Free Concierge Service
Text or call 1-877-GREET-WELL
Ask AIAI
Ask AIAI
Why travelers choose Greetwell

Curated by our team

Every experience is hand selected and approved by Greetwell.

Personal concierge

Real humans available to help before, during, and after your booking.

Intimate & authentic

Including unique in-home experiences you won't find anywhere else.

Easy booking & cancellation

Reserve in minutes with free cancellation on most experiences.

Greetwell

Experiences that stay with you long after the trip

Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

About

  • Our Story
  • For Experience Providers
  • For Hospitality Partners
  • For Developers

Resources

  • Travel Guides
  • Destinations
  • Categories
  • Experience Gift Cards
  • Help Center
[email protected]1-877-GREET-WELL

Safe & Secure Payments

© 2026 Greetwell, Inc. All rights reserved.
Privacy PolicyTerms
Free Concierge Service
Text or call 1-877-GREET-WELL
Ask AIAI
Ask AIAI
Best 242

things to do in South Dennis, MA

Showing 169-192 of 242 results
3-Hour Waterskiing Lesson in Nantucket

3-Hour Waterskiing Lesson in Nantucket

Get on the water with gear provided for a classic skiing session

5.0 • 43 reviews
$1,272
Private Shark Watching Tour in Harwich

Private Shark Watching Tour in Harwich

Explore Shark Alley by private motorboat with expert guidance and aerial spotting

4.8 • 134 reviews
$2,150& up
Shark Tour in Harwich

Shark Tour in Harwich

Scan the water for sharks with a naturalist guide and aerial spotting support

4.8 • 134 reviews
$335/ person
8-Hour Kayak & Paddleboard Rental in Mashpee

8-Hour Kayak & Paddleboard Rental in Mashpee

Set out on a self-guided paddle through Popponesset Bay

5.0 • 208 reviews
$96/ equipment
90-Minute SUP Yoga Class in Mashpee

90-Minute SUP Yoga Class in Mashpee

Find your balance with a guided yoga flow on calm Cape Cod waters

5.0 • 193 reviews
$64/ person
Striped Bass & Bluefish Fishing & Whale Watching Charter

Striped Bass & Bluefish Fishing & Whale Watching Charter

Private charter to fish for striped bass and bluefish and look for whales

4.9 • 179 reviews
$1,214
4-Hour Private Boat Charter in Provincetown

4-Hour Private Boat Charter in Provincetown

Choose your beach and use the boat as your home base for swimming and relaxing

4.9 • 179 reviews
$843
Kids Kayak & Paddleboard Tour Series in Oak Bluffs

Kids Kayak & Paddleboard Tour Series in Oak Bluffs

Build kayaking and paddleboard skills on a 4-day kids series at Sengekontacket Pond

4.9 • 162 reviews
$345/ person
Oak Bluffs 1.5-Hour Private Kayak Lesson

Oak Bluffs 1.5-Hour Private Kayak Lesson

Build paddling skills at any level with a private lesson

4.9 • 162 reviews
$159/ kayak
Nantucket Group Wakeboarding & eFoiling Session

Nantucket Group Wakeboarding & eFoiling Session

Make waves together with coached wakeboarding, eFoiling, and tubing

5.0 • 43 reviews
$2,938& up
Sandwich Kayaking & Glassblowing Experience

Sandwich Kayaking & Glassblowing Experience

Paddle Scorton Creek and create your own blown-glass piece

5.0 • 208 reviews
$283/ person
Cape Cod Ice Cream Paddleboard Tour

Cape Cod Ice Cream Paddleboard Tour

A relaxed guided paddle with a midway ice cream boat stop

5.0 • 193 reviews
$90/ person
Nantucket 3-Hour Wing Foiling Lesson

Nantucket 3-Hour Wing Foiling Lesson

Build wing-foiling skills with tailored instruction and boat support

5.0 • 43 reviews
$770& up
Harwich Sunset Cruise

Harwich Sunset Cruise

Share a sunset motorboat ride through the harbor

4.8 • 134 reviews
$85/ person
14' Catamaran Rental on Pleasant Bay

14' Catamaran Rental on Pleasant Bay

Take the helm of a forgiving catamaran for easy bay sailing

4.8 • 134 reviews
$143/ boat
Paddleboard Scorton Creek Guided Tour

Paddleboard Scorton Creek Guided Tour

Stand-up paddleboard tour up Scorton Creek with an ACA Certified guide

5.0 • 208 reviews
$110/ person
Cape Cod Guided Pirate Paddle Tour

Cape Cod Guided Pirate Paddle Tour

Paddle through a clue-filled pirate quest with a water cannon showdown

5.0 • 193 reviews
$85/ person
2-Hour Kids Sea Creature Cruise in Provincetown

2-Hour Kids Sea Creature Cruise in Provincetown

Cruise for seals, fish, and lobster traps with the kids

4.9 • 179 reviews
$604
Provincetown Seal & Lighthouse Cruise

Provincetown Seal & Lighthouse Cruise

See seals and three historic lighthouses from Provincetown Harbor

4.9 • 179 reviews
$551
4-Hour Sea Kayaking Tour In Martha's Vineyard

4-Hour Sea Kayaking Tour In Martha's Vineyard

Paddle open-ocean routes to remote spots with guides on Martha’s Vineyard

4.9 • 162 reviews
$186/ kayak
Sunrise Kayak & SUP Tour in Oak Bluffs

Sunrise Kayak & SUP Tour in Oak Bluffs

Paddle at sunrise with breakfast and coffee included

4.9 • 162 reviews
$64/ kayak
Sunset Harbor Cruise in Nantucket

Sunset Harbor Cruise in Nantucket

Take in Nantucket Harbor views as the day turns toward sunset

5.0 • 43 reviews
$933
2-Hour Stand-Up Paddleboard Tour on Popponesset River

2-Hour Stand-Up Paddleboard Tour on Popponesset River

Beginner stand-up paddleboard tour with ACA-certified guidance

5.0 • 208 reviews
$110/ person
Full Moon Kayak Tour On Popponesset Bay

Full Moon Kayak Tour On Popponesset Bay

Paddle Popponesset Bay at sunset and into the full moonlight

5.0 • 208 reviews
$182/ kayak
1…789…11
Bike Rentals57Boat Tours28Sailing23Kayaking Tours21Boat Rentals15
More
  • Paddleboarding13
  • Stand Up Paddle Boarding13
  • Private Fishing Charters8
  • Fishing Charters7
  • Yacht Charters7
  • Whale Watching6
  • Sunrise and Sunset Tours5
  • Water Skiing5
  • Bus Van and Limo Tours3
  • Kiteboarding3
  • Scenic Flights3