sanctuary Beach Resort ($250)
    Monterey Bay Eco Tours: Tour for two of the Elkhorn Slough aboard a 37′ electric catamaran to view the largest population of Southern Sea Otters in the world
    – Adventures by the Sea: embrace the opportunity to discover Monterey by land and by sea with Adventures Passes for two, to include kayak rentals or ½ day on e-bikes
    – Monterey Touring Vehicles: discover a once-in-a-lifetime experience of driving a classic car on the California Coast to include a ½ day classic car experience ($269 value)
  • – $200 donation to local Monterey County charity, Rancho Cielo Youth Campus, made in the name of the winner
    – Kind Traveler: gift box to include eco-conscious travel products to inspire kind travel ($250 value)
    – SAMBAZON: gift box to include a portable Blend Jet blender, coupons and more ($200 value)
    – Spirituality & Health Magazine: one-year subscription
    – Awaken Your Passion: gift box to include mugs, a coasters collection, and tee’s, each designed to invoke self-reflection
    – Gogh Jewelry: gift box to include a $500 gift card towards conscious jewelry that empowers
    – Midori Bikinis: ethical, UPF 50, and sustainable swimwear gift box
    – $300 Visa cash card towards travel expenses
  • open to anyone who is at least twenty-one (21) years of age and a resident of the United States of America and the District of Columbia (excluding residents of Alaska, Hawaii, Rhode Island, overseas military installations, Puerto Rico, and other U.S. Territories)
  • Read about craft beer in Monterey
  • Enter by March 17, 2023

Win a trip to Jamaica

  • You could win a 4-night stay for two at Azul Beach Resort Negril in Jamaica and enjoy an all-inclusive escape embraced by some of the most beautiful beachfront settings in the Caribbean. This Gourmet Inclusive® Experience features a variety of restaurants serving international cuisine enhanced by breathtaking Caribbean views, Azul Beach Resort Negril combines Karisma’s all-inclusive luxury with a Caribbean paradise brimming with beauty.
  • + Gogh Jewelry Design: $500 eco conscious travel inspired jewelry
  • + $250 beachwaver.com Gift Card to get beach ready
  • + $150 cash from Your Tango
  • + $250 cash from Matt’s Flights
  • + $100 cash from The Canopy
  • open to anyone who is at least eighteen (18) years of age and has reached the age of majority in their jurisdiction of residence at the time of opt-in (19 in Alabama and Nebraska; 21 in Mississippi) and a resident of the United States of America and the District of Columbia (excluding residents of Alaska, Hawaii, Rhode Island, overseas military installations, Puerto Rico, and other U.S. Territories)
  • Enter by March 18, 2023

Win a trip to Puerto Rico

  • – 3 nights at the Motel Rincon with accommodations for two
  • – $500 AMEX Gift Card for travel
  • – $250 restaurant credit for tropical cocktails at Casa Isleña
  • – One day of surf lessons for two with Mar Azul Surf Shop
  • open to anyone who is at least eighteen (18) years of age and has reached the age of majority in their jurisdiction of residence at the time of opt-in (19 in Alabama and Nebraska; 21 in Mississippi) and a resident of the United States of America and the District of Columbia (excluding residents of Alaska, Hawaii, Rhode Island, overseas military installations, Puerto Rico, and other U.S. Territories)
  • Enter by March 20, 2023

Win a trip to Las Vegas, Nevada

  • One (1) Grand Prize consisting of two (2) orchestra tickets to winner’s choice of one (1) participating Maroon 5 concert at Dolby Live in Las Vegas, NV during 2023 residency year; one (1) double-occupancy standard hotel room for winner and one (1) guest for two (2) nights / three (3) days during the selected concert; two (2) Allegiant travel vouchers in the amount of $300 each; and a $200.00 pre-paid cash card to use toward ground transportation
  • open only to natural persons who are legal residents of the 50 United States (and the District of Columbia) who have a valid social security or tax ID number, and who are at least twenty-one (21) years old
  • Enter by March 20, 2023

Go on an adventure at home or when you’re away with a tour or activity via Get Your Guide.

Which travel giveaway are you most excited about winning this week?

Why not share this post with your friends? If they win, maybe they’ll take you!

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