Things to do in Dennis

    Discover amazing Dennis activities and premium in-home experiences.

    Nestled where cranberry bogs meet wide, windswept beaches, Dennis captures the quiet magic of old Cape Cod. In this charming village, shingled cottages and sandy lanes invite you to slow down and savor a sense of timeless coastal ease—where every salty breeze carries echoes of summer days gone by.

    Popular Activities in Dennis

    Best of Martha's Vineyard 3-Hour Full Island Tour

    Cover all six towns in 3 hours with history and film highlights—ideal for first-time visitors

    4.6 345 reviews
    $69/ person

    Bike Rental Delivery for 1–6 Days

    Get bikes delivered to you with electric, standard, and kids options.

    3.1 9 reviews
    $40/ bike

    Daily Bike Rental Pickup in Oak Bluffs

    Explore Oak Bluffs with flexible 1–6 day bike rentals and many models to choose from

    3.1 9 reviews
    $20/ bike

    Martha's Vineyard Island Tour & Menemsha Feast

    Customize your island tour with a Menemsha seafood picnic and complimentary wine

    Daily Bike Rental Delivery

    Enjoy bike delivery with 1–6 day rentals for all ages

    4.6 152 reviews
    $20/ bike

    Daily Bike Rentals in Oak Bluffs

    Explore the island on quality e-bikes and pedal bikes for 1–6 days

    4.6 152 reviews

    Cape Cod Bay Fishing Charter with Expert Crew

    Cast lines in Cape Cod Bay with experienced crew and soak in scenic coastal views

    5.0 11 reviews

    Tandem Kayak Rental in Hyannis for Two

    Enjoy flexible 24-hour to one-month kayak rentals and explore at your own pace.

    4.8 69 reviews

    Flexible Canoe Rental in Hyannis: 1 Day to 4 Weeks

    Enjoy hassle-free paddling with flexible rental periods and no age restrictions.

    4.8 69 reviews

    Hyannis Paddleboard Rental: 24hr to Monthly

    Explore Cape Cod waters with flexible 24-hour to month-long paddleboard rentals.

    4.8 69 reviews

    Cape Cod Half Day Striper Fishing Charter

    Chase striped bass on Cape Cod during a flexible 4.5-hour private charter for up to six guests

    5.0 65 reviews

    Monomoy Seal Watching Cruise in Harwich Port

    Cruise shallow channels to observe Gray seals and historic lighthouses with a naturalist guide.

    4.6 297 reviews
    $20/ person

    Cape Cod Evening Cocktail & Ice Cream Cruise

    Sip, Savor & Cruise: Narrated Harbor Views with Cocktails and Ice Cream Treats Onboard

    4.4 54 reviews
    $28/ person

    Cape Cod Sunset Cocktail & Ice Cream Cruise

    Watch Cape Cod's vibrant sunset while enjoying onboard cocktails and treats

    4.4 54 reviews
    $31/ person

    Shark Center General Admission in Chatham

    Explore interactive exhibits and learn about Great White Sharks during a self-guided visit.

    4.5 372 reviews
    $8/ person

    3-Hour Morning Cruise in Wellfleet Harbor

    Start your day with a private 3-hour cruise to secluded beaches and tidal islands around Wellfleet Harbor.

    5.0 60 reviews

    Private 3-Hour Day Cruise in Wellfleet, MA

    Discover remote beaches and swim in secluded waters during a customizable private charter for up to six guests.

    5.0 60 reviews

    Private 2Hr Sunset Sail with BYOB & 6 Guest Max

    Catch Cape Cod’s vibrant evening colors on a private charter for up to six guests with BYO food and drinks.

    5.0 60 reviews

    Mashpee Kayak Rental: 3 Hour Bay Access

    Explore Popponesset Bay with quality gear and the freedom to paddle for up to three hours.

    4.9 445 reviews

    Lawrence Pond Kayak & Paddleboard Rental

    Paddle Lawrence Pond at your own pace with included gear and flexible 2–3 hour rental.

    4.9 445 reviews

    Sandwich Marsh Kayak & Paddleboard Rental 2–3 Hr

    Paddle scenic Cape Cod marshes at your own pace with quality gear included.

    4.9 445 reviews

    Cape Cod Canal Full Day Bike Rental

    Pedal scenic canal paths at your own pace with quality bikes and included gear

    4.9 445 reviews

    Cape Cod Bike Rental with Gear in Sandwich MA

    Pedal scenic Cape Cod trails with quality bikes and gear included for four hours.

    4.9 445 reviews

    Cape Cod Sunset Kayak Tour in Sandwich MA

    Paddle Popponesset Bay to Ockway Bay with an ACA-certified guide and enjoy brilliant evening colors

    4.9 445 reviews

    Sandwich Cape Cod Kayaking Tour with ACA Guide

    Explore secluded beaches and wildlife with ACA-certified guides

    4.9 445 reviews

    Cape Cod Sunset Paddleboard Tour in Sandwich

    Watch a Cape Cod sunset from the water with an ACA-certified guide

    4.9 445 reviews
    $100/ person

    Wildlife Kayaking on Scenic Scorton Creek

    Watch wildlife on a relaxed Scorton Creek paddle with ACA certified guides

    4.9 445 reviews

    Half-Day Private Sail & Swim in Cape Cod Bay

    Spend half a day sailing Cape Cod Bay with a private crew and optional swim stop.

    4.9 35 reviews
    $1,199

    Provincetown Private Whale Watching on Stellwagen

    Search for whales on Stellwagen Bank aboard a boat reserved exclusively for your group.

    4.6 46 reviews

    Provincetown Whale Watch at Stellwagen Bank

    Discover feeding and nursing whales at Stellwagen Bank on an intimate boat tour

    4.6 46 reviews
    $175/ person

    Humpback Encounters on Private 3.5Hr Cruise

    Experience close encounters with humpbacks and finbacks on an exclusive 3.5-hour charter

    4.9 166 reviews

    Provincetown Sunset Cruise Past Historic Lighthouses

    Relax aboard the Beth Ann as you glide past Provincetown’s iconic lighthouses at sunset

    4.9 166 reviews

    Watch Humpback Whales & Cape Cod Sunset

    Search for humpback and finback whales then savor a colorful Cape Cod sunset aboard the Beth Ann.

    4.9 166 reviews

    Provincetown Sailing Tour on Historic Bay

    Treat yourself to a memorable afternoon sail

    5.0 35 reviews
    $32/ person

    2-Hour Sunset Sail in Provincetown Harbor

    Enjoy a relaxing two-hour cruise as daylight fades over the water

    5.0 35 reviews
    $30/ person

    Advanced Electric Bike Rental on Martha's Vineyard

    Ride up to 20 MPH with pedal assist and throttle to explore the island with ease

    3.1 9 reviews
    $79/ bike

    Parasailing in Oak Bluffs: 600 Foot Flight

    Soar 600 feet above the water with a dry deck takeoff and landing

    4.3 34 reviews
    $35/ person

    Jet Ski Rental in Oak Bluffs, Martha's Vineyard

    Ride a Yamaha WaveRunner for an exhilarating hour on Martha's Vineyard waters.

    4.3 34 reviews

    Martha's Vineyard Sunset Tour with Dinner

    Watch the sun set over Menemsha Beach aboard a comfy shuttle with dinner options and local commentary

    $50/ person

    Martha's Vineyard Tour of 6 Towns in 3 Hours

    Discover all six Martha's Vineyard towns in a small-group guided bus tour.

    $65/ person

    In-Home Experiences

    Full-Day E-Bike Rental in Hyannis with Gear

    Ride scenic Cape Cod trails with helmet and lock included

    4.8 69 reviews

    Private Beach Cruise in Provincetown

    Cruise to Provincetown's pristine beaches for sun, scenery, and seaside fun.

    Electric Beach Cruiser Rental in Edgartown

    Cover more ground effortlessly with pedal-assist power on colorful cruisers.

    4.8 88 reviews

    Experience the Charm of Dennis

    Dennis is a picturesque town where the serene beauty of Cape Cod meets sandy beaches, quaint villages, and vibrant cultural spots. Known for its historic sea captain's homes and stunning sunsets over Cape Cod Bay, Dennis offers visitors a perfect blend of relaxation and exploration. The gentle ocean breeze carries hints of saltwater as you stroll along Mayflower Beach or explore the charming shops in Dennis Village.

    Start your adventure with a bike ride on the scenic Cape Cod Rail Trail that winds through lush forests and cranberry bogs. In summer, catch an outdoor performance at the renowned Cape Playhouse—the oldest professional summer theater in America—or enjoy fresh seafood at one of many local eateries. As autumn arrives, immerse yourself in nature’s palette by hiking trails lined with golden leaves or visiting nearby Scargo Tower for panoramic views that stretch to Provincetown.

    Whether you're kayaking on Swan Pond River or exploring art galleries filled with local talent, Dennis provides endless opportunities for memorable experiences. Join a guided tour to learn about maritime history or simply relax on warm sands while savoring ice cream from an iconic seaside stand. With its welcoming atmosphere and diverse activities year-round, this coastal gem promises both tranquility and discovery around every corner.

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