How about a cruise? We did a cruise in the Caribbean last Feb on Royal Caribbean and it was heavenly. First day out and last day back were a bit chilly as we headed back in to Port Jersey, but many cruise lines have ships ported in Florida that you can fly to depart from.
It is actually great, food is included, though you can pay extra for specialty dining. Many nonalcoholic drinks are included, though you can pay extra for alcohol, and some sorts of wine/beer packages, or soda/froufrou coffee packages. You bop between island ports, you just unpack once and get to visit 4 or 5 [or more depending on how long a cruise you take] there is generally swimming pool, hot tub, pretty much all the food you can snarf, and you get to sightsee multiple places. Generally you tip once at the end [unless you barhop on the boat, or order from room service]
As an idea, this is part of the menu from last Feb’s cruise:
NIGHT ONE - Bon Voyage Dinner
STARTERS
Strawberry, Kiwi & Pineapple Medley
Smoke Fish Tapenade
Vidalia Onion Tart
Sopa de Tortilla
Hot and Sour Shrimp soup
Child Watermelon Gazpacho
Caesar Salad or Spinach Salad
MAIN COURSE
Truffled wild mushroom linguini alfredo
Slow-Roasted Prime Rib
Grilled Mediterranean Quesadilla
Pan-seared golden sea bass
Pan-seared fresh atlantic salmon
Aloo Gobi Methi
DESSERTS
Strawberry Pavlova
Chocolate Cherry Cake
Savarin
Low-fat blueberry and peach cobbler
Sugar-Free chocolate pot de Crème
NIGHT Two - Captain’s Gala (Formal Night)
STARTERS:
Shrimp Cocktail
Escargot Bourguignonne
Lobster Bisque
Oxtail Broth
Golden Pear Soup
Caesar Salad
MAIN COURSE:
Shrimp Ravioli
Grilled Seafood Brochett
Filet Mignon
Roasted Duck
Sauteed Seasonal Mushrooms
Potato Curry
DESSERTS:
Bittersweet Chocolate Souffle
Double Strawberry Cheesecake
Marinated Cherry Bake
Low-fat Berry Mouse
Sugar-free coconut vanilla layer cake
NIGHT THREE
STARTERS
Exotic Fruits w/ mojito jelly
Crab and Shrimp Salad
Beef and Veal Tortellaci
Jalapeno potato soup
Chicken Consomme
Caesar Salad
Seasonal Salad
MAIN COURSE
Parmesan-Crusted Turkey Tenderloin
Cornmeal-Dusted Tilapia
Slow-Roasted Beef Shoulder Filet
Asparagus and Brie Tart
Penne Tarantina
Gobi Ki Sabzi
DESSERTS
Choca-Chino Trilogy
Banana and Baileys Irish Cream brulee custard baked under a caramel crust
Magic Mango Parfait
Low-Fat Exotic pineapple and coconut cake
Steamed Sugar Free vanilla and berry custard w/ fresh berries
NIGHT FOUR - Venetian Feast
STARTERS
Caprese Salad
Antipasti
Scallop Risotto
Creamy Roasted Garlic Soup
Minestrone
Strawberry bisque
Caesar Salad
Insalata Mista – mixed greens, crisp zucchini, sweet red bell peppers and black olives
MAIN COURSE
Rigatoni Pasta
Garlic Tiger Shrimp
Chicken Marsala
Lamb Shank w/Rosemary
Eggplant and Roma Tomato Bake
Kaju Paneer Dhansak
DESSERTS
Warm Chocolate Cake
Raspberry Panna Cotta
Tiramisu
Low-Fat angel food cake w/ grand marnier marinated strawberries
Sugar-Free Chocolate mint cake
NIGHT FIVE - Chef’s Dinner
STARTERS
Eggplant and Kalamata Olive Tartare
Seafood Salad
Creamed wild mushroom in Puff Pastry
Cream of Asparagus
Double Duck Consomme
Roasted Peach Soup
Caesar Salad
House Salad
MAIN COURSE
Thai BBQ Chicken Breast
New England Bay Scallops and Ziti
Fisherman’s Plate
Slow-Roasted Aged Prime Rib
Greek-Style Vegetarian Moussaka
Kabuli Chana
DESSERTS
Dessert Sampler
Cherries Jubilee
Low Fat Double Passion Fruit Cheesecake
Sugar Free Red Berry Tart