Reliable Private Air Charter to Key West

Back to Blogs

Reliable Private Air Travel To Key West

Ah… Key West. Perhaps the only city in the United States that truly believes it is its own micro country they call the “Conch Republic”. Heck, they even have their own flag that’s more recognizable than many state flags. If you think it’s just for fun, it certainly doesn’t seem it when you visit this laid-back culture that truly is like being in another country.  The city doesn’t seem to wake up early. Most people, in fact, eat breakfast at a time that many consider “brunch”. It’s not surprising when you take into consideration that the city doesn’t seem to go to sleep very early, either.

Getting here isn’t always easy. Driving will spoil your weekend as there is only one way in and one way out. The airlines only offer direct flights from their respective hubs and frequently cancel their flights. At Odyssey Airways, we are frequently called by people who have fallen victim to a canceled flight and in need of getting to Key West in a hurry. Although it is rarely the most economical way to travel to Key West, private air charters are certainly the most reliable way. If you have several couples traveling with you, the cost difference between private air charters and the cramped airlines is marginal. Factor in the value of your time and patience and a private charter flight to Key West is the only way to travel, especially for some of these popular Key West events:

Key West Events 2020

May 2020 Key West Events

  • May 6 – 10, 2020 – MUSIC – 25th Annual Key West Song Writers Festival – Features more than two-hundred top songwriters performing at a variety of venues in Key West, including a concert on the Sunset Pier of the Ocean Key House at 1 Duval Street and a free concert on Duval Street. For more information, visit the Key West Song Writers Festival website.
  • May 10, 2020 – HOLIDAYMother’s Day in Key West – Celebrate your mom in style! Local restaurant have numerous brunches available – dine indoor or outdoor, oceanfront or air-conditioned. Happy day mothers! We love you!!
  • May 11, 2020 – LGBT37th Annual Queen Mother Pageant – Drag queens compete for title of “Queen Mother,” judged by their often hilarious, always talented performance in evening gown, talent, and interview skills. THIS YEAR’S EVENT HAS NOT BEEN CONFIRMED. Last year’s details include: Benefits Compassionate Care Hospice and One Human Family Foundations. Cost is $25 for general admission, or tables from $200-$500 (these sell out fast). Door open at 7pm, show starts at 8pm. LaTeDa, 1125 Duval Street.
  • May 16 – 17, 2020 – RUNNING13th Annual Keys 100 Ultra – 100 and 50 mile ultra marathons starting near Key Largo and in Marathon FL, finishing in Key West. Cost: $150 to $275 for individuals (depending on race length and time of registration), and $720 to $840 for teams (depending on race length and time of registration).

June 2020 Key West Events

  • June [DATE NOT YET ANNOUNCED], 2020 – FOOD Tropical Fruit Fiesta – Held on the grounds of the Truman Little White House, this event features a display Key West’s numerous tropical fruits, including mango, papaya, Key Lime, Spanish lime, jackfruit, starfruit and others. Tastings, lectures, and opportunity to purchase locally grown produce. Growers compete for award of best fruits in each category. Fun event with genuine local color. 9am-1pm, Truman Little White House, 111 Front Street. FREE to attend.
  • June 3 – 7, 2020 – LGBTKey West Pridefest – Event honoring diversity, openness and freedom in the city that is consistently recognized as one of the world’s top gay and lesbian vacation destinations. Includes a mix of: dance and cocktail parties, contests, shows, forums, activities on the water, tours, street fair and the Pride Parade along Duval Street. For more information, visit the Key West Pridefest website.
  • June 6, 2020 – SWIMMING 44th Annual Swim Around Key West – Presented by the Key West Athletic Association, this 12.5 mile swim around the island of Key West must be completed in 8 hours and typically has 200 participants, including solo and team swimmers. Cost for registration by March 15 is $165 for a solo swimmer, $300 for two-person relay, and $420 for three-person relay.  For more information, visit the 44th Annual Swim Around Key West website.
  • June 20, 2020 – SWIMMINGFKCC Swim Around Key West – Swimmers, accompanied by kayakers, circumnavigate the island of Key West, a distance of over 12 miles. For more information, call 305-809-3562 or visit the FKCC Swim Around Key West website.
  • June 26, 2020 – LITERATURE6th Annual Mystery Fest Key West – Over twenty South Florida’s writers convene in Key West for three days of discussions and interactions. Cost is $195 for the weekend events. For more information, visit the 6th Annual Mystery Fest Key West website.

July 2020 Key West Events

  • July 1 – 5, 2020 – LOCAL COLORKey West Mermaid Festival – Family-friendly event featuring mermaids in costume.  Offers swimming with mermaids, parties, Duval Street parade on Saturday, vending, and more.
  • July 4, 2020 – INDEPENDENCE DAYKey West 4th of July Fireworks – Dazzling fireworks show is launched from the White Street pier on the south side of the island of Key West. Begins shortly after sunset. Popular tradition is to view the fireworks from the water aboard a boat. More information and reservations for boat options at Key West July 4th Fireworks Cruises. For more information, visit the Key West 4th of July Fireworks website.
  • July 2 – 6, 2020 – FOOD – 8th Annual Key Lime Festival – Key Limes, grown abundantly on the island, are necessary to make true Key Lime pie. This four-day fest celebrates the tiny local lime, with pie-baking contests, cooking classes, and pie-eating contest. For more information, visit the 8th Annual Key Lime Festival website.
  • July 18 – 21, 2020 – FISHING20th Annual Del Brown Permit Tournament – Considered by anglers to be the hardest and most rewarding fish to catch in shallow water on fly, this tournament is named after the early innovator of the sport Del Brown, who showed that you can catch a permit on fly – more than once in a lifetime. In practice, it is a feat of a lifetime, but if you have skills, pattern, and luck, then you just may have a chance. For more information, call 305-744-0903.
  • July 18, 2020 – RUNNINGHemingway 5k Sunset Run & Paddle Board Race – Running race through Key West. This year, the event has expanded to include a paddleboard competition. Cost is $45-85 to register, depending on which events you participate in. For more information, visit the Hemingway 5K Sunset Run& Paddle Board Race website.
  • July 23 – 26, 2020 – HEMINGWAY Hemingway Days & Sloppy Joe’s 40th Annual Papa Look-a-Like Contest – Over 100 Hemingway look-a-likes compete for prizes and notoriety as most resembling the famous writer, judged by previous contest winners. Sloppy Joe’s Bar – 6:30 pm – 201 Duval Street.
  • July 29 – 30, 2020 – FISHING Lobster Mini-Sport Season – Two-day event draws hundreds of often frenzied recreational boaters in search of Florida lobster. Many rules apply, including: Bag limit: 6 per person per day for Monroe County. Possession limit – on the water: equal to the daily bag limit. Possession limit – off the water: equal to the daily bag limit on the first day, and double the daily bag limit on the second day. Possession limits are enforced on and off the water. Minimum size limit: must be larger than 3? carapace, measured in the water. A reminder that possession and use of a measuring device is required at all times, and night diving is prohibited in Monroe County (only during the sport season). Florida Saltwater Fishing License plus lobster endorsement/stamp required. Please respect other boaters, stay away from shorelines, ecological reserves, no-take zones, and canals, use a dive flag, and do no harm to the sensitive coral and eco-system.

August 2020 Key West Events

  • August 6 – 9, 2020 – SEAFOOD24th Annual Key West Lobsterfest – Everyone will be partying on Duval Street, except the lobsters. Marking the official opening of lobster season, this crustacean-focused event features street fairs, live music, and arts & crafts. Street fair with free live concert on Saturday, noon-11pm, lower Duval Street. For more information, visit the 24th Annual Key West Lobsterfest website.
  • August 12 – 16, 2020 – LBGTTropical Heat – All male, adults-only celebration of Key West’s gay community and lifestyle. Events include all-male themed parties and adult-oriented entertainment. For more information, visit the Tropical Heat website.

September 2020 Key West Events

  • September 2 – 6, 2020 – LGBT – Womenfest Key West 2020 – Lesbians and friends converge on Key West for a week of activities, including late night dancing, pool parties, comedy shows, sunset sails, competitive bull riding, and lots of music. Visit the Womenfest Key West 2020 website for more information
  • September 3 – 7, 2020 – PARTY11th Annual Key West Brew Fest – Labor-day weekend event featuring more than 150 different beers – including many award-winning microbrews. Events include seminars, tastings, pool parties, and meals. Big event is the Signature Tasting on Saturday, September 2 at South Beach ($75 per person for that event, advance tickets required).
  • September 7, 2020 – HOLIDAYLabor Day 2020 in Key West – Picnics, BBQ, beaches, and a day of leisure, all activities Key West is known for. Expect warm ocean temperatures, balmy nights, and a laid back crowd.

October 2020 Key West Events

  • October 15, 2020 – SEAFOODOfficial 2020 Stone Crab Season Opening – In mid-October, the most delicious local seafood becomes available, the stone crab. With a porcelain-like shell and briny meat, this crab is considered a sustainable resource in that only the claws are taken and the crab is released back into the wild to grow new ones. Stone crab is only native to this region and is considered a seafood delicacy. October 15 is a special day for locals who eagerly await the opening of the stone crab season in Key West.
  • October 16 – 17, 2020 – PARTY39th Annual Goombay Fest – This street party brings out all the locals to Bahama Village and features street fair cuisine (conch ceviche made fresh is popular), vendors selling a variety of wares, and live music at the bottom of Petronia. Don’t miss the party inside Blue Heaven. This is a family-friendly event and NOT the time to be wearing body paint or showing too much skin. 12noon – 12midnight. Petronia Street starting at Duval Street. FREE to attend.
  • October 16 – 25, 2020 – FANTASY FEST41st Annual Key West Fantasy Fest – Week-long celebration and Key West’s biggest party of the year – with many adult-only events. This year’s theme is “Roaring 2020’s & Future Fictions.”  Be creative with your costume!
  • October 22, 2020 – LOCAL COLOR –  38th Annual Headress Ball – Costume contest featuring dazzling headdresses created over many months and worn and displayed in this awe inspiring event. HUGE works of art, each more inventive and imaginative then the previous. Grand prize is $1500. Truman Waterfront Amphiteater, end of Southard Street. Buy tickets early as this event sells out.
  • October 29 – 31, 2020 – MUSIC29th Annual Meeting of the Minds 2020 – Parrothead convention and nirvana benefiting charity. Many events are members only. Live shows usually include members of Jimmy Buffett’s band. Highlights include the Margaritaville Street Fest on Friday from 1pm – 5:30pm on the 500 block of Duval Street (near Fleming Street) which is FREE and open to the public. For more information, visit the 29th Annual Meeting of the Minds 2020 website.

November 2020 Key West Events

  • November [DATE TO BE ANNOUNCED], 2020 – RUNNING28th Annual ABC 5K Walk/Run – Sponsored by Zonta, this running race benefits women’s health screenings and breast cancer awareness in the Lower Florida Keys. Race begins and ends at Salute on Higgs Beach.  Registration cost is $25 – $35, depending on when you register. For more information, call 305-393-5200.
  • November [DATE TO BE ANNOUNCED], 2020 – BOATING 39th Annual Key West World Championship – Considered the pinnacle of offshore powerboat racing. Top powerboat & superboat offshore racers compete for title of World Champion. Spectators line the Key West harbor to see the 100+ mph action. Good viewing from Fort Zachary Taylor State Park at the end of Southard Street. For more information, call 305-296-6166.
  • November [DATE TO BE ANNOUNCED], 2020 – ARCHITECTUREGarden Lecture Series – With the largest number of wood-framed historic structures in the United States, the architecture of Key West is a local and national treasure.  This lecture, held in the garden of Key West’s oldest house, will discuss the history, form, and influences of the local architecture.  Tickets cost $25 per person, 7pm start time, 322 Duval Street.
  • November 26, 2020 – HOLIDAYThanksgiving in Key West 2020 – Traditional turkey is served in a tropical setting as residents and visitors celebrate the annual holiday. Many local restaurants have special Thanksgiving menus.

December 2020 Key West Events

  • December [DATE TO BE ANNOUNCED], 2020 – HOLIDAYTree Trimming Party – The dock-front Schooner Wharf Bar hosts this annual holiday tree decorating party, craft fair, and toy drive.  Bring an ornament and get a free holiday cocktail; prizes for best ornaments. Features live island music by The Last Mango. 5pm, 202 William Street.
  • December [DATE TO BE ANNOUNCED], 2020 – HOLIDAYKey West Lighted Bike Parade – To benefit Wesley House Family Services, this neighborhood parade features bicycles adorned with holiday lights and decoration.  Ride ends on Appelrouth Lane (off Duval St), where there will be a Holiday block party.  Begins at 7pm (check-in is at 5pm), Bayview Park.  FREE with donation of unwrapped child’s gift.
  • December [DATE TO BE ANNOUNCED], 2020 – HOLIDAYKey West Holiday Parade – Extremely popular with children due to the shower of candy given out by the parade. Parade begins at Bayview Park in Key West, then heads down Truman Ave to Duval Street. Best viewing is along Truman Ave in Old Town, Key West. FREE.
  • December [DATE TO BE ANNOUNCED], 2020 – SPORTSTRIKW Triathalon – Athletes swim, run, and bike among Key West’s ideal scenery and conditions. Up to 1000 competitors are expected. Two race distances are available: Sprint and the twice-as-long Olympic. For more information, visit the TRIKW Triathalon website.
  • December [DATE TO BE ANNOUNCED], 2020 – ARTCharity Art Auction – To benefit Wesley House Family Services, this auction includes pieces donated by the estate of Judge Tegan Slaton and his widow Rosemary Enright. The event begins at 5:30 p.m. with a reception featuring appetizers by the Iron Chefs, and signature rum drinks by the Hemingway Rum Company. Cost is $20 and can be applied to art purchases.  Viewing of auction lots, and appetizers, at 5:30pm. Auction begins at 6:30pm.  201 Simonton Street.
  • December [DATE TO BE ANNOUNCED], 2020 – HOLIDAY30th Annual Key West Lighted Boat Parade – Vessels of every size and shape deck their hulls and light up the night with their creativity and originality to the delight of locals and visitors alike. Santa Claus has been spotted at the helm, ditching his sleigh for a center console or sailboat with mistletoe hanging from the mast. His first mates have included gingerbread men and the Grinch. Other times, dolphins have replaced cold-weather reindeer, ushering in Santa’s sleigh packed with lighted presents. Boats will come into the Key West Bight (Historic Seaport) and pass in front of the judges’ stand at Schooner Wharf Bar. Festivities start at 6 p.m. with the Gerald Adams Steel Your Heart Band, and the parade begins at 8 p.m. Live music all evening with yuletide favorites, plus a traditional ham dinner served from our galley.
  • December [DATE TO BE ANNOUNCED], 2020 – HOLIDAY7th Annual Parade of Paws & Holiday Bazaar – Benefiting the Florida Keys SPCA, this family-friendly event features pet parade, holiday bazaar, local vendors, live music, and smooch-a-pooch booth.  Santa will be there to take photos with your pets.  10am-2pm at Higgs Dog Park, White Street & Atlantic Blvd.  For more information, call 305-294-4857.
  • December 10 – 18, 2020 – HOLIDAYHanukkah in Key West 2020 – Key West is home to one of Florida’s oldest Jewish communities – with Jews settling here when the City was incorporated in 1832. The first Key West Congregation, B’nai Zion was founded in 1887. Today, during Hanukkah, a large menorah is lit in from of the synagogue each night of the holiday, with Rabbi and congregants gathering for the “festival of lights”. A latke and salmon feast is held the first night. Stop by 750 United Street and celebrate.
  • December 25, 2019 – HOLIDAYChristmas in Key West 2020 – Whatever gift you wish for, spending Christmas in Key West might be at the top of the list. While it never snows, and sometimes a palm tree is substituted for a traditional tree, there still is plenty of Christmas spirit in Key West. Look for historic homes that have added twinkle and magic with lights and displays. And to all a good night!
  • December [DATE TO BE ANNOUNCED], 2020 – ARCHITECTURE61st Annual Key West House & Garden Tour – Visit five Key West homes and tropical gardens. 4pm – 8pm. Tickets are $35 and are available at the 61st Annual Key West House & Garden Tour website.
  • December 31, 2020 – CELEBRATIONKey West New Year’s Eve – Celebrations include the lowering of the Conch Shell over Sloppy Joe’s on lower Duval Street, the lowering of famous Key West drag queen Sushi (riding a huge high-heeled shoe) over the Bourbon Street Complex on upper Duval Street, and the lowering of the “pirate wench” from the mast of a schooner in the Historic Seaport.

No items found.

Contact us today for your private air charter to Key West at (813) 207-5002 or at

Quote your flight quickly!

Quote my flight