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The Best Naples Activities for Seniors and Over 50s (Updated January 2026)

Naples, USA
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Naples Tours

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13 Results
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  • 10,000 Islands Boat Excursion - 3.5-Hour Dolphins & Shelling Tour
    4.9 (47)

    10,000 Islands Boat Excursion - 3.5-Hour Dolphins & Shelling Tour

    This is a premier experience in the Marco Island area and is superb for the entire family... from toddlers to the grandparents. It is a...

     3 hours 30 minutes  Free Cancellation  Instant Confirmation
    from
    $169.95
    from
    $169.95
  • Naples Sunset Cruise - Complimentary Charcuterie and wine
    Likely to Sell Out
    Likely to Sell Out
    5.0 (46)

    Naples Sunset Cruise - Complimentary Charcuterie and wine

    Whether you're a cozy couple, a lively family, or a tight-knit squad of friends, this adventure is your ticket to a shared moment of bliss....

     2 hours  Free Cancellation  Instant Confirmation
    from
    $110
    from
    $110
  • Naples Sunset Cruise 40' Vessel
    Likely to Sell Out
    Likely to Sell Out
    4.9 (18)

    Naples Sunset Cruise 40' Vessel

    Experience the magical Naples sunset while cruising on our Edison Explorer. This 90-minute sunset cruise takes you from historic Tin City Waterside Shops out to...

     1 hour 30 minutes  Instant Confirmation
    from
    $72.35
    from
    $72.35
  • Everglades Small Group Guided Boating & Walking Tour Expedition
    4.8 (58)

    Everglades Small Group Guided Boating & Walking Tour Expedition

    This is a premier learning experience in the Everglades Area and is superb for the entire family... from toddlers to the grandparents. Limited to just...

     3 hours 30 minutes  Free Cancellation  Instant Confirmation
    from
    $199.95
    from
    $199.95
  • PRIVATE Sunset & Sightseeing Boat Trip of Naples Bay and the Gulf
    4.9 (31)

    PRIVATE Sunset & Sightseeing Boat Trip of Naples Bay and the Gulf

    Price, as shown, is for the boat trip (group price) and not per adult! Maximum are 5 guests regardless of age. If your group is...

     2 hours 20 minutes  Free Cancellation  Instant Confirmation
    from
    $375
    from
    $375
  • Ten Thousand Islands Eco/Dolphin Tour
    Likely to Sell Out
    Likely to Sell Out
    5.0 (13)

    Ten Thousand Islands Eco/Dolphin Tour

    On this Eco Tour we will observe local marine life up close in its natural habitat, as well as search for rare shells on a...

     3 hours  Free Cancellation  Instant Confirmation
    from
    $550
    from
    $550
  • Private Sunset Eco Tour of Marco & 10,000 Islands
    Likely to Sell Out
    Likely to Sell Out
    5.0 (3)

    Private Sunset Eco Tour of Marco & 10,000 Islands

    Come see an amazing sunset on the Gulf! Some of the best sunsets in the world are in SW Florida—best seen on a sunset boat...

     2 hours 30 minutes  Free Cancellation  Instant Confirmation
    from
    $500
    from
    $500
  • Naples Sightseeing Day Cruise 40' Vessel
    Likely to Sell Out
    Likely to Sell Out
    5.0 (1)

    Naples Sightseeing Day Cruise 40' Vessel

    Experience the beauty of Naples, Florida while cruising on the Edison Explorer vessel. This 90-minute sightseeing cruise takes you from historic Tin City Waterside Shops...

     1 hour 30 minutes  Instant Confirmation
    from
    $65.65
    from
    $65.65
  • Florida Audio Tour Bundle 3 Self-Guided Sightseeing Tours
    5.0 (1)

    Florida Audio Tour Bundle 3 Self-Guided Sightseeing Tours

    Embark on an unforgettable journey through Florida's diverse landscapes with our Florida Self-Guided Audio Tour Bundle! Cruise the iconic Overseas Highway to Key West, uncovering...

     4 days  Free Cancellation  Instant Confirmation
    from
    $31.99
    from
    $31.99
  • Ten Thousand Islands Sunset, Beach and Eco Tour
    Likely to Sell Out
    Likely to Sell Out
    New To The Site!

    Ten Thousand Islands Sunset, Beach and Eco Tour

    Witness an incredible sunset only Florida can provide, all while relaxing in luxury on our first class boat. During this excursion we'll stop off at...

     3 hours  Free Cancellation  Instant Confirmation
    from
    $350
    from
    $350
  • Everglades Pirate and Beach Adventure
    Likely to Sell Out
    Likely to Sell Out
    New To The Site!

    Everglades Pirate and Beach Adventure

    Ahoy Matey! If you are captivated by stories of infamous pirates and legendary mobsters, then this is the tour for you! The Ten thousand Islands...

     3 hours  Free Cancellation  Instant Confirmation
    from
    $375
    from
    $375
  • Sunset Photography Private Tour on Marco Island
    New To The Site!

    Sunset Photography Private Tour on Marco Island

    unlimited guests can participate! seriously bring a group up to 100 people. package includes your choice of 40 high resolution digital photos complex edited.  additional...

     1 hour  Instant Confirmation
    from
    $650
    from
    $650
  • Explore Naples with a Fun Scavenger Hunt by Operation City Quest
    New To The Site!

    Explore Naples with a Fun Scavenger Hunt by Operation City Quest

    To play Operation City Quest in Naples, you'll use an app to gather points by completing exciting tasks and finding objects around the city in...

     2 hours  Free Cancellation  Instant Confirmation
    from
    $10
    from
    $10
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We guarantee the lowest price on all the tours available to book on our site. We'll refund the difference if you find the exact tour cheaper online until 48 hours before your tour starts.

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The following conditions apply to all lowest price guarantee refund requests:

  • The lowest price guarantee is available to any customer who makes a qualifying purchase through our website. The qualifying purchase must be a minimum of US$20 (or equivalent).
  • The lowest price guarantee covers retail and prepaid rates available to the general public. This does not include discounts or promotions you may receive (or be eligible for) from third-party sites or organizations such as AAA or AARP or special offers made as part of a membership program, corporate discount, daily deal, group, or rewards program.
  • Cool Marco Island promotions cannot be combined with the lowest price guarantee.
  • If you find a lower retail or prepaid rate for the same tour, offered on the same date, time and priced in the same currency as your original purchase, on any other website between the time you book on Cool Marco Island and 48 hours before your trip starts, we will refund the difference.
  • The lowest price guarantee does not apply where a lower overall price is found by breaking down the purchased tour into one or more parts sold separately.
  • Cool Marco Island reserves the right to verify the lower price details. Examples of acceptable forms of verification include a web screenshot or a web address.
  • All refund decisions will be made at the sole discretion of Cool Marco Island.

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Cool Marco Island wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Cool Marco Island over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.

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Cool Rewards

  • Cool Rewards is a loyalty program operated by Cool Destinations. Rewards may be earned by any eligible person holding a Cool Destinations account, subject to the Cool Destinations customer Terms of Use.

Earning rewards

  • Rewards can be earned by making bookings on the Cool Destinations website. You will be able to see the value of the rewards you can earn during the booking process.
  • Earned rewards will be issued in a pending state and will move to a confirmed state 24 hours after the start time of the experience.
  • Earned rewards will be available to redeem once they are no longer in a pending state.
  • For bookings that are moved to a different travel date, the rewards will be redeemable after the amended travel date.
  • If a booking where rewards were issued is canceled, the earned rewards will not be redeemable and will be moved to a canceled state.

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  • To redeem rewards, you must be logged into your Cool Destinations account.
  • Any available rewards will be automatically applied the next time you make a booking, and their value will be deducted from your order at checkout, unless you choose not to apply them, which requires you to indicate this via the toggle switch. Bookings made using rewards are subject to the standard Cool Destinations Customer Terms of Use.
  • You will not be able to redeem only a portion of your available rewards at checkout. It is only possible to redeem all or none of your available rewards.
  • There is no minimum order value required to redeem your rewards. This means that you can pay for 100% of your order with rewards.
  • Rewards are non-transferable and cannot be redeemed for cash.
  • If rewards are redeemed against a booking that is canceled or refunded, the rewards will be reissued to your account.

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  • You can check your Cool Destinations account to see the rewards you have collected at any time. You are responsible for ensuring that your rewards balance is correct.
  • We reserve the right to modify these Cool Rewards Terms and Conditions at any time, with or without notice, including the rules for earning and redeeming rewards. Any changes will be reflected in the updated Terms and Conditions.
  • We reserve the right to terminate the Cool Rewards program and cease issuing any further rewards on future bookings. All pending and available rewards balances will be honored.
  • By earning and redeeming rewards, you agree to these Terms and Conditions, as well as any subsequent changes made to them.